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Open AccessReview

A Comprehensive Review on the Medicinal Plants from the Genus Asphodelus

1
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Professor Gama Pinto, 1649-003 Lisbon, Portugal
2
Department of Infectious Diseases, National Reference Laboratory of Antibiotic Resistances and Healthcare Associated Infections, National Institute of Health Doutor Ricardo Jorge, 1649-016 Lisbon, Portugal
*
Author to whom correspondence should be addressed.
Plants 2018, 7(1), 20; https://doi.org/10.3390/plants7010020
Received: 14 February 2018 / Revised: 5 March 2018 / Accepted: 10 March 2018 / Published: 13 March 2018
(This article belongs to the Special Issue Medicinal Plants and Natural Product Research)

Abstract

Plant-based systems continue to play an essential role in healthcare, and their use by different cultures has been extensively documented. Asphodelus L. (Asphodelaceae) is a genus of 18 species and of a total of 27 species, sub-species and varieties, distributed along the Mediterranean basin, and has been traditionally used for treating several diseases particularly associated with inflammatory and infectious skin disorders. The present study aimed to provide a general review of the available literature on ethnomedical, phytochemical, and biological data related to the genus Asphodelus as a potential source of new compounds with biological activity. Considering phytochemical studies, 1,8-dihydroxyanthracene derivatives, flavonoids, phenolic acids and triterpenoids were the main classes of compounds identified in roots, leaf and seeds which were correlated with their biological activities as anti-microbial, anti-fungal, anti-parasitic, cytotoxic, anti-inflammatory or antioxidant agents.
Keywords: anthracene derivatives; antimicrobial; Asphodelus; ethnomedicine; skin diseases anthracene derivatives; antimicrobial; Asphodelus; ethnomedicine; skin diseases

1. Introduction

The genus Asphodelus Linnaeus belongs to family Asphodelaceae Jussieu and is native to temperate Europe, the Mediterranean, Africa, the Middle East, and the Indian Subcontinent, and now naturalized in other places (New Zealand, Australia, Mexico, southwestern United States, etc.) [1]. It reaches its maximum diversity in the West of the Mediterranean, particularly in the Iberian Peninsula and in North-West Africa [2].
The family consists of three subfamilies: Asphodeloideae Burnett (including 13 genera), Hemerocallidoideae Lindley (including 19 genera) and Xanthorrhoeoideae M.W. Chase (with only one genus). This botanical family, now called Asphodelaceae, has had a complex history; its circumscription and placement in an order have varied widely. In the Cronquist system of 1981, members of the Asphodelaceae were placed in the order Liliales Perleb [3,4]. Cronquist had difficulty classifying the less obviously delineated lilioid monocots; consequently, he placed taxa from both the modern orders Asparagales Link and Liliales into a single family, Liliaceae Jussieu [5]. The decision to group three formerly separate families, Asphodelaceae, Hemerocallidaceae and Xanthorrhoeaceae, into a single family first occurred in 2003 as an option in the II Angiosperm Phylogeny Group (APG) classification for the orders and families of flowering plants. The name used for the broader family was then Xanthorrhoeaceae Dumortier [6], and the earlier references to this family were related only to subfamily Xanthorrhoeoideae. These changes were a consequence of improvements in molecular and morphological analysis and also a reflection of the increased emphasis on placing families within an appropriate order [5,7,8]. Later in 2009, the APG III classification dropped the option of keeping the three families separate, using only the expanded family, still under the name Xanthorrhoeaceae [7]. Anticipating a decision to conserve the name Asphodelaceae over Xanthorrhoeaceae, the APG IV classification of 2016 used Asphodelaceae as the name for the expanded family [9].
According to the World Checklist of Selected Plant Families (WCSP), there are 32 accepted names with more than 150 homo- and heterotypic synonyms for all species, subspecies and varieties of the genus Asphodelus L. namely, Asphodelus acaulis Desfontaines, Asphodelus aestivus Brotero, Asphodelus albus Miller (subsp. albus; subsp. carpetanus Z. Díaz & Valdés; subsp. delphinensis (Grenier & Godron) Z. Díaz & Valdés; subsp. occidentalis (Jordan) Z. Díaz & Valdés), Asphodelus ayardii Jahandiez & Maire, Asphodelus bakeri Breistroffer, Asphodelus bento-rainhae P. Silva (subsp. bento-rainhae; subsp. salmanticus Z. Díaz & Valdés), Asphodelus cerasiferus J. Gay, Asphodelus fistulosus Linnaeus (subsp. fistulosus; subsp. madeirensis Simon), Asphodelus gracilis Braun-Blanquet & Maire, Asphodelus lusitanicus Coutinho (var. lusitanicus; var. ovoideus (Merino) Z. Díaz & Valdés), Asphodelus macrocarpus Parlatore (subsp. macrocarpus; subsp. rubescens Z. Díaz & Valdés; var. arrondeaui (J. Lloyd) Z. Díaz & Valdés), Asphodelus ramosus Linnaeus (subsp. distalis Z. Díaz & Valdés; subsp. Ramosus); Asphodelus refractus Boissier, Asphodelus roseus Humbert & Maire, Asphodelus serotinus Wolley-Dod, Asphodelus tenuifolius Cavanilles, and Asphodelus viscidulus Boissier [1]. However, on the Missouri Botanical Garden database (Tropicos), more two accepted names (Asphodelus cerasifer Gay and Asphodelus microcarpus Salzmann & Viviani) were recorded [10]. Considering all the above-mentioned data 18 species and of a total of 27 species, sub-species and varieties must be considered for the Asphodelus genus.
Among all the species, A. aestivus and A. fistulosus are inscribed as “Least Concern” and A. bento-rainhae as “Vulnerable” species on International Union for the Conservation of Nature (IUCN) Red List of Threatened Species [11].
Botanical and systematic descriptions of this genus have been discussed by several taxonomists in various flora publications. The plants are hardy herbaceous perennials with narrow tufted radical leaves and an elongated stem bearing a spike of white or yellow flowers. Many have a small rhizomatous crown and thick, fleshy roots [12].
Different ethnomedical uses were described to Asphodelus species. Different parts of the plant including leaf, fruit, seed, flower, and root are used as traditional herbal medicines, alone or in mixtures to treat various ailments. In Iberian Peninsula, the following general medicinal uses were described: by rubbing with the cut tubers for the treatment of skin eczema, the ashes of the roots were used against the alopecia, and the leaves and stems decoction was used for the treatment of paralysis and the juice of fresh capsules for earache treatment [2]. Medicinal usage of the Asphodelus genus is also common in North African, and West and South Asian countries. Beside its medicinal uses, in Iberian Peninsula the alcohol obtained by fermentation of the tubers is extracted and used as fuel [2] and the local people of Iran, Turkey and Egypt use the root tubers of A. aestivus and A. microcarpus to produce a strong glue used by shoemakers and cobblers [2,13,14], and as yellow and brown dyes to dye the wool [2].
Root tubers are used as daily food, after being moistened and fried beforehand to eliminate the astringent compounds, and also the young stem, the leaves and the roasted seeds [2,15].
This study aims to present a comprehensive and updated review of documented ethnomedicinal and ethnopharmacological studies including chemical and biological data concerning Asphodelus genus.

2. Results and Discussion

Table 1 summarizes the ethnomedicinal data about the Asphodelus species including specific information on the plant parts as well as the geographical region where the plant is used. In Table 2 the principal chemical studies and identified compounds of the genus are presented. Table 3 and Table 4 summarize the principals of in vitro and in vivo biological activity assays on the total extracts and isolated compounds.

2.1. Ethnomedical Studies

Ethnomedicinal records showed that among the 18 species of the genus Asphodelus, only five species namely A. aestivus, A. fistulosus, A. microcarpus, A. ramosus, and A. tenuifolius have been documented for their traditional uses (Table 1). Most commonly, these species were used as anti-inflammatory and anti-infective agents. In particular, A. aestivus, A. fistulosus and A. microcarpus were reported to be used in dermatomucosal infections in various countries including Cyprus, Egypt, Libya, Palestine, and Spain [16,17,18,19,20]. A. microcarpus, A. ramosus and A. tenuifolius were generally indicted as anti-inflammatory agents specifically for the treatment of psoriasis, eczema, and rheumatism [21,22,23,24,25,26,27,28]. A. aestivus and A. tenuifolius are also used for ulcer treatment in Turkey, India, and Pakistan [26,27,28,29]. A. ramosus and A. tenuifolius have frequently been reported as diuretics among the inhabitants of Egypt, India, Pakistan, and Turkey [24,25,27,28,29,30,31].

2.2. Phytochemical Studies

Phytochemical studies as shown in Table 2, revealed the presence of different groups of compounds namely anthraquinones (either in the free or in the glycoside form), phenolic acids, flavonoids, and triterpenoids from A. acaulis, A. albus, A. aestivus, A. cerasiferus, A. fistulosus, A. microcarpus, A. ramosus, and A. tenuifolius.
Roots were mainly reported to have anthraquinone derivatives such as chrysophanol and aloe-emodin, triterpenoids, and naphthalene derivatives, while aerial parts mostly exhibited the presence of flavonoids such as luteolin, isovitexin and isoorientin, phenolic acids, and few anthraquinones. Fatty acids, namely myristic, palmitic, oleic, linoleic, and linolenic, were found in seeds and roots. Only A. aestivus and A. microcarpus were studied for essential oil characterization of flowers [22,35].

2.3. Reported Biological Activities

In vitro and in vivo biological studies concerning Asphodelus extracts are presented in Table 3 and those reported from identified pure compounds are shown in Table 4. In some of the studies, no data were obtained concerning the tested doses and/or inhibitory values.
The ethanol and aqueous extracts of A. aestivus leaf showed moderate anti-fungal activity against Aspergillus niger [33], and whole plant ethanol extracts exhibited weak activity against Staphylococcus aureus with minimum inhibitory concentration (MIC) = 42 mg/mL) and Klebsiella pneumoniae (MIC = 60 mg/mL) [67]. Both leaf and root extracts showed strong antioxidant activity [15,68]. The root extract also showed significant anti-inflammatory properties, specifically anti-ulcer activity which is one of the documented uses in Turkish traditional medicine [32]. Root and leaf extracts showed antitumoral activity against human cancer cells (lung and prostate) through DNA damage [68,69].
The aerial parts extracts of A. luteus showed strong anti-fungal activity against Trichophyton violaceum (MIC = 18 µg/mL), Microsporum canis (MIC = 25 µg/mL), and Trichophyton mentagrophytes (MIC = 30 µg/mL) supporting their traditional use in dermatomucosal infections [18] and weak activity against methicillin-resistant Staphylococcus aureus (MRSA) isolates (MIC = 1.25–2.5 mg/mL) [70]. Moreover, the methanol root extracts showed moderate antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl free radicals (DPPH; IC50 = 0.54 mg/mL) [61].
The aerial parts and root extracts of A. microcarpus showed moderate antioxidant [47,61] and moderate to weak cytotoxic activities [48,49,71]. The ethanol extracts of leaves demonstrated strong antiviral activity against Ebola virus (EBOV) in the concentration of 0.1–0.3 µg/mL [49]. Although the leaf seems to have stronger antimicrobial activity in comparison with roots, in general, both exhibit weak or no antimicrobial/antifungal activity [20,48,49,70]; however, compounds isolated from root tubers extracts showed potent activity such as asphodelin A against S. aureus (MIC = 16 µg/mL), Escherichia coli (MIC = 4 µg/mL), Pseudomonas aeruginosa (MIC = 8 µg/mL), Candida albicans (MIC = 64 µg/mL) [19] and Botrytis cinerea (MIC = 128 µg/mL) and asphodoside B against MRSA (IC50 = 1.62 μg/mL) [51]. Other isolated compounds from root extracts showed different biological activity; for instance, ramosin showed potent cytotoxic activity against leukemia cell lines [21], aestivin showed potent antimalarial activity against chloroquine-sensitive and resistant strains of Plasmodium falciparum with IC50 of 0.8–0.7 μg/mL [21] and 3,4-dihydroxy-methyl benzoate exhibited anti-parasitic activity against Leishmania donovani promastigotes with IC50 of 33.2 µg/mL [54].
Root extracts of A. ramosus showed positive in vivo anti-inflammatory activity, confirming the traditional uses of the plant in inflammatory disorders [23].
Several root, seed, aerial parts, fruit, and leaf extracts of A. tenuifolius showed strong anti-microbial/antifungal against K. pneumoniae, P. aeruginosa, E. coli, S. aureus, Proteus mirabilis, C. albicans, Aspergillus fumigatus, Vibrio cholerae, Salmonella typhi, and Candida glabrata, among other pathogens [24,27,30,34,72,73]. Of note, there is no ethnomedical report of antimicrobial use of A. tenuifolius.
The whole plant extract showed in vivo hypotensive and diuretic activity in normotensive rats [74]. The root extract of this species showed anti-oxidant activity (DPPH test, IC50 = 2.006 µg/mL) [25] and asphorodin, a compound isolated from the whole plant extract, exhibit a potent inhibition of lipoxygenase enzyme, (IC50 = 18.1 µM) [26], which may have an important role as an anti-inflammatory agent. The biological properties of A. tenuifolius extracts prove their ethnomedical use mostly as anti-inflammatory or diuretic [24,25,26,27,28,30,31,34].

3. Materials and Methods

Ethnobotanical data was collected by our team in Portugal and relevant literature was reviewed until December 2017, by probing scientific databases (PubMed, Scopus, Google Scholar, b-on, Web of knowledge) and other web sources such as records from WCSP, IUCN, APG and the Missouri Botanical Garden database. Various keywords were used during the bibliographic research including: ASPHODELUS SPECIES; TRADITIONAL USES; ETHNOMEDICINAL EVIDENCE; BIOLOGICAL ACTIVITIES; ISOLATED MOLECULES; PHYTOCHEMISTRY. Information was gathered and summarized in table form where appropriate.

4. Conclusions

In conclusion, among the 18 species of the genus Asphodelus, only 30 percent of the species namely A. aestivus, A. fistulosus, A. microcarpus, A. ramosus, and A. tenuifolius have been documented for their traditional uses. In phytochemical studies 50 percent of the species (A. acaulis, A. aestivus, A. albus, A. cerasifer, A. fistulosus, A. macrocarpus, A. microcarpus, A. ramosus, A. tenuifolius) have been evaluated for their constituents however there is no documented data related to traditional uses of A. acaulis, A. albus and A. cerasiferus.
All the species with ethnomedical documented data were submitted to biological activity tests, showing a total or partial correlation with their traditional use as anti-microbial, anti-fungal, anti-parasitic, cytotoxic, anti-inflammatory, or antioxidant agents.
Root tubers plant part were mainly reported to have anthraquinone derivatives, triterpenoids, and naphthalene derivatives, while aerial parts mostly exhibited the presence of flavonoids, phenolic acids, and few anthraquinones.
Considering the previous phytochemical studies, 1,8 dihydroxyanthracene derivatives (e.g., aloe-emodin and chrysophanol) were the most common reported anthraquinones of A. aestivus, A. luteus and A. microcarpus extracts which could be responsible for the reported antimicrobial/fungal activities [78,80]. Aloe-emodin as a potent cytotoxic compound might be related to the reported anti-tumoral activity of A. aestivus [68,78].
Flavonoids namely luteolin and apigenin derivatives were frequently reported from the aerial parts of all studied Aphodelus species, which according to their known antioxidant and anti-inflammatory properties [81,82], could be correlated to their traditional uses in inflammatory diseases in agreement with the reported biological studies. Phenolic acids, namely caffeic acid and chlorogenic acid reported from aerial parts and root tubers might be responsible for the general antioxidant activity presented in the biological studies.
Phytosterols (e.g., fucosterol, β-sitosterol, and stigmasterol) and β-amyrin were the most common found triterpenoids from roots and seeds. According to the literature, β-amyrin possess antibacterial/antifungal properties [83] which complement the reported biological activities of A. tenuifolius.
The present study allowed the importance and potential of the genus Asphodelus as a source of new compounds to be ascertained, with biological activity and new herbal products based on Asphodelus genus used in traditional medicine being ascertained, as well as its quality, mode of action, and safety of use. It should be pointed out that, to the best of our knowledge, the latter aspect (the safety of Asphodelus species) has not yet been the object of in-depth studies.

Acknowledgments

The authors wish to thank the Fundação para a Ciência e Tecnologia (FCT) for financial support of iMed.ULisboa project (UID/DTP/04138/2013) as well as a doctoral fellowship granted to the first author (SFRH/BD/125310/2016). This work was supported by the National Research Foundation (FCT), in Portugal, having no role in the data collection and analysis, interpretation of the findings, preparation of the manuscript, or the decision to submit the manuscript for publication. None of the authors has a conflict of interest.

Author Contributions

Maryam Malmir and Olga Silva did the literature review and wrote the first draft of the manuscript; Beatriz Silva-Lima and Manuela Caniça gave scientific involvement and evaluated critically the literature review; Rita Serrano was associated with the edition of the paper.

Conflicts of Interest

The authors declare no conflict of interest.

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Table 1. Ethnomedicinal uses of the Asphodelus species.
Table 1. Ethnomedicinal uses of the Asphodelus species.
SpeciesPart UsedCountryTraditional Uses/ApplicationReferences
A. aestivusL, RTurkeyPeptic ulcers[32]
RTurkeyHaemorrhoids, burns, wounds and nephritis[33]
NICyprus, SpainSkin diseases[16]
A. fistulosusNIEgypt, LibyaFungal infections[17]
A. luteus *WPPalestineDermatomucosal infections[18]
A. microcarpusFR, L, REgyptEar-ache, withering and paralysis[13,14]
RPalestineDermatomucosal infections[18]
REgyptEctodermal parasites, jaundice, microbial infections and psoriasis[19,20,21]
NIAlgeriaEar-ache, eczema, colds and rheumatism[22]
A. ramosusRNorth-AfricaInflammatory disorders[23]
NITurkeyAnti-tumoral, diuretic and emmenagogue[29]
A. tenuifoliusLIndiaDiuretic, inflammatory disorders and ulcers[24]
L, SEEgyptDiuretic[30]
R, SEIndiaAntipyretic, diuretic, colds and hemorrhoids, inflammatory disorders, rheumatic pain, ulcers and wounds[25,27]
SEPakistanulcers and inflammatory disorders[26]
WPIndiaDiuretic, inflammatory disorders, bite of bees and wasps, ulcers[28,34]
NIPakistanDiuretic[31]
SE: Seed; L: Leaf; WP: Whole plant; FR: Fruit; R: Root; NI: Not indicated, * Asphodelus luteus L.—synonym of Asphodeline lutea was formerly included in the family Asphodelaceae.
Table 2. Identified compounds reported from Asphodelus genus.
Table 2. Identified compounds reported from Asphodelus genus.
SpeciesPart UsedClassName of CompoundsReferences
A. acaulisLFlavonoidsLuteolin; apigenin[36]
RAnthraquinonesChrysophanol; asphodelin; 10,7′-bichrysophanol[37]
A. aestivusFLn-alkenesHexadecanoic acid (35.6%), pentacosane (17.4%), tricosane (13.4%), heptacosane (8.4%), heneicosane (4.5%), phytol (4.5%), tetracosane (3%), hexacosane (2%), hexahydrofarnesyl acetone (1.7%), tetradecanoic acid (1.4%), docosane (1.3%), nonadecane (1%)[35]
LAmino acidsAdenosine; tryptophan; phenylalanine[38]
AnthraquinonesAloe-emodin; aloe-emodin acetate; chyrosphanol 1-O-gentiobioside
FlavonoidsIsovitexin; isoorientin; isoorientin 4′-O-β glucopyranoside; 6′′-O-(malonyl)-isoorientin; 6′′-O-[(S)-3-hydroxy-3-methylglutaroyl]-isoorientin
Phenolic acidChlorogenic acid
SEFatty acidsButyric acid; nervoic acid[39]
A. albusLAnthraquinonesAloe-emodin; chrysophanol[36,40]
FlavonoidLuteolin[36]
RAnthraquinonesChrysophanol; asphodelin; 10,7′-bichrysophanol[37]
Fatty acidsMyristic (5.3%); palmitic (18.5%); stearic (2.1%); oleic (13.5%); linoleic (44.1%); linolenic (9.9%); arachidic (2.7%); behenic (1.2%); lignoceric (2.1%) acids[41]
Triterpenoidsβ-sitosterol; β-amyrin; campesterol; stigmasterol; fucosterol
A. albus var. delphinensisRAnthraquinonesAsphodeline; microcorpine; aloe-emodine; chrysophanole[42]
A. cerasiferLAnthraquinonesAloe-emodin[36]
FlavonoidsIsoorientin; luteolin; luteolin 7-glucoside[36,43]
RAnthraquinonesAsphodeline; microcorpine; aloe-emodine; chrysophanole[41]
* A. delphinensisLFlavonoidsIsoorientin; luteolin; luteolin 7-glucoside[43]
A. fistulosusAPAnthraquinonesAsphodelin; asphodelin 10′-anthrone; aloesaponarin II; aloe-emodin; chrysophanol; desoxyerythrolaccin[17]
FlavonoidsChrysoeriol; luteolin
LAnthraquinonesDianhydrorugulosin; aloe-emodin; chrysophanol; 1,8 hydroxy-dianthraquinone[44]
RAnthraquinonesChrysophanol; asphodelin; 10,7′-Bichrysophanol[37]
SEAnthraquinonesDianhydrorugulosin; aloe-emodin; chrysophanol; 1,8 hydroxy-dianthraquinone[44]
CarbohydratesSucrose; raffinose; stachyose[45]
Fatty acidsMyristic (0.5%); palmitic (5.7%); stearic (3.6%); oleic (33.1%); linoleic (54.9%)[45,46]
Triterpenoidsβ-sitosterol; β-amyrin[45]
** A. luteusLAnthraquinonesAloe-emodin[36]
*** A. mauritii SennenLAnthraquinonesAloe-emodin; chrysophanol[36]
FlavonoidsLuteolin
A. microcarpusFLTerpenoidsGermacrene D (78.3%); germacrene B (3.9%); a-elemene (3.8%); caryophyllene (3.3%)[22]
FlavonoidsLuteolin; luteolin-6-C-glucoside; luteolin-O-hexoside; luteolin-7-O-glucoside; luteolin-O-acetylglucoside; luteolin-O-deoxyhesosylhexoside; methyl-luteolin, naringenin; apigenin[47]
Phenolic acids3-O caffeoylquinic acid; 5-O caffeoylquinic acid
LAnthraquinoneChrysophanol, 10 (chrysophanol-7-yl)-10-Hydroxychrysophanol-9-antrone, asphodoside C, Dianhydrorugulosin; aloe-emodin[44,48]
FlavonoidsLuteolin-6-C-glucoside; luteolin-6-c-acetilglucoside; luteolin-C-glucoside; luteolin, isoorientin[43,49]
Phenolic acids5-O caffeoylquinic acid; cichoric acid; cumaril exosa malic acid[49]
RAnthraquinonesDianhydrorugulosin; aloe-emodin; chrysophanol; asphodelin; microcarpin, 8 methoxychrysophanol; emodin; 10-(chrysophanol-7′-yl)-10-hydroxychrysophanol-9-anthrone; aloesaponol-III-8-methyl ether; ramosin; aestivin, asphodosides A-E, chrysophanol dianthraquinone; 5,5′-bichrysophanol; chrysophanol-8-mono-β-d-glucoside; Methyl-1,4,5-trihydroxy-7-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate; 6 methoxychrysophanol[21,44,50,51,52,53,54]
ArylcoumarinsAsphodelin A 4′-O-d-glucoside; asphodelin A[19]
CarbohydratesRaffinose; sucrose; glucose; fructose[55]
Fatty acidsPalmitic; stearic; oleic; linoleic; linolenic; arachidic; behenic; lignoceric; myristic acids[55,56]
Naphthalene derivatives2-acetyl-1,8-dimethoxy-3 methylnaphthalene; 1,6-dimethoxy-3-methyl-2-naphthoic acid[21]
Mucilage Composed of glucose; galactose; arabinose[55]
Triterpenoidsβ-sitosterol-β-d-glucoside, fucosterol[13,55]
SEAnthraquinonesAloe-emodin; chrysophanol; chrysophanol-8-mono-β-d-glucoside[44]
Carbohydrates Sucrose; raffinose; stachyose; melibiose[45]
Fatty acidsMyristic; palmitic; stearic; oleic; linoleic acids
Triterpenoidsβ-sitosterol; β-amyrin
A. ramosusFLFlavonoidsLuteolin[57]
Phenolic acidsCaffeic acid; chlorogenic acid; p-hydroxy-benzoic acids
LFlavonoidsLuteolin; 7-O-glucosyl luteolin; 7-O-glucosyl apigenin; isoorientin; isoswertiajaponin (7-methyl orientin); isocytisoside (4′-methyl vitexin)[29]
RAnthraquinoneRamosin; (−)-10′-C-[β-d-xylopyranosyl]-; (−)-10′-C-[β-d-glucopyranosyl-(1-4)-β-d-glucopyranosyl]-1,1′,8,8,10,10′-hexa hydroxy -3,3′-dimethyl-10,7′ bianthracene-9,9′-dione; 10′-deoxy-10-epi-ramosin; 10-(chrysophanol-7′-yl)-10-hydroxychrysophanol-9-anthrone; 7′-(Chrysophanol-4-yl)-chrysophanol-10′anthrone10′-C-α-rhamnopyranosyl; -C-β-xylopyranosyl; -C-β-antiaropyranosyl; -C-α-arabinopyranosyl; -C-β-quinovoopyranosyl[58,59,60]
WPFlavonoidsNaringin, quercetin, kaemferol[61]
Phenolic acidsGallic acid, chlorogenic acid, vanilic acid, cafeic acid
A. tenuifoliusAPFlavonoidsLuteolin; luteolin-7-O-β-d-glycopyranoside; apigenin, chrysoeriol[30]
RNaphthalene derivatives1,8-dimethylnaphthalene; 2-acetyl-8-methoxy-3-methyl-1-naphthol; 2-acetyl-1,8-dimethoxy-3-methylnaphthalene[62]
Triterpenoidsβ-sitosterol; stigmasterol
SEEster1-O-17methylstearylmyoinositol[63]
Fatty acidsMyristic (3.96%); palmitic (13.84%); oleic (15.60%); linoleic (62.62%); linolenic (2.60%)[64,65]
WPAmino acidsCrystine; serine; glycine; proline; alanine, glycin; serine; alanine and valine in the form of protein[66]
Carbohydratesd-glucose; lactose; d-glucuronic acid; d-arabinose; d-fructose, d-ribose
Chromone2-hentriacontyl-5,7-dihydroxy-8-methyl-4H-1-benzopyran-4-one[31]
TriterpenoidsAsphorodin; asphorin A; asphorin B; β-sitosterol; β-amyrin[26,28,31]
AP: Aerial Part; FL: Flower; FR: Fruit; L: Leaf; R: Root; SE: Seed; WP: Whole plant; NI: Not indicated; * The accepted name is Asphodelus albus subsp. delphinensis (Gren. & Godr.). ** Asphodelus luteus L.—synonym of Asphodeline lutea was formerly included in the family Asphodelaceae. *** The accepted name is Asphodelus macrocarpus subsp. rubescens.
Table 3. In vitro and in vivo biological studies reported from the Asphodelus genus.
Table 3. In vitro and in vivo biological studies reported from the Asphodelus genus.
SpeciesPartExtractTest/AssayResultReference
A. aestivusLAqueous, EthanolIn vitro anti-fungal activity (A. niger)—Agar well diffusion method (zone of inhibition in cm−1)Ethanol extract (0.25 and 0.5 mg/mL) showed higher activity than aqueous extract (0.25 and 0.5 mg/mL) and similar activity for concentrations of 1 mg/mL.
Both extracts were less active than Fluconazole (100 µ/mL)
[33]
In vitro antioxidant activity—β-carotene bleaching effect, metal chelating, total antioxidant activity, DPPH, ABTS, superoxide radical scavenging activity, hydroxyl radical scavenging activity, DMPD, nitric oxide scavenging activityAqueous extract presented higher activity in metal chelating and radical scavenging assays (DPPH, IC50 aqueous = 4.58 mg/mL and IC50 methanol = 9.54 mg/mL, superoxide, hydroxyl, DMPD)
Ethanol extract presented higher activity in β-carotene bleaching effect and total antioxidant activity
Aqueous and ethanolic extracts presented similar radical scavenging activity in ABTS and NO assays. Both extracts presented significantly inferior results when compared to reference substances
A. aestivusLAcetone, MethanolIn vitro antioxidant activity—β-carotene, reducing power assay, DPPH, ABTS, inhibition of linoleic acid peroxidation, superoxide radical scavenging assaysReducing power and total antioxidant activity were higher in acetone extract; free radical and superoxide radical scavenging activity were higher in methanol extract (DPPH, IC50 methanol = 0.16 mg/mL and IC50 acetone = 0.50 mg/mL)
Acetone extract presented higher activity in Reducing power and total antioxidant activity (inhibition of linoleic acid peroxidation)
Methanol extract presented higher activity in superoxide radical scavenging and free radical scavenging activity (β-carotene, ABTS and DPPH, IC50 methanol =0.16 mg/mL, IC50acetone = 0.50 mg/mL)
[15]
A. aestivusL, RDichloromethane n-HexaneIn vitro cytotoxic activity—MTT assay against human lung cell cancer (A549) and prostate cell cancer (PC3)Root:
Dichloromethane: A549 (IC50 = 16 µg/mL); PC3 (IC50 = 19 µg/mL)
n-Hexane: PC3 (IC50 = 80 µg/mL)
Leaves:
Dichloromethane: A549 (IC50 = 90 µg/mL)
[69]
A. aestivusRAqueous (decoction)In vivo anti-inflammatory—Ethanol induced gastric ulcer model in ratsDecoction gave significant protection against the lesions[32]
A. aestivusRAqueous (infusion and decoction) Diethyl ether, Ethyl acetate, MethanolIn vitro antioxidant activity—DPPH assayDiethyl ether (IC50 = 22.46 µg/mL) have a higher scavenging activity than Ethyl acetate (IC50 = 188.90 µg/mL), both have lower activity than reference substance, rutin (7.77 µg/mL). Methanol and aqueous extract had no scavenging activity[68]
In vitro cytotoxic & apoptotic activity—MCF-7 breast cancer cells-trypan blue exclusion assay, comet assay, Hoechst 33,258, propidium iodide double stainingMethanol and aqueous extracts exhibited strong cytotoxic activities. All extracts showed significant DNA damaging and apoptotic activities.
A. aestivusSEPetroleum etherIn vitro antimicrobial/fungal activity—broth microdilution methodActive against S. aureus (MIC = 512 µg/mL), Enteroococcus faecalis (MIC = 512 µg/mL), K. pneumoniae (MIC = 512 µg/mL) and C. albicans (MIC = 512 µg/mL)
Not active against Bacillus cereus, Staphylococcus epidermidis, E. coli, P. aeruginosa, S. typhimurium, Salmonella enterica, Candida krusei and Candida parapsilosis
[39]
A. aestivusWPn-Butanol, EthanolIn vitro anti-microbial/fungal activity—well and disk diffusion methodActive against S. aureus (MIC: 42 mg/mL), K. pneumoniae (MIC: 60 mg/mL), E. coli (MIC: 90 mg/mL), C. albicans (MIC: 90 mg/mL)[67]
A. aestivusWPAqueousIn vitro antioxidant activity—DPPH assayInhibition % = 62.5[75]
A. fistulosus var. tenuifoliusNINIIn vitro anti-microbial/fungal activityPositive to S. aureus and no activity against E. coli, Proteus vulgaris, Salmonella sp., P. aeruginosa, C. albicans[76]
A. luteus *APAqueousIn vitro anti-fungal activity—Agar dilution methodActivity against T. violaceum (MIC = 18 µg/mL), M. canis (MIC = 25 µg/mL) and T. mentagrophytes (MIC = 30 µg/mL)[18]
A. luteus *AP
R
Methanol, Petroleum EtherIn vitro anti-microbial activity—agar diffusion test; tetrazolium microplate assay (MIC)Against MRSA isolates
Methanol extract:
MIC (AP) = 1.25–2.5 mg/mL
MIC (R) = 0.65–1.25 mg/mL
Petroleum ether extract:
Root extract had higher activity than aerial part extract
[70]
A. luteus *RMethanolIn vitro antioxidant activity—DPPH assayIC50 (methnol)= 0.54 mg/mL, IC50 (reference, BHT) = 0.017 mg/mL[61]
A. microcarpusAPAqueousIn vitro anti-fungal activity—Agar dilution methodWeak activity against T. violaceum (MIC = 25 µg/mL) and no activity against M. canis and T. mentagrophytes[18]
A. microcarpusAP
R
MethanolIn vitro anti-microbial activity—agar diffusion test; tetrazolium microplate assay (MIC)Against MRSA isolates
Methanol extract:
MIC (AP) = 1.25–5 mg/mL
MIC (R) = 1.25–2.5 mg/mL
[70]
A. microcarpusFL
L
R
Aqueous, Ethanol, MethanolIn vitro antimelanogenic activity—tyrosinase inhibition (mushroom tyrosinase assay and mouse melanoma cells viability), kojic acid as positive controlAntimelanogenic activity
Ethanol extract (F) had the highest tyrosinase inhibition activity in mushroom assay and melanoma cell assay
[47]
In vitro antioxidant activity—DPPH and ABTS (reference—Trolox)Antioxidant activity
DPPH (best activity)
Ethanol extract (F): IC50 = 28.4 µg/mL
Ethanol extract (L): IC50 = 55.9 µg/mL
Trolox: IC50 = 3.2 µg/mL
A. microcarpusLEthanolIn vitro antimicrobial/fungal activity—micro broth dilution methodActive against Bacillus clausii (MIC = 250 µg/mL), S. aureus (MIC = 250 µg/mL), Staphylococcus haemolyticus (MIC = 250 µg/mL) and E. coli (MIC = 500 µg/mL).
No activity against Streptococcus spp. and yeasts
[49]
In vitro antiviral activity (IFN-β induction)—luciferase reporter gene assayAntiviral activity
Active against EBOV in concentration of 0.1–3 µg/mL
In vitro cytotoxicity-Cell viability of A549 cells, positive control (camptothecin)Cytotoxicity
IC50 (extract) > 100 µg/mL
IC50 (camptothecin) = 0.54 µg/mL
A. microcarpusLMethanolIn vitro antimicrobial/fungal—two-fold serial dilution techniqueAntimicrobial activity
Active against S. aureus (MIC = 78 µg/mL), Bacillus subtilis (MIC = 156 µg/mL), Salmonella spp. (MIC = 313 µg/mL), E. coli (MIC = 125 µg/mL), Aspergillus flavus (MIC = 125 µg/mL), C. albicans (MIC = 78 µg/mL)
[48]
In vitro antiviral activity—CPE inhibition assay against HSV-1 and HAV-10Antiviral activity
Moderate activity against Hepatitis A virus (HAV-10) and no activity against Herpes Simplex Virus (HSV-1)
In vitro cytotoxicity—viability assay against human tumor cell lines of the lung (A-549), colon (HCT-116), breast (MCF-7) and prostate (PC3). Cisplatin as standardCytotoxicity
Highest activity against human lung carcinoma cells (A-549), IC50 = 29.3 µg/mL
A. microcarpusRMethnolIn vitro antioxidant activity—DPPH assayIC50 (Methnol) = 0.30 mg/mL, IC50 (reference, BHT) = 0.017 mg/mL[61]
A. microcarpusRMethanolIn vitro anti-microbial—Disk diffusion assayNo activity against S. aureus, B. subtilis and E. coli[20]
A. microcarpusWPAqueous, EthanolIn vitro antioxidant activity—DPPH assayEthanol extract (100 µg/mL) with moderate activity (inhibition percentage—60.3%) higher than aqueous extract (100 µg/mL, inhibition percentage—49.5%)[71]
In vitro cytotoxic activity—Trypan blue technique for Ehrlich Ascites Carcinoma Cells (EACC)Weak anti-cancer activity of both extracts
A. ramosusRAqueous, Chloroform, Ethanol, MethanolIn vivo anti-inflammatory—Arachidonic acid test (mouse ear oedema)
Carrageenan test (sub-plantar oedema)
Arachidonic acid test: Positive activity from chloroform and ethanol extracts
Carrageenan test: No activity was observed
[23]
A. ramosusWPAqueous, Methanol, Methanol 50%In vitro antioxidant activity—DPPH assay at 35 °C and 65 °CAqueous extract at 65 °C had the highest inhibition percentage[77]
A. tenuifoliusAPButanol, Ethyl acetate, Methylene-chlorideIn vitro anti-microbial/fungal activity—Disc diffusion methodAll extracts showed antimicrobial activity, the methylene-chloride as the most active against S. aureus (MIC = 1.6 mg/mL), E. faecalis (MIC = 1.0 mg/mL), E. coli (MIC = 1.8 mg/mL) and P. aeruginosa (MIC = 0.15 mg/mL)
All extracts showed antifungal activity against C. albicans, C. parapsilosis, C. glabrata, C. krusei.
[30]
A. tenuifoliusFRAcetone, Aqueous, Benzene, Chloroform, Methanol, Petroleum etherIn vitro anti-microbial/fungal activity—Kirk-bauer disc diffusion methodSignificant activity against S. aureus (acetone, MIC = 125 µg/mL); S. epidermidis (acetone, MIC = 125 µg/mL; chloroform and methanol, MIC = 250 µg/mL); P. vulgaris (methanol, MIC = 250 µg/mL; chloroform, MIC = 125 µg/mL), P. mirabilis (benzene, MIC = 125 µg/mL; acetone and methanol, MIC = 250 µg/mL; chloroform, MIC = 500 µg/mL) E. coli (acetone, chloroform and methanol, MIC = 125 µg/mL); K. pneumoniae (acetone and methanol, MIC = 125 µg/mL; chloroform and benzene, MIC = 500 µg/mL); P. aeruginosa (acetone, MIC = 250 µg/mL; chloroform, MIC = 500 µg/mL); C. albicans (acetone, MIC = 125 µg/mL); A. fumigatus (benzene and chloroform, MIC = 250 µg/mL; acetone, MIC = 500 µg/mL)[27]
A. tenuifoliusLAcetone, MethanolIn vitro anti-microbial/fungal activity—Agar disc diffusion methodMethanol extract positive against S. aureus, B. cereus, Citrobacter freundii, Candida tropicalis and acetone extract was positive against K. pneumoniae, C. tropicalis and Cryptococcus luteolus[24]
A. tenuifoliusRMethanolIn vitro antioxidant activity—DPPH, ABTS+, NO, OH, O2, ONOO assays, Oxidative DNA damagePositive activity, DPPH (IC50 = 2.006 µg/mL), ABTS·+ (IC50 = 156.94 µg/mL), NO (nd), OH (IC50 = 50.13 µg/mL), O2 (IC50 = 425.92 µg/mL) and ONOO- (IC50 = 3.390 µg/mL), oxidative DNA damage: 1.85 µg/mL of extract prevented DNA damage.[25]
A. tenuifoliusRBenzene, Chloroform, Ethyl acetate, Methanol, Petroleum etherIn vitro anti-microbial/fungal activity—Disc diffusion methodAll extracts were active against B. subtilis, P. vulgaris, P. aeruginosa, Trichophyton rubrum, E. coli, K. pneumoniae, Shigella sonnei, S. aureus, C. albicans, A. niger and A. flavus[72]
A. tenuifoliusSEAqueous, Ethanol, Methanol, Petroleum etherIn vitro anti-microbial/fungal activity—modified Kirby Bauer disc diffusion methodPetroleum ether: no antibacterial activity
Ethanol: activity against P. aeruginosa, Vibrio cholerae and S. aureus (MIC = 16 µg/mL); P. mirabilis, S. typhi, Shigella flexneri and Serratia marcescens (MIC = 32 µg/mL).
Methanol: activity against S. aureus (MIC = 16 µg/mL); V. cholerae, P. aeruginosa, S. typhi, S. flexneri and S. marcescens (MIC = 16 µg/mL)
Aqueous: activity against V. cholerae, S. aureus, S. typhi and S. flexneri (MIC = 32 µg/mL); P. aeruginosa and P. mirabilis (MIC = 16 µg/mL).
No antifungal activity against C. albicans and A. niger
[34]
A. tenuifoliusWPMethanolIn vitro antimicrobial/fungal activity—disk diffusion method
In vitro anti-parasitic activity—trophozoites growth inhibition assay
Good activity against E. coli and moderate activity against S. aureus, S. typhi, K. pneumoniae, P. aeruginosa, C. albicans and A. niger
Active against Giardia lamblia (IC50 = 219.82 µg/mL) and Entamoeba histolytica (IC50 = 344.62 µg/mL)
[73]
A. tenuifoliusWPAqueous In vivo hypotensive activity—blood pressure (BP) measure after parenteral administration of aqueous extracts in rats. Acetylcholine and verapamil as positive controls in co administration with atropineHypotensive activity
The extract decreased blood pressure in normotensive rats (35.2% decrease with 30 mg/Kg), similar to Verapamil. The response was independent from atropine effect
[74]
In vivo diuretic activity—measure of rat urine output and urinary electrolytes. After 6 hr administration. Saline solution and furosemide as controlsDiuretic activity
Significant increase in urinary volume and electrolytes excretion with 300 and 500 mg/Kg
AP: Aerial Part; FL: Flower; FR: Fruit; L: Leaf; R: Root; SE: Seed; WP: Whole plant; NI: Not indicated; * Asphodelus luteus L.—synonym of Asphodeline lutea was formerly included in the family Asphodelaceae. ABTS+: 2,2′-azinobis-(3-ethylbenzothiazole-6-sulphonate) radical cation, DMPD: N,N-dimethyl-p-phenylenediamine dihydrochloride, DPPH: 2,2-diphenyl-1-picrylhydrazyl radical, NO: nitric oxide radical, O2.–: superoxide anion radical , ·OH: hydroxyl radical, ONOO-: Peroxynitrite radicals, EBOV: Ebola virus.
Table 4. In vitro and in vivo biological studies reported from pure compounds isolated from Asphodelus genus.
Table 4. In vitro and in vivo biological studies reported from pure compounds isolated from Asphodelus genus.
SpeciesPure CompoundsTest/AssayResultReference
A. microcarpusAsphodelin A 4′-O-β-d-glucoside (1), Asphodelin A (2)In vitro antimicrobial/fungal activity—micro dilution assayS. aureus (MIC1 = 128 µg/mL, MIC2 = 16 µg/mL), E. coli (MIC1 = 128 µg/mL, MIC2 = 4 µg/mL), P. aeruginosa (MIC1 = 256 µg/mL, MIC2 = 8 µg/mL), C. albicans (MIC1 = 512 µg/mL, MIC2 = 64 µg/mL) and B. cinerea (MIC1 = 1024 µg/mL, MIC2 = 128 µg/mL[19]
3-methyl anthraline, chrysophanol, and aloe-emodinePsoriasisPositive (patent)[78,79]
1,6-dimethoxy-3-methyl-2-naphthoic acid (1), asphodelin (2), chrysophanol (3), 8 methoxychrysophanol (4), emodin (5), 2-acetyl-1,8-dimethoxy-3-methylnaphthalene (6), 10-(chrysophanol-7′-yl)-10-hydroxychrysophanol-9-anthrone (7), aloesaponol-III-8-methyl ether (8), ramosin (9), aestivin (10)In vitro anti-parasitic activityCompounds 3 and 4 showed moderate to weak against a culture of L. donovani promastigotes (IC50 = 14.3 and 35.1 μg/mL, respectively)[21]
In vitro cytotoxic activity-Human acute leukemia HL60 cells/human chronic leukemia 562 cellsCompounds 7 and 9 exhibited a potent cytotoxic activity against leukemia LH60 and K562 cell lines
In vitro antimalarial activity—chloroquine sensitive & resistant strains of Plasmodium falciparum (plasmodial LDH activity)Compound 10 showed potent antimalarial activities against both chloroquine-sensitive and resistant strains of P. falciparum (IC50 = 0.8–0.7 μg/mL) without showing any cytotoxicity to mammalian cells
In vitro anti-microbial/fungal activityCompound 4 exhibited moderate antifungal activity against Cryptococcus neoformans (IC50 = 15.0 μg/mL), compounds 5, 7 and 10 showed good to potent activity against methicillin resistant S. aureus (MRSA) (IC50 = 6.6, 9.4 μg/mL and 1.4 μg/mL respectively). Compounds 5, 8 and 9 displayed good activity against S. aureus (IC50 = 3.2, 7.3 and 8.5 μg/mL, respectively)
Methyl-1,4,5-trihydroxy-7-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate (1), (1R) 3,10-dimethoxy-5-methyl-1H-1,4 epoxybenzo[h]isochromene (2), 3,4-dihydroxy-methyl benzoate (3), 3,4-dihydroxybenzoic acid (4), 6 methoxychrysophanol (6)In vitro anti-parasitic activityCompound 3 showed activity against a culture of L. donovani promastigotes (IC50 = 33.2 µg/mL)[54]
In vitro anti-microbial/activityCompound 1 showed a potent activity against methicillin resistant S. aureus (MRSA) and S. aureus (IC50: 1.5 and 1.2 µg/mL, Respectively)
5 Compounds, Asphodosides A–EIn vitro anti-microbial activityCompounds 24 showed activity against methicillin resistant S. aureus (MRSA) (IC50: 1.62, 7.0 and 9.0 µg/mL, respectively). activity against S. aureus (non-MRSA), IC50 = 1.0, 3.4 and 2.2 µg/mL, respectively[51]
A. tenuifoliusAsphorodinIn vitro anti-inflammatory-inhibition of lipoxigenase enzymePotent inhibitory activity (IC50 = 18.1 µM), Reference: baicalein (22.6 µM)[26]
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