Abstract
Lantana camara L., commonly known as pigeon berry, is a herbaceous plant of growing scientific interest due to the high medicinal value. In fact, despite being categorized as an invasive species, it has been used for a long time to treat different diseases thanks to the many biological activities. Triterpenes, flavonoids, phenylpropanoids, and iridoid glycosides are the bioactive compounds naturally occurring in L. camara that have demonstrated anticancer, antifilarial, nematocidal, antibacterial, insecticidal, antileishmanial, antifungal, anti-inflammatory, and antioxidant properties. The aim of this review is to update the information concerning the chemistry and biological activity of L. camara extracts and their constituents, including semisynthetic derivatives, revising the literature until June 2024. We believe that the data reported in this review clearly demonstrate the importance of the plant as a promising source of medicines and will therefore stimulate further investigations.
1. Introduction
According to the latest Angiosperm Phylogeny Group classification (APG IV), the genus Lantana L. is one of the 32 genera belonging to the family Verbenaceae J. St. Hill., in the order Lamiales [1]. This genus comprises 133 species with accepted names according to the December 2023 WFO classification [2] (latest access: 31 May 2024). However, this number may change in the future due to the description of new species or the segregation into other genera [3]. Moreover, the taxonomic classification of the genus is difficult, since species are not stable and widespread hybridization occurs, while morphological characters vary with age.
A recent phylogenetic study of the tribe Lantaneae Endl. stated that the genus Lantana L. is not monophyletic and placed the species Lantana camara L. into the section Lantana sect. Lantana together with L. horrida Kunth, L. depressa Small, L. leonardiorum Moldenke, L. sabrida Sol., and L. strigocamara R.W. Sanders [4].
L. camara L., which is the most widespread species of the genus, is an evergreen aromatic spiny hairy shrub, usually 0.5–3 m high (Figure 1), bearing flowers of different colors, from red to pink, white, yellow, orange, and violet. The stems and branches are sometimes armed with prickles or spines; the leaves are opposite, simple with large petioles, and oval blades, which are rugged and hairy and have a bluntly toothed margin. The plant is known by different popular names, such as pigeon berry [5], wild red sage [6], cuasquito, angel lip, flowered sage, black sage, shrub verbena, white sage, and wild sage [7]. It is native to tropical and subtropical Central and South America, from where it was introduced to other countries, and it has spread all over the world [8] (Figure 2). L. camara is considered an invasive obnoxious weed of pastures, orchards, and forest areas, as well as a cultivated ornamental or garden hedge plant [9,10,11]. The poisonous properties of the plant have been known for a long time, especially to livestock; on the other hand, toxicity to humans from fruit ingestion has also been reported. Due to the plant cosmopolitan distribution and the innate ability to produce hybrids, some varieties and subspecies are known [12], and have been proposed in a taxonomic revision of Lantana L. sect. Lantana [13]. However, because of the intrinsic taxonomic complexity [14], in this review, all of the subspecies and varieties have not been treated separately, but have been incorporated into a single species, L. camara L. sensu lato.
Figure 1.
Lantana camara L.: (A) entire plant; (B) flowers; (C) fruits (photos by the authors).
Figure 2.
Worldwide distribution of Lantana camara L. [11].
L. camara is one of the most important herbal medicines in the world. For example, it is well known in the Ayurvedic medicinal system with the Sanskrit names of Chaturangi and Vanacchedi. Different parts of the plant are used as traditional remedies for the treatment of various human ailments, such as itches, cuts, ulcers, swellings, bilious fever, catarrh, asthma and bronchitis, eczema, chicken pox, tetanus, malaria, tumors, stomachache, toothache, headache, scabies, leprosy, rheumatism, and as an antiseptic agent to treat wounds [4,5,15,16]. The essential oil has shown antibacterial, antifungal, cytotoxic, and mosquito-repellent effects. L. camara has been found to display a variety of biological properties, including antiarthritic, anti-aspergillus, antibacterial, anticancer, cardioactive, anti-fertility, antifilarial, hepatoprotective, anti-hyperglycemic, anti-hyperlipidemic, anti-inflammatory, insecticidal, antimicrobial, antimutagenic, anxiolytic, nematocidal, antioxidant, anti-proliferative, anti-protozoal, antipyretic, antithrombin, antitumor, antiulcerogenic, antiurolithiasis, antiviral, and wound-healing properties. Moreover, the plant extracts have been reported to inhibit the enzymes acetylcholinesterase, alpha amylase, carboxylesterase, cyclooxygenase-2, inducible nitric oxide synthase (iNOS), glutathione-S-transferase (GST), 5-lipoxygenase (5-LOX), protein kinase C, and xanthine oxidase [17,18]. Phytochemical studies conducted by different research groups have led to the isolation of essential oils, various steroids, terpenoids, saponins, iridoids, flavonoids, phenylethanoids, naphthoquinones, coumarins, polyphenols and other phenolics, and alkaloids [17,18,19,20,21,22,23]. Interestingly, the genus Lantana is free of diterpenoids [17].
The information concerning the phytochemistry and the biological activities of L. camara L. published until March 2000 has been condensed in previous reviews [17,18,21,24]. Moreover, recent studies on ecological aspects, chemical constituents, semisynthetic derivatives [25,26,27], and the biological and pharmacological activities of L. camara have been reviewed [17,18,20,21,22,23,28,29,30,31,32,33,34,35]. However, these publications, although dealing with different aspects of the plant, are largely incomplete. Therefore, the purpose of this review is to update and complete the information about L. camara L. to serve as a starting point for further investigations of the plant.
2. Research Strategies and Literature Sources
To prepare this review, the literature from 14 March 2000 until 10 June 2024 has been retrieved from the following databases: Pub-Med (https://pubmed.ncbi.nlm.nih.gov/, accessed on 10 June 2024), Google Scholar (https://scholar.google.com/, accessed on 9 March 2024), Scopus (https://www.scopus.com/, accessed on 9 March 2024), MDPI (https://www.mdpi.com/, accessed on 9 March 2024), NIH (https://www.nih.gov/, accessed on 9 March 2024), Elsevier (https://www.elsevier.com/, accessed on 9 March 2024), Scielo (https://scielo.org/es/, accessed on 9 March 2024), and Bio One (https://bioone.org/, accessed on 9 March 2024). The most relevant papers dedicated to the phytochemistry and the in vitro and in vivo biological effects of L. camara extracts, isolated chemical compounds, and semisynthetic derivatives were initially considered. Subsequently, among the more than 1600 articles published on L. camara, the manager software Mendeley Desktop software version 1.19.8 was used led us to select and review the research papers mainly dedicated to the above-mentioned topics. Moreover, all duplicated articles and gray sources were removed. After this first selection, a total of approximately 200 articles directly related to the topics of the present review were further reduced to 176 based on the relevance of the information provided by each of them. The systematic search of databases for relevant articles published on L. camara to compile this review is shown in Figure 3.
Figure 3.
Flowchart for the search process and selection of the studies considered for the review.
3. Results
3.1. Ethnobotany
In Table 1 we have reported the distribution of L. camara L. in different regions and countries of the world, together with the local vernacular names, the part of the plant used and the preparation methods of traditional remedies.
Table 1.
Distribution and traditional uses of Lantana camara L. in various continents and countries of the world.
Table 1.
Distribution and traditional uses of Lantana camara L. in various continents and countries of the world.
| Region | Country | Vernacular Name | Part of the Plant | Preparation Method | Traditional Uses | Ref. |
|---|---|---|---|---|---|---|
| Africa | Congo (Bouenza Department) | Lantana (Kunyi) | Leaves | Decoction | Antidiarrheal | [36] |
| Democratic Republic of Congo (Bukavu and Uvira) | Mwamuganga (Mashi), Mavi ya kuku (Swahili), Makereshe (Nande) | Leaves | Decoction | Antimalarial | [37] | |
| Democratic Republic of Congo (Kisantu and Mbanza-Ngungu) | Nsudi nsudi (Kikongo) | Leaves and fruits | Decoction; administered by rectal route | To treat cough by the Ntându and Ndibu ethnic groups; to treat hemorrhoids | [38] | |
| Ethiopia (Libo-Kemkem District) | NR | Leaves | Infusion | Antidiarrheal | [39] | |
| Ethiopia (Mana Angetu District) | NR | Leaves | Decoction | To treat skin infections, gonorrhea, and “evil eye” | [40] | |
| Ethiopia (Wonago Woreda) | Yewof kollo (Amharic) | Stems | Infusion | Antidiarrheal | [41] | |
| Ethiopia (Sheko District) | Michi-charo (Sheko) | Leaves | Topical | To treat “Michi”, a type of febrile illness | [42] | |
| La Réunion | Galabert, Corbeille d’or (French) | Leaves | Decoction, infusion | Antimalarial | [43] | |
| Guinea (Low, middle, upper, and forest ecological zones) | Tagani (NR) | Leaves | Decoction | Soussous, Malinké, Guerzé, Konon, and Manon ethnic groups use the plant to treat infectious diseases | [44] | |
| Kenya (Central Province) | Rûîthiki, Mûkenia (Kikuyu) | Leaves | Crushed; directly applied to the ear to treat otitis | Kikuyu ethnic group uses the plant to treat common cold by inhaling crushed leaves | [45,46] | |
| Kenya (Embu and Mbeere Districts) | Mûkenia (Kikuyu) | Leaves | Decoction | Antimalarial | [47] | |
| Kenya (Formerly: Bondo District, now Siaya County) | Nyabend winy (Luo) | Leaves and roots | Decoction | To treat cough | [48] | |
| Kenya (Msambweni District) | Mjsasa (Digo) | Leaves | Decoction | Digos, Durumas, and Kambas ethnic groups use the plant as an antimalarial | [49] | |
| Kenya (Rusinga Island and Rambira) | NR | Leaves and seeds | Burnt for fumigation | Used as a mosquito repellent | [50] | |
| Madagascar (Antsiranana) | Kalabera (NR) | Aerial parts | Decoction | To treat cough, hypertension, and fever | [51] | |
| Nigeria (Ibadan) | Wild sage (English) | Leaves | Burnt for fumigation | Used as an insect repellent | [52] | |
| Uganda (Budiope County) | Kapanga (Lusoga) | Leaves | Burnt for fumigation; decoction | Used as a mosquito repellent; antimalarial | [53] | |
| Uganda (Budondo Subcounty) | Kapanga (Lusoga), Tickberry (English) | Leaves | Burnt for fumigation | Used as a housefly and insect repellent | [54] | |
| Uganda (Otwal and Ngai Subcounties) | NR | Leaves and roots | Maceration | Used to treat ringworms, cataracts, snake bites, and epilepsy | [55] | |
| Asia | China (Xishuangbanna) | Luo-ya-min (Chinese) | Leaves | Burnt for fumigation | Used as a mosquito repellent | [56] |
| India (Assam) | Bhoot-phool (Hindi) | Bark | Burnt for fumigation; decoction | Used as an insect repellent; antimalarial | [57] | |
| India (Dharmapuri District) | NR | Leaves | Decoction, infusion | Antimalarial | [58] | |
| India (Jharkhand State) | Puttu (NR) | Leaves | Decoction, pounded | To treat several skin and respiratory diseases | [59] | |
| India (NR) | NR | Leaves | Decoction | Antiseptic, antimalarial, and antirheumatic | [60] | |
| Philippines (Paroc) | Gainis (NR) | Leaves and stems | Burnt for fumigation | Used as an insect repellent | [61] | |
| Vietnam (Hướng Hóa District) | Thục Klay (NR) | Roots | Decoction | Van Kieu ethnic group uses the plant alone or associated with roots of Mangifera indica and barks of Erythrina variegata to treat abdominal pain and diarrhea | [62] | |
| Yemen (Hajjah District) | NR | Flowers, leaves, and seeds | Burnt for fumigation | Used as an insect repellent | [63] | |
| North and Central America | Mexico (Querétaro) | Alfombrilla, Gobernadora, Ororuz (Spanish) | Leaves and stems | Decoction | To treat scorpion and insect stings; antidiarrheal and antiparasitic | [64] |
| Mexico (Chiapas) | Jøtskuy (Zoque), Cinco negritos (Spanish) | Stems | Decoction | Antidiarrheal, antiparasitic, and antirheumatic | [65] | |
| Mexico (Puebla) | Cinco negritos (Spanish) | Aerial parts | Decoction | Antidiarrheal | [66] | |
| South America | Brazil (Minas Gerais) | Cambará (Tupi) | Leaves | Decoction, infusion | To treat respiratory diseases; antipyretic and antirheumatic | [67] |
| Suriname (Pikin Slee) | NR | Leaves | Decoction | The Saramaccan Marron ethnic group uses the plant for the anti-inflammatory, antiparasitic, and depurative properties | [68] | |
| Colombia (Antioquia Department) | Venturosa (Spanish) | Stems | Decoction; steam bath | To treat snake bites | [69] | |
| The Caribbean | France (Guadeloupe) | Mille-fleurs (French) | Flowers | Decoction, infusion | To treat flu syndrome | [70] |
NR: not reported.
3.2. Phytochemistry
A total of 168 compounds have been described with different names in the considered period. They include both specialized metabolites isolated from non-volatile fractions of L. camara as well as semisynthetic derivatives. The distribution pattern of these compounds includes steroids and triterpenoids (75.6%), flavonoids (14.3%), fatty acids and other miscellaneous compounds (8.9%), and iridoid glucosides (1.2%).
Triterpenoids and Steroids
Steroids and pentacyclic triterpenoids are the predominant constituents isolated in the indicated period from the non-volatile fractions of L. camara or obtained by semisynthesis. Steroids (Table 2) are only a few and include common phytosterols such as stigmasterol (1), β-sitosterol (3), and campesterol (5), in addition to the rare spirostane saponin yamogenin II (6), which has a unique aglycone moiety. One hundred and twenty-one triterpenoids (Table 3) have been described in the years considered in this review. Their molecular structures belong to only five families, i.e., the protostane, euphane, lupane, oleanane, and ursane ones. The last two skeletons are by far the most common. Alisol A (7) is the only protostane isolated from L. camara, while euphanes are represented by eight triterpenoids (8–15). The structures of most of them are characterized by a D7 double bond, an oxidized α-substituent at C-4, and a γ-lactone E ring that is trans-fused to the cyclopentane D ring and bears an unsaturated homoprenyl chain. The small lupane family (16–18) includes the rare lantabetulic acid (17), which is characterized by an ether β-bridge connecting C-3 with C-25, and the highly bioactive betulinic acid (18). A total of 78 oleanane triterpenoids (19–96), including 34 synthetic ones, and 31 ursane derivatives (97–127), including 6 synthetic ones, have been described in the considered period. The two skeletons differ from the position of the methyl groups C-29 and C-30, which are positioned on the quaternary carbon C-20 in the oleanane compounds, while they are trans-oriented on the tertiary carbons C-19 and C-20 in the ursane derivatives.
The great variety of oleanane triterpenoids from L. camara derive from a combination of differently placed double bonds and different oxygenated groups that decorate the basic skeleton. A β-COOH, as in compound 30, or a β-COOMe group, as in 33, is usually linked to C-17, with cis-orientation to βH-18. When a carboxylic group is absent at C-17, a D17(18) double bond occurs, as in triterpenoid 49; a D12(13) double bond is usually present, as in 22, while, very rarely, a double bond occurs between C-11 and C-12, as in 21, or between C-1 and C-2, as in 78. One compound (54) containing a 9(11),12(13)-diene system has also been isolated. A carbonyl group is usually present at C-3, as in 26, or at C-11, as in 20; in one compound, 40, a CO occurs at C-22. An acetal system formed by a β-epoxide bridge between C-25 and C-3 and an α-OH (or, very rarely, an α-alkoxy) group at C-3 is frequently present in oleanane structures, as in 29 or 40. A few compounds are known to contain a lactone ring formed by a β-oxygen atom at C-13 bonded to a β-CO group at C-17, as in 43. One example (34) of a triterpenoid bearing a β-epoxy ring at C-21/C-22 has been isolated from L. camara. A free βOH group usually occurs at C-3, as in 31, at C-22, as in 26, and at C-24, as in 28; very rarely, an OH is present at C-2, as in 78, or at C-19, as in 25, at C-7, as in 23, C-9, as in 64, and C-12, as in 43. One 3-O-acyl (compound 38) and one 3-O-β-D-glucosyl derivative (84) have been isolated. The 22-βOH is usually esterified with an acyl group, e.g., an acetyl, as in 42, a propanoyl, as in 46, a butanoyl, as in 50, an isobutanoyl, as in 51, an angelyl [(Z)-2-methylbut-2-enoyl], as in 48, and a senecioyl (3-methylbut-2-enoyl) residue, as in 49; rarer are the esters with (S)-2-mehylbutanoic acid, as the triterpenoid 66, and (S)-3-hydroxy-2-methylidenebutanoic acid, as 69.
Most of these structural characteristics are shared by the ursane triterpenoids due to the close biosynthetic origin of the oleanane and ursane families. A unique ursane triterpenoid is the 3-O-β-D-glucosyl derivative 127, in which stearic acid is esterified to the 4-OH group of a glucosyl moiety.
The flavonoids (Table 4) are represented by 19 flavones (128–146), which are mainly apigenin and luteolin derivatives. A semisynthetic derivative (144) is included. Three rare O-methyl flavonols (147–149) and two isoflavones, i.e., 5,7-dihydroxy-6,3′,4′-trimethoxy isoflavone (150) and triglycoside 151, have also been isolated. The two iridoids 152 and 153 (Table 5) are the 1-O glucosides of the common aglycones genipin and 4a-OH genipin. The fatty acids 154–162 (Table 6) include common saturated and unsaturated long-chain homologues from C14 to C32. Finally, the small group of miscellaneous metabolites 163–168 (Table 7) includes the toxic cyanogenic glucoside linamarin (164), the common aliphatic alcohols phytol (165), and triacontane-1-ol (167).
Compounds isolated from L. camara and semisynthetic derivatives are listed in the following Table 2, Table 3, Table 4, Table 5, Table 6 and Table 7. The compounds with the same molecular skeleton are grouped and are then listed by increasing molecular formulae. Compounds with the same molecular formula are listed in alphabetic order.
Table 2.
Steroids isolated from non-volatile fractions of Lantana camara.
Table 2.
Steroids isolated from non-volatile fractions of Lantana camara.
| Nº | Compound Name | Molecular Formula | Molecular Weight | Skeleton Type | Part of the Plant/Solvent | Reference |
|---|---|---|---|---|---|---|
| (1) | Stigmasterol (Stigmasta-5,22-dien-3β-ol) | C29H48O | 412.702 | Stigmastane | Leaves/methanol Stems/methanol | [71] |
| (2) | 7-Oxo-β-sitosterol 3β-Hydroxy-stigmast-5-en-7-one | C29H48O2 | 428.701 | Stigmastane | Stems/methanol Roots/chloroform | [19,71] |
| (3) | β-Sitosterol Stigmast-5-en-3β-ol (Figure 4) | C29H50O | 414.718 | Stigmastane | Aerial parts/petroleum ether Aerial parts/96% ethanol Fruits/chloroform Leaves/methanol Stems/95% ethanol, methanol Roots/chloroform Leaves, stems, and roots/ petroleum ether | [19,72,73,74] |
| (4) | β-Sitosterol 3-O-β-D-glucopyranoside 3-O-β-D-Glucopyranosyl-stigmast-5-en-3β-ol | C35H60O6 | 576.859 | Stigmastane | Aerial parts/methanol Leaves/methanol Stems/95% ethanol, methanol | [15,71,74,75,76,77] |
| (5) | Campesterol Campest-5-en-3β-ol | C28H48O | 400.691 | Campestane | Leaves/methanol Stems/methanol | [71] |
| (6) | Yamogenin II (25S)-Spirostan-5-ene-3β,21-diol-3-O-α-L-rhamnopyranosyl-(1″33→2′)-[α-L-rhamnopyranosyl-(1‴→4′)]-β-D-glucopyranoside (Figure 4) | C45H72O17 | 885.054 | Spirostane | Leaves/methanol | [78,79] |
Table 3.
Triterpenoids isolated from non-volatile fractions of Lantana camara and semisynthetic derivatives.
Table 3.
Triterpenoids isolated from non-volatile fractions of Lantana camara and semisynthetic derivatives.
| Nº | Compound | Molecular Formula | Molecular Weight | Skeleton Type | Part of the Plant/Solvent | Reference |
|---|---|---|---|---|---|---|
| (7) | Alisol A | 490.725 | Protostane | Roots/chloroform | [19] | |
| (8α,9β,11β,14β,23S,24R)-11,23,24,25-tetrahydroxy-protost-13(17)-en-3-one | C30H50O5 | |||||
| (Figure 4) | ||||||
| (8) | Lantrieuphpene B (Figure 4) | C31H44O5 | 496.688 | Euphane | Aerial parts/methanol | [80] |
| (9) | Lantrieuphpene C (Figure 4) | C31H46O5 | 498.704 | Euphane | Aerial parts/methanol | [80] |
| (10) | Euphane monolactone A (Figure 4) | C32H46O6 | 526.714 | Euphane | Leaves/acetonitrile | [72] |
| (11) | Euphane monolactone B (Figure 4) | C32H46O7 | 542.713 | Euphane | Leaves/acetonitrile | [72] |
| (12) | Lantrieuphpene D (Figure 4) | C32H48O6 | 528.730 | Euphane | Aerial parts/methanol | [80] |
| (13) | Lantrieuphpene A (Figure 4) | C33H46O7 | 554.724 | Euphane | Aerial parts/methanol | [80] |
| (14) | Euphane monolactone C (Figure 4) | C40H58O14 | 762.890 | Euphane | Leaves/acetonitrile | [72,80] |
| (15) | Euphane monolactone D (Figure 4) | C42H60O15 | 804.927 | Euphane | Leaves/acetonitrile | [72] |
| (16) | Betulonic acid 3-oxo-lup-20(29)-en-28-oic acid (Figure 5) | C30H46O3 | 454.695 | Lupane | Leaves/methanol Stems/methanol Leaves and stems/petroleum ether | [61,71,79] |
| (17) | Lantabetulic acid 3,25-β-epoxy-3α-hydroxy-lup-20 (29)-en-28-oic acid (Figure 5) | C30H46O4 | 470.694 | Lupane | Leaves and stems/petroleum ether | [81] |
| (18) | Betulinic acid 3β-hydroxy-lup-20 (29)-en-28-oic acid | C30H48O3 | 456.711 | Lupane | Aerial parts/methanol Leaves/methanol Stems/methanol Leaves and stems/petroleum ether | [71,72,78,79,82] |
| (19) | Camaradienone 3,25-β-epoxy-3α-hydroxy-28-nor-oleana-12,17-dien-11-one (Figure 5) | C29H42O3 | 438.652 | Oleanane | Aerial parts/methanol | [15] |
| (20) | Lantanoic acid 3,25-β-epoxy-3α-hydroxy-11-oxo-olean-12-en-28-oic acid (Figure 5) | C30H44O5 | 484.677 | Oleanane | Aerial parts/methanol | [83] |
| (21) | 3β-Hydroxy-olean-11-en-28,13-β-olide (Figure 5) | C30H46O3 | 454.695 | Oleanane | HD * | [74] |
| (22) | Oleanonic acid 3-Oxo-olean-12-en-28-oic acid (Figure 5) | C30H46O3 | 454.695 | Oleanane | Aerial parts/ethanol, methanol Leaves/ethanol Leaves and stems/methanol, petroleum ether Stems/ethanol, methanol Roots/ethyl acetate, methanol, n-hexane–ethyl acetate–methanol (1:1:1) | [15,71,73,74,75,76,77,78,79,81,82,83,84,85,86,87,88] |
| (23) | Camarin 7α-hydroxy-3-oxo-olean-12-en-28-oic acid (Figure 5) | C30H46O4 | 470.694 | Oleanane | Aerial parts/methanol | [89,90] |
| (24) | 4-epi-Hederagonic acid 24-hydroxy-3-oxo-olean-12-en-28-oic acid (Figure 5) | C30H46O4 | 470.694 | Oleanane | Aerial parts/ethanol Leaves and stems/petroleum ether | [84] |
| (25) | 19α-Hydroxy-oleanonic acid (S)-19α-hydroxy-3-oxo-olean-12-en-28-oic acid (Figure 5) | C30H46O4 | 470.694 | Oleanane | Aerial parts/methanol | [80] |
| (26) | 22β-Hydroxy-oleanonic acid 22β-hydroxy-3-oxo-olean-12-en-28-oic acid (Figure 5) | C30H46O4 | 470.694 | Oleanane | Aerial parts/ethanol HD Leaves/acetonitrile Leaves and stems/petroleum ether | [75,84,91,92,93,94,95,96,97] |
| (27) | Lantanolic acid 3,25-β-epoxy-3α-hydroxy-olean-12-en-28-oic acid (Figure 5) | C30H46O4 | 470.694 | Oleanane | Aerial parts/methanol HD Leaves/chloroform, methanol, petroleum ether Leaves and stems/petroleum ether Roots/ethanol | [15,75,77,79,82,84,89,90,92, 98] |
| (28) | 22β-Hydroxy-4-epi-hederagonic acid (Figure 5) | C30H46O5 | 486.693 | Oleanane | Aerial parts/ethanol | [84] |
| (29) | Lantacamaric acid A 3,25-β-epoxy-3α,24-dihydroxy-olean-12-en-28-oic acid (Figure 5) | C30H46O5 | 486.693 | Oleanane | Leaves and stems/methanol | [85] |
| (30) | Lantaninilic acid 3,25-β-epoxy-3α,22β-dihydroxy-olean-12-en-28-oic acid (Figure 5) | C30H46O5 | 486.693 | Oleanane | Aerial parts/methanol HD * Leaves and stems/methanol | [75,82,83,85,89,90] |
| (31) | Oleanolic acid 3β-hydroxy-olean-12-en-28-oic acid (Figure 6) | C30H48O3 | 456.711 | Oleanane | Aerial parts/ethanol, methanol Leaves/methanol Leaves and stems/petroleum ether Stems/ethanol, methanol Roots/ethanol, ethyl acetate, (52.5% methanol/47.5% ethyl acetate), (60% chloroform/40% methanol), n-hexane–ethyl acetate–methanol (1:1:1) | [15,19,74,75,76,77,79,80,82,84,86,87,90,91,98,99,100,101,102] |
| (32) | 22β-Hydroxy-oleanolic acid 3β,22β-dihydroxy-olean-12-en-28-oic acid (Figure 6) | C30H48O4 | 472.710 | Oleanane | Aerial parts/ethanol HD * Roots/ethanol | [84,95,96] |
| (33) | Methyl lantanoate methyl 3,25-β-epoxy-3α-hydroxy-11-oxo-olean-12-en-28-oate (Figure 6) | C31H46O5 | 498.704 | Oleanane | HD * | [83] |
| (34) | 21,22-β-Epoxy-3β-hydroxy-olean-12-en-28-oic acid, isolated as Methyl 21,22-β-epoxy-3β-hydroxy-olean-12-en-28-oate (Figure 6) | C31H48O4 | 484.721 | Oleanane | Roots/n-hexane–ethyl acetate–methanol (1:1:1) | [74] |
| (35) | Methyl 22β-hydroxy-oleanonate methyl 22β-hydroxy-3-oxo-olean-12-en-28-oate (Figure 6) | C31H48O4 | 484.721 | Oleanane | HD * | [93,94] |
| (36) | Methyl lantaninilate methyl 3,25-β-epoxy-3α,22β-dihydroxy-olean-12-en-28-oate (Figure 6) | C31H48O5 | 500.720 | Oleanane | HD * | [75] |
| (37) | 22β-Acetyloxy-oleanonic acid 22β-acetyloxy-3-oxo-olean-12-en-28-oic acid (Figure 6) | C32H48O5 | 512.731 | Oleanane | HD * | [94] |
| (38) | Lantanone 3β-acetyloxy-11-oxo-olean-12-en-28-oic acid (Figure 6) | C32H48O5 | 512.731 | Oleanane | Aerial parts/ethanol | [101] |
| (39) | Methyl 3,25-β-epoxy-3α-methoxy-22-oxo-olean-12-en-28-oate (Figure 6) | C32H48O5 | 512.731 | Oleanane | HD * | [103] |
| (40) | 22β-Acetyloxy-4-epi-hederagonic acid (Figure 6) | C32H48O6 | 528.730 | Oleanane | Aerial parts/ethanol | [104] |
| (41) | Lancamarinic acid 22β-acetyloxy-3,25-β-epoxy-3α-hydroxy-olean-12-en-28-oic acid (Figure 6) | C32H48O6 | 528.730 | Oleanane | Aerial parts/methanol | [105] |
| (42) | Lancamarolide 22β-acetyloxy-3,25-β-epoxy-3α,12α-dihydroxyolean-28,13-β-olide (Figure 6) | C32H48O7 | 544.729 | Oleanane | Aerial parts/methanol | [82] |
| (43) | Lancamaric acid 3,25-β-epoxy-3α-ethoxy-olean-12-en-28-oic acid (Figure 6) | C32H50O4 | 498.748 | Oleanane | Aerial parts/methanol | [85] |
| (44) | Oleanolic acid 3-O-acetate 3β-acetyloxy-olean-12-en-28-oic acid (Figure 6) | C32H50O4 | 498.748 | Oleanane | Aerial parts/methanol HD * Roots/n-hexane–ethyl acetate–methanol (1:1:1) | [74,77,102,106] |
| (45) | Methyl 22β-acetyloxy-oleanonate methyl 22β-acetyloxy-3-oxo-olean-12-en-28-oate (Figure 6) | C33H50O5 | 526.758 | Oleanane | HD * | [94] |
| (46) | 22β-Propanoyloxy-oleanonic acid 22β-propanoyloxy-3-oxo-olean-12-en-28-oic acid (Figure 6) | C33H50O5 | 526.758 | Oleanane | HD * | [94] |
| (47) | Methyl 22-O-acetyl-lantaninilate methyl 22β-acetyloxy-3,25-β-epoxy-3α-hydroxy-olean-12-en-28-oate (Figure 6) | C33H50O6 | 542.757 | Oleanane | HD * | [103,107] |
| (48) | Lantadienone 22β-angelyloxy-3,25-β-epoxy-3α-hydroxy-28-nor-oleana-12,17-dien-11-one (Figure 7) | C34H48O5 | 536.753 | Oleanane | Aerial parts/methanol | [15] |
| (49) | Lantigdienone 3,25-β-epoxy-3α-hydroxy-11-oxo-22β-senecioyloxy-28-nor-olean-12,17-diene (Figure 7) | C34H48O5 | 536.753 | Oleanane | Aerial parts/methanol | [108] |
| (50) | 22β-Butanoyloxy-oleanonic acid 22β-butanoyloxy-3-oxo-olean-12-en-28-oic acid (Figure 7) | C34H52O5 | 540.785 | Oleanane | HD * | [94] |
| (51) | Lantadene D 22β-isobutyryloxy-3-oxo-olean-12-en-28-oic acid (Figure 7) | C34H52O5 | 540.785 | Oleanane | Aerial parts/ethanol HD * Leaves/acetonitrile, methanol, petroleum ether | [19,84,94,97] |
| (52) | Methyl 22β-propanoyloxy-oleanonate methyl 22β-propanoyloxy-3-oxo-olean-12-en-28-oate (Figure 7) | C34H52O5 | 540.785 | Oleanane | HD * | [92] |
| (53) | 24-Hydroxylantadene D 22β-isobutyryloxy-24-hydroxy-3-oxo-olean-12-en-28-oic acid (Figure 7) | C34H52O6 | 556.784 | Oleanane | Aerial parts/ethanol | [84] |
| (54) | Lantrigloylic acid 3,25-β-epoxy-3α-hydroxy-22β-senecioyloxy-olea-9 (11),12-dien-28-oic acid (Figure 7) | C35H50O6 | 566.779 | Oleanane | Aerial parts/methanol | [90] |
| (55) | Camangeloyl acid 3,25-β-epoxy-3α-hydroxy-22β-[(Z)-2-methyl-2-butenoyloxy]-11-oxo-olean-12-en-28-oic (Figure 7) | C35H50O7 | 582.778 | Oleanane | Aerial parts/methanol | [15,77,83,89,106] |
| (56) | Camarinin 3,25-β-epoxy-3α-hydroxy-22β-(3-methyl-2-butenoyloxy)- 11-oxo-olean-12-en-28-oic (Figure 7) | C35H50O7 | 582.778 | Oleanane | Aerial parts/methanol | [83,84,89,90,107] |
| (57) | Lantadene A nitrile 22β-angelyloxy-28-ciano-3-oxo-olean-12-ene (Figure 7) | C35H51NO3 | 533.797 | Oleanane | HD * | [93] |
| (58) | Lantadene A acyl chloride 28-chloro-22β-angelyloxy-3,28-dioxo-olean-12-ene (Figure 7) | C35H51ClO4 | 571.239 | Oleanane | HD * | [93] |
| (59) | 22β-Angelyloxy-3-oxo-olean-28,13-β-olide (Figure 7) | C35H52O5 | 552.796 | Oleanane | HD * | [108] |
| (60) | Lantadene A (Rehmannic acid) 22β-angelyloxy-3-oxo-olean-12-en-28-oic acid (Figure 7) | C35H52O5 | 552.796 | Oleanane | Aerial parts/methanol, ethanol Leaves/acetone, acetonitrile, ethanol, ethyl acetate, methanol, petroleum ether, methanol–water (70:30) Leaves and stems/methanol, petroleum ether Roots/n-hexane–ethyl acetate–methanol (1:1:1); ethanol Stems/ethanol, methanol | [108] |
| (61) | Lantadene B 3-oxo-22β-senecioyloxy- olean-12-en-28-oic acid (Figure 7) | C35H52O5 | 552.796 | Oleanane | Aerial parts/ethanol, dichloromethane, methanol, petroleum ether Leaves/acetonitrile, 96% ethanol, ethyl acetate Leaves/methanol, (70% methanol/30% water) Leaves and stems/petroleum ether Stems/methanol Roots/ethanol | [15,19,79,82,84,91,95,96,98,109,110,111,112,113,114,115,116] |
| (62) | Camaric acid 3,25-β-epoxy-3α-hydroxy-22β-[(Z)-2-methyl-2-butenoyloxy]-olean-12-en-28-oic acid (Figure 7) | C35H52O6 | 568.795 | Oleanane | Aerial parts/dichloromethane, methanol Leaves and stems/methanol Roots/n-hexane–ethyl acetate–methanol (1:1:1) | [15,74,77,80,82,84,90,98,99,117,118] |
| (63) | 3,25-β-Epoxy-3α-hydroxy-22β-[(E)-2-methyl-2-butenoyloxy]-olean-12-en-28-oic acid (Figure 7) | C35H52O6 | 568.795 | Oleanane | Aerial parts/ethanol | [84] |
| (64) | 9-Hydroxy-lantadene A 22β-angelyloxy-9-hydroxy-3-oxo-olean-12- en-28-oic acid (Figure 7) | C35H52O6 | 568.795 | Oleanane | Leaves/ethyl acetate, methanol | [119,120] |
| (65) | 24-Hydroxylantadene B ≡ 24-Hydroxy-22β-senecioyloxy-oleanonic acid 24-hydroxy-3-oxo-22β-senecioyloxy-olean-12-en-28-oic acid (Figure 7) | C35H52O6 | 568.795 | Oleanane | Aerial parts/ethanol Leaves/ethyl acetate Leaves and stems/methanol | [84,99,116] |
| (66) | 24-Hydroxy lantadene X 24-hydroxy-3-oxo-22β-[(E)-2-methylbut-2-enoyloxy]- olean-12-en-28-oic acid (Figure 7) | C35H52O6 | 568.795 | Oleanane | Aerial parts/ethanol | [84] |
| (67) | Icterogenin ≡ 24-Hydroxy-lantadene A ≡ 24-Hydroxy-22β-angelyloxy-oleanonic acid 24-hydroxy-3-oxo-22β-[(Z)-2-methylbut-2-enoyloxy]- olean-12-en-28-oic acid (Figure 7) | C35H52O6 | 568.795 | Oleanane | Aerial parts/ethanol, methanol Leaves/acetone, ethanol Leaves/ethyl acetate, methanol Leaves and stems/methanol, petroleum ether | [19,79,80,81,82,84,99,109,116,118,121] |
| (68) | Lantanilic acid 3β,25-β-epoxy-3α-hydroxy-22β-senecioyloxy-olean-12-en-28-oic acid (Figure 7) | C35H52O6 | 568.795 | Oleanane | Aerial parts/dichloromethane, ethanol, methanol Leaves/ethanol, ethyl acetate, methanol, petroleum ether Leaves and stems/methanol Roots/chloroform | [15,19,72,77,79,81,84,85,98,99,100,109,116,122,123] |
| (69) | Camarolic acid 3,25-β-epoxy-3α-hydroxy-22β-[(S)-3-hydroxy-2-methylidenebutanoyloxy] olean- 12-en-28-oic acid (Figure 7) | C35H52O7 | 584.794 | Oleanane | Aerial parts/methanol | [82,90] |
| (70) | Lantacamaric acid B 3,25-β-epoxy-3α,24-dihydroxy-22β-senecioyloxy-olean-12-en-28-oic acid (Figure 7) | C35H52O7 | 584.794 | Oleanane | Leaves and stems/methanol | [85] |
| (71) | Lantadene A amide 28-amino-22β-angelyloxy-3,28-dioxo-olean-12-ene (Figure 7) | C35H53NO4 | 551.812 | Oleanane | HD * | [93] |
| (72) | Lantadene C 22β-[(S)-2-methylbutanoyloxy]-3-oxo-olean-12-en-28-oic acid (Figure 7) | C35H54O5 | 554.812 | Oleanane | HD * Leaves/acetonitrile, ethyl acetate, methanol Leaves and stems/petroleum ether | [91,94,109, 116,124] |
| (73) | Methyl 22β-butanoyloxy-oleanonate methyl 22β-butanoyloxy-3-oxo-olean-12-en-28-oate (Figure 7) | C35H54O5 | 554.812 | Oleanane | HD * | [94] |
| (74) | Methyl 22β-isobutyryloxy-oleanonate methyl 22β-isobutyryloxy-3-oxo-olean-12-en-28-oate (Figure 7) | C35H54O5 | 554.812 | Oleanane | HD * | [94] |
| (75) | Reduced lantadene A 22β-angelyloxy-3β-hydroxy-olean-12-en-28-oic acid (Figure 8) | C35H54O5 | 554.812 | Oleanane | Aerial parts/ethanol HD * Leaves/methanol, acetonitrile Roots/ethanol | [84,91,95] |
| (76) | Reduced lantadene B 3β-hydroxy-22β-senecioyloxy-olean-12-en-28-oic acid (Figure 8) | C35H54O5 | 554.812 | Oleanane | Aerial parts/ethanol HD * Leaves/acetonitrile, methanol Roots/ethanol | [84,91,95] |
| (77) | Reduced lantadene C 3β-hydroxy-22β-[2-methylbutanoyloxy]-olean-12-en-28-oic acid (Figure 8) | C35H56O5 | 554.812 | Oleanane | Aerial parts/ethanol | [84] |
| (78) | Methyl 22β-angelyloxy-2-hydroxy-3-oxo-olean-1,12-diene- 28-oate (Figure 8) | C36H52O6 | 580.806 | Oleanane | HD * | [124] |
| (79) | Lancamarinin methyl 3,25-β-epoxy-3α-hydroxy-11-oxo-22β-senecioyloxy-olean-12-en- 28-oate (Figure 8) | C36H52O7 | 596.805 | Oleanane | HD * Aerial parts/methanol | [105] |
| (80) | Methyl camangeloylate methyl 3,25-β-epoxy-3α-hydroxy-22β-[(Z)-2′-methyl-2′-butenoyloxy]-11-oxo-olean-12-en-28-oate (Figure 8) | C36H52O7 | 596.805 | Oleanane | HD * | [77] |
| (81) | Lantadene A methyl ester methyl 22β-angelyloxy-3-oxo-olean-12-en-28-oate (Figure 8) | C36H54O5 | 566.823 | Oleanane | HD * Leaves and stems/petroleum ether | [93,124] |
| (82) | Methyl 22-β-angelyloxy-lantanolate methyl 22β-angelyloxy-3,25-β-epoxy-3α-hydroxy-olean-12-en-28-oate (Figure 8) | C36H54O6 | 582.822 | Oleanane | HD * | [82] |
| (83) | Methyl camarolate methyl 3,25-β-epoxy-3α-hydroxy-22β-[(S)-3-hydroxy-2-methylidenebutanoyloxy] olean-12-en-28-oate (Figure 8) | C36H54O7 | 598.821 | Oleanane | HD * | [90] |
| (84) | 3-O-β-D-Glucosyl oleanolic acid 3-O-β-D-glucopyranosyloxy-olean-12-en-28-oic acid (Figure 8) | C36H58O8 | 618.852 | Oleanane | Leaves/methanol | [125,126] |
| (85) | 22β-Benzoyloxy-oleanonic acid 22β-benzoyloxy-3-oxo-olean-12-en-28-oic acid (Figure 8) | C37H50O5 | 574.802 | Oleanane | HD * | [94] |
| (86) | Methyl 22β-benzoyloxy-oleanonate methyl 22β-benzoyloxy-3-oxo-olean-12-en-28-oate (Figure 8) | C38H52O5 | 588.829 | Oleanane | HD * | [94] |
| (87) | 3β-(2-Acetyloxybenzoyloxy)-22β-hydroxy-olean-12-en-28-oic acid (Figure 8) | C39H54O7 | 634.854 | Oleanane | HD * | [96] |
| (88) | 3β-[(R,S)-2-(4-Isobutylphenyl)propanoyloxy]-22β-hydroxy-olean-12-en-28-oic acid (Figure 8) | C43H64O5 | 660.980 | Oleanane | HD * | [96] |
| (89) | 3β-{2-[2-(2,6-Dichlorophenylamino)phenyl]acetyloxy}-22β-hydroxy-olean-12-en-28-oic acid (Figure 8) | C44H57Cl2NO5 | 750.842 | Oleanane | HD * | [96] |
| (90) | 3β-[(+)-(S)-2-(6-Methoxy-2-naphthyl)propanoyloxy]-22β-hydroxy-olean-12-en-28-oic acid (Figure 8) | C44H60O6 | 684.958 | Oleanane | HD * | [96] |
| (91) | 3β-[(R,S)-2-(3-Benzoylphenyl)propanoyloxy]-22β-hydroxy-olean-12-en-28-oic acid (Figure 9) | C46H60O6 | 708.980 | Oleanane | HD * | [96] |
| (92) | 3β,22β-Di-(2-acetyloxybenzoyloxy)-olean-12-en-28-oic acid (Figure 9) | C48H60O10 | 796.998 | Oleanane | HD * | [96] |
| (93) | 3β,22β-Di-[(R.S)-2-(4-isobutylphenyl)propanoyloxy]-olean-12-en-28-oic acid (Figure 9) | C56H80O6 | 849.250 | Oleanane | HD * | [96] |
| (94) | 3β,22β-Di-{2-[2-(2,6-dichlorophenylamino)phenyl]acetyloxy}-olean-12-en-28-oic acid (Figure 9) | C58H66Cl4N2 O6 | 1028.974 | Oleanane | HD * | [96] |
| (95) | 3β,22β-Di-[(+)-(S)-2-(6-methoxy-2-naphthyl)propanoyloxy]-olean-12-en-28-oic acid (Figure 9) | C58H72O8 | 897.206 | Oleanane | HD * | [96] |
| (96) | 3β,22β-Di-[(R,S)-2-(3-benzoylphenyl)propanoyloxy]-olean-12-en-28-oic acid (Figure 9) | C62H72O8 | 945.250 | Oleanane | HD * | [96] |
| (97) | Camarolide 3-oxo-urs-11-en-28,13-β-olide (Figure 10) | C30H44O3 | 452.679 | Ursane | Aerial parts/methanol | [85] |
| (98) | 3,24-Dioxo-urs-12-en-28-oic acid (Figure 10) | C30H44O4 | 468.678 | Ursane | Leaves/solvent not reported | [127] |
| (99) | Camaranoic acid 3,25-β-epoxy-3α-hydroxy-11-oxo-urs-12-en-28-oic acid (Figure 10) | C30H44O5 | 484.677 | Ursane | Aerial parts/methanol | [81,83,118] |
| (100) | Ursonic acid 3-oxo-urs-12-en-28-oic acid (Figure 10) | C30H46O3 | 454.695 | Ursane | Aerial parts/methanol Leaves and stems/petroleum ether | [81,83,84,85] |
| (101) | 11α-Hydroxy-3-oxo-urs-12-en-28-oic acid (Figure 10) | C30H46O4 | 470.694 | Ursane | Aerial parts/methanol | [82] |
| (102) | Lantic acid 3,25-β-epoxy-3α-hydroxy-urs-12-en-28-oic acid (Figure 10) | C30H46O4 | 470.694 | Ursane | Aerial parts/methanol Leaves/chloroform Leaves and stems/dichloromethane–methanol (1:1), petroleum ether | [75,83,98] |
| (103) | 11-Oxo-β-boswellic acid 3α-hydroxy-11-oxo-urs-12-en-24-oic acid (Figure 10) | C30H46O4 | 470.694 | Ursane | Leaves/ethyl acetate | [120] |
| (104) | Pomonic acid 19α-hydroxy-3-oxo-urs-12-en-28-oic acid (Figure 10) | C30H46O4 | 470.694 | Ursane | Aerial parts/ethanol, methanol Roots/ n-hexane–ethyl acetate–methanol (1:1:1) | [74,77,80,84] |
| (105) | Lantoic acid 3,25-β-epoxy-3α,22β-dihydroxy-urs-12-en-28-oic acid (Figure 10) | C30H46O5 | 486.693 | Ursane | Aerial parts/methanol Leaves/petroleum ether | [81,84,90,118] |
| (106) | Ursolic acid 3β-hydroxy-urs-12-en-28-oic acid; urs-12-en-3β-ol-28-oic acid (Figure 10) | C30H48O3 | 456.711 | Ursane | Aerial parts/methanol Leaves/methanol | [19,79,89,90,121,125] |
| (107) | Pomolic acid 3β,19α-dihydroxy-urs-12-en-28-oic acid (Figure 10) | C30H48O4 | 472.710 | Ursane | Aerial parts/methanol Stems/methanol Roots/chloroform, ethanol | [84,89,90,98] |
| (108) | α-Amyrin urs-12-en-3β-ol | C30H50O | 426.729 | Ursane | Aerial parts/96% ethanol, petroleum ether | [73,74] |
| (109) | 3β,19α-Dihydroxy-ursan-28-oic acid (Figure 10) | C30H50O4 | 474.726 | Ursane | Roots/ n-hexane–ethyl acetate–methanol (1:1:1) | [74] |
| (110) | Methyl camaranoate methyl 3,25-β-epoxy-3α-hydroxy-11-oxo-urs-12-en-28-oate (Figure 10) | C31H46O5 | 498.704 | Ursane | HD * | [83] |
| (111) | Ursoxy acid 3,25-β-epoxy-3α-methoxy-urs-12-en-28-oic acid (Figure 10) | C31H48O4 | 484.721 | Ursane | Aerial parts/methanol | [106] |
| (112) | Methyl 25-hydroxy-3-deoxy-ursen-12-en-28-oate (Figure 10) | C31H50O3 | 470.738 | Ursane | HD * | [128] |
| (113) | Methyl 3β,19α-dihydroxy ursan-28-oate (Figure 10) | C31H52O4 | 488.753 | Ursane | HD * | [74] |
| (114) | Camarinic acid 22β-acetyloxy-3,25-β-epoxy-3α-hydroxy-12-ursen-28-oic acid (Figure 10) | C32H48O6 | 528.730 | Ursane | Aerial parts/methanol Leaves/chloroform Leaves and stems/dichloromethane–methanol (1:1) | [16,83,98, 109] |
| (115) | Methyl ursoxylate methyl 3,25-β-epoxy-3α-methoxy-urs-12-en-28-oate (Figure 10) | C32H50O4 | 498.748 | Ursane | Aerial parts/methanol HD * | [106] |
| (116) | Ursethoxy acid 3,25-β-epoxy-3α-ethoxy-urs-12-en-28-oic acid (Figure 10) | C32H50O4 | 498.748 | Ursane | Aerial parts/methanol | [129] |
| (117) | Methyl camaralate methyl 22β-acetoxy-3,25-β-epoxy-3α-hydroxy-urs-12-en-28-oate (Figure 10) | C33H50O6 | 542.757 | Ursane | Aerial parts/methanol HD * | [77,98] |
| (118) | Methyl ursethoxylate methyl 3,25-β-epoxy-3α-ethoxy-urs-12-en-28-oate (Figure 10) | C33H52O4 | 512.775 | Ursane | Aerial parts/methanol | [129] |
| (119) | Lantacin 3β,19α-dihydroxy-22β-senecioyloxy-urs-12-en-28-oic acid (Figure 10) | C35H54O6 | 570.811 | Ursane | Aerial parts/methanol | [84,89,118] |
| (120) | Lantaiursolic acid 3β-isovaleroyloxy-19α-hydroxy-urs-12-en-28-oic acid (Figure 10) | C35H56O5 | 556.828 | Ursane | Roots/ethanol | [118] |
| (121) | Camaracinic acid 22β-angelyloxy-3,25-β-epoxy-3α-methoxy-12-ursen-28-oic acid (Figure 11) | C36H54O6 | 582.822 | Ursane | Aerial parts/methanol | [82] |
| (122) | Camaryolic acid 3,25-β-epoxy-3α-methoxy-22β-senecioyloxy-urs-12-en-28-oic acid (Figure 11) | C36H54O6 | 582.822 | Ursane | Aerial parts/methanol | [77,82] |
| (123) | Methyl lantacinate methyl 3β,19α-dihydroxy-22β-senecioyloxy- urs-12-en-28-oate (Figure 11) | C36H56O6 | 584.838 | Ursane | HD * | [84] |
| (124) | Methyl camaracinate methyl 22β-angelyloxy-3,25-β-epoxy-3α-methoxy-12-ursen-28-oate (Figure 11) | C37H56O6 | 596.849 | Ursane | HD * | [82] |
| (125) | Methyl camaryolate methyl 3,25-β-epoxy-3α-methoxy-22β-senecioyloxy-urs-12-en-28-oate (Figure 11) | C37H56O6 | 596.849 | Ursane | HD * | [82] |
| (126) | Ursangilic acid 22β-angelyloxy- 3,25-β-epoxy-3α-ethoxy-urs-12-en-28-oic acid (Figure 8) | C37H56O6 | 596.849 | Ursane | Aerial parts/methanol | [106] |
| (127) | Urs-12-en-3β-ol-28-oic acid 3-O-β-D-glucopyranosyl-4′- octadecanoate (Figure 11) | C54H92O9 | 885.321 | Ursane | Leaves/methanol | [125,126] |
* HD: semisynthetic derivative.
Table 4.
Flavonoids isolated from non-volatile fractions of Lantana camara and semisynthetic derivatives.
Table 4.
Flavonoids isolated from non-volatile fractions of Lantana camara and semisynthetic derivatives.
| N.º | Compound | Molecular Formula | Molecular Weight | Flavonoid Type | Part of the Plant/Solvent | Reference |
|---|---|---|---|---|---|---|
| (128) | Hispidulin 4′,5,7-trihydroxy-6-methoxyflavone (Figure 12) | C16H12O6 | 300.266 | Flavone | Leaves/ethanol Stems/methanol | [63,79,84] |
| (129) | Pectolinarigenin 5,7-dihydroxy-4′,6-dimethoxyflavone (Figure 12) | C17H14O6 | 314.293 | Flavone | Leaves/methanol | [19,79,84,130] |
| (130) | Tricin 4′,5,7-trihydroxy-3′,5′-dimethoxyflavone (Figure 12) | C17H14O7 | 330.292 | Flavone | Leaves/methanol | [79] |
| (131) | Apigenin 7-O-β-D-galacturonide 7-O-β-D-galacturonyl-4′,5,7-trihydroxyflavone (Figure 12) | C21H18O11 | 446.364 | Flavone | Flowers/methanol–water (70:30) | [131] |
| (132) | Anthemoside Apigenin 7-O-β-D-glucopyranoside 7-O-β-D-glucopyranosyl- 4′,5,7-trihydroxyflavone (Figure 12) | C21H20O10 | 432.381 | Flavone | Flowers/methanol–water (70:30) | [132] |
| (133) | Isovitexin 6-C-β-D-glucopyranosyl-4′,5,7-trihydroxyflavone (Figure 12) | C21H20O10 | 432.381 | Flavone | Flowers/ methanol–water (70:30) | [132] |
| (134) | Vitexin 8-C-β-D-glucopyranosyl-4′,5,7-trihydroxyflavone (Figure 12) | C21H20O10 | 432.381 | Flavone | Flowers/ methanol–water (70:30) | [132,133] |
| (135) | Juncein Luteolin 4′-O-β-D-glucopyranoside 4′-O-β-D-glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone (Figure 12) | C21H20O11 | 448.380 | Flavone | Flowers/methanol–water (70:30) | [132] |
| (136) | Luteolin 7-O-β-D-galactopyranoside 7-O-β-D-galactopyranosyl-3′,4′,5,7-tetrahydroxyflavone (Figure 12) | C21H20O11 | 448.380 | Flavone | Flowers/methanol–water (70:30) | [132] |
| (137) | Luteoloside Luteolin 7-O-β-glucopyranoside 7-O-β-D-glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone (Figure 12) | C21H20O11 | 448.380 | Flavone | Flowers/methanol–water (70:30) | [132] |
| (138) | 6-Methoxy scutellarin 7-O-β-glucuronyl-4′,5,7-trihydroxy-6-methoxyflavone (Figure 12) | C22H20O12 | 476.390 | Flavone | Leaves and stems/methanol | [85] |
| (139) | Linaroside 7-O-β-D-glucopyranosyl-5,7-dihydroxy-4′,6-dimethoxyflavone (Figure 13) | C23H24O11 | 476.434 | Flavone | Aerial parts/ methanol Leaves/ methanol | [16,124,134] |
| (140) | Lantanoside 7-O-(6-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxy-4′,6-dimethoxyflavone (Figure 13) | C25H26O12 | 518.471 | Flavone | Aerial parts/methanol | [16,134] |
| (141) | Apigenin 7-O-β-D-galacturonyl- (2″→1‴)-O-β-D-galacturonide (Figure 13) | C27H26O17 | 622.488 | Flavone | Flowers/methanol–water (70:30) | [132] |
| (142) | Luteolin 7-O-β-D-galacturonyl-(2″→1‴)-O-β-D-galacturonide (Figure 13) | C27H26O18 | 638.487 | Flavone | Flowers/methanol–water (70:30) | [132] |
| (143) | Luteolin 7-O-β-D-glucuronyl-(2″→1‴)-O-β-D-glucuronide (Figure 13) | C27H26O18 | 638.487 | Flavone | Flowers/methanol–water (70:30) | [132] |
| (144) | Acetyl lantanoside 7-O-(2,6-O-diacetyl-β-D-glucopyranosyl)-5,7-dihydroxy-4′,6-dimethoxyflavone (Figure 13) | C27H28O13 | 560.508 | Flavone | HD * | [16,134] |
| (145) | Acacetin-7-O-β-D-rutinoside 7-O-β-D-rutinosyl-5,7-dihydroxy- 4′-methoxyflavone (Figure 13) | C28H32O14 | 592.550 | Flavone | Leaves/methanol | [79] |
| (146) | Pectolinarin 7-O-β-D-rutinosyl -5,7-dihydroxy-4′,6-dimethoxyflavone (Figure 13) | C29H34O15 | 622.576 | Flavone | Aerial parts/ ethanol Leaves/ ethanol, methanol | [19,84,133] |
| (147) | 3,7-O-Dimethylquercetin 3′,4′,5-trihydroxy-3,7-dimethoxyflavone (Figure 13) | C17H14O7 | 330.292 | Flavonol | Leaves/acetone | [127] |
| (148) | 3,5,7,8-Tetrahydroxy-3′,6-dimethoxyflavone (Figure 13) | C17H14O8 | 346.291 | Flavonol | Leaves/methanol | [79] |
| (149) | 6-Methoxykaempferol-7-O-β-D-glucoside 7-O-β-D-glucopyranosyl-3,4′,5,7-tetrahydroxy-6-methoxyflavone (Figure 13) | C22H22O12 | 478.406 | Flavonol | Flowers/95% methanol | [135] |
| (150) | 5,7-Dihydroxy-6,3′,4′-trimethoxy isoflavone (Figure 13) | C18H15O7 | 343.311 | Isoflavone | Leaves/methanol | [79] |
| (151) | Gautin 5,7-dihydroxy-6,3′,4′-trimethoxy isoflavone-5-O-α-L-rhamnopyranosyl-7-O-β-D-arabinopyranosyl-(1‴→4″)-O-β- D-xylopyranoside (Figure 13) | C34H42O19 | 754.691 | Isoflavone | Leaves/methanol | [79] |
* HD: semisynthetic derivative.
Table 5.
Iridoid glucosides isolated from non-volatile fractions of Lantana camara L.
Table 5.
Iridoid glucosides isolated from non-volatile fractions of Lantana camara L.
| N.º | Compound | Molecular Formula | Molecular Weight | Part of the Plant/Solvent | Reference |
|---|---|---|---|---|---|
| (152) | Geniposide methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) oxan-2-yl] oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (Figure 14) | C17H24O10 | 388.369 | Leaves and stems/ methanol Roots/ ethanol | [91] |
| (153) | Theviridoside methyl (1S,4aR,7aR)-4a-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) oxan-2-yl] oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate (Figure 14) | C17H24O11 | 404.368 | Aerial parts and roots/ ethanol Leaves and stems/ methanol Roots/ methanol | [91] |
Table 6.
Fatty acids isolated from non-volatile fractions of Lantana camara L.
Table 6.
Fatty acids isolated from non-volatile fractions of Lantana camara L.
| N.º | Compound | Molecular Formula | Molecular Weight | Part of the Plant/Solvent | References |
|---|---|---|---|---|---|
| (154) | Myristic acid tetradecanoic acid | C14H28O2 | 228.376 | Aerial parts/petroleum ether | [73] |
| (155) | Palmitic acid hexadecanoic acid | C16H32O2 | 256.430 | Aerial parts/methanol/petroleum ether Stems/ethanol | [73,77,82] |
| (156) | Linoleic acid (9Z,12Z)-octadeca-9,12-dienoic acid | C18H32O2 | 280.452 | Aerial parts/petroleum ether | [73] |
| (157) | Oleic acid (9Z)-octadec-9-enoic acid | C18H34O2 | 282.468 | Aerial parts/petroleum ether | [73] |
| (158) | Stearic acid octadecanoic acid | C18H36O2 | 284.484 | Aerial parts/methanol Stems/ethanol | [77,82] |
| (159) | Arachidic acid eicosanoid acid (Figure 14) | C20H40O2 | 312.538 | Aerial parts/petroleum ether | [73] |
| (160) | Behenic acid docosanoic acid (Figure 14) | C22H44O2 | 340.592 | Aerial parts/methanol | [77,82] |
| (161) | Lignoceric acid tetracosanoic acid (Figure 14) | C24H48O2 | 368.646 | Aerial parts/methanol | [106] |
| (162) | Lacceroic acid dotriacontanoic acid (Figure 14) | C32H64O2 | 480.862 | Aerial parts/methanol | [106] |
Table 7.
Other compounds isolated from non-volatile fractions of Lantana camara L.
Table 7.
Other compounds isolated from non-volatile fractions of Lantana camara L.
| N.º | Compound | Molecular Formula | Molecular Weight | Part of the Plant/Solvent | References |
|---|---|---|---|---|---|
| (163) | Ethyl-β-D-galactopyranoside (Figure 14) | C8H16O6 | 208.210 | Stems/ ethanol | [15] |
| (164) | Linamarin 2-(β-D-Glucopyranosyloxy)-2-methylpropanenitrile (Figure 14) | C10H17NO6 | 247.247 | Leaves and stems/ methanol | [99] |
| (165) | Phytol 3,7,11,15-tetramethyl-2-hexadecen-1-ol (Figure 14) | C20H40O | 296.539 | Leaves and stems/ petroleum ether | [75] |
| (166) | Di-(2-ethylhexyl) phthalate (Figure 14) | C24H38O4 | 390.564 | Fruits/ chloroform | [73] |
| (167) | Triacontan-1-ol (Figure 14) | C30H62O | 438.825 | Aerial parts/ petroleum ether | [73] |
| (168) | Trilinolein Glyceryl trilinoleate (Figure 14)) | C56H96O6 | 865.37 | Fruits/ chloroform | [73] |
The chemical structures of steroids, triterpenes, flavonoids, iridoid glycosides, fatty acids, and miscellaneous compounds isolated from L. camara or obtained by semisynthesis are depicted in Figure 4, Figure 5, Figure 6, Figure 7, Figure 8, Figure 9, Figure 10, Figure 11, Figure 12, Figure 13 and Figure 14. The structures of very well-known compounds have been omitted.
Figure 4.
Structures of compounds 3, and 6–15.
Figure 4.
Structures of compounds 3, and 6–15.
Figure 5.
Structures of compounds 16, 17, and 19–30.
Figure 5.
Structures of compounds 16, 17, and 19–30.
Figure 6.
Structures of compounds 31–47.
Figure 6.
Structures of compounds 31–47.
Figure 7.
Structures of compounds 48–74.
Figure 7.
Structures of compounds 48–74.
Figure 8.
Structures of compounds 75–90.
Figure 8.
Structures of compounds 75–90.
Figure 9.
Structures of compounds 91–96.
Figure 9.
Structures of compounds 91–96.
Figure 10.
Structures of compounds 97–107 and 109–120.
Figure 10.
Structures of compounds 97–107 and 109–120.
Figure 11.
Structures of compounds 121–127.
Figure 11.
Structures of compounds 121–127.
Figure 12.
Structures of compounds 128–138.
Figure 12.
Structures of compounds 128–138.
Figure 13.
Structures of compounds 139–151.
Figure 13.
Structures of compounds 139–151.
Figure 14.
Structures of compounds 152, 153, and 159–168.
Figure 14.
Structures of compounds 152, 153, and 159–168.
3.3. Biological Activities
A great variety of biological effects exerted by several extracts of different parts of L. camara have been tested in vitro and, more rarely, also in vivo (Table 8). The most relevant biological properties included significant anti-inflammatory and analgesic effects of a leaf aqueous extract [136]; a moderate antibacterial activity of leaf alcoholic and aqueous extracts against Escherichia coli, Proteus vulgaris, and Vibrio cholerae [121], and against Bacillus subtilis, Klebsiella pneumoniae, Staphylococcus aureus, and Pseudomonas aeruginosa [137]; the inhibitory properties of a 70% aqueous ethanolic flower extract against the growth of the Mycobacterium tuberculosis H37RV strain [138]; the antidiabetic effects of an aqueous leaf extract [125]; the moderate antidiarrheal effects of an ethanol leaf extract [100]; the significant antioxidant properties of methanol leaf and flower extracts [139]; the high in vitro antiparasitic activity of dichloromethane and methanol extracts of the leaves/aerial parts against Leishmania amazonensis promastigotes [64,67,109], and dichloromethane and ethyl acetate leaf extracts against the chloroquine-sensitive strains 3D7 and D10, and the chloroquine-resistant strain W2, of Plasmodium falciparum [43,58,140]; the potent in vitro nematocidal activity of a methanol extract of the aerial parts and its partitions against the larvae of the root-knot nematode Meloidogyne incognita; the significant in vitro anti-COVID-19 activity of 95% ethanol extracts of the leaves and flowers from different cultivars [103]; the significant cancer reduction and increased survival rate of mice exhibited by a methanol leaf extract [141]; the high in vitro cytotoxicity of different leaf extracts [43,58,142]; the DNA-protective effects of an aqueous leaf extract [143]; the significant hepatoprotective effects of a methanol leaf extract [130]; the high insecticidal, larvicidal, and termiticidal activities of different extracts, especially of the leaves in polar solvents, against several insects (mosquitos, moths, termites, weevils, and bugs) [52,59,86,144,145,146,147,148,149,150,151,152,153]; the wound-healing effects of ethanol and water leaf extracts [108,154].
In summary, the alcoholic and aqueous leaf extracts seem to exhibit the highest and widest biological properties. In our opinion, the most promising biological effects of the extracts, which have attracted the greatest interest from several research groups, are the antiparasitic, nematocidal, and insecticidal properties.
Concerning the bioactivities of the compounds isolated from L. camara and the semisynthetic derivatives (Table 9), potent nematocidal effects against Meloidogyne incognita larvae (mortality ˃ 80%) were shown by different oleanane triterpenoids, such as camaric acid (62), camarin (23), camarinin (56), lantanilic acid (68), lantanolic acid (27), the ursane triterpenoids camarinic acid (114), lantacin (119), lantic acid (102), lantoic acid (105), pomolic acid (107), and ursolic acid (106), and the flavonoids linaroside (139) and lantanoside (140). Other interesting properties were the in vitro antiparasitic activity (IC50 < 10 μM) towards Leishmania mexicana promastigotes exhibited by camaric acid (62) and lantanilic acid (68). On the other hand, the in vitro cytotoxicity of most triterpenoids towards different human tumor cell lines was from moderate to very weak (IC50 = 20–80 μM) or null (IC50 ˃ 100 μM), except for the high activity (IC50 < 10 μM) exhibited by camaric acid (62), lantacamaric acid B (70), and lantanilic acid (68) towards HL-60 (JCRB0085) leukemia cells, icterogenin (67) towards colon cancer HCT-116 and lymphocytic leukemia L1210 cells, lantadene B (61) towards lung carcinoma A549 cells, oleanolic acid (31) towards drug-resistant human ovarian carcinoma IGROV-1 cells, and oleanonic acid (22) towards leukemia HL-60 and Ehrlich ascites carcinoma (EAC) cells. However, the in vivo antitumor activity, measured by the percent mice survival and percent overall papilloma incidence, was observed only for large doses of the administered compound, such as, for example, the ester 78. Interesting in vivo antidiabetic effects were exhibited by urs-12-en-3β-ol-28-oic acid 3-O-β-D-glucopyranosyl-4′-octadecanoate (127). In vitro high antibacterial activity against the Mycobacterium tuberculosis strain H37Rv was exhibited by acetyl lantanoside (144). Powerful in vitro protein tyrosine phosphatase inhibition effects (IC50 < 10 μM) were determined for camaric acid (62), di(2-ethylhexyl) phthalate (166), 24-hydroxylantadene B (65), 22β-hydroxy-oleanolic acid (32), 22β-hydroxy-oleanonic acid (25), lantadenes A (71), B (62) and D (54), lantanilic acid (68), oleanolic acid (31), oleanonic acid (22), and reduced lantadenes A (75), B (76), and C (77). The in vitro anti-inflammatory activity was determined by measuring the inhibition of the following two inflammatory mechanisms: 22β-hydroxy-oleanonic acid (26) and lantadene A (60) and B (61) strongly inhibited the TNF-α-induced NF-ΚB activation (IC50 < 10 μM), but they were ineffective (IC50 ˃ 100 μM) against cyclooxygenase-2 (COX-2).
L. camara is also known for the toxicity to animals causing hepatotoxicity, photosensitization, and jaundice. Lantadene A (60) is the main toxic pentacyclic triterpenoid present in this weed.
Table 8.
Biological activities of different extracts of Lantana camara L. a,*.
Table 8.
Biological activities of different extracts of Lantana camara L. a,*.
| Biological Activity | Part of the Plant/Solvent | Model | Results | Reference |
|---|---|---|---|---|
| Analgesic, anti-inflammatory | Leaves/water | The anti-inflammatory activity assay was carried out using carrageenan-induced lung edema and pleurisy mice. An analgesic effect assay was carried out using the formalin pain test. | Significant (p < 0.05) anti-inflammatory and analgesic activity, and minimal toxic effects. | [136] |
| Antibacterial | Leaves/ dichloromethane–methanol (1:1) | The in vitro antibacterial activity of a crude extract was screened at concentrations of 1000 μg/mL and 500 μg/mL against Bacillus cereus var mycoides (ATCC 11778), B. pumilus (ATCC 14884), B. subtilis (ATCC 6633), Bordetella bronchiseptica (ATCC 4617), Micrococcus luteus (ATCC 9341), Staphylococcus aureus (ATCC 29737), S. epidermidis (ATCC 12228), Escherichia coli (ATCC 10536), Klebsiella pneumoniae (ATCC 10031), Pseudomonas aeruginosa (ATCC 9027), and Streptococcus faecalis (MTCC 8043). | Except for E. coli and P. aeruginosa, a complete inhibition of bacterial growth was observed at both concentrations. | [60] |
| Leaves, stems, and roots/methanol | The in vitro antibacterial activity of a crude extract was screened against Bacillus cereus (ATCC 14579), Mycobacterium fortuitum (ATCC 6841), and Staphylococcus aureus (ATCC 6538). | B. cereus and M. fortuitum: MIC and MBC values > 1000 μg/mL; S. aureus: MIC = 250 μg/mL, MBC > 1000 μg/mL. | [44] | |
| Leaves/methanol | A crude extract was tested in vitro with the disk diffusion method against Escherichia coli, Proteus vulgaris, and Vibrio cholerae. | Inhibition zone diameter = 50 mm. | [121] | |
| Leaves/ methanol, ethanol, water | Crude extracts were tested against Bacillus subtilis (ATCC 6059), Klebsiella pneumoniae, Staphylococcus aureus (ATCC 6538), and Pseudomonas aeruginosa (ATCC 7221). | MIC values (mg/mL) of a methanol extract: B. subtilis and K. pneumoneae = 8; S. aureus and P. aeruginosa = 5. MIC values (mg/mL) of an ethanol extract: B. subtilis = 10, K. pneumoneae = 12, S. aureus = 6.5, P. aeruginosa = 8. MIC values (mg/mL) of an aqueous extract: B. subtilis and S. aureus = 8, P. aeruginosa = 10. | [137] | |
| Flowers/70% aqueous ethanol | A crude extract was tested against the Mycobacterium tuberculosis H37RV strain at different concentrations (25, 50, and 100 μg/mL). | All concentrations inhibited the growth of M. tuberculosis H37RV from the first to the sixth week. | [138] | |
| Leaves/methanol | Crude extracts were tested against the Mycobacterium smegmatis mc2155 strain, M. tuberculosis H37Rv strain, and rifampicin-resistant M. tuberculosis TMC-331 strain. | MIC values (μg/mL) determined for M. smegmatis mc2155 strain = 574 ± 196; M. tuberculosis H37Rv strain = 574 ± 196; M. tuberculosis TMC-331 strain = 176 ± 33. | [155] | |
| Aerial parts/methanol | The in vitro antibacterial activity of a crude extract was tested against E. coli (ATCC25922), Klebsiella pneumoniae, Pantoea sp., and Shigella flexneri. | MIC values determined for all tested bacteria = 25 μg/mL. | [156] | |
| Leaves/methanol | A crude extract was tested with the disk diffusion method against Helicobacter pylori. | Inhibition zone diameter = 20 mm. | [128] | |
| Leaves and flowers/water, methanol, acetone, benzene | Crude flower and leaf extracts showed the highest inhibitory effects against B. subtillis. Extracts separated by column chromatography displayed weaker inhibitory effects against B. subtillis than crude extracts. | Inhibition area ranging from 6 to 9 mm. Inhibition area ranging from 3 to 7 mm. | [157] | |
| Anticoagulant | Leaves, flowers, and roots/70% aqueous ethanol | The in vitro anticoagulant activity of crude extracts was tested at concentrations of 0.125, 0.25, 0.50, and 1 mg/mL. | The concentration of 1 mg/mL exhibited the highest anticoagulant activity; values expressed as prothrombin time: flowers = 21.7 ± 3 s; leaves = 16.9 ± 2.4 s; roots = 21.5 ± 2.8 s. | [158] |
| Antidiabetic | Leaves/water | Wistar albino rats (150–200 g); dose 1 = 250 mg extract/kg body weight and dose 2 = 500 mg extract/kg body weight were administered orally for 21 days. | Blood glucose levels: dose 1: at the 8th day = 183.83 ± 4.29 mg/dL; at the 14th day = 165.50 ± 4.26 mg/dL; at the 21st day = 136.83 ± 1.99 mg/dL. Dose 2: at the 8th day = 180.50 ± 3.07 mg/dL; at the 14th day = 157.83 ± 5.28 mg/dL; at the 21st day = 124.67 ± 2.40 mg/dL. | [125] |
| Antidiarrheal | Leaves/ethanol | Group II of male mice (Laca strain; 20–25 g) received 1% leaf powder for ten days; groups III–VI received a single dose of 125, 250, 500, and 1000 mg extract/kg body weight; subsequently, castor oil-induced diarrhea was evaluated. | % Intestinal transit: group II: 34.78 ± 3.52; group III: 1 ± 0.01; group IV: 26.46 ± 6.82; group V: 31.74 ± 1.49; group VI: 38.67 ± 6.60. Mean defecation in 4 h: group III: 9 ± 1.18; group IV: 9 ± 2.06; group V: 1 ± 0.05; group VI: total constipation. | [100] |
| Leaves/80% aqueous methanol | Groups III–V of Swiss albino mice (6–88 weeks; 20–30 g) received a single dose of 100, 200, and 400 mg extract/kg body weight; subsequently, castor oil-induced diarrhea was evaluated. | The most effective dose was 400 mg/kg body weight with a 67.9% inhibition of diarrhea and an antidiarrheal index of 87.6. | [159] | |
| Antifungal | Leaves/dicloromethane–methanol (1:1) | The antifungal activity of a crude extract was tested at concentrations of 1000 μg/mL and 500 μg/mL against Candida albicans (MTCC 10231), Aspergillus niger (MTCC 1344), and Saccharomyces cerevisiae (ATCC 9763). | Complete inhibition was observed at both concentrations. | [60] |
| Leaves, stems, and roots/methanol | The in vitro antifungal activity of a crude extract was tested against Candida albicans (ATCC 10231). | MIC and MBC values > 1000 μg/mL. | [44] | |
| Leaves/methanol | A crude extract was tested in vitro with the disk diffusion method against Aspergillus niger and Candida albicans. | Inhibition zone diameter = 0.5 mm. | [79] | |
| Leaves/methanol, water | Crude extracts were tested against Aspergillus fumigatus and A. flavus. | % Inhibition of the methanol extract: A. fumigatus = 71.4; A. flavus = 66.4. % Inhibition of the water extract: A. fumigatus = 61.5; A. flavus = 57.8. | [137] | |
| Antioxidant | Leaves, flowers, fruits, roots, and stems/methanol | Phytochemical analysis: Folin–Ciocalteu assay; gallic acid and ascorbic acid as reference standard. The in vitro antioxidant activity was tested by the following different methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, with ascorbic acid as a reference standard; xanthine oxidase inhibition assay, with allopurinol as a reference standard; Griess–Ilosvay method, with allopurinol as a reference standard. | Leaves: total phenols > 100 mg/g extract; DPPH assay: IC50 = 16.02 ± 0.04 μg/mL; xanthine oxidase inhibition assay: IC50 < 20 μg/mL; Griess–Ilosvay method: IC50 < 10 ± 2 μg/mL. Flowers: total phenols > 100 mg/g extract; DPPH assay: IC50 = 28.92 ± 0.19 μg/mL; xanthine oxidase inhibition assay: IC50 > 20 μg/mL; Griess–Ilosvay method: IC50 < 10 ± 2 μg/mL. Fruits: total phenols < 100 mg/g extract; DPPH assay: IC50 = 90.11 ± 0.57 μg/mL; xanthine oxidase inhibition assay: IC50 > 20 μg/mL; Griess–Ilosvay method: IC50 > 10 ± 2 μg/mL. Roots: total phenols > 100 mg/g extract; DPPH assay: IC50 = 31.52 ± 0.74 μg/mL; xanthine oxidase inhibition assay: IC50 > 20 μg/mL; Griess–Ilosvay method: IC50 < 10 ± 2 μg/mL. Stems: total phenols > 100 mg/g extract; DPPH assay: IC50 = 46.96 ± 2.51 μg/mL; xanthine oxidase inhibition assay: IC50 < 20 μg/mL; Griess–Ilosvay method: IC50 > 10 ± 2 μg/mL. | [139] |
| Leaves and roots/ethanol | Phytochemical analyses: Folin–Ciocalteu assay, with gallic acid as a reference standard; aluminum chloride method, with quercetin as a reference standard; quantification of phenolics and flavonoids by HPLC-DAD. In vitro antioxidant activity was determined by the following different methods: thiobarbituric acid reactive substances (TBARS) assay with phospholipids; iron chelation assay; deoxyribose degradation assay; ferric-reducing antioxidant power (FRAP). | Leaves: total phenols: 227.10 ± 9.07; Gallic Acid Equivalents (GAE μg/mg), 22.7%; total flavonoids: 46.55 ± 1.50; quercetin equivalents (QuercE μg/mg), 4.6%; caffeic acid (10.75 ± 0.04 mg/g), 1.07%; quercetin (2.87 ± 0.01 mg/g, 0.28%); TBARS assay: basal IC50 = 57.69 ± 4.01 μg/mL; induced Fe2+ IC50 = 32.48 ± 3.51 μg/mL; iron chelation assay: IC50 = 214.20 ± 2.50 μg/mL; deoxyribose degradation assay: IC50 = 285.64 ± 20.63 μg/mL; FRAP assay: 8.28 ± 0.07 mM Fe 2+/g extract. Roots: total phenols = 211.80 ± 7.94 (GAE μg/mg), 21.3%; total flavonoids = 33.64 ± 1.52 (QuercE μg/mg, 3.3%); caffeic acid (8.27 ± 0.01 mg/g, 0.82%), rutin (5.35 ± 0.03 mg/g, 0.53%); TBARS assay: basal IC50 = 168.92 ± 7.36 μg/mL; induced Fe2+ IC50 = 63.84 ± 4.56 μg/mL; iron chelation assay: IC50 = 448.19 ± 4.50 μg/mL; deoxyribose degradation assay: IC50 = 276.89 ± 31.26 μg/mL; FRAP assay: 11.64 ± 0.10 mM Fe2+/g extract. | [160] | |
| Leaves/methanol | The concentration of lipid peroxides (LPOs) in the stomach mucosa of Wister albino rats used in ulcerogenic models was indirectly measured by the TBARS assay; the concentration of reduced glutathione was also determined. | LPO: 29.23 ± 0.35 and 27.7 ± 0.50 nmol/g; GSH: 181.52 ± 0.83 and 202.9 ± 1.08 μg/g. | [128] | |
| Leaves/methanol | DPPH assay. | IC50 = 74.3 μg/mL. | [130] | |
| Leaves/methanol | Quantitative analysis of phytochemicals: total phenolic content, total flavonoid content, and total tannin content. In vitro antioxidant activity (DPPH radical scavenging activity assay and hydroxyl radical scavenging activity assay). | Total phenolic content: 40.859 ± 0.017 (mg GAE/g dry sample). Total flavonoid content: 53.112 ± 0.199 (mg rutin/g dry sample). Total tannin content: 0.860 ± 0.038 (mg/g dry sample). DPPH assay: IC50 ≥ 0.2 mg/mL. Hydroxyl radical assay: IC50 ≤ 0.2 mg/mL. | [137] | |
| Leaves/ethyl acetate | Total phenolic content and DPPH assay. | Total phenolic content: 2419.6 mg/L GAE. DPPH assay: IC50 = 36.18 mg/mL. | [161] | |
| Aerial parts/methanol | The antioxidant capacity of a crude extract was evaluated by the FRAP and the DPPH assays. | FRAP: 8.17 ± 0.04 mmol/g, DPPH: IC50 = 16.13 ± 0.35 μg/mL. | [156] | |
| Leaves/water | DPPH, metal chelating activity, and FRAP assays. | DPPH assay: IC50 = 42.66 μg/mL; metal chelating activity assay: IC50 = 1036.4 μg/mL; FRAP test: dose-dependent activity. | [162] | |
| Leaves/methanol | DPPH and FRAP assays. | DPPH: IC50 = 24.80 ± 0.52 μg/mL; FRAP: IC50 = 21.61 ± 0.26 μg/mL. | [143] | |
| Antiparasitic | Leaves and stems/dichloromethane; dichloromethane–methanol (1:1); water | Leishmania amazonensis (MHOM/77BR/LTB0016) promastigotes and amastigotes. | Dichlorometane extract: IC50 = 11.7 ± 4.4 μg/mL and IC50: 21.8 ± 2.4 μg/mL; dichloromethane–methanol (1:1) and water extracts: IC50 > 200 μg/mL. | [64] |
| Leaves/methanol Aerial parts/dichloromethane | Leishmania amazonensis (MHOM/Br/75/Josefa) isolated promastigotes and L. chagasi (MHOM/Br/74/PP75) isolated promastigotes. The in vitro antiparasitic activity of a crude extract and 18 fractions obtained by open-column chromatographic separation were tested against Leishmania amazonensis (MHOM/BR/77/LTB0016) promastigotes and L. mexicana isolated amastigotes. | IC50 = 14 μg/mL and IC50 > 250 μg/mL. Crude extract: IC50 = 21.8 ± 2.4 μM and IC50 = 42.6 ± 1.9 μM. The most active fractions against L. amazonensis amastigotes were as follows: FII, IC50 = 9.1 ± 3.4 μM; FX, IC50 = 7.9 ± 0.3 μM; FXI, IC50 = 8.0 ± 1.1 μM; FXVI, IC50 = 8.5 ± 1.7 μM. | [67] [109] | |
| Leaves/dichloromethane | Dichloromethane extracts of two different batches were tested against the chloroquine-sensitive strain 3D7 and chloroquine-resistant strain W2 of Plasmodium falciparum, and by the parasite dehydrogenase lactate essay. Five female Swiss mice (10 weeks old; 25 ± 2 g), infected by Plasmodium berghei NK173, received a single dose of 50 mg extract/kg body weight daily for 4 days intraperitoneally. | 3D7: IC50 = 8.7 ± 1 and 14.1 ± 8.4 μg/mL; W2: IC50 = 5.7 ± 1.6 and 12.2 ± 2.9 μg/mL. 5% growth inhibition. | [43] | |
| Leaves/ethyl acetate | The extract was tested on chloroquine-resistant strains (3D7 and INDO) of Plasmodium falciparum. | 3D7: IC50 = 19 ± 0.57 μg/mL; INDO: IC50 = 20 ± 1.5 μg/mL. | [58] | |
| Leaves and twigs/dichloromethane–methanol (1:1); water | Crude extracts were tested in vitro against the chloroquine-sensitive strain D10 of Plasmodium falciparum and by the parasite dehydrogenase lactate assay. | IC50 = 11 μg/mL; IC50 < 1000 μg/mL. | [140] | |
| Aerial parts/methanol | The in vitro nematocidal activity of crude extract and its partitions were screened against Meloidogyne incognita larvae, at concentrations of 0.5%, 0.25%, and 0.125% after 48 h. | At a 0.5% concentration, the methanol extract: 85% mortality; ether insoluble partition: 90% mortality; methanolic acidic partition: 88% mortality; ether soluble partition: 75% mortality; n-hexane soluble partition: 60% mortality; n-hexane insoluble partition: 50% mortality. | [99] | |
| Antiulcerogenic | Leaves/methanol | Wister albino rats (150–200 g) were divided into 4 groups; groups 2 and 3 received 250 and 500 mg extract/kg orally. Aspirin-induced ulcerogenesis in a pyloric ligated system (APL); ethanol-induced ulcer model (EIM); cysteamine-induced duodenal ulcer model (Cys). | Ulcer index inhibition: APL: 46.61% and 73.97%; EIM: 55.60% and 63.39%; CYS: 41.43% and 68.90%. | [103] |
| Antiviral | Leaves and flowers/95% ethanol | The in vitro anti-COVID-19 activity of crude extracts from different cultivars were screened by the plaque reduction assay. | Spreading sunset cultivar: flowers: IC50 = 4.188 μg/mL; leaves: IC50 = 8.751 μg/mL. Chelsea gem cultivar: flowers: IC50 = 3.671 μg/mL; leaves: IC50 = 3.181 μg/mL. Nivea cultivar: flowers: IC50 = 15.050 μg/mL; leaves: IC50 = 6.820 μg/mL. Drap d’or cultivar: flowers: IC50 = 5.015 μg/mL; leaves: IC50 = 8.715 μg/mL. | [103] |
| Anxiolytic | Leaves/methanol | Ursolic acid stearyl glucoside (UASG) was isolated from the leaves of L. camara using column chromatography. The compound was administered to the animals in a dose-dependent manner to evaluate its effects at different concentrations | A dose-dependent effect, with higher doses of UASG (25 and 50 mg/kg) leading to more pronounced anxiolytic effects. UASG reduced the anxiety and increased the locomotor activity. The anxiolytic effects of UASG were comparable to those of diazepam (1 mg/kg), a standard anxiolytic drug, indicating that UASG may have a similar therapeutic potential. | [163] |
| Chemoprotective effect | Leaves/methanol | Female Swiss albino mice (6 weeks old; 18–22 g). Group III received 400 mg extract/kg body weight, which was given orally as a suspension in water and carboxymethyl cellulose, twice a week (100 nmol/100 μL), applied for 20 weeks topically. | A significant reduction in cancer (76.4%) was observed, and the survival rate was 75%. | [141] |
| Cytotoxic | Leaves and stems/dichloromethane (a); dichloromethane–methanol (1:1) (b); water (c). | BALB/c mice peritoneal macrophages. | (a): CC50 > 100 μg/mL; (b): CC50 > 200 μg/mL; (c): CC50 = 125.9 ± 3.1 μg/mL. | [64] |
| Leaves/dichloromethane | The cytotoxicity of dichloromethane extracts from two different batches was tested in vitro towards normal human fetal lung fibroblasts WI-38. | IC50 = 69.5 ± 12.1 μg/mL and IC50 = 97.2 ± 2.4 μg/mL. | [43] | |
| Leaves/ethyl acetate | HeLa cells and the MTT assay. | IC50 = 42 ± 2.3 μg/mL. | [58] | |
| Leaves/ethanol | Tested towards Hela cancer cells. | IC50 = 43.54 μg/mL. | [142] | |
| Leaves/methanol | Vero cells. | IC50 values at 24 h exposure = 361.44 ± 10.68 μg/mL; at 48 h exposure = 319.37 ± 99.80 μg/mL. | [103] | |
| DNA protection | Leaves/water | H2O2 photolysis by UV radiation in the presence of pBR322 plasmid DNA and an aqueous extract (50 g). | Treatment with the extract at the evaluated dose completely protected the plasmid DNA. | [162] |
| Hemolytic | Leaves/water | The hemolytic activity of a crude extract and the hexane–ethyl acetate (50:50), chloroform, methanolic, and ethanolic partitions were screened at different concentrations (125, 250, 500, and 1000 μg/mL). | CC50 values (μg/mL): aqueous extract = 8035.9; hexane–ethyl acetate (50:50) phase = 4470.4; chloroform phase = 2739.8; methanolic phase = 12332.0; ethanolic phase = 9496.4. | [107] |
| Hepatoprotective effect | Leaves/methanol | In vivo acetaminophen-induced hepatotoxicity on a mice model. The mice of groups III and IV received a dose of 25 and 75 mg extract/kg daily for 7 days before receiving a single dose of acetaminophen. The mice of groups V and VI received a dose of 25 and 75 mg extract/kg daily for 7 days before receiving a single dose of acetaminophen. Subsequently, the serum glutamate oxaloacetate transaminase (SGOT), serum glutamate pyruvate transaminase (SGPT), and alkaline phosphatase (ALP) activities were measured. | Among all of the tested groups, pretreatment with a 75 mg extract/kg significantly reduced the SGOT = 144.5 ± 3.74 (UI/L), SGPT = 112.4 ± 9.1 (UI/L), and ALP = 96.8 ± 3.2 (UI/L) activities compared to control groups. | [130] |
| Leaves/methanol (Lantadenes concentrated fraction) | A Ginkgo biloba methanolic extract (GBME) was evaluated against lantadenes-induced hepatic damage in guinea pigs. Guinea pigs (200–250 g) were divided into 5 groups. Group I: negative control; group II received 25 mg lantadenes/kg body weight; group III received 25 mg lantadenes/kg body weight + 100 mg GBME/kg body weight; group IV received 25 mg lantadenes/kg body weight + 200 mg GBME/kg body weight; group V: positive control, received 100 mg silymarin/kg body weight. The drugs were administered orally in gelatin capsules daily for 14 days. Analysis by HPLC of the lantadenes fraction (72.82% lantadene A). | Serum protein levels of group IV were significantly lower than group II. | [164] | |
| Insecticidal/larvicidal/termiticidal | Leaves/methanol, n-hexane | Methanol and n-hexane extracts were tested in vivo against Anopheles stephensi (Liston). | The methanol extract was more active than the n-hexane extract. The optimal dose for the repellent activity was 2 mg/mL. | [52] |
| Aerial parts/ethanol | Phthorimae operculella (Zeller). | High insecticidal effect against Phthorimae operculella (Zeller); no ovocidal effects. | [144] | |
| Leaves/ethyl acetate, methanol | Tested against Anopheles stephensi (Liston) and Culex quinquefasciatus (Say) larvae. | Ethyl acetate extract: 500 ppm, 30 min: 98% mortality and 500 ppm, 30 min: 93% mortality. Methanol extract: 500 ppm, 30 min: 82% mortality and 500 ppm, 30 min: 86% mortality. | [145] | |
| Whole plant/ethanol | The in vitro larvicidal activity of the methanol and petroleum ether partitions from extracts of different parts of the plant were assayed with the brine shrimp lethality test. | Methanol partitions: leaves: LC50 = 18 μg/mL; roots: LC50 = 17 μg/mL; twigs and stems: LC50 = 0.3 μg/mL. Petroleum ether partitions: leaves: LC50 = 54 μg/mL; roots: LC50 = 47 μg/mL; twigs: LC50 = 62 μg/mL; stems: LC50 = 3.6 μg/mL. | [86] | |
| Leaves/chloroform | The termiticidal activity of several extracts was screened against Microcerotermes beesoni. | Most active extract: LD50 = 5 μg/insect. | [146] | |
| Leaves and seeds/powder | Applied to Zea mays L. against Sitophilus zeamais. | 63.3% mortality of Sitophilus zeamais on the twenty-eighth day. | [147] | |
| Leaves/n-hexane | Different concentrations (10%, 5%, 2.5%, 1.25%, 0.1%, 0.05%, 0.025%, 0.0125%, and 0.00625%) of a crude extract were tested against Dysdercus koenigii Fabricius nymphs for 24 h and monitored for 7 days. | Survival of nymphs at 10%, 5%, 2.5%, and 1.25% concentrations = 65.33%, 66.67%, 72%, and 85.33%. Reduction in the longevity at 10% and 5% concentrations = 5.54 and 5.95 days. | [148] | |
| Leaves and flowers/ethanol | Crude extracts were tested against Anopheles arabiensis and Culex quinquefasciatus larvae. | Flowers: A. arabiensis, LC50 = 15.84 ppm; C. quinquefasciatus, LC50 = 21.37 ppm. Leaves: A. arabiensis, LC50 = 9.54 ppm; C. quinquefasciatus, LC50 = 5.01 ppm. | [149] | |
| Whole plant/water, acetone, chloroform, ethanol, and methanol | The larvicidal activity of different concentrations (25, 50, 75, 100, and 150 ppm) of crude extract was screened for 24 h against Aedes aegypti, Anopheles stephensis, and Culex quinquefasciatus. | The most active extracts: methanol: A. aegypti, LC50 = 39.54 ppm; A. stephensis, LC50 = 35.65 ppm; C. quinquefasciatus, LC50 = 35.36 ppm; ethanol: A. aegypti LC50 = 60.93 ppm; A. stephensi, LC50 = 79.03 ppm; C. quinquefasciatus, LC50 = 50.17 ppm. | [150] | |
| Leaves/diluted aqueous juice | Different concentrations (25, 50, 75, and 100 ppm) were tested against Aedes aegypti, Anopheles subpictus, and Culex quinquefasciatus larvae during 6, 12, and 24 h. | LC50 values ranged from 47.47 to 101.68 ppm. | [151] | |
| Leaves/acetone | The insecticidal activity of different concentrations (100, 200, 300, 400, and 500 ppm) of a crude extract was tested against Aedes aegypti L. larvae and pupae for 24 h. | Larvae: LC50 = 198.52 ppm; pupae: LC50 = 309.64 ppm. | [59] | |
| Leaves/water | The insecticidal activity of different concentrations (62.5, 125, 250, 500, and 1000 ppm) of a crude extract was tested against Aedes aegypti L. and Culex quinquefasciatus Say larvae for 24 h. | A. aegypti L.: LC50 = 35.48 ppm; C. quinquefasciatus: LC50 = 35.19 ppm. | [152] | |
| Leaves/95% ethanol | Different concentrations (250–3000 ppm) of a crude extract were tested against Anopheles arabiensis Patton larvae. | LC50 = 477.53 ppm. | [153] | |
| Phytotoxic | Leaves/water | Different concentrations (0%, 1.25%, 2.5%, 3.75%, and 5%, v/v) of a crude extract were tested on Bidens pilosa seeds. | The aqueous extract reduced the viability of Bidens pilosa seeds during phase III of germination. At any concentration, the aqueous extract inhibited the root and epicotyl growth. | [154] |
| Leaves/methanol–water (70:30) | A crude extract, at the concentration of 5 g/L, was tested on Eichhornia crassipes (Mart.) Solms and Microcystis aeruginosa Kütz. | E. crassipes: complete inhibition; M. aeruginosa: 66.1% inhibition. | [110] | |
| Leaves and callus/water | The inhibition of seed germination by crude extracts was tested on Brassica campestris var. chinensis, Ipomoea aquatica Forsk., Sorghum bicolor L., and Zea mays L. | Extract concentration that caused 50% inhibition of seed germination: B. campestris: leaves = 0.62%, callus = 0.65%; I. aquatica: leaves = 0.94%, callus = 0.45%; S. bicolor: leaves = 0.95%, callus = 1.19%; Z. mays: leaves = 4.39%, callus = 3.05%. | [165] | |
| Leaves/water | An aqueous leaf leachate was tested on Eichhornia crassipes (Mart.) Solms. | The concentration of 5% was the most toxic after 21 days. | [166] | |
| Callus/water | An aqueous leaf leachate was tested on Salvinia molesta Mitchell. | The concentration of 1% was the most toxic after 7 days. | [167] | |
| Callus/water | A crude extract encapsulated in calcium alginate beads was tested on Brassica campestris var. chinensis. | Beads with 5% extract had no effect on the germination rate, while beads with 1–4% extract did not reduce the total weight of fresh seedlings. | [168] | |
| Wound-healing effects | Leaves/water Leaves/ethanol | Daily topical application of 100 mg extract/kg body weight on wounds of male Sprague Dawley rats (200–220 g). Bovine dermatophilosis caused by Dermatophilus congolensis was treated with ointments containing L. camara leaf ethanolic extracts once a day for 10 days. | Mean epithelization time and % of wound healing: placebo group = 19 ± 0.14 days and 88%; tested group = 17.20 ± 0.12 days and 98%. Wound healing was observed between the third and fourth day of application without recurrence. | [169] [108] |
a Biological activities are ordered in alphabetic order. * MIC = minimum inhibitory concentration; MBC = minimum bactericidal concentration; IC50 = sample concentration causing 50% inhibition; LC50 = sample concentration that causes 50% mortality; CC50 = sample concentration causing 50% cytotoxicity.
Table 9.
Bioactivities determined for the compounds isolated from Lantana camara and semisynthetic derivatives.
Table 9.
Bioactivities determined for the compounds isolated from Lantana camara and semisynthetic derivatives.
| Compound a,* (Nº) | Biological Activity | Reference |
|---|---|---|
| Acetyl lantanoside * (144) | In vitro antibacterial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294): 98% inhibition, MIC < 11.15 μM. | [16,134] |
| 22β-Acetyloxy-oleanonic acid * (37) | In vitro cytotoxic activity towards human leukemia HL-60 cells: IC50 = 75.09 ± 0.09 μM; human cervical carcinoma Hela cells: IC50 = 72.75 ± 0.29 μM; colon 502,713 cells: IC50 = 67.1 ± 0.04 μM; lung carcinoma A549 cells: IC50 = 71.77 ± 0.15 μM. | [94] |
| 22β-Benzoyloxy-oleanonic acid * (85) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 88.38 ± 0.15 μM; Hela cells: IC50 = 80.55 ± 0.15 μM; colon 502,713 cells: IC50 = 89.07 ± 0.04 μM; lung A549 cells: IC50 > 100 μM. | [94] |
| 22β-Butanoyloxy-oleanonic acid * (50) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 39.94 ± 0.23 μM; Hela cells: IC50 = 42.16 ± 0.15 μM; colon 502,713 cells: IC50 = 46.6 ± 0.28 μM; lung A549 cells: IC50 = 50.11 ± 0.09 μM. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a]anthracene/12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg/kg body weight administered orally for 20 weeks: 80% mice survival and 17.2% overall papilloma incidence. | [94] |
| Camaric acid (62) | In vitro nematocidal activity towards Meloidogyne incognita larvae: 95% mortality at 0.5% concentration after 48 h. In vitro antiparasitic activity towards Leishmania mexicana promastigotes: IC50 = 2.52 ± 0.08 μM. In vitro protein tyrosine phosphatase 1B inhibition assay: IC50 = 5.1 μM [84]. In vitro cytotoxic activity towards HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 1.71 ± 0.10 μM. In vitro anti-inflammatory activity (inhibition of LPS-induced NO production in BV-2 cells): IC50 > 3 μM. | [80,82,84,99,117,118] |
| Camarin (23) | In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at 1 mg/mL concentration after 48 h. | [90] |
| Camarinic acid (114) | In vitro antimicrobial and antifungal activity index values: E. coli = 2, S. aureus = 0.95, P. aeruginosa = 0.15, S. typhi = 0.7, C. albicans = 0.2, T. mentagrophytes = 2.3. In vivo antimutagenic evaluation: micronucleus test (2.75 mg mitomycin D/kg body weight and 6.75 mg/kg body weight given orally to Swiss strain mice, once a day-48 h): 76.7% reduction in the number of micronucleated polychromatic erythrocytes. In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at 1% concentration after 24 h. In vitro antiparasitic activity against Leishmania major promastigotes: IC50 = 89 ± 0.3 μM. | [16,78] |
| Camarinin (56) | In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at 1 mg/mL concentration after 48 h. | [90] |
| Di-(2-ethylhexyl) phthalate (166) | In vitro antibacterial activity (disk diffusion method), zone inhibition diameter: Escherichia coli = 20 mm, Staphylococcus aureus = 22 mm, Salmonella typhimurium = 21 mm, Pseudomonas aerugionosa = 23 mm. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 8.1 μM. | [73,84] |
| Ethyl-β-D-galactopyranoside (163) | Inactive in an in vitro antiparasitic activity assay towards Brugia malayi. | [74] |
| 3-O-β-D-Glucosyl oleanolic acid (84) | In vivo antiulcer activity: aspirin-induced and ethanol-induced ulcer models; Albino Wistar rats (150–200 g) were divided into 4 groups. Groups III and IV received 25 and 50 mg compound/kg body weight, respectively, orally once a day for 5 days. Ulcer index: 3.48± 0.83 and 1.99 ± 0.34, respectively; protection: 21.24 and 38.37%, respectively. | [126] |
| Hispidulin (128) | In vitro protein tyrosine phosphatase inhibition assay: IC50 > 33 μM. | [72,79,84] |
| 9-Hydroxy-lantadene A (64) | In vitro antifungal activity against Fusarium subglutinans (PPRI 6740), F. solani (PPRI 19147), F. graminearum (PPRI 10728), and F. semitectum (PPRI 6739): MIC ˃ 1000 μM; against F. proliferatum (PPRI 18679): MIC = 70.32 μM. In vitro cytotoxic activity towards Raw 264.7 cells: IC50 ˃ 100 μM. | [120] |
| 24-Hydroxy-lantadene B ≡ 24-Hydroxy-22β-senecioyloxy-oleanonic acid (65) | Binding affinity to the antiapoptotic protein Bcl-xL: Ki = 5.3 μM. In vitro cytotoxic activity towards papilloma KB cells: IC50 = 35.5 μM; colon carcinoma HCT-116 cells: IC50 = 11.4 μM; breast adenocarcinoma MCF7 cells: IC50 = 42.5 μM; lymphocytic leukemia L1210 cells: IC50 = 12.3 μM. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 7.3 μM. | [84,116] |
| 24-Hydroxy-lantadene D (53) | In vitro protein tyrosine phosphatase inhibition assay: IC50 >18 μM. | [84] |
| 22β-Hydroxy- oleanolic acid (32) | In vitro cytotoxic activity: tested on multiple cancer cells. In vitro anti-inflammatory activity (TNF-α-induced NF-ΚB activation inhibitory activity): IC50 ˃10 μM; COX-2 inhibition: IC50 ˃100 μM. In vitro cytotoxic activity towards A549 cells: IC50 ˃10 μM. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 7.9 μM. | [80,84,95,96] |
| 22β-Hydroxy-oleanonic acid (26) | In vitro antitumor activity: Epstein–Barr virus early antigen activation assay induced by 12-O-tetradecanoylphorbol-13-O-acetate (TPA) in Raji cells: 35.3% inhibition at 100 mol tested compound/1 mol TPA. In vivo hepatotoxicity evaluation (adult female guinea pigs received 125 mg compound/kg body weight orally in gelatin capsules): bilirubin: 0.67 ± 0.001 mg/100 mL, SGOT: 46.1 ± 0.4 U/L, SGPT: 39 ± 0.3 U/L; nontoxic. In vitro cytotoxic activity towards HL-60, Hela, colon 502,713, and lung A549 cells: IC50 > 100 μM; A549 cells: IC50 ˃ 10 μM [94]. In vitro anti-inflammatory activity (inhibitory activity of TNF-α-induced NF-ΚB activation): IC50 = 6.42 ± 1.24 μM; COX-2 inhibition: IC50 ˃ 100 μM. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 6.9 μM. | [84,92,93,94,95,96] |
| 11α-Hydroxy-3-oxo-urs-12-en-28-oic acid (101) | In vitro nematocidal activity against Meloidogyne incognita larvae: 70% mortality at 0.25% concentration after 72 h. | [82] |
| Icterogenin (67) | Binding affinity to the antiapoptotic protein Bcl-xL: Ki = 7.6 μM. In vitro cytotoxic activity towards KB cells: IC50 = 15 μM; HCT-116 colon cancer cells: IC50 = 5.8 μM; MCF7 cells: IC50 = 11.3; L1210 lymphocytic leukemia cells: IC50 = 6.8 μM; HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 34.2 ± 0.7 μM. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 11 μM. In vitro anti-inflammatory activity (inhibition of LPS-induced NO production in BV-2 cells): IC50 > 3 μM. DPPH radical scavenging activity: IC50 = 169.7 μg/mL. | [109] |
| Lancamarinic acid (41) | In vitro screening against a variety of Gram-positive and Gram-negative bacteria (disk diffusion method). | [105] |
| Lancamarolide (42) | In vitro nematocidal activity against Meloidogyne incognita larvae: 80% mortality at 0.25% concentration after 48 h. | [81] |
| Lantacamaric acid A (29) | In vitro cytotoxic activity towards HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 30.8 ± 2.7 μM. | [99] |
| Lantacamaric acid B (70) | In vitro cytotoxic activity towards HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 6.60 ± 0.46 μM. | [99] |
| Lantacin (119) | In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at 1 mg/mL concentration after 48 h. | [81,90] |
| Lantadene A (Rehmannic acid) (60) | In vitro larvicidal activity: very toxic in the brine shrimp lethality test; insecticidal activity at 5.0 mg/mL towards Spodoptera littoralis Biosduval: 40% lethality after 48 h; fecundity inhibition assay in Clavigralla tomentosicollis Stal.: 50% fecundity suppression; inactive towards Aphis craccivora Koch. In vivo antimotility effect evaluation (Laca strain male mice (20–25 g) received a single injection of 85 and 170 mg compound/kg body weight): % intestinal transit = 39.47 ± 10.05 and 27.34 ± 4.58, respectively. Phytotoxic activity towards Eichhornia crassipes (Mart.) Solms and Microcystis aeruginosa Kutz: ErC50 = 24.78 and 21.34 mg/L, respectively. In vivo hepatotoxicity evaluation (adult female guinea pigs received 125 mg compound/kg body weight orally in gelatin capsules): bilirubin = 8.74 ± 2.5 mg/100 mL, SGOT = 696.3 ± 3.1 U/L, SGPT = 305.2 ± 3.9 U/L; toxic. In vitro cytotoxicity towards HL-60 cells: IC50 = 35.81 ± 0.40 and 35 ± 1 μM; HeLa cells: IC50 = 42.15 ± 0.09 and 42 ± 8 μM; colon 502,713 cells: IC50 = 38.53 ± 0.09 and 38 ± 5 μM μM; lung A549 cells: IC50 = 39.43 ± 0.21, 39 ± 1 μM μM, and 2.84 ± 0.72 μM; KB cells: IC50 = 15.8 μM; HCT-116 cells: IC50 = 41.8 μM; MCF7 cells: IC50 = 44.7 and ˃ 100 μM; L1210 cells: IC50 = 16.3 μM; HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 25.4 ± 3.1 μM; LNcap prostatic cancer cells: IC50 ˃ 100 μM; RWPE-1 prostatic cancer cells: IC50 ˃ 100 μM. Lantadene A-gold nanoparticles reduced MCF-7 (breast cancer cells) viability, upregulated the p53 expression, and downregulated the BCL-2 expression. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a]anthracene-12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight administered orally for 20 weeks: 80–100% mice survival and 17.9–18.1% overall papilloma incidence. Binding affinity to the antiapoptotic protein Bcl-xL: Ki > 100 μM. Antioxidant activity in a dose-dependent manner. Toxicity evaluation: toxic (2 g) orally to sheep; nontoxic to lambs (167 mg compound/kg body weight administered orally in gelatin capsules) and guinea pigs (667 mg compound/kg body weight administered orally in gelatin capsules). In vitro antiparasitic activity against Leishmania major promastigotes: IC50 = 20.4 ± 0.1 μM. In vitro anti-inflammatory activity (inhibition of TNF-α-induced NF-ΚB activation): IC50 = 1.06 ± 0.46 μM; COX-2 inhibition: IC50 ˃ 100 μM. In vitro nematocidal activity towards Meloidogyne incognita larvae: 70% mortality at 0.5% concentration after 48 h. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 5.2 μM. DPPH radical scavenging activity: IC50 = 93.94 μM. | [78,82,84,86,91,92,93,94,95,96,99,100,105,109,110,111,112,113,114,115,116] |
| Lantadene A acyl chloride * (58) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 47.79 ± 0.24 μM; Hela cells: IC50 = 46.21 ± 0.17 μM; colon 502,713 cells: IC50 = 49.19 ± 0.17 μM; lung A549 cells: IC50 = 50.07 ± 0.14 μM. | [93] |
| Lantadene A methyl ester * (81) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 34.04 ± 0.26 and 34 ± 1.4 μM; Hela cells: IC50 = 37.93 ± 0.09 and 37 ± 5 μM; colon 502,713 cells: IC50 = 37.22 ± 0.15 and 37 ± 8 μM; lung A549 cells: IC50 = 33.87 ± 0.09 and 33 ± 5 μM. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a]anthracene-12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight administered orally for 20 weeks: 87.5–100% mice survival and 13.6–19.6% overall papilloma incidence. | [112] |
| Lantadene A nitrile * (57) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 70.43 ± 0.22 μM; Hela cells: IC50 = 74.0 ± 0.09 μM; colon 502,713 cells: IC50 = 78.68 ± 0.15 μM; lung A549 cells: IC50 = 82.80 ± 0.18 μM. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a]anthracene-12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight given orally for 20 weeks: 75% mice survival and 24.9% overall papilloma incidence. | [93] |
| Lantadene B (61) | Phytotoxic activity against Eichhornia crassipes (Mart.) Solms and Microcystis aeruginosa Kütz: ErC50 = 19.53 and 17.37 mM, respectively. Binding affinity to the antiapoptotic protein Bcl-xL: Ki > 100 μM. In vitro cytotoxic activity against KB cells: IC50 = 25.3 μM; HCT-116 cells: IC50 = 11.4 μM; MCF-7 cells: IC50 = 44 μM and ˃ 100 μM; L1210 cells: IC50 = 16.1 μM; A549 (lung carcinoma) cells: IC50 = 1.19 ± 0.28 μM. In vitro cytotoxic activity (MTT test) towards MCF-7 breast cancer cells: IC50 = 1.13 μM. In vitro anti-inflammatory activity (inhibition of TNF-α-induced NF-ΚB activation): IC50 = 1.56 ± 0.04 μM; COX-2 inhibition: IC50 ˃ 100 μM. In vitro nematocidal activity against Meloidogyne incognita larvae: 60% mortality at 0.25% concentration after 48 h; against Leishmania mexicana promastigotes, IC50 = 23.45 ± 2.15 μM. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 5.5 μM. DPPH radical scavenging activity: IC50 = 76.45 μM. | [82,84,95,96,109,110,116,117,124] |
| Lantadene C (72) | Binding affinity to the antiapoptotic protein Bcl-xL: Ki > 100 μM. In vitro cytotoxic activity towards KB cells: IC50 = 15.8 μM; HCT-116 cells: IC50 = 41.8 μM; MCF7 cells: IC50 = 44.7 and ˃ 100 μM; L1210 cells: IC50 = 16.3 μM; HL-60 cells: IC50 ˃ 100 μM; Hela cells: IC50 ˃ 100 μM; colon 502,713 cells: IC50 ˃ 100 μM; lung A549 cells: IC50 ˃ 100 μM. DPPH radical scavenging activity: IC50 ˃ 100 μM. | [84,116] |
| Lantadene D (51) | In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a]anthracene-12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight given orally for 20 weeks: approximately 85% mice survival and 30% overall papilloma incidence. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 7.9 μM [84]. | [84,97] |
| Lantanilic acid (68) | In vitro nematocidal activity against Meloidogyne incognita larvae: 98.66% mortality at 0.5% concentration after 48 h. In vitro antiparasitic activity against Leishmania mexicana promastigotes: IC50 = 9.50 ± 0.28 μM; L. major promastigotes: IC50 = 21.3 ± 0.02 μM; brine shrimp toxicity assay: LC50 = 49.20 μM. In vitro antibacterial and antifungal activity: diameter of inhibition zone at a concentration of 500 μg/mL against S. aureus = 1.7 mm and against C. albicans = 9.3 mm. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 7.5 μM [84]. In vitro cytotoxic activity towards HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 4.00 ± 0.67 μM. In vitro anti-inflammatory activity (inhibition of LPS-induced NO production in BV-2 cells): IC50 > 3 μM. | [78,80,81,84,98,99,118,122,123] |
| Lantaninilic acid (30) | In vitro antiparasitic activity against Leishmania major promastigotes: IC50 = 164 ± 0.8 μM. In vitro nematocidal activity against Meloidogyne incognita larvae: 60% mortality at a concentration of 0.125% after 48 h. In vitro cytotoxic activity towards HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 68.4 ± 15.4 μM. | [78,82] |
| Lantanolic acid (27) | In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at a concentration of 1 mg/mL after 24 h. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 13 μM. | [84,90] |
| Lantanoside (140) | In vitro nematocidal activity against Meloidogyne incognita larvae: 95% mortality at a concentration of 1% after 48 h. In vitro antibacterial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294): 37% inhibition, MIC > 12.05 μM. | [16,134] |
| Lantic acid (102) | In vitro antimicrobial activity (bioautography assays): minimum growth inhibition values for B. subtilis (ATCC 6633), M. luteus (ATCC 9341), S. aureus (ATCC 6538P), and P. mirabilis (ATCC 14153) = 0.3 μg; B. cereus (ATCC 11778) = 0.1 μg; S. faecalis (ATCC 8043) and P. aeruginosa (ATCC 25619) = 1.1 nmol; E. coli (ATCC 25922) = 0.17 nmol. In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at a concentration of 1 mg/mL after 24 h. | [90] |
| Lantoic acid (105) | In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at a concentration of 1 mg/mL after 24 h. In vitro antiparasitic activity against Leishmania major promastigotes: IC50 = 97 ± 0.02 μM. | [81,90] |
| Lantrieuphpene A (13) | In vitro anti-inflammatory activity (inhibition of LPS-induced NO production in BV-2 cells): IC50 > 30 μM. | [80] |
| Lantrieuphpene B (8) | In vitro anti-inflammatory activity: inhibition of LPS-induced NO production in BV-2 cells, IC50 = 24 ± 0.30 μM; ROS and NO levels in LPS-stimulated zebrafish embryos significantly decreased in a concentration-dependent manner. Western blotting: iNOS protein expression decreased in a dose-dependent manner on pretreated cells. | [80] |
| Lantrieuphpene C (9) | In vitro anti-inflammatory activity: inhibition of LPS-induced NO production in BV-2 cells, IC50 = 27.98 ± 0.98 μM; ROS and NO levels in LPS-stimulated zebrafish embryos significantly decreased in a concentration-dependent manner. Western blotting: iNOS protein expression decreased in a dose-dependent manner on pretreated cells. | [80] |
| Lantrieuphpene D (12) | In vitro anti-inflammatory activity: inhibition of LPS-induced NO production in BV-2 cells, IC50 > 10 μM. | [80] |
| Linaroside (139) | In vitro nematocidal activity against Meloidogyne incognita larvae: 90% mortality at a concentration of 1% after 48 h. In vitro antibacterial activity against the Mycobacterium tuberculosis strain H37Rv (ATCC 27294): 30% inhibition, MIC = 13.12 μM. In vitro antioxidant activity (DPPH test): IC50 = 149.09 mM. | [16,134,162] |
| Methyl 22β-acetyloxy-oleanonate * (45) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 72.75 ± 0.29 μM; Hela cells: IC50 = 70.6 ± 0.10 μM; colon 502,713 cells: IC50 = 67.48 ± 0.15 μM; lung A549 cells: IC50 = 71.77 ± 0.10 μM. | [94] |
| Methyl 22β-angelyloxy-2-hydroxy-3-oxo-olean-1,12-diene-28-oate (78) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 26 ± 6 μM; HeLa cells: IC50 = 31 ± 5 μM; colon 502,713 cells: IC50 = 32 ± 1 μM; lung A549 cells: IC50 = 28 ± 4 μM. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a]anthracene-12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight administered orally for 20 weeks: approximately 100% mice survival and 17.2% overall papilloma incidence. | [124] |
| Methyl 22β-benzoyloxy-oleanonate * (86) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 81.52 ± 0.08 μM; Hela cells: IC50 = 86.10 ± 0.08 μM; colon 502,713 and lung A-549 cells: IC50 > 100 μM. | [94] |
| Methyl 22β-butanoyloxy-oleanonate * (73) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 34.79 ± 0.14 μM; Hela cells: IC50 = 36.23 ± 0.38 μM; colon 502,713 cells: IC50 = 38.03 ± 0.09 μM; lung A549 cells: IC50 = 40.37 ± 0.09 μM. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a]anthracene-12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight administered orally for 20 weeks: 80% mice survival and 12.4% overall papilloma incidence. | [94] |
| Methyl 22β-hydroxy-oleanonate * (35) | In vitro cytotoxicity towards HL-60 cells: IC50 ˃ 100 μM; Hela cells: IC50 > 100 μM; colon 502,713 cells: IC50 ˃ 100 μM; lung A549 cells: IC50 ˃ 100 μM. | [91,94] |
| Methyl 22β-isobutyryloxy-oleanonate * (74) | In vitro cytotoxicity towards HL-60 cells: IC50 = 71.19 ± 0.09 μM; Hela cells: IC50 = 74.08 ± 0.38 μM; colon 502,713 cells: IC50 = 68.67 ± 0.09 μM; lung A549 cells: IC50 = 76.06 ± 0.14 μM. | [94] |
| Methyl 22β-propanoyloxy-oleanonate * (52) | In vitro cytotoxicity towards HL-60 cells: IC50 = 44.75 ± 0.39 μM; Hela cells: IC50 = 48.81 ± 0.15 μM; colon 502,713 cells: IC50 = 41.42 ± 0.15 μM; lung A549 cells: IC50 = 52.52 ± 0.39 μM. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a] anthracene-12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight administered orally for 20 weeks: 80% mice survival and 17.9% overall papilloma incidence. | [94] |
| Oleanolic acid (31) | In vitro larvicidal activity: 30% lethality in the brine shrimp lethality test against Spodoptera littoralis Biosduval after 48 h at a concentration of 10.95 mM. Inactive in the fecundity inhibition assay against Clavigralla tomentosicollis Stal. and Aphis craccivora Koch. In vitro nematocidal activity against Meloidogyne incognita larvae: 70.33% mortality at a concentration of 0.5% after 48 h. In vitro antifilarial activity against Brugia malayi: LC100 = 136.85 μM. In vivo antifilarial activity against Brugia malayi in rodel model Mastomys coucha (100 or 200 mg compound/kg body weight administered intraperitoneally for 5 days): macrofilaricidal efficacy = 9.09% and 18.18%, respectively; percent female sterility = 49.22 ± 10.57 and 56.50 ± 9.50, respectively. In vitro cytotoxic activity towards HCT-15 cells: IC50 = 52 μM; SW-620 cells: IC50 = 25 μM; A549 cells: IC50 = 52 μM; IGROV-1 cells: IC50 = 8 μM; IMR-32 cells: IC50 = 61 μM. In vitro antiparasitic activity against Leishmania major promastigotes: IC50 = 53 ± 0.02 μM. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 2 μM. In vitro anti-inflammatory activity (inhibition of LPS-induced NO production in BV-2 cells): IC50 > 60 μM. | [75,78,80,84,86,87,118] |
| Oleanonic acid (22) | In vitro larvicidal activity: 20% lethality in the brine shrimp lethality test against Spodoptera littoralis Biosduval: after 48 h at a concentration of 10.996 mM. Inactive in the fecundity inhibition assay towards Clavigralla tomentosicollis Stal. and Aphis craccivora Koch. In vitro antifilarial activity against Brugia malayi: LC100 = 68.73 μg/mL. In vivo antifilarial activity against Brugia malayi in rodel model Mastomys coucha (100 or 200 mg compound/kg body weight administered intraperitoneally for 5 days), macrofilaricidal efficacy: inactive; % female sterility: 56.56 ± 9.49 and 29.71 ± 6.52, respectively. In vitro cytotoxic activity towards EAC cells: IC50 = 7.1 ± 1.3 μM; A375 cells: IC50 = 10.9 ± 1.5 μM; Hep2 cells: IC50 = 59.3 ± 1.1 μM; U937 cells: IC50 = 16.5 ± 1.3 μM; HL-60 human promyelocytic leukemia cells (JCRB0085): IC50 = 9.79 ± 2.13 μM; PMBC cells: IC50 > 100 μM. In vitro nematocidal activity against Meloidogyne incognita larvae: 80% mortality at a concentration of 0.5% after 48 h. In vitro protein tyrosine phosphatase inhibition essay: IC50 = 6.9 μM [84]. | [26,75,82,84,86,88,99] |
| 11-Oxo-β-boswellic acid (103) | In vitro antifungal activity against Fusarium subglutinans (PPRI 6740) and F. semitectum (PPRI 6739): MIC = 1.338 mM; F. proliferatum (PPRI 18679): MIC = 2.762 mM; F. solani (PPRI 19147) and F. graminearum (PPRI 10728): MIC = 5.311 mM. In vitro cytotoxicity towards Raw 264.7 cells: IC50 ˃ 100 μM. | [120] |
| Pomolic acid (107) | In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at a concentration of 1 mg/mL after 24 h. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 10.6 μM. | [84,90] |
| Pomonic acid (104) | In vitro protein tyrosine phosphatase inhibition assay: IC50 = 10.5 μM. In vitro anti-inflammatory activity (inhibition of LPS-induced NO production in BV-2 cells): IC50 > 30 μM. | [80,84] |
| 22β-Propanoyl- oxy-oleanonic acid * (46) | In vitro cytotoxic activity towards HL-60 cells: IC50 = 50.12 ± 0.32 μM; Hela cells: IC50 = 54.29 ± 0.09 μM; colon 502,713 cells: IC50 = 48.22 ± 0.09 μM; lung A549 cells: IC50 = 56.19 ± 0.26 μM. In vivo antitumor activity: squamous cell carcinogenesis induced by 7,12-dimethylbenz[a] anthracene/12-O-tetradecanoylphorbol-13-O-acetate in Swiss albino mice (LACCA/female); 50 mg compound/kg body weight administered orally for 20 weeks: 80% mice survival and 19.6% overall papilloma incidence. | [94] |
| Reduced lantadene A (22β-angelyloxy-3β-hydroxy-olean-12-en-28-oic acid) (75) | Evaluation of toxicity to sheep: 80 mg compound/kg body weight administered orally in gelatin capsules: nontoxic; 80 mg compound/kg body weight, dissolved in DMSO, intraruminal administration: toxic. Evaluation of toxicity to Wistar female rats: 15 mg compound/kg body weight administered orally in olive oil: toxic. In vitro antitumor activity: Epstein–Barr virus early antigen activation assay induced by 12-O-tetradecanoylphorbol-13-O-acetate (TPA) in Raji cells: 30.6% inhibition at a concentration of 100 mol compound/1 mol TPA. In vitro cytotoxicity was tested towards multiple cancer cells. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 7.2 μM. | [84,91,95] |
| Reduced lantadene B (3β-hydroxy-22β-senecioyloxy-olean-12-en-28-oic acid) (76) | In vitro cytotoxicity was tested towards multiple cancer cells. In vitro protein tyrosine phosphatase inhibition assay: IC50 = 5.1 μM. | [95] |
| Reduced lantadene C 3β-hydroxy-22β-[2-methylbutanoyloxy]-olean-12-en-28-oic acid (77) | In vitro protein tyrosine phosphatase 1B inhibition assay: IC50 = 7.3 μM. | [84] |
| β-Sitosterol (3) | In vitro antiparasitic activity against Brugia malayi: LC100 > 1.2 mM. Antibacterial activity (disk diffusion method): diameter of inhibition zone = 14 mm for Escherichia coli, 19 mm for Staphylococcus aureus, 17 mm for Salmonella typhimurium, 24 mm for Pseudomonas aeruginosa. The cytotoxic potential was tested in vitro by an MTT assay against T47D (breast cancer cells) and HeLa (cervical cancer cells): IC50 = 24.06 and 24.86 µM, respectively. | [73,74,170] |
| β-Sitosterol 3-O-β-D-glucopyrano-side (4) | In vitro antiparasitic activity against Brugia malayi: LC100 > 0.86 mM. | [71] |
| Stearic acid (158) | In vitro antiparasitic activity against Brugia malayi: LC100 > 1.7 mM. | [74,77] |
| Trilinolein (168) | In vitro antibacterial activity (disk diffusion method): diameter of inhibition zone = 20 mm for Escherichia coli, 19 mm for Staphylococcus aureus, 18 mm for Salmonella typhimurium, 21 mm for Pseudomonas aeruginosa. | [73] |
| Urs-12-en-3β-ol-28-oic acid 3-O-β-D-glucopyrano- syl-4′-octadecano- ate (127) | In vivo antidiabetic activity: Wistar albino rats (150–200 g) received 0.3 mg/kg body weight orally for 21 days. Blood glucose levels: 8th day = 183.56 ± 3.61 mg/dL, 14th day = 143.43 ± 2.79 mg/dL, 21st day = 118.67 ± 2.40 mg/dL. In vivo anxiolytic activity: dose-dependent effect. | [125] |
| Ursolic acid (106) | In vitro nematocidal activity against Meloidogyne incognita larvae: 100% mortality at a concentration of 1 mg/mL after 48 h. In vitro antiparasitic activity against Leishmania major promastigotes: IC50 = 12.4 ± 0.03 μM. | [78,90] |
a Compounds are ordered in alphabetic order. Cytotoxicity values (IC50) are expressed in μM for homogeneity. * Semisynthetic derivative. ErC50 = concentration of test substance which caused 50% reduction in growth rate relative to the control for a 72 h exposure.
A few compounds isolated from L. camara were also submitted to molecular docking studies (Table 10) towards the active site of RNA-dependent RNA polymerase (RdRp) of SARS-CoV-2. The highest binding energy (around 6 kcal/mol) was determined for camarolic acid (69) and lantoic acid (105). These values, when compared to remdesivir (−5.75 kcal/mol), indicated that compounds 69 and 105 can serve as promising anti-COVID-19 candidates. Moreover, lantrieuphpene B (8) and C (9) exhibited a high binding affinity (a binding energy of around 9 kcal/mol) to the TYR-341, TYR-367, and ASP-376 residues of inducible Nitric Oxide Synthase (iNOS). In addition, a recent in silico study has evaluated 20 selected constituents of L. camara as potent inhibitors of the human enzymes acetylcholinesterase (hAchE), carbonic anhydrase II (hCA-II), and carboxylesterase 1 (hCES-1), which are pharmacological targets for the treatment of neurodegenerative diseases, glaucoma, obesity, and type 2 diabetes [171]. All of the twenty ligands docked effectively with the CA-II enzyme. Only ursonic acid (100) was ineffective in both docking and binding with AchE and CES-1, while lantic acid (102) exhibited the least atomic binding energy with all three enzymes. The glucosyl flavone camaroside [17] exhibited the maximum binding energy (−9.34 kcal/mol) with hAchE, while the phenylethanoid glycoside isonuomioside A [17] demonstrated the highest binding energy (−9.72 kcal/mol) with hCA-II, and the flavone pectolinarin (146) showed the highest binding energy (−9.21 kcal/mol) with hCES-1 [172].
Table 10.
In silico studies of compounds isolated from Lantana camara.
Table 10.
In silico studies of compounds isolated from Lantana camara.
| Compound (Nº) | Docking Value | Reference |
|---|---|---|
| Camaranoic acid (99) | Molecular docking into the active site of SARS-CoV-2 RNA-dependent RNA polymerase (RdRp): binding free energy = 1.272 kcal/mol. | [81] |
| Camaric acid (62) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding free energy = −3.198 kcal/mol. | [81] |
| Camarolic acid (69) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding free energy = −6.73 kcal/mol. | [81] |
| Icterogenin (67) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding energy = −2.311 kcal/mol. | [81] |
| Lantabetulic acid (17) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding free energy = −2.958 kcal/mol. | [81] |
| Lantacin (119) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding free energy = −2.919 kcal/mol. | [81] |
| Lantaiursolic acid (120) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding free energy = −3.867 kcal/mol. | [81] |
| Lantanilic acid (68) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding free energy = −3.633 kcal/mol. | [81] |
| Lantoic acid (105) | Molecular docking into the active site of SARS-CoV-2 RdRp: binding free energy = −6.07 kcal/mol. | [81] |
| Lantrieuphpene B (8) | Binding free energy = −9.8 Kcal/mol with TYR-341, TYR-367, and ASP-376 residues of iNOS (inducible Nitric Oxide Synthase). | [80] |
| Lantrieuphpene C (9) | Molecular binding free energy = −9.3 Kcal/mol with TYR-341, TYR-367, and ASP-376 residues of iNOS. | [80] |
| β-Sitosterol (3) | Molecular binding free energies towards Bcl-2 and HPV16 E7 protein receptors: −8.11 and −7.276 kcal/mol, respectively | [170] |
Finally, in unusual applications, leaf, fruit, flower, root, and seed extracts of Lantana camara have been used to prepare several metal (Ag, Au, Fe, Cu, Zn, Pd, and Pt) [173] and metal oxide (ZnO, SrO, CuO, NiO, and Y2O3) nanoparticles with potential photocatalytic, electrochemical, anticancer, antiarthritic, and antibacterial properties, and other medical applications. The biomass and leaves of L. camara have also been used as a sustainable alternative for the removal of antibiotics and metals, such as Pb (II), Zn (II), and Mn (II) from contaminated rivers and waste waters [171,174,175,176].
4. Conclusions
This review, reporting on the recently published information on the phytochemistry and bioactivities of L. camara, clearly demonstrates that this species continues to be one of the most investigated plants due to the various traditional uses, the rich phytochemical contents of the extracts, and the wide variety of biological activities exhibited by total extracts, several isolated compounds, and the many semisynthetic derivatives.
Perspectives. In our opinion, among the various biological effects exhibited by specialized metabolites from L. camara (Table 8 and Table 9), the nematocidal and antiparasitic properties of several compounds and the antimalarial effects of leaf extracts against the chloroquine-sensitive strains 3D7 and D10, and the chloroquine-resistant strain W2, of Plasmodium falciparum deserve further investigations with in vivo and in the field tests. Given the various structural features of active compounds, there may also be an opportunity to conduct QSAR studies and to clarify the mechanism(s) of action, and to identify the molecular target(s) and the biological processes involved in the nematocidal and antiparasitic properties. Moreover, the interesting antidiabetic and anti-COVID-19 properties in vitro of leaf extracts and a few isolated compounds must be confirmed by additional in silico and in vivo studies. Computational strategies involving artificial intelligence and machine learning algorithms are expected to help in the full exploration of the biological space of natural molecules from L. camara, and to identify the unexplored human receptors and enzymes to which they can bind. Semisynthesis is an important technique to harness nature’s diversity for novel drugs. In this regard, semisynthetic efforts to prepare analogs of natural products isolated from L. camara to enhance their biological properties are limited and, therefore, they must be intensified.
Finally, preclinical and clinical research studies, which are missing so far, are necessary to evaluate the efficacy and safety of the products with the most promising medicinal properties.
Author Contributions
Conceptualization, J.R. and C.A.; methodology, N.E.-O.; software, L.N.C.; validation, J.R., N.E.-O. and L.N.C.; investigation, N.E-O.; writing—original draft preparation, C.A. and J.R.; writing—review and final editing, J.R., C.A., L.N.C. and G.V.; supervision, J.R. and G.V.; project administration, J.R. All authors have read and agreed to the published version of the manuscript.
Funding
This research was funded by the Universidad Técnica Particular de Loja (UTPL). Nº Grant: PROY_PROY_ARTIC_QU_2022_3652.
Data Availability Statement
All data are available on database reported.
Acknowledgments
We are grateful to the Universidad Técnica Particular de Loja (UTPL) for supporting open-access publication.
Conflicts of Interest
The authors declare no conflicts of interest.
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