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Molecules 2015, 20(7), 13422-13495; https://doi.org/10.3390/molecules200713422

Review
Secondary Metabolites from Rubiaceae Species
Bioprospection and Biotechnology Laboratory, Technology and Innovation Coordenation, National Research Institute of Amazonia, Av. André Araújo, 2936, Petrópolis, Manaus, AM 69067-375, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Marcello Iriti
Received: 13 June 2015 / Accepted: 13 July 2015 / Published: 22 July 2015

Abstract

:
This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion.
Keywords:
Rubiaceae; Rubioideae; Cinchonoideae; Ixoroideae; iridoids; alkaloid; anthraquinones; triterpenes

1. Introduction

The Rubiaceae family is characterized by the production of bioactive metabolites with great pharmacological potential. These metabolites can be used as chemotaxonomic markers even for genera and subfamilies [1,2]. Usually, taxa are classified according to different botanical characteristics; classical taxonomic systems only consider the plant morphological characters, while modern systems correlate their various combinations, including the chemical composition. Studies correlating classical plant taxonomy to chemical data can be found as far back as 1699 [3].
Phytochemical compounds can be a useful tool for characterizing, describing and classifying plant species. The distribution of secondary metabolites in Rubiaceae follows patterns that may help characterize the botanical group (subfamily, tribe or genera). These patterns relative to chemotaxonomy are often used to establish the botanical origin [4].
In recent years, Rubiaceae species have been thoroughly studied from a phytochemical viewpoint. However, very few studies have used this knowledge as a tool in taxonomic studies. When conducting bioprospecting studies of a plant, all botanical and chemotaxonomic information is of great importance, since it increases the likelihood of finding bioactive compounds, which enables the discovery of new Nature-originated drugs [5]. Therefore, the present study aims to conduct a literature survey on phytochemical studies addressing species of Rubiaceae published from 1990 to 2014, and describe their secondary metabolites occurrence and distribution in the subfamilies, tribes and main genera of this family.

2. Taxonomic Classification of Rubiaceae

The Rubiaceae family has a cosmopolitan distribution, mostly concentrated in the tropics. Being one of the largest in the Magnoliopsida class, it ranks fourth in diversity of species among Angiosperms [4]. It includes approximately 637 genera and 13,000 species [5,6]. In Brazil, nearly 120 genera and 1400 species occur, representing one of the most important economic, ornamental and medicinal plant families in the Brazilian flora [7].
The Rubiaceae family taxonomic classification is complex and there are still some gaps which have to be filled. According to the classification of Robbrecht [8], the Rubiaceae family is divided into four subfamilies: Rubioideae, Cinchonoideae, Antirheoideae and Ixoroideae. However, more recent studies suggest this family to be divided into three subfamilies: Rubioideae, Cinchonoideae and Ixoroideae, as some authors do not recognize Antirheoideae as a subfamily, since molecular studies have shown it to be polyphyletic with no standardized occurrence of a chemical marker [9,10,11,12,13,14,15,16]. Due to the abundance of species, the subfamilies were divided into 43 tribes (an intermediate clade between genus and subfamily) [16], which are listed in Figure 1.
Due to the lack of studies that can complement the extant information on geographical distribution, morpho-anatomical characteristics and molecular data, there are still genera and species not allocated into any tribe [16]. The evaluation of the chemical profile of these species may indicate a more complete phylogenetic distribution, since the secondary metabolites are the results of adaptation and evolution of a specific taxon to environment [17]. Thus, the profile of secondary metabolites distribution can bring new information for the taxonomic classification of this family.
Figure 1. Subfamilies and tribes belonging to the Rubiaceae family [16].
Figure 1. Subfamilies and tribes belonging to the Rubiaceae family [16].
Molecules 20 13422 g001

3. Chemical and Biological Aspects of Rubiaceae

The Rubiaceae family presents a large diversity of substances such as iridoids, indole alkaloids, anthraquinones, terpenoids (diterpenes and triterpenes), flavonoids and other phenolic derivatives, with emphasis on production of bioactive alkaloids [2]. Alkaloids are secondary metabolites that can generate various drugs with important pharmacological effects and used to find out physiological responses and biochemical mechanisms of action [18].
The number of described products, the structural diversity and pharmacological activities reported for various species of Rubiaceae demonstrate this family to be a promising source of new bioactive substances, which may give rise to new products as active molecules or even drug prototypes. Many of these plants have widespread use in folk medicine and some showed anti-inflammatory, analgesic, antibacterial, mutagenic, antiviral, antioxidant, effect on vascular diseases as well as activity on the central nervous system [19].
In the Ixoroideae subfamily, the genus Coffea is one of the most economically important, mainly the species Coffea arabica, popularly known as coffee, which has caffeine as one of its principal chemical components. This substance acts as stimulant of the central nervous system, as well as vasoconstrictor, bronchodilator and diuretic, besides being one of the components of migraine drugs [18]. Genipa, the Brazilian jenipapo (Genipa americana) with antiangiogenic, anti-inflammatory and antioxidant activity [20,21,22] is another important genus from which genipin was isolated, a colorless iridoid, used by indigenous people to tattoo their skin, since it produces a black coloration when it reacts with skin proteins. Its fruits are used to make wines, liqueurs, jams, soft drinks, etc. [23].
In the Cinchonoideae subfamily, Cinchona species are the source of quinine, isolated in 1820 by Pelletier and Caventou [24], and which for about 200 years was the only active substance against malaria, and can be considered as responsible for the development of synthetic antimalarials [1,25]. More than 50 new substances were isolated from alkaloid-rich Uncaria species [19], as Uncaria tomentosa, known as “unha de gato”, is one of most used plants in Brazilian folk medicine. Studies have shown that alkaloids isolated from this plant have immunostimulant and antitumor activity [26,27]. Other groups of substances such as triterpenes and procyanidins presented anti-inflammatory activity [28,29].
Psychotria, belonging to the Rubioideae subfamily, are plants that produce substances with activity on the central nervous system, such as Psychotria viridis, popularly known as “ayahuasca” which means “soul wine”. P. viridis is used in religious ceremonies in association with Banisteriopsis caapi, a species from the Malpighiaceae family [30,31]. Their hallucinogenic effect is due to the synergy that occurs between the alkaloid N,N-dimethyltryptamine (DMT), present in the leaves of P. viridis, and β-carboline indole alkaloids (harmine, harmaline and tetrahydroharmine) present in the bark of B. caapi [32]. Cephaelis is another important genus, especially C. ipecacuanha, a plant traditionally used by the Brazilian population, an important source of emetine, an alkaloid with emetic, antihelminthic and expectorant effects [33,34]. In Brazil, species of Palicourea are considered responsible for about half of all cattle deaths brought about by natural poisoning [35]. Some selected isolated compounds from Rubiaceae species are shown in Table 1 and Figure 2.

4. Chemotaxonomic Considerations

Chemotaxonomic studies use chemical characteristics, particularly secondary metabolites from a group of organisms to determine their taxonomic classification [36]. This correlation between phytochemical compounds and morphological data becomes an important tool to determine plant classification, phylogeny and evolution [37,38,39].
The plant evolution process, from a morphological point of view, occured by the successive appearance of small weeds, larger herbs, shrubs and, finally, trees achieving the climax with primitive angiosperms. Then, the evolutionary polarity became inverted, woody plant being gradually replaced by herbaceous plants [40,41]. As explained by Gottlieb: “The most conspicuous evolutionary trend in the gross morphology of land plants concerns the successive appearance of small weeds, larger herbs, shrubs and, finally, trees. This trend had attained or even had passed its climax with the primitive angiosperms and within this division the evolutionary polarity became inverted, woody plants being gradually replaced by herbaceous plants.
Table 1. Some metabolites isolated from Rubiaceae.
Table 1. Some metabolites isolated from Rubiaceae.
GeneraClassSubstanceStructure *
CephaelisAlkaloidEmetineI
LactoneChelidonic acidII
AlkaloidCephalinIII
AlkaloidPsycotrinIV
CinchonaAlkaloidQuinineV
TriterpeneCincholic acidVI
TriterpeneQuinovic acidVII
AlkaloidQuinidineVIII
AlkaloidCinchonineIX
AlkaloidCinchonidineX
CoffeaMethyl xantineCaffeineXI
DiterpeneCafestolXII
AnthraquinoneGaliosinXIII
AnthraquinoneCopareolatinXIV
AnthraquinoneMunjistinXV
CorynantheAlkaloidYohimbineXVI
GaliumIridoideMacedonineXVII
GenipaMonoterpeneGenipinXVIII
HedyotisAnthraquinoneAlizarinXIX
LanderbergiaAlkaloidQuinidineVIII
AlkaloidCinchonineIX
AlkaloidCinchonidineX
MorindaAnthraquinoneAlizarinXIX
MussaendaTriterpeneArjunolic acidXX
OldenlandiaAnthraquinoneAlizarinXIX
PsychotriaAlkaloidPsycotrinIV
AlkaloidCephalinIII
RelbuniumAnthraquinonePurpurinXXI
RemijiaAlkaloidQuinidineVIII
AlkaloidCinchonineIX
AlkaloidCinchonidineX
RubiaAnthraquinonePurpurinXXI
AnthraquinoneAlizarinXIX
* shown in Figure 2.
Figure 2. Different classes of compounds isolated from Rubiaceae.
Figure 2. Different classes of compounds isolated from Rubiaceae.
Molecules 20 13422 g002
These successional phenomena are paralleled by micromolecular compositions. The ubiquitous flavonoids excepted, polyketides and terpenoids dominate the chemical compositions of bryophytes and pteridophytes. Shikimate-derived aromatics became numerically significant only in gymnosperms and attain predominance over other biosynthetic classes in primitive angiosperms. Concomitantly, here secondary metabolism reflects the trend from woody to herbaceous forms by inactivation of cinnamoyl/cinnamyl-derivatives through two phenomena: (i) extension of the shikimate pathway by reduction of cinnamyl alcohols to allylphenols and propenylphenols and (ii) gradual curtailment of the final steps of the shikimate pathway. The former alternative is most frequent in the primitive magnolialean block, where oxidative oligomerization of the precursors leads to neolignans. The first consequence of the latter alternative, the accumulation of phenylalanine and tyrosine, again very frequent in the magnolialean block, occurs also in the rosiflorean block. Oxidative elaboration of these amino acids leads to benzylisoquinolines. Further shortening of the shikimate pathway is restricted to the rosiflorean block. It leads to the accumulation of chorismic acid, the precursor of anthranilate- and of tryptophane-derived alkaloids, and of shikimic acid, the precursor of gallic acid- and ellagic acid-derived tannins. With gallic acid, the possibilities of diversifying the production of micromolecules through gradual curtailment of the shikimate pathway seem to be exhausted. In the most highly advanced, mostly sympetalous, angiosperms, shikimate-derived secondary metabolites play a relatively minor role. In these lineages, the full potential of acetate utilization leads to polyacetylenes, while mevalonate utilization leads to steroidal alkaloids, iridoids, alkaloids, sesquiterpene lactones, etc. In comparison with the polyketides and terpenoids of less advanced plant groups mentioned above, these compounds all show a high state of oxidation.” [40].
Regarding the distribution of the major secondary metabolites in Rubiaceae, indole alkaloids are indicated as the main chemical markers of this family [42,43,44,45,46]. Iridoids, anthraquinones, triterpene glycosides, flavonoids, lignoids, terpenes and phenols derivatives, were also reported [47]. Indole alkaloids occur just in families belonging to the Gentianales order (Loganiaceae, Rubiaceae, Apocynaceae and Naucleaceae), where one observes monoterpene indole alkaloids mainly [48]. The occurrence of indole alkaloids out of Gentianales order is quite rare and when found they are usually simple indole alkaloids.
A good correlation between the biosynthetic pathways and morphological aspects of the Ixoroideae, Cinchonoideae and Rubioideae subfamilies is obtained by evaluating chemical data, combined with the parameters cited by Robbrecht [8]. Each one of these subfamilies presents a different and typical profile of indole alkaloids, iridoids and anthraquinones which are considered as Rubiaceae chemotaxonomic markers [49]. Other studies based on chemotaxonomic data obtained by gas chromatography coupled to mass spectrometry show that the iridoid glycosides are present in several different species belonging to the Rubiaceae subfamilies [50,51,52]. Monoterpene indole alkaloids, especially which are derivatives of tryptamine and monoterpene (iridoid) secologanin are another predominant class in Rubiaceae. Quinoline alkaloids, which are products from the monoterpene indole and isoquinoline alkaloids rearrangement, yielding emetine-type alkaloids, are also characteristic of Rubiaceae, however, strychnine class alkaloids are not present in this family. Other alkaloid types are quite heterogeneous leading to a hard chemotaxonomic correlation [53].
Several studies have reported the use of chemical data to assist plant taxonomy [53]. Interest in this area increased due to the appearance of fast and accurate analytical techniques. However, there are still limitations on the application of chemical data in systematics. Even with a growing number of phytochemical studies, there are still many plants that remain without any chemical study.

5. Data Obtained Through the Bibliographic Survey

The present study sought to survey phytochemical studies of all species of Rubiaceae published in ScienceDirect and CAS SciFinder websites between 1990 and 2014. The data compiled in this review show the distribution of the studied species classified by their respective tribes and subfamilies as well as the isolated compounds and their chemical classes (Table 2).
Based on the obtained data, the main occurrence of iridoids, anthraquinones, triterpenes, indole alkaloids and alkaloids belonging to different chemical subclasses, was observed. The chemical profile, as expressed by the occurrence of major categories of secondary metabolites (alkaloids, anthraquinones and iridoids) showed to be quite different for each subfamily. Furthermore, the study of specific classes may contribute to chemotaxonomic correlations, since there are compounds with restricted distribution [54]. These same classes of substances served as a distribution pattern to create and modify plant classification systems as proposed by Dahlgren [54].
In Ixoroideae subfamily, the iridoids are found as chemotaxonomic markers, in Cinchonoideae the indole alkaloids predominate over other substances and in Rubioideae the anthraquinones are the major class of secondary metabolites (Figure 3). These global findings corroborate those found in the Brazilian Rubiaceae chemotaxonomic study by Bolzani [15].
Other studies also describe indole alkaloids as the class of substances of major occurrence in Cinchonoideae, especially in Guettardeae tribe [50,55]. Studies by Wijinsma and Verpoorte [56] and Bolzani et al. [15] describe the occurrence of standardized chemical markers: iridoids in Ixoroideae; indole alkaloids in Cinchonoideae and anthraquinones in Rubioideae. These data corroborate the one presented in this review.
Therefore, it was observed triterpenes widely distributed in all subfamilies, therefore a chemotaxonomic correlation cannot be established. The occurrence of a common pattern in secondary metabolism may suggest, strongly, taxons having a common ancestor. Thus, if there are morphological similarities, they can either be due to a common ancestry or convergent evolution [54]. Furthermore, the seco-iridoids are iridoids precursors and also participate in the biosynthesis of monoterpene indole alkaloids, so they may be involved in two distinct chemotaxonomic subdivisions [57,58]. Thus, different species may exhibit different chemical substance classes, but having the same precursor, which may indicates a phylogenetic relationship [59,60,61,62,63,64].
Table 2. Compounds isolated from Rubiaceae species, organized by subfamily and tribe.
Table 2. Compounds isolated from Rubiaceae species, organized by subfamily and tribe.
SubfamilyTribeSpeciesCompound (s)References
CinchonoideaeCHIChiococca albaTriterpene glycosides: chiococcasaponins I–V[65]
Cetoalcohols: 4-hydroxy-heptadecan-7-one; 5-hydroxy-octadecan-11-one
Phenylcoumarines: 5,7,4′-trimethoxy-4-phenylcoumarine
Lignans: exostemin; matairesinol; d-mannitol
[66]
Seco-iridoids: albosides I–III[67]
Nor-seco-pimarane: merilactone[68]
Triterpene: 3-β-hydroxyolean-12,15-dien-28-oic acid[69]
Triterpene glycosides: O-α-d-apiofuranosyl (1→3)-[α-d-apiofuranosyl (1→4)]-α-l-rhamnopyranosyl (1→2)-α-l-arabinopyranosyl 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12,15-dien-28-oate; 28-O-α-d-apiofuranosyl (1→3)-α-l-rhamnopyranosyl (1→2)-α-l-arabinopyranosyl 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12,15-dien-28-oate[70]
Ent-kaurane diterpenes: 1-hydroxy-18-nor-kaur-4,16-dien-3-one; 15-hydroxy-kaur-16-en-3-one; kaur-16-en-19-ol; kaurenoic acid; merilactone; ribenone[71]
Ent-kaurane: ent-17-hydroxy-16α-kauran-3-one[72]
Chiococca braquiataFlavonoids: 4′-methoxykaempferol-7-(acetyloxy)-3,5-O-α-l-rhamnoside; apigenin; 7-O-methoxyquercetrin; quercetrin
Triterpenes: α-amirin; β-amirin; ursolic acid; oleanolic acid
[73]
Coutarea hexandraCoumarins: 5-O-β-d-glucopyranosyl-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one; 5-O-β-d-galactopyranosyl-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one
Cucurbitacins: 23,24-dihydrocucurbitacin F; 23,24-dihydro-25-acetylcucurbitacin F; 2-O-β-d-glucopyranosyl-23,24-dihydrocucurbitacin F
[74]
Exostema acuminatumNor-diterpenes: ent-16,17-diidroxicauran-19-nor-4-en-3-one;
ent-16,17-dihydroxy-kauran-19-nor-4-en-3-one
Phenylcoumarins: 5,7,4′-trimethoxy-4-phenylcoumarin;
7,4′-dimethoxy-5-hydroxy-4-phenylcoumarin;
5,7,4′-trimethoxy-3′-hydroxy-4- phenylcoumarin;
5,7,4′-trimethoxy-8-hydroxy-4-phenylcoumarin (exostemin I);
5,7,4′-trimethoxy-8,3′-dihydroxy-4′-phenylcoumarin;
[75]
7,4′-dimethoxy-5,3′-hydroxy-4′-phenylcoumarin[75]
Exostema caribaeumPhenylcoumarin: 5-O-β-d-galactopyranosyl-7-methoxy-3′, 4′-dihydroxy-4-phenylcoumarin[76]
Hintonia latifloraPhenylcoumarin: 5-O-(6′′acetyl-β-d-glucopyranosyl)-7,3′,4′-trihydroxy-4-phenylcoumarin
Phenylstyrene: 6-O-β-d-glucopyranosyl-2,3′,4β-trihydroxy-4-methoxy-β-phenylstyrene
[77]
Hintonia standleyanaPhenylcoumarin: 3-O-β-d-glucopyranosyl-23,24-dihydrocucurbitacin F; 5-O-[β-d-apiofuranosyl-(1→6)-β-d-glucopyranosyl]-7-methoxy-3′,4′-dihydroxy-4-phenyl-coumarin; desoxycordifolinic acid[78]
CINCinchona ledgerianaQuinolinic alkaloids: quinine; quinidine; cinchonidine and cinchonine[79,80]
Cinchona robustaAnthraquinones: robustaquinones A–H; 1,3,8-trihydroxy-2-methoxyanthraquinone; copareolatin 6-methyl ether[81]
Ladenbergia oblongifoliaAlkaloids: epicinchonicinol; cinchonidicinol; mixture of dihydrocinchonicinol and dihydrocinchonidicinol[82]
Remijia peruvianaQuinolinic alkaloids: quinine; cuprein; cinchonine; acetylcupreine; N-ethylquinine[83]
Alkaloids: remijinine; epiremijinine; 5-acetylapocinchonamine; N-acetyldeoxy-cinchonicinol; N-acetylcinchonicinol[84]
Sickingia tinctoriaIndole alkaloids: sickingin; 5-carboxystrictosidine; ophiorines A–B; lyalosidic acid[85]
Sickingia williamsiiIndole alkaloids: sickingin; 5α-carboxystrictosidine; ophiorines A–B; lyalosidic acid[85]
GUEAntirhea acutataTriterpene-methyl ester: nor-seco-cycloartane[86]
Antirhea lucidaIndole alkaloids: N,N-methyl-3′-indolylmethyl-5-methoxytryptamine; N,N-dimethyltryptamine; 6-methoxy-2-methyl-1,2,3,4-tetrahydro-13-carboline[87]
Antirhea portoricensisIndole alkaloids: 20-epiantirhine; isoantirhine; antirhine; yohimbol; epi-yohimbol; 19(S)-hydroxydihydrocorinanteol[88]
Chomelia obtusaTriterpenes: 3-O-β-d-quinovopyranosyl-28-O-β-d-glycopyranosyl quinovic acid; 3-O-β-d-quinovopyranosyl-28-O-β-d-glycopyranosyl cincholic acid; ursolic acid; oleanolic acid
Flavonoids: (3-O-β-d-glycopyranosyl quercetin; 3-O-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] quercetin;
3,5-O-dicaffeoyl quinic acid; 4,5-O-dicaffeoyl quinic acid
[89]
Guettarda grazielaeTriterpenes: α-amyrin acetate; cycloartenone; 3β,19α,23-trihydroxyurs-12-ene; 3-β-O-β-d-glucopyranosylquinovic acid; 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic; acid ursolic acid[90]
Iridoid: guettardodiol
Seco-iridoid: sarracenin; 7α-morroniside; 7β-morroniside
[91]
Guettarda noumeanaQuinolinic alkaloids: cupreine; dihydrocupreine;
N-methyldihydroquinicinol; N-methylquinicinol
[92]
Guettarda pohlianaTriterpenes: ursolic acid; oleanolic acid; pomolic acid; rotundic acid; 3β,6β,19α,23-tetra-hydroxyurs-12-en-28-oic acid; clethric acid
Monoterpene: 5-O-caffeoylquinic acid; loliolide
Seco-iridoid: secoxiloganin
[93]
Triterpenes glycosides: 28-O-β-d-glycopyranosyl-3-O-β-d-quinovopyranosyl quinovic acid; 28-O-β-d-glycopyranosyl-3-O-β-d-glycopyranosyl quinovic acid; 3-O-β-d-glycopyranosyl quinovic acid; 28-O-β-d-glycopyranosyl-3-O-β-d-glycopyranosyl cincholic acid; quinovic acid; daucosterol
Phenolic compound: 4,5-O-dicaffeoylquinic acid
[94]
Guettarda speciosaPhenolic compounds: 1-O-α-d-glucuronide 3-O-benzoyl ester; guettardionoside
Indole alkaloid: cadambine
Iridoid glycoside: sweroside; morroniside
Steroids: ecdysone; icariside D1
Triterpene: quinovic glycoside C
[95]
Machaonia brasiliensisSteroids: 3β-O-β-glucopyranosyl stigmasterol; 3β-O-β-glucopyranosyl sitosterol
Seco-iridoid: secologanoside
Flavonoid: 7-O-β-glucopyranosyl quercetagetin
Clorogenic acids: 4,5-O-dicaffeoylquinic acid; 5-O-caffeoylquinic acid.
[96]
Neolamarckia cadambaIndole alkaloids: neolamarckines A–B[97]
Neolaugeria resinosaOxindole alkaloids: neolaugerine; isoneolaugerine; 15-hydroxyneolaugerine[98]
Timonius timonTriterpenes: 3β,6β,23-trihydroxy-olean-12-en-28-oic acid; 3β,6β,19α,23-tetrahydroxy-olean-12-en-28α-oic acid[99]
HAM/HILChione venosa var. venosaAcetophenone derivatives: ortho-hydroxy-acetophenone-azine; acetophenone-2-O-β-d-glucopyranoside; acetophenone-2-O-[β-d-apiofuranosyl-(1→6′)-O-β-d-glucopyranosyl]
Iridoid glycosides: 4α-morroniside; sweroside; diderroside
Triterpene: daucosterol
[100]
HAMDeppea blumenaviensisβ-carboline alkaloids: deppeaninol[101]
Hamelia magnifloraIndole alkaloids: magniflorine; ajmalicine[102]
Hamelia patensIndole alkaloids: (−)-hamelin; tetrahydroalstonin; aricine; pteropodine; isopteropodine; uncarine F; speciophylline; palmirine; mitraphylline; rumberine[103]
HYMHymenodictyon excelsumTriterpenes: 3β-hydroxy-11-oxours-12-en-28-oic acid; 3β-hydroxy-27-p-(Z)-coumaroyloxyolean-12-en-28-oic acid; 3-oxo-11α,12α-epoxyurs-13β,28-olide; 3β-hydroxy-11α,12α-epoxyurs-13β,28-olide; 3β-hydroxyurs-11-en-13(28)-lactone; oleanolic acid; uncarinic acid E (3β-hydroxy-27-(E)-p-coumaroyloxyolean-12-en-28-oic acid; ursolic acid; ursonic acid; 3β-(formyloxy)-urs-12-en-28-oic acid[104]
Hymenodictyon floribundumGlycosides: scopolin; himexelsin or xeroboside; scopoletin[105]
Iridoids: floribundane A–B[106]
ISEIsertia haenkeanaIndole alkaloids: dihydroquinamine; epidihydroquinamine; apodihydrocinchonamine; 3-carbomethoxy-5-(l′-hydroxyethyl) pyridine[107]
Isertia pittieriTriterpene glycosides: pyrocincholic acid 3β-O-α-d-quinovopyranosyl-28-[β-d-glucopyranosyl(1→6)-β-d-glucopyranosyl] ester; pyrocincholic acid 3β-O-β-d-quinovopyranosyl(1→6)-α-d-glucopyranosyl-28-[-β-d-glucopyranosyl(1→2)-β-d-glucopyranosyl] ester; quinovic acid 3α-O-R-l-rhamnopyranosyl(28→1)-β-d-glucopyranosyl ester; quinovic acid 3β-O-β-d-glucopyranosyl(1→4)-R-l-rhamnopyranosyl-(28→1)-β-d-glucopyranosyl ester[108]
NAUAdina cordifoliaCoumarins: umbelliferone; skimmin; 7-methoxycoumarin and 7-hydroxy-8-acetyl coumarin[109]
Adina racemosaFlavonoid glycosides: quercetin
3-O-R-l-rhamnopyranosyl(16)-(3-O-trans-p-coumaroyl)-α-d-galactopyranoside; quercetin 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-p-coumaroyl)-R-l-rhamnopyranosyl(1→2)]-(4-O-trans-p-coumaroyl)-α-d-galactopyranoside; kaempferol 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-p-coumaroyl)-R-l-rhamno-pyranosyl(1→2)]-(4-O-trans-p-coumaroyl)-β-d-galactopyranoside; quercetin 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-p-coumaroyl)-R-l-rhamnopyranosyl(1→2)]-(3-O-trans-p-coumaroyl)-β-d-galactopyranoside; quercetin 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-caffeoyl)-R-l-hamnopyranosyl-(1→2)]-(3-O-trans-p-coumaroyl)-β-d-galactopyranoside
[110]
Secoiridoid glucosides: adinosides A–E; grandifloroside 11-methyl ester[111]
Adina rubellaTriterpenes glycosides: quinovic acid 3-O-β-d-glucopyranosyl (l→4)-β-d-fucopyranoside; quinovic acid 3-O-β-d-glucopyranosyl (1→4)-β-d-fucopyranoside (28→1)-β-d-glucopyranosyl ester; quinovic acid 3-O-β-d-glucopyranosyl (1→4)-α-l-rhamnopyranosyl-(28→1)-β-d-glucopyranosyl ester; quinovic acid 3-O-β-d-glucopyranosyl (1→2)-β-d-glucopyranosyl-(28→1)-β-d-glucopyranosyl ester[112]
27-Nor-triterpene glycosides: rubellosides C–D[113]
Adina polycephalaIridoids: genipin-1-O-α-l-rhamnopyranosyl (1→6)-α-d-glucopyranoside[114]
Cephalanthus glabratusOxindole alkaloids: tetrahydroalstonine; mitraphylline; uncarine E[115]
Cephalanthus occidentalisTriterpenes glycosides: 3-O-α-glucopyranosylcincholic acid; cincholic acid 28-O-α-glucopyranosyl ester; 3-O-β-glucopyranosyl-(1→4)-β-fucopyranosylcincholic acid; 3-O-β-glucopyranosyl-(1→4)-β-fucopyranosylcincholic acid 28-O-β-glucopyranosyl ester; 3-O-β-glucopyranosylcincholic acid 28-O-α-arabinopyranosyl-(1→2)-β-glucopyranosyl ester; 3-O-β-glucopyranosylquinovic acid 28-O-α-arabinopyranosyl-(1→2)-β-glucopyranosyl ester[116]
Corynanthe pachycerasIndole alkaloids: corynanthine; α-yohimbine; dihydrocorynanthine; corynantheine; corynantheidine[117]
Mitragyna diversifoliaMonoterpe indole alkaloids: mitradiversifoline; specionoxeine-N(4)-oxide; 7-hydroxyisopaynantheine; 3-dehydropaynantheine; 3-isopaynantheine-N(4)-oxide[118]
Mitragyna inermis27-Nor-glycosides triterpene: inermisides I–II
Triterpenes: quinovic acid; 3-O-[β-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl]; β-d-glucopyranosyl-[3-O-(β-d-glucopyranosyl)]-quinovic acid; 3-O-(β-d-6-deoxy-glucopyranosyl) quinovic acid
[119]
Indole alkaloids: naucleactonin D; nauclefilline; angustoline; angustine; naucleficine; nauclefidine
Triterpenes: barbinervic acid; quinovic acid; 3-O-α-l-rhamnopyranoside acid; betulinic acid; oleanolic acid; ursolic acid; strictosamide
[120]
Oxindole alkaloids: mitraphylline; isomitraphylline; speciophylline; pteropodine[121]
Mitragyna parvifoliaOxindole alkaloids: 16,17-dihydro-17β-hydroxyisomitraphylline; 16,17-dihydro-17β-hydroxymitraphylline; 2-isomitraphylline; mitraphylline[122]
Mitragyna rotundifoliaTriterpene glycosides: quinovic acid 3-O-β-d-6-deoxy-glucopyranoside 28-O-β-d-glucopyranosyl ester; quinovic acid 27-O-α-l-rhamnopyranosyl ester; 3-O-α-l-rhamnopyranoside; quinovic acid 27-O-β-d-glucopyranosyl ester; quinovic acid 3-O-6-deoxy- glucopyranoside; quinovic acid 27-O-β-d-glucopyranosyl ester; cincholic acid 3-O-β-d-6-deoxy-glucopyranoside; cincholic acid 28-O-β-d-glucopyranosyl ester[123]
Mitragyna speciosaIndole alkaloids: mitragynine; speciogynine; speciociliatine; 7-hydroxy-mitragynine; paynantheine[124]
Nauclea cadambaGluco-indole alkaloids: 3β-dihydroisocadambine; cadambine; 3α-dihydrocadambine; 16-carbomethoxynaufoline; nauclechine; 5,11,12,5α-tetrahydroindolo[3,2-g]-pyridino-[4,3-b]indolizine[125]
Nauclea diderrichiiTriterpene glycosides: quinovic acid 3-O-α-l-rhamnopyranosyl (28→1)-β-d-gluco-pyranosyl ester; quinovic acid 3-O-β-d-glucopyranosyl (1→2)-d-glucopyranoside; quinovic acid 3-O-β-l-fucopyranosyl (28→1)-β-d-glucopyranosyl ester[126]
Indole alkaloids: 3α-5α-tetrahydrodeoxycordifoline; cadambine acid[127]
Nauclea latifoliaIndole alkaloids: latifoliamides A–E; angustoline[128]
Nauclea officinalisIndole alkaloids: naucleficines A–E; naucleidinal; angustoline[129]
Indole alkaloids: naucline; angustine; angustidine; nauclefine; naucletine[130]
Triterpenes: 3β,19α,23,24-tetrahydroxyurs-12-en-28-oic acid; 2β,3β,19α,24-tetrahydroxyurs-12-en-28-oic acid; 3-oxo-urs-12-ene-27; 28-dioic acid; quinovic acid 3-β-rhamnopyranoside[131]
Nauclea orientalisTetrahydro-β-carboline monoterpene alkaloid glucosides: naucleaorine; epimethoxynaucleaorine; strictosidine lactam
Triterpenes: oleanolic acid; 3,4,5-trimethoxyphenol; 3-hydroxyurs-12-en-28-oic acid methyl ester; 3α,23-dihydroxyurs-12-en-28-oic acid; 3α,19α,23-trihydroxyurs-12-en-28-oic acid methyl ester
[132]
Indole alkaloids: nauclealines A–B; naucleosides A–B; strictosamide; vincosamide; pumiloside[133]
Indole alkaloids: naucleaorals A–B[134]
Nauclea pobeguiniiIndole alkaloids: naucleidinal; magniflorine; naucleofficine D; diastereoisomers of 3,14-dihydroangustoline; strictosidine; desoxycordifoline; 3α,5α-tetrahydrodeoxycordifoline lactam
Phenolic compound: kelampayoside A
[135]
Indole alkaloid: nauclequinine; nauclefoline; nauclefidine[136]
Neonauclea purpureaQuinolinic alkaloid: 2,6-dimethoxy-1,4-benzoquinone[137]
Indole alkaloids: cadambine; α-dihydrocadambine
Neonauclea sessilifolia Triterpene glycosides: 3-O-β-d-glucopyranosyl quinovic acid; 3-O-β-d-glucopyranosyl-(1→2)-β-d-quinovopyranosyl quinovic acid; 3-O-β-d-quinovopyranosyl pyrocincholic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester; 3-O-α-l-rhamnopyranosyl-(1→4)-β-d quinovopyranosyl pyrocincholic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester[138]
Triterpene: ursolic acid[139]
Chromone-secoiridoid glycosides: sessilifoside; 7′′-O-β-d glucopyranosylsessilifoside
Indole alkaloid glycosides: neonaucleosides A–C
Glycosides: 5-hydroxy-2-methylchromone-7-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside; sweroside; loganin; grandifloroside; quinovic acid 3β-O-β-d-quinovopyranoside-28-O-β-d-glucopyranoside
[140]
Ochreinauclea maingayiiIndole alkaloids: neonaucline; cadamine; naucledine[141]
Pausinystalia johimbeMonoterpene indole alkaloid: yohimbine[142]
Uncaria attenuataOxindole alkaloids: corynoxine; corynoxine B; isocorynoxeine; epi-allo-corynantheine; dihydrocorynantheine pseudoindoxyl
Indole alkaloids: 19-epi-3-iso-ajmalicine
Triterpene: ursolic acid
[19]
Uncaria borneensisAlkaloids: isorhynchophylline; rhynchophylline; isocorynoxeine; corynoxeine;
Indole alkaloids: allo-yohimbine; pseudo-yohimbine; 3-epi-β-yohimbine
[143]
Uncaria callophyllaIndole alkaloids: dihydro-corynantheine; gambirine; isogambirine; gambireine; rotundifoline; callophylline; callophyllines A–B; yohimbine; pseudoyohimbine; β-yohimbine; α-yohimbine[144]
Indole alkaloids: callophyllines A–B; 3-epi-β-yohimbine; gambirine[144]
Uncaria cordata var. cordata and Uncaria cordata var. ferrugineaIndole alkaloids: dihydrocorynantheine[143]
Uncaria ellipticaPentacyclic oxindole alkaloids: formosanine; isomitraphylline; mitraphylline
Indole alkaloids: ajmalicine
[145]
Triterpenes: 3β,6β,19α-trihydroxy-23-oxo-urs-12-en-28-oic acid; 3β,6β,19α,23-trihydroxy-23-oxo-urs-en-28-oic acid; 3,6-dioxo-19α-hydroxy-urs-12-ene-28-oic acid; 3β,6β-diacetoxi-19-hydroxy-urs-12-ene-28-oic acid; quinovic acid 3β-O-β-d-quinopyranosyl-(28→1)-β-d-glucopyranosyl ester[145]
Uncaria gambirProanthocyanidins: gambiriins A1–A2 ; gambiriins B1–B2; (+)-catechin; (+)-epicatechin; procyanidin B1; procyanidin B3; gambiriin[146]
Uncaria glabrataMonoterpene indole alkaloids: 14α-hydroxyrauniticine; rauniticine; uncarine C–E; glabratine; deoxycordifoline[147]
Uncaria guianensisIndole alkaloid: 3-isoajmalicine
Oxindole alkaloids: isomitraphylline; mitraphylline; isomitraphylinic acid
[38]
Indole alkaloid: ajmalicine
Oxindole alkaloids: formosanine or uncarine B; isomitraphylline; mitraphylline
[148]
Triterpenes: quinovic acid 3β-O-β-d-quinovopyranoside; quinovic acid 3β-O-β-d-fucopyranosyl-(27→1)-β-d-quinovopyranosyl ester; quinovic acid 3β-O-[β-d-glucopyranosyl-(1→3)-β-d-fucopyranosyl]-(27→1)-β-d-glucopyranosyl ester; quinovic acid 38-O-β-d-fucopyranoside[149]
Uncaria hirsutaBis(monoterpenoid) indole alkaloid glucosides: hirsutaside D; bahienoside A–B; neonaucleoside B[150]
Phenolic compound: chlorogenic acid
Alkaloid: uncarine B
Flavonoids: quercitrin; rutin; hiperin; neohesperidin
[151]
Uncaria lanosa var. glabrata and Uncaria lanosa var. ferreaPentacyclic oxindole alkaloids: isopteropodine; pteropodine[143]
Uncaria longiflora var. longifloraAlkaloids: isorhynchophylline; rhynchophylline; iso-corynoxeine; corynoxeine[143]
Uncaria longiflora var. pteropodaPentacyclic oxindole alkaloids: pteropodine; isopteropodine[143]
Pentacyclic oxindole alkaloids: pteropodine; isopteropodine[152]
Uncaria macrophyllaOxindole alkaloids: rhynchophylline; isorhynchophylline; corynoxine; corynoxine B[153]
Uncaria rhynchophylla Indole alkaloids: tetrahydroalstonine; tetrahydroalstonine-N-oxide; akuamigine; (4R)-akuamigina-N-oxide; (4S)-akuamigine-N-oxide; corynantheine; dihydrocorynantheine; dihydrocorynantheine-N-oxide; hirsuteine; geissoschizine methyl ether; hirsutine N-oxide; akuamigine pseudoindoxyl; rauniticine pseudoindoxyl; 3-isorauninticine pseudoindoxyl; dihydrocorynantheine pseudoindoxyl; vallesiachotamine; vincoside lactam; strictosamide; rhynchophyne; 2′-O-β-d-glucopyranosyl-11-hydroxyvincoside lactam; angustine; angustoline; angustidine[154]
Sesquiterpene indole alkaloids: (5S)-5-carboxystrictosidine; 3,4-dehydro-(5S)-5-carboxystrictosidine
Indole alkaloids: cadambine; 3α-dihydrocadambine; 3β-isodihydrocadambine
Pentacyclic oxindole alkaloids: isorhynchophylline; rhynchophylline; corynoxeine; isocorynoxeine; corynoxeine; rhynchophylline N-oxide; isorhynchophylline N-oxide; macrophylline A; 18-19-dehydrocorynoxinic acid; 22-O-demethyl-22-O-β-d-glucopyranosyl isocorynoxeine
[154]
Oxindole alkaloids: rhynchophylline; corynoxeine; corynanteine; hirsutine[155]
Oxindole alkaloids: isocorynoxeine; isorhynchophylline; orynoxeine; rhynchophylline
Indole alkaloids: corynanteine; dihydrocorynanteine
[156]
Pentacyclic oxindole alkaloids: 22-O-demethyl-22-O-β-glucopyranosyl isorhynchophylline; 22-O-demethyl-22-O-β-glucopyranosyl rhynchophylline; 22-O-demethyl-22-O-β-glucopyranosyl isocorynoxeine; isorhynchophylline acid; 9-hydroxy isocorynoxeine; 18,19-dehydrocorynoxinic acid; 18,19 dehydrocorynoxinic acid B; rhynchophyllic acid; 9-hydroxycorynoxeine; isocorynoxeine N-oxide; rhynchophylline acid N-oxide; corynoxeine N-oxide; isocorynoxeine; rhynchophylline; isorhynchophylline N-oxide; isorhynchophylline; corynoxeine
Indole alkaloid: vincoside lactam
Phenolic compounds: chlorogenic acid; neochlorogenic; cryptochlorogenic; quinic acid; cis-5-caffeoylquinic acid; procyanidin b1; procyanidin b2; catechin; epi-catechin; rutin
[157]
Uncaria salaccensisOxindole alkaloids: 3-oxo-7-hydroxy-3,7-secorhynchophylline[158]
Uncaria sinensisAlkaloids: isohynchophyllic acid; pteropodic acid; 3α-dihydrocadambine; 3β-isodihydrocadambine[159]
Proanthocyanidin: procyanidin B-1[160]
Uncaria tomentosa Pentacyclic alkaloids: isomitraphylline; mitraphylline; uncarine F; speciophylline; isopterophylline; pterophylline; isocorynoxeine
Tetratacyclic alkaloids: corynoxeine; isorincophylline; rincophylline
[161]
Alkaloids: cinchonain Ia; cinchonain Ib[162]
Oxindole alkaloids: uncarines C–E; mitraphylline; isomitraphylline
Iridoid glycosides: 7-deoxyloganic acid
[163]
Triterpenes glycosides: 3-oxo-6β-19α-dihydroxyurs-12-en-28-oic acid; 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic acid;
3β-methoxy-16α-hydroxyurs-12,19(29)-dien-27,28-dioic acid;
3β-hydroxyurs-12-en-27,28-dioic acid
[164]
Oxindole alkaloids: pteropodine; isopteropodine; speciophylline; uncarine F; mitraphylline; isomitraphylline; rincophylline; isorincophylline[165]
Oxindole alkaloids: mitraphylline[166,167]
Indole alkaloid: 3-isoajmalicine[168]
Alkaloids: cinchonain Ia; cinchonain Ib[162]
Iridoids: tomentosides A–B
Phenolic compound: (−)-epi-cathequin
[169]
Triterpenes: oleanolic acid; 3β,6β,19α-trihydroxyurs-12-en-28-oic acid[170]
Triterpenes: 3β,6β,19α-trihydroxyurs-12-en-23-al-28-oic acid; 3β,19α-dihydroxy-6-oxo-urs-12-en-23-al-28-oic acid; 3β,19α-dihydroxy-6-oxo-urs-12-en-23-ol-28-oic acid[171]
Triterpene: 23-nor-24-esomethylene-3β,6β-19α-trihydroxyurs-12-en-28 oic acid; 3β,6β,19α-trihydroxyurs-12-en-28-oic acid; 3-oxo-6β,19α-dihydroxyurs-12-en-28 oic acid; oleanic acid[169]
Uncaria villosaIndole alkaloids: villocarines A–D[172]
IxorideaeALBAlberta magnaIridoids: (+)-5-acetaldehyde-l-formyl-2-methylcyclopentan; 5-acetaldehyde-1-formyl-2- methylcyclopent-1-ene; 1,4α,5,6,7α-hexahydro-1-hydroxy-7-methylcyclopenta-pyran-4-carboxaldeyde; 4,4α,5,7α-tetrahydro-1-hydroxy-4-(hydroxymethylene)-7-methylcyclopentane-pyran-3-(1H)-one; 5-deoxystansioside; 6,10-bisdeoxyaucubin; boschnaloside[173]
COFCoffea spAlkaloid: caffeine[174]
Coffea bengalensisAlkaloid: caffeine
Diterpene: 16-epicafestol
[175]
Nematostylis anthophyllaTriterpene glycosides: randianin; 2′′-O-acetylrandianin; 6′′-O-acetylrandianin[176]
Tricalysia dubiaDiterpenes: tricalysiol A–B; tricalysiolide B; tricalysioside G tricalysioside L[177]
Ent-kaurane glycosides: tricalysiosides A–G[178]
Tricalysia okelensisEnt-kaurane glycosides: ent-kauran-3α,16α,17-triol-19-al 3-O-[5-O-vanilloyl-β-d-apiopyranosyl(1→6)]-β-d-glucopyranoside; ent-kauran-3α,16α,17-triol-19-al; 3-O-[5-O-E-sinapoyl-β-d-apiopyranosyl(1→6)]-β-d-glucopyranoside[179]
CONCalycophyllum spruceanumSeco-iridoids: 7-methoxydiderroside,6′-O-acetyldiderroside; 8-O-tigloyldiderroside; loganetin; loganin; secoxyloganin; kingiside; diderroside[180]
Chimarrhis turbinataIndole monoterpene alkaloids: strictosidine; strictosidine acid; 5α-arboxystrictosidine; isovallesiachotamine; vallesiachotamine; turbinatine; 3,4-dehydro-strictosidine; turbinatine
β-Carboline alkaloids: cordifoline; deoxycordifoline; harman-3-carboxylic acid
[181]
Crossopteryx febrifugaTriterpene glycosides: 3β-(α-l-rhamnopyranosyloxi)-28-O-(β-d-glucopyranosyl)urs-12,20(30)-diene-27,28-dioic acid[182]
Emmenopterys henryiTriterpenes: 3β,19α,23-trihydroxyurs-12-en-24-al-28-oic acid; 3β,19α,24-trihydroxy-23-norurs-12-en-28-oic acid; 3β,12β-dihydroxy-5α-pregnane-14,16-dien-20-one; and 12β-hydroxy-5α-pregnane-14,16-dien-3,20-dione; 3β,19α,23,24-tetrahydroxyurs-12-en-28-oic acid; pomolic acid; 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic acid; 3β,6β,23-trihydroxyolean-12-en-28-oic acid; 3β,6β,19α,23-tetrahydroxyolean-12-en-28-oic acid; 3β,23,24-trihydroxyolean-12-en-28-oic acid; 3β,12β-dihydroxy-5α-pregnane-16-en-20-one; 12β-dihydroxy-5α-pregnane-16-en-3,20-dione[183]
Pogonopus speciosusAlkaloids: 1′,2′,3′,4′-tetradehydrotubulosine; tubulosine; psychotrine[184]
Pogonopus tubulosusAlkaloid: tubulosine[185]
Alkaloids: tubulosine; psychotrine; cephaeline[186]
Simira glazioviiAlkaloids: aribin; ophiorine B; lyaloside
Monoterpenes: methyl 3,4-dimethoxycinamate
[187]
Simira eliezerianaDiterpenes: simirane A [(5R,6R,8R,9R,10S,11S,13S)-6 β,11β -dihydroxy-2,4(18),15-erythroxylatrien-1-one]; simirane B [(5S,8R,9R,10S,11S,13S)-11-hydroxy-2,4(18),15-erythroxylatrien-1-one][188]
GARAlibertia edulisIridoids: 6β-hydroxy-7-epigardoside methyl ester[189]
Alibertia macrophyllaDiterpene: ent-kaurane-2β,3α,16α-triol
Triterpenes: lupenone; germanicone; α-amirenone; β-amirenone; lupeol; oleanolic acid; ursolic acid
Glucosidic iridoids: 6α-hydroxygeniposide; 6β-hydroxygeniposide; gardenoside; shanziside methylester
Phenolic acids: protocatechuic; vanilic; caffeic
[190]
Alibertia myrciifoliaCoumarin: scopoletin[64]
Flavonoid: corymbosin[191]
Iridoid: 10-O-vanilloylgeniposidic acid[192]
Triterpenes: pomolic acid methyl ester; ursolic acid methyl ester; oleanolic acid methyl ester[193]
Alibertia sessilisPhenolic compounds: 3,4,5-trimethoxyphenyl-1-O-β-d-(5-O-syringoyl)-apiofuranosyl-(1→6)-β-d-glucopyranoside
Iridoids: geniposidic acid; geniposide; 6α-hydroxygeniposide; 6β-hydroxygeniposide
Lignans glycosides: (+)-lyoniresinol-3α-O-β-d-glucopyranoside; (−)-lyoniresinol-3α-O-β-d-glucopyranoside
[64]
Flavonoids: quercetin-3-O-β-d-(2′′-O-trans-p-coumaroyl)-rutinoside; kaempherol-3-O-β-d-(2′′-O-trans-p-coumaroyl)-rutinoside
Triterpenes: oleanolic acid; ursolic acid; epi-betulinic acid
Iridoids: gardenoside; deacetylasperuloside; 10-dehydrogardenoside; β-gardiol; α-gardiol
[46]
Burchellia bubalinaIridoids: β-gardiol; α-gardiol; garjasmine[60]
Canthium gilfillaniiIridoid: geniposidic acid[61]
Catunaregam niloticaTriterpene glycosides: 28-O-β-d-glucopyranosyl-3-O(O-α-l-rhamnopyranosyl-(1→3)-O-β-d-glucopyranosyl]-(1→3)]-β-d-glucopyranosyl) oleanolate; 3-O-[2′,3′-di-O-(β-d-glucopyranosyl)-β-d-glucopyranosyl] oleanolic acid; 3-O-(O-α-l-rhamnopyranosyl-(1→3)-O-[O-β-d-glucopyranosyl-(1→3)]-β-d-glucopyranosyl) oleanolic acid; 3-O-[O-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl] oleanolic acid[194]
Catunaregam spinosaTriterpene glycosides: catunarosides A–D; swartziatrioside; aralia-saponin V–IV[195]
Coptosapelta flavescensAnthraquinones: 1,4-dimethoxy-2-methylanthraquinone; 2-amino-3-methoxycarbonyl-1,4-naphtoquinone[196]
Duroia hirsutaIridoid: plumericin[197]
Iridoid lactone: duroin
Flavonol: ether flavonol-3-O-methyl
[198]
Duroia macrophyllaTriterpenes: oleanolic acid; ursolic acid[199]
Gardenia collinsaeTriterpenes: 20R,24R-epoxy-3-oxodammarane-25ξ, 26-diol; C-24-epimer; 20R,24R-ocotilone[200]
Gardenia gummiferaCycloartane triterpenes: dikamaliartanes A–F
Flavonoid: 3′,5,5′-trihydroxy-4′,6,7,8-tetramethoxyflavone
[201]
Gardenia jasminoides Coumarines: ferrulic acid; skimmin; uracil; 5,8-di-(3-methyl-2,3-dihydroxy-butyloxypsoralen); 3-O-α-d-glucopyranosyl-(1→4)-β-d-glucopyranosyloxypeucedanin[202]
Iridoids: genipin 1-O-β-d-d-isomaltoside; 1,10-di-O-β-d-glucopyranoside; genipin 1-O-β-d-gentiobioside; geniposide; scandoside methyl ester; deacetylasperulosidic acid methyl ester; 6-O-methyldeacetylasperulosidic acid methyl ester; gardenoside[59]
Iridoids: 8-epi-apodantheroside; 7β,8β-epoxy-8α-dihydrogeniposide[203]
Iridoids: 6′-O-[(E)-sinapoyl] gardoside; 4′′-O-[(E)-p-coumaroyl]-gentiobiosylgenipin; 6′-O-[(E)-caffeoyl]-deacetylasperulosidic acid methyl ester[204]
Iridoid: 6-O-sinapoylgeniposide[205]
Monoterpenes: gardenone; gardendiol[206]
Carotenoids: crocetin; crocetin mono (β-d-glucosyl) ester; crocetin di-(β-d-glucosyl) ester; crocetin mono-(β-gentiobiosyl) ester; crocetin (β-d-glucosyl)-(β-gentiobiosyl) ester; crocin [crocetin-di-(β-gentiobiosyl)ester]; crocetin (β-gentiobiosyl)-(β-neapolitanosyl) ester; crocetin-di-(β-neapolitanosyl) ester[207]
Monoterpenes: jasminosides J–K; 6′-O-trans-sinapoyljasminoside B; 6′-O-trans-sinapoyljasminoside L; jasminosides M–P; jasminoside C; jasminol E; sacranoside B[208]
Flavonoid: luteolin-7-O-β-d-glucopyranoside
Triterpenes: ursolic acid; oleanolic acid; methyl 3,4-di-O-caffeoylquinate; methyl 5-O-caffeoyl-3-O-sinapoylquinate; methyl 3,5-di-O-caffeoyl-4-O-(3-hydroxy-3-methyl)glutaroylquinate; methyl 5-O-caffeoyl-4-O-sinapoylquinate
Glycosides: 2-methyl-l-erythritol-4-O-(6-O-trans-sinapoyl)-β-d-glucopyranoside; 2-methyl-l-erythritol-1-O-(6-O-trans-sinapoyl)-β-d-glucopyranoside
[209]
Iridoids: 6′-O-trans-p-coumaroyl geniposidic acid; 11-(6-O-trans-sinapoyl glucopyranosyl)-gardendiol; 10-(6-O-trans-sinapoyl glucopyranosyl)gardendiol; 6′′-O-trans-sinapoylgenipin gentiobioside; 6′′-O-trans-cinnamoylgenipin gentiobioside; 10-O-succinoylgeniposide; 6′-O-acetylgeniposide; 6′′-O-trans-p-coumaroylgenipin gentiobioside[210]
Iridoids: gardaloside[211]
Iridoids: garjasmine; dunnisin; α-gardiol; β-gardiol; diffusoside A diffusoside B; genameside C; deacetylasperulosidic acid[212]
Gardenia jasminoides var. radicansIridoid glycoside: 6′′-O-trans-feruloylgenipin gentiobioside; 2′-O-trans-p-coumaroylgardoside; 2′-O-trans-feruloylgardoside[213]
Gardenia lucidaCycloartane triterpenes: dikamaliartanes A–F
Flavonoid: 3′,5,5′-trihydroxy-4′,6,7,8-tetramethoxyflavone
[201]
Gardenia saxatilisTriterpenes: lupenone; lupeol; betulinic acid; messagenic acid A; messagenic acid B; oleanolic acid; ursolic acid; acid (27-O-feruloyloxybetulinic acid; 27-O-p-(Z)- and 27-O-p-(E)-coumarate esters of betulinic acid and a mixture of uncarinic acid E (27-O-p-(E)-coumaroyloxyoleanolic acid) and 27-O-p-(E)-coumaroyloxyursolic acid[214]
Gardenia sootepensisSesquiterpene: sootepdienone[215]
Gardenia thailandicaFlavonoids: 5,7-dihydroxy-7,2′,3′,4′,5′,6′-hexamethoxyflavone; 5,7-dihydroxy-2′,3′,4′,5′,6′-pentamethoxyflavone; 5-hydroxy-7,2′,3′,4′,5′-pentamethoxyflavone; 5,7-dihydroxy-2′,3′,4′,5′-tetramethoxyflavone
Triterpenes: thailandiol; gardenolic acid; quadrangularic E acid; 3β-hydroxy-5α-cycloart-24(31)-en-28-oic acid
[216]
Gardenia fructusIridoids: genipin 1-O-β-gentiobioside; 10-O-acetylgeniposide; 6α-hydroxygeniposide; 6β-hydroxygeniposide; gardenoside; picrocrocinic acid; 6′-O-sinapoyljasminoside; 10-O-(4′′-O-methylsuccinoyl) geniposide; jasminosides Q–R; 6-O-p-coumaroylgeniposide; 6′-O-acetylgeniposide; 6′-O-sinapoylgeniposide[217]
Iridoids: geniposidic acid; genipin 1-β-gentiobioside; geniposide; genipin
Flavonoids: rutin; crocin-1; crocin-2
Phenolic compound: chlorogenic acid
[218]
Iridoid glycosides: gardenoside; genipin 1-O-β-d-isomaltoside; genipin 1,10-di-O-β-d-glucopyranoside; genipin 1-O-β-d-gentiobioside; geniposide; scandoside methyl ester; deacetylasperulosidic acid methyl ester[59]
Genipa americanaIridoids: genipaol; genipin; tarenoside; geniposidic acid; geniposide; genamesides A–D; genipin-gentiobioside; gardenoside; gardendiol; shanzhiside[219]
Monoterpenes: genipacetal; genipic acid; genipinic acid
Genipa spruceanaCycloartane triterpene: genipatriol[220]
Lamprothamnus zanguebaricusPhenolic acids: 1-(3-hydroxy-4-methoxy-5-methylphenyl)-ethanone; 1-(3-hydroxy-4-methoxyphenyl)-ethanone[221]
Oxyanthus pallidusCycloartane glycosides: pallidiosides A–C
Triterpenes: oleanolic acid; 3-O-β-d-glucopyranosyl-β-sitosterol
[222]
Oxyanthus pyriformisCyanogenic glycosides: prunasin; amygdalin[223]
Oxyanthus speciosusPhenolic compounds: 2-(2-hydroxy)-ethanol-β-d-glucopyranoside[61]
Cyanogenic glycosides: holocalin[223]
Pavetta owariensisProanthocyanidins: pavetannin A1; pavetannin A2; cinnamtannin B1; pavetanninB1; pavetannin B3; pavetannin B5; pavetannin B6[224]
Psydrax lividaPhenolic compounds: psydroside
Monoterpene: psydrin
[61]
Randia dumetorumIridoid: 11-methylixoside[225]
Triterpenes: α-l-arabinosyl(1→3)-β-galactopyranosyl(1→3)-3-β-hydroxyolean-12-en-28-methyloate[226]
Randia FormosaTriterpenes glycosides: randiasaponins I–VII; ilexoside XXVII; ilexoside XXXVII[227]
Randia siamensisTriterpenes: ursolic acid; pseudoginsenoside-RP 1; pseudoginsenoside-RT 1[228]
Randia spinosaIridoid glycosides: randinoside; galioside; deacetylasperulosidic acid methyl ester; scandoside methyl ester; geniposide; gardenoside[229]
Rothmannia macrophyllaIridoids: macrophylloside[230]
Rothmannia urcelliformisIridoid: genipin
Iridoid alcaloidal: gardenamide A; 4-oxonicotinamide-1-(1′-β-d-ribofuranoside)
[231]
Schumanniophyton problematicumAlkaloids: rohitukine; rohitukine N-oxide; flavopiridol[232]
Scyphiphora hydrophyllaceaIridoid: scyphiphorin A1–A2; scyphiphorin B1–B2[233,234]
Tocoyena brasiliensisTriterpene glycosides: 3-O-β-d-quinovopyranosyl quinovic acid; 3-O-β-d-glucopyranosyl quinovic acid; 28-O-β-glucopyranosyl ester derivative of quinovic acid
Flavonoid: ramnazin-3-O-rutinoside
[235]
Tocoyena bullataIridoid glycoside: gardenoside[236]
Tocoyena formosaIridoids: α-gardiol; β-gardiol; gardenoside[237]
IXOEnterospermum madagascariensisSesquiterpenes: 2-hydroxy-10-epi-zonarene; 2,15-dihydroxycalamenene; guaia-4,6-dien-3-one[238]
Enterospermum pruinosumTriterpenes glycosides: longispinogenin; 3,16-di-O-β-d-glucopyranoside; triacetyllongispinogenin; diglucoside[239]
Ixora coccinea Triterpene: ursolic acid[240]
Proanthocyanidins: ixoratannin A-2; epicatechin; procyanidin A2; cinnamtannin B-1
Flavonoids: kaempferol-7-O-α-l-rhamnoside; kaempferol-3-O-α-l-rhamnoside; quercetin-3-O-α-l-rhamnopyranoside; kaempferol-3,7-O-α-l-dirhamnnoside
[241]
Triterpenes: lupeol; ixorene; 17β-dammara-12,20-diene-3β-ol[242,243]
Fenolic compounds: 3-O-caffeoylquinic acid; 5-O-caffeoylquinic acid; catechin; epicatechin; rutin; quercetin; kaempferol; quercetin 3-O-glucoside; quercetin 3-O-galactoside; kaempferol 7-O-glucoside[244]
MUSHeinsia crinataTriterpene glycosides: heinsiagenin A-3β-O-(β-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→6)-[α-l-rhamnpyranosyl-(1→2)]-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside); heinsiagenin A-3β-O-(α-l-rhamnopynosyl-(1→2)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside)[245]
Mussaenda dona auroraIridoid glycoside: shanshiside D[246]
Mussaenda erythrophyllaFlavonoid: 5-hydroxy-7,4′-dimethoxyflavones;
Phenolic compounds: 3-iso-cumaryloxycyclopropane-1-oic acid; 4-hydroxy-3-methoxy cinnamic acid
[247]
Mussaenda incanaIridolactona: shanzhilactone
Iridoid glycosides: barlerin; mussaenoside
Triterpene: lupeol
[248]
Mussaenda macrophyllaIridoid: 6-epi-barlerin[249]
Mussaenda roxburghiiIridoid: shanzhiol[250]
Mussaenda pubescensMonoterpenes: mussaenins A–C[251]
Triterpene glycosides: mussaendosides R-S; 6 α-hydroxygeniposide; 3β-O-β-d-glucopyranosyl quinovic acid 28-O-β-d-glucopyranosyl ester[252]
OCTVillaria odorataAlkenoyloxy alkenol: villarinol[253]
Iridoids: morindolide; hydrophylin A; hydrophylin B
Sesquiterpene: vomifoliol
[254]
PAVPavetta owariensisProanthocyanidins: proanthocyanidin A-2; proanthocyanidin A-4; pavetannin A
Flavonoids: (+)-catechin; (−)-epicatechin; (+)-epicatechin
[224]
Tarenna attenuataIridoids: tarenninosides A–G[255]
Tarenna gracilipesCycloartane glycosides: tareciliosides H–M[256]
Cycloartane glycosides: tareciliosides A–G[257]
Tarenna madagascariensisIridoids: tarennin; gardenoside; geniposidic acid
Phenolic compounds: p-cumaric acid; cafeic acid; chlorogenic acid
Flavonoids: kaempferol 3-O-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside; kaempferol 3-O-α-l-rhamnopyranoside-7-O-α-l-rhamnopyranoside; quercetin 3-O-α-l-rhamnopyranoside-7-O-α-l-rhamnopyranoside; kaempferol 3-O-α-l-(3′′-O-acetyl)-rhamnopyranoside-7-O-α-l-rhamnopyranoside; kaempferol 3-O-α-l-(4′′-O-acetyl) rhamnopyranoside-7-O-α-l-rhamnopyranoside
[258]
POSMolopanthera paniculataIridoid glycosides: barlerin; shanzhiside methyl ester[259]
SABSabicea brasiliensisPhenolic compounds: 5-O-caffeoylquinic acid; 3,5-O-dicaffeoylquinic acid; 4,5-O-dicaffeoylquinic acid
Coumarine: scopoletin
Triterpene: ursolic acid
[260]
Sabicea grisea var. griseaSteroid: octacosanol[261]
Coumarine: scopoletin
Phenolic compounds: ethyl caffeate; salicylic acid
Steroid: 3-O-β-d-glucopyranosylsitosterol
Triterpene: vanillic acid
[262]
VANCanthium berberidifoliumIridoid glycosides: 6-O-β-d-apiofuranosyl-mussaenosidic acid
Phenolic diglycosides: canthosides A–D
[263]
Canthium multiflorumIridoid: 6-oxo-genipin; macrophylloside; garjasmine; gardenine; gardenamide; deacetylasperulosidic acid; 6α-hydroxygeniposide; galioside; aitchisonide B
Triterpenes: vanillic acid 4-O-β-d-(6-O-benzoylglucopyranoside); oleanolic acid; quinovic acid
[264]
Canthium schimperianumCyanogenic glycoside esterified with an iridoid glycoside: 2R-[(2-methoxybenzoyl-genoposidyl)-5-O-β-d-apiofuranosyl-(1→6)-β-glucopyranosyl-oxy]-2-phenyl acetonitrile; oxyanthin[265]
Fadogia agrestisMonoterpene glycosides: (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-β-d-glucopyranosyl-(12)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-(2-O-((2E,6Z)-8-hydroxy-2,6-dimethyloctadienoyl)-α-l-rhamnopyranosyl)-(1→3)-α-l-rhamnopyranosyl) oxy]-octadien-1-yl α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-(2-O-((2E,6Z)-8-hydroxy-2,6-dimethyloctadienoyl)-α-l-rhamnopyranosyl)-(1→3)-4-O-acetyl-α-l-rhamnopyranosyl) oxy]-octadien-1-yl α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-(2-O-((2E,6Z)-8-hydroxy-2,6-dimethyloctadienoyl)-α-l-rhamnopyranosyl)-(1→3)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranoside[266]
Fadogia ancylanthaTriterpene glycosides: 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-[R-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl] ester; 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-[-d-apiofuranosyl-(1→2)-β-d-glucopyranosyl] ester[267]
Fadogia hombleiCoumarine: scopoletin
Flavones: luteolin; quercetin-3-O-β-d-galactoside
Triterpenes: lupeol; betulinic acid; 3β-dodecanoyllup-20(29)-en-28-al; lup-20(29)-en-3β-ylhexadecanoate; oleanolic acid; ursolic acid
Lignan: 4,4′-dihydroxy-3,3′-dimethoxy-7,9′; 7′,9-diepoxylignan-((−)-pinoresinol)
[268]
Vangueria spinosaProanthocyanidin: (−)-epicatechin-3-O-β-glucopyranoside[269]
*Augusta longifoliaTriterpenes: ursolic acid; acyl lupeol
Coumarin: scopoletin
Flavonoids: naringenin; kaempferol; quercetin; myricitrin; rutin
[270]
Myrioneuron nutansAlkaloid: myrobotinol[271]
Wendlandia formosanaIridoid glycosides: 10-O-caffeoyl scandoside methyl ester; 6-methoxy scandoside methyl ester; scandoside methyl ester; methyl deacetyl asperulosidate; 10-O-caffeoyl daphylloside
Triterpene: ursolic acid
[272]
Wendlandia tinctoriaIridoid glycosides: 5-dehydro-8-epi-adoxosidic acid; 5-dehydro-8-epi-mussaenoside; 10-O-dihydroferuloyldeacetyldaphylloside; wendoside; 8-epi-mussaenoside[273,274]
Iridoids: 5-dehydro-8-epi-adoxosidic acid; wendoside[273]
RubioideaeARGArgostemma yappiiPyrrolidinoindole alkaloid: (+)-isochimonanthine[275]
COUAnthocephalus chinensisSeco-iridoid glycoside: 3′-O-caffeoylsweroside; loganine; 8-epikingiside; loganic acid; sweroside
Phenolic apiglycosides: kelampayosides A–B
Indole alkaloids: cadambine; strictosidine lactam; 5α-carboxystrictosidine; desoxycordifoline
[276]
Coussarea brevicaulisTriterpenes: 3-epi-spathodic acid; coussaric acid; barbinervic acid; scutellaric acid[277]
Coussarea hydrangeifoliaPhenylpropanoid glycosides: 1′-O-benzyl-α-l-rhamnopyranosyl-(1′′→6′)-β-d-glucopyranoside; α-l-xylopyranosyl-(4′′→2′)-(3-O-β-d-glucopyranosyl)-10-O-(E)-caffeoyl-β-d-glucopyranoside; 1,6-di-O-caffeoyl-β-d-glucopyranoside; 1-O-(E)-caffeoyl-β-d-glucopyranoside 1-O-(E)-feruloyl-β-d-glucopyranoside[278]
Coussarea paniculataTriterpenes: lupeol; lupeyl acetate; botulin; betulinic acid; 3-epi-betulinic acid; 3-epi-betulinaldehyde; oleanolic acid; ursolic acid; lup-20(29)-en-3β,25-diol; lup-20(29)-en-11R-ol-25,3β-lactone; 3-deoxybetulonic acid[279]
Coussarea platyphyllaTriterpenes: betulonic acid; betulinic acid
Iridoid: monotropein
Diterpene: trans-phytol
[280]
Cruckshanksia pumilaIridoids: asperuloside; 7-α-methoxysweroside; swertiamarine[246,281]
Heterophyllaea pustulataAnthraquinones: soranjidiol; soranjidiol-1-methyl ether; rubiadin; rubiadin-1-methyl ether; damnacanthal; damnacanthol[282]
Anthraquinones: soranjidiol; rubiadin; rubiadin-1-methyl ether[283]
KNOKnoxia corymbosaChromone glycosides: corymbosins K1–K4; noreugenin; undulatoside A[284]
Knoxia valerianoidesAnthraquinones: 2-hydroxymethylknoxiavaledin; 2-ethoxymethylknoxiavaledin; 2-formylknoxiavaledin[285]
Anthraquinones: lucidin; lucidin-ω-methyl ether; rubiadin; damnacanthol; 1,3,6-trihydroxy-2-methoxymethylanthraquinone; 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone; 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-β-primeveroside; vanillic acid[286]
Pentas busseiPentacyclic cyclol-type naphthohydroquinone: eriobrucinol; methyl 5,10-dihydroxy-7-methoxy-1,1,3α-trimethyl-1a,2,3,3a,10c,10d-hexahydro-1H-4-oxacyclobuta[cd]-indeno[5,6-a]naphthalene-9-carboxylate[287]
Benzochromene: methyl-5,10-dihydroxy-7-methoxy-3-methyl-3-[4-methyl-3-pentenyl]-3H-benzo[f]chromene-9-carboxylate[288]
Pentas lanceolataAnthraquinones: 5,6-dihydroxydamnacanthol; nordamnacanthal ; lucidin-ω-methyl ether; damnacanthol[289]
Iridoid: tudoside; 13(R)-epi-gaertneroside; 13(R)-epi-epoxygaertneroside; (E)-uenfoside; (Z)-uenfoside[290]
Pentas longifloraQuinones: pentalongin; mollugin[291]
Quinones: pentalongin; mollugin; trans-3,4-dihydroxy-3,4-dihydromollugin; methyl-2,3-epoxy-3-prenyl-1,4-naphthoquinone-2-carboxylate; tectoquinone; 3-hydroxymollugin[289]
Pentas micranthaAnthraquinones: tectoquinone; lucidin-ω-methyl ether; damnacanthol; rubiadin-1-methyl ether; rubiadin; damnacanthal; 5,6-dihydroxydamnacanthol; munjistin methyl ester[292]
Pentas schimperiAnthraquinones: schimperiquinones A–B; cleomiscosin A; 2-hydroxymethylanthraquinone
Triterpene: oleanolic acid
[293]
Triterpenes: oleanolic acid; ursolic acid[294]
LASLasianthus fordiiIridoid glycosides: asperuloside; deacetylasperuloside; methyl deacetyl-asperuloside; megastigmane glucoside; lasianthionoside A–C[295]
Lasianthus gardneriTriterpenes: lupenone; lupeol; ursolic acid; canaric acid; 3,4-seco-lupane[296]
Lasianthus wallichiiIridoids: iridolactone; iridoid dimer of asperuloside; asperulosidic acid[297]
Ronabea emeticIridoid glycosides: asperuloside; 6-hydroxygeniposide; deacetylasperulosidic acid; asperulosidic acid[298]
MORCoelospermum billardieriIridoids: coelobillardin[299]
Morinda citrifolia Anthraquinone glycosides: digiferruginol-1-methylether-11-O-β-gentiobioside; digiferruginol-11-O-β-primeveroside; damnacanthol-11-O-β-primeveroside; 1-methoxy-2-primeverosyloxymethyl-anthraquinone-3-olate; 1-hydroxy-2-primeverosyloxymethyl-anthraquinone-3-olate; 1-hydroxy-5,6-dimethoxy-2-methyl-7-primeverosyloxyanthraquinone[300]
Anthraquinones: alizarin or 1,2-dihydroxyanthraquinone[301]
Anthraquinones: 5,15-dimethylmorindol; alizarin 1-methyl ether; anthragallol 1,3-dimethyl ether; anthragallol 2-dimethyl ether; 6-hydroxy-anthragallol-1,3-dimethyl ether; demorindone-5-dimethylether
Iridoids: morindacin; asuperlosidic acid; deacetylasperulosidic acid
[302]
Fatty acid glucosides: 1,6-di-O-octanoyl-β-d-glicopiranose; 6-O-(-β-d-glucopyranosyl)-1-O-decanoyl-β-d-glicopyranose[303]
Iridoid glycosides: 6R-hydroxyadoxoside; 6β,7β-epoxy-8-epi-splendoside; americanin A; narcissoside; asperuloside; asperulosidic acid; borreriagenin; citrifolinin B epimer a; citrifolinin B epimer b; cytidine; deacetylasperuloside; dehydromethoxygaertneroside; epi-dihydrocornin; methylR-d-fructofuranoside; methyl-β-d-fructofuranoside; nicotifloroside
Fatty acid glycoside : β-sitosterol 3-O-β-d-glucopyranoside
[304]
Iridoid glycosides: 9-epi-6α-methoxy geniposidic acid[305]
Iridoids: morindacin[302]
Triterpenes: 1-O-(3′-methylbut-3′-enyl)-β-d-glucopyranose; 1-n-butyl-4-(5′-formyl-2′-furanyl)methylsuccinate; 4-epi-borreriagenin
Iridoid glycosides: asperulosidic acid; deacetylasperulosidic acid; 1-n-butyl-4-methyl-2-hydroxysuccinate; 1-n-butyl-4-methyl-3-hydroxysuccinate
[306]
Iridoid glycoside: citrifoside[307]
Morinda coreiaIridoid glycosides: yopaaosides A–C; 10-O-acetylmonotropein; 6-O-acetylscandoside
Phenolic glycosides: 3,4,5-trimethoxyphenyl 1-O-β-apiofuranosyl (1′→6′′)-β-glucopyranoside
[308]
Morinda ellipticaAnthraquinones: 2-formyl-1-hydroxyanthraquinone; 1-hydroxy-2-methylanthraquinone; nordamnacanthal; damnacanthal; lucidin-ω-methyl ether; rubiadin; soranjidiol; morindone; rubiadin-l-methyl ether; alizarin-l-methyl ether; morindone-5-methyl ether[309,310,311]
Morinda longissimaCoumarine: scopoletin[312]
Morinda lucidaAnthraquinones: oruwal; oruwalol; damnacanthal; nor-damnacanthal; soranjidiol; alizarin-l-methyl ether; rubiadin; rubiadin-l-methyl ether; 2-methylanthraquinone; anthraquinone-2-aldehyde; l-hydroxy-2-methylanthraquinone; l-methoxy-2-methyl-anthraquinone; hexacosanoic acid[313]
Morinda morindoidesFlavonoids: quercetin; quercetin 7,4'-dimethylether; luteolin 7-glucoside; apigenin 7-glucoside; quercetin 3-rhamnoside; kaempferol 3-rhamnoside; quercetin 3-rutinoside; kaempferol 3-rutinoside; chrysoeriol 7-neohesperidoside[314]
Flavonoids: quercetin; quercetin-3-O-rutinoside; kaempferol-7-O-rhamnosylsophoroside; chrysoeriol-7-O-neohesperidoside; quercetin-7,4′-dimethylether; quercetin-3-O-rhamnoside; kaempferol-3-O-rhamnoside; kaempferol-3-O-rutinoside; apigenin-7-O-glucoside; luteolin-7-O-glucoside; kaempferol; apigenin; luteolin
Iridoids: epoxygaertneroside; methoxygaertneroside; gaertneroside; gaertneric acid
[315]
Iridoid: 6′-O-acetyl-3′′-methoxygaertneroside[316]
Morinda officinalisMonoterpene: monotropein[317]
Anthraquinones: 1,3,8-trihydroxy-2-methoxy anthraquinone; 2-hydroxy-1-methoxy-anthraquinone; rubiadin[318]
Morinda pandurifoliaAnthraquinones: soranjidiol; lucidin-ω-methyl ether; damnacanthal; 1-methoxy-2-methyl anthraquinone; 3-hydroxy-1-methoxy-2-methoxymethyl anthraquinone; anthragallol; nordamnacanthal; flavopurpurin; damnacanthal; lucidin; soranjidiol
Iridoid glycoside: asperulosidic acid
[319]
Morinda royocAnthraquinones: nordamnacanthal; damnacanthal; lucidin; soranjidiol; rubiadin 1-methylether[320]
Morinda umbellatanor-Iridoids: umbellatolides A–B[321]
OPHLerchea bracteataAlkaloids: dihydrocorynantheol; dihydrositsirikine; β-hunterburnin methoclhoride; α-hunterburnine methoclhoride; dihydrocorynantheol; melinonine B; methobromide; yombine methobromide; 4-methylanthirine; diploceline; malindine; iso-malindine; dihydro-3-epi-corynantheol methoclhoride (lercheine)[322]
Myrioneuron faberiAlkaloid: myriberine A[323]
Ophiorrhiza blumeanaIndole alkaloids: bracteatine; ophiorrhizine; ophiorrhizine-12-carboxylate; cinchonamine[324]
Ophiorrhiza bracteataIndole alkaloids: bracteatine[325]
Ophiorrhiza communisIndole alkaloids: harman; strictosidinic acid[326]
Ophiorrhiza hayatanaAnthraquinones: ophiohayatones A–C[327]
Ophiorrhiza kunstleriIndole alkaloids: ophiorrhines A–B[328]
Ophiorrhiza liukiuensisMonoterpene glycosides: demethylsecologanol; 3-O-glucosylsenburiside II
Indole alkaloids: camptothecin; 9-methoxycamptothecin; pumiloside; (3R)-deoxypumiloside; 10-methoxycamptothecin; estrictosamide; lyalosidic acid; ophiorrhines A–B; harman
Iridoids: loganic acid; loganin; swertiaside A
Triterpene: ursolic acid; epi-vogeloside
Monoterpene: sweroside
Flavonoid: hyperin
Coumarin: scopoletin
[329]
β-Carbolinic alkaloids: lyalosidic acid; lyaloside; 10-hydroxylyalosidic acid; ophiorrhines A–B; ophiorrhines methyl ester A–B[330]
Ophiorrhiza japonicaβ-Carbolinic alkaloids: lyaloside; lyalosidic acid; 10-hydroxylyalosidic acid; ophiorrhines A–B; ophiorrhines methyl ester A–B
Ophiorrhiza pumila Pentacyclic alkaloid: camptothecin[331]
Anthraquinones:1-hydroxy-2-methylanthraquinone; 3-hydroxy-2-methylanthraquinone; 3-hydroxyanthraquinone-2-carbaldehyde; 1-hydroxy-2-hydroxymethylanthraquinone; 3-hydroxy-2-hydroxymethylanthraquinone; 1,3-dihydroxy-2-methylanthraquinone[332]
Alkaloids: camptothecin; 9-methoxycamptothecin; pumiloside; (3R)-deoxypumiloside[329]
Alkaloids: camptothecin; (3S)-pumiloside; (3S)-deoxypumiloside; (3R)-deoxy-pumiloside; strictosamide[333]
Alkaloids: camptothecin; pumiloside; (3S)-deoxypumiloside; (3R)-deoxypumiloside; strictosamide 9-methoxycamptothecin[330]
Ophiorrhiza rosaceaIndole alkaloids: ophiorrhines A and B[328]
Ophiorrhiza rugosa var decumbensAnthraquinones: 1-hydroxy-2-hydroxymethyl-3-methoxyanthraquinone; 2-n-butoxy-methyl-1,3-dihydroxyanthraquinone[334]
Ophiorrhiza trichocarponIndole alkaloids: ophiorrhisides A–F; 3,4,5,6-tetradehydrodolichantoside; lyaloside; dolichantoside; 5-oxostrictosidine[335]
Ophiorrhiza tomentosaIndole alkaloids: harman; strictosidinic acid[326]
PAEPaederia foetidaePhenolic acid: ethyl p-methoxy-trans-cinnamate[336]
Paederia scandensIridoid glycosides: paederoside; paederoside B; asperuloside; paederosidic acid; methylpaederosidate; saprosmoside E[337]
Iridoid glycosides: paederoside; asperuloside; paederosidic acid; asperulosidic acid; paederosidic acid methyl ester; geniposide[338]
Iridoid glycosides: paederosidic acid; paederoside; asperulosidic acid; asperuloside; geniposidic acid; deacetylasperulosidic acid; decatilasperuloside methyl ester[339]
Iridoid: 6β-O-β-d glucosylparderosic acid[340]
Iridoid glycosides: asperuloside; paederoside; scanderoside[341,342]
Iridoid glycosides: 6′-O-E-feruloyl monotropein; 10-O-E-feruloyl monotropein[343]
Iridoid glycoside: paederoside B[344]
PRIRennellia ellipticaAnthraquinone: 1,2-dimethoxy-6-methyl-9,10-anthraquinone; 1-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone; nordamnacanthal; 2-formyl-3-hydroxy-9,10-anthraquinone; damnacanthal; lucidin-ω-methyl ether; 3-hydroxy-2-methyl-9,10-anthraquinone; rubiadin; 3-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone; rubiadin-1-methyl ether; 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone[345]
PSYCamptotheca acuminataAlkaloids: camptothecin; 10-hydroxycamptothecin[346]
Carapichea affinisAlkaloids: cephaeline; emetine; ipecoside; 6-O-methylipecoside; 6-O-methyl-trans-cephaeloside; borucoside[347]
Cephaelis acuminataAlkaloids: 2-O-β-d-glucopyranosyldemethylalangiside; demethylalangiside; 6′′-O-β-d-glucopyranosylipecoside; 6′′-O-α-d-glucopyranosylipecoside; ipecoside; (4R)-4-hydroxy-6,7-di-O-methyl ipecoside; (4S)-4-hydroxy-6,7-di-O-methylipecoside; 6,7-di-O-methylipecoside tetraacetate[348]
Alkaloids: emetine; cephaeline; neocephaeline 7-O-demethylcephaeline; 10-O-demethylcephaeline; 2′-n-(1′′-deoxy-1′′-β-d-buctopyranosyl) cephaeline; 2′′-n-(1′′-deoxy-1′′-β-d-fructopyranosyl) pyranosyl[349]
Cephaelis acuminataAlkaloids: neocephaeline; 7′-O-demethylcephaeline; 10-O-demethylcephaeline; 2′-n-(10-deoxy-10-β-d-fructopyranosyl) cephaeline; 2′-n-(10-deoxy-10′′-β-d-fructopyranosyl) neocephaeline; emetine; cephaeline; psychotrine; protoemetine; 9-demethylprotoemetinol; isocephaeline[349]
Cephaelis dichroaIndole alkaloids: vallesiachotamine lactone; vallesiachotamine; strictosamide; strictosidine; angustine[350]
Cephaelis ipecacuanhaTetrahydroisoquinoline-monoterpene glucosides: 3-O-demethyl-2-O-methylalangiside; alangiside or ipecoside; 6-O-methylipecoside; 7-O-methylipecoside; 3-O-demethyl-2-O-methylalangiside; 2-O-methylalangiside[351]
Alkaloids: emetine; cephaeline; psychotrine; emetamine; O-methylpsycotrine[352]
Chassalia curviflora var. ophioxyloidesIndole alkaloids: alstrostine A; rudgeifoline[353]
Margaritopsis cymuligeraPyrrolidinoindoline alkaloids: hodgkinsine; quadrigemine C[354]
Palicourea acuminataIndole alkaloid: strictosidinic acid; methylester strictosidine; palicoside; bahienoside B; 5α-carboxystrictosidine; desoxycordifoline; lagamboside; vallesiachotamine[355]
Palicourea adustaMonoterpenoid glucoindole alkaloids: lyaloside; tetra-(O-acetyl)-lyaloside; (E)-O-(6′)-cinnamoyl-4′′-hydroxy-3′′-methoxylyaloside; (E)-tetra-(O-acetyl)-O-(6′)-cinnamoyl-4′-hydroxy-3′-methoxylyaloside; (E)-tetra-(O-acetyl)-O-(6′)-cinnamoyl-4′′-hydroxy-3′′,5′′-dimethoxylyaloside[356]
Palicourea croceaMonoterpenoid indole alkaloids: 3,4-dihydro-1-(1-β-d-glucopyranosyloxy-1,4α,5,7-tetrahydro-4-methoxycarbonylcyclopenta[c]pyran-7-yl)-β-carboline-N2-oxide; croceaine A; psychollatine[357]
Palicourea coriaceaGlucoindole alkaloids: 3-epi-strictosidinic acid; strictosidinic acid; strictosidinic ketone
Alkaloid: calycanthine
Triterpene: ursolic acid
[358]
Palicourea croceaMonoterpene Indole Alkaloids: croceaines A–B[359]
Palicourea rigidaIndole alkaloid: vallesiachotamine[360]
Prismatomeris connataAnthraquinone glycosides: 1-O-methylrubiadin 3-O-β-primeveroside; damnacanthol 3-O-β-primeveroside; rubiadin 3-O-β-primerveroside; lucidin 3-O-β-primeverosideo; 1,3-dihydroxy-2-(methoxymethyl) anthraquinone 3-O-β-primerveroside; digiferruginol ω-gentiobiose[361]
Phenolic compound glycoside: prismaconnatoside[362]
Prismatomeris malayanaAnthraquinone: 1,3-dihydroxy-5,6-dimethoxy-2-methoxymethyl-9,10-anthraquinone; 2-hydroxymethyl-1-methoxy-9,10-anthraquinone; tectoquinone; 1-hydroxy-2-methyl-9,10-anthraquinone; rubiadin; rubiadin-1-methyl ether; 1,3-dihydroxy-5,6-dimethoxy-2-methyl-9,10-anthraquinone; nordamnacanthal; damnacanthal[363]
Prismatomeris tetrandraIridoids: prismatomerin[364,365]
Psychotria bahiensisBis(monoterpenoid) indole alkaloid glucosides: bahienoside A; bahienoside B; 5R-carboxystrictosidine; angustine; strictosamide; (E)- and (Z)-vallesiachotamine[366]
Psychotria barbifloraβ-Carbolinic alkaloids: harman; strictosidinic acid[367]
Psychotria brachycerasMonoterpene indole alkaloids: brachycerine[368]
Psychotria camponutansPyranonaphthoquinones: pentalongin; psychorubrin; 1-hydroxy-3,4-dihydro-1H-benz[g]isochromene-5,10-dione[369]
Psychotria colorataAlkaloids: (−)-calycanthine; isocalycanthine; (+)-chimonanthine; hodgkinsine; quadrigemine C; (8-8a),(8′-8′a)-tetradehydroisocalycanthine 3a(R),3′a(R)[370]
Psychotria calocarpaAlkaloids: psychotriasine[371]
Psychotria correaeIndole alkaloids: isodolichantoside; correantoside; 10-hydroxycorreantoside; correantines A–C e 20-epi-correantine B
C13-Norisoprenoids: megastigm-5-ene-3,9-diol; S(+)-dehydrovomifoliol
Carotenoids: lutein
[372]
Psychotria glomerulataQuinoline alkaloids: glomerulatines A−C; calycanthine; iso-calycanthine[373]
Psychotria ipecacuanhaAlkaloids: emetine; cephaeline[374]
Psychotria leiocarpaIndole alkaloids: umbellatine; brachicerine; lyaloside; strictosamide; myrianthosines A–B; n,β-D-glucopyranosyl vincosamide quadrigemine A
Iridoid glucosides: asperuloside; deacetylasperuloside; loganin
[375]
Psychotria myrianthaIndole alkaloids: strictosidinic acid[376]
Indole alkaloids: strictosidinic acid[377]
Psychotria nudaAlkaloid: strictosamide[378]
Psychotria lyciifloraAlkaloids: meso-chimonanthine; hodgkinsine; N-demethyl-meso- chimonanthine; quadrigemine C; isopsycotridine B; psychotridine; quadrigemine I; oleoidine; caledonine[379]
Psychotria oleoides
Psychotria prunifoliaAlkaloids: strictosamide; 10-hydroxyiso-deppeaninol; N-oxide-10-hydroxy-antirhine[380]
Indole-β-carboline alkaloids: 10-hydroxyisodeppeaninol; N-oxide-10-hydroxy-antirhine; 14-oxoprunifoleine; strictosamide[381]
Indole-β-carboline alkaloids: 14-oxoprunifoleine; strictosamide; 10-hydroxyantirhine N-oxide; 10-hydroxyisodeppeaninol[382]
Psychotria suterellaIndole alkaloids: lyaloside; naucletine; strictosamide[383]
Psychotria umbellataIndole alkaloids: psycollatine[384]
Psychotria vellosianaTriterpenes: squalene; lupeolids
Coumarin: scopoletin
[385]
Psychotria viridisAlkaloid: dimethyltryptamine[386]
Rudgea jasminoidesAnthraquinone: 1,4-naphthohydroquinone[387]
PUTPlocama pendulaNaphthohydroquinones: mollugin 6-methyl ether; plocanaphthin
Lignans: syringaresinol; pinoresinol; lariciresinol
Coumarin: scopoletin
[388]
Anthraquinones: balonone; balonone; methyl ether; plocamanones A–C; knoxiadin; 5,6-dimethyl ether; plocamanone D; chionone; isozyganein dimethyl ether; lucidin 1,3-dimethyl ether; lucidin; 1-hydroxy-2-methyl-9,10-anthraquinone; tectoquinone; rubiadin 3-methyl ether; rubiadin 1-methyl ether; rubiadin dimethyl ether; rubiadin; lucidin 3-methyl ether; munjistin ethyl ester; ibericin; damnacanthol ω-ethyl ether; alizarin dimethyl ether; alizarin 1-methyl ether; anthragallol 1,2-dimethyl ether; 3-hydroxy-2-(hydroxymethyl)-9,10-anthraquinone[389]
Triterpenes: 3-epi-pomolic acid 3α-acetate; baloic acid; meth; 19α-hydroxyoleanonic acid; 3β-hydroxyolean-11,13(18)-dien-28-oic acid; 3α-acetoxy-19α-hydroxyursa-12-en-28-oic acid; baloic acid;19α-hydroxyoleanonic acid[390]
Putoria calabricaFlavonoids: calabricosides A–B
Iridoid: asperuloside; paederosidic acid; paederoside
Lignan glycosides: liriodendrin; dihydrodehydrodiconiferyl alcohol-4-O-β-d-glucopyranoside; 7S,8R,8′R-(–)-lariciresinol-4,4′-bis-O-β-d-glucopyranoside.
[391]
SPEBorreria verticillataIndole alkaloids: spermacoceine; borrerine; borreverine; isoborreverine[392]
Indole alkaloids: verticillatines A–B
Iridoids: scandoside methyl ester; 6′-O-(2-glyceryl) scandoside methyl ester; asperuloside acid
[393]
Dunnia sinensisIridoid: dunnisinine
Iridoid glycoside: dunnisinoside
[394]
Galianthe brasiliensisIridoid glycosides: asperuloside; deacetylasperuloside; mixture of Z- and E-6-O-p-coumaroylscandoside methyl ester[395]
Galianthe ramosa Phenolic compound: epicatechin
Triterpene: ursolic acid
β-carboline indole alkaloid: 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl) cyclopentanol
[396]
β-carboline alkaloid: 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl) cyclopentanol; 9-methoxyindole alkaloid[396]
Galianthe thalictroidesβ-carboline indole alkaloid: 1-methyl-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol; 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol
Anthraquinones: 1-methylalizarin; morindaparvin-A
Coumarin: scopoletin
[397]
Hedyotis auriculariaβ-Carboline alkaloid: auricularine[398]
Hedyotis capitellataβ-Carboline alkaloids: capitelline; cyclocapitelline; isocyclocapitelline; hedyocapitelline; hedyocapitine
Hedyotis chrysotrichaβ-Carboline alkaloid: chrysotricine
Hedyotis capitellataAnthraquinones: capitellataquinone A–D; rubiadin; anthragallol; 2-methyl ether; alizarin-1-methyl eter; digiferruginol; lucidin-3-O-β-glucoside[399]
β-Carboline alkaloids: capitelline; (−)-isocyclocapitelline; (+)-cyclocapitelline; isochrysotricine; chrysotricine[400]
β -Carboline alkaloids: capitelline; (+)-isocyclocapitelline; (+)-cyclocapitelline; isochrysotricine; chrysotricine[401]
Hedyotis chrysotrichaβ-Carboline alkaloid: chrysotricine[402]
Hedyotis corymbosaIridoid glucosides: asperuloside; scandoside methyl ester[403]
Iridoids: hedycoryside A–C[404]
Hedyotis crassifoliaTriterpenes: ursolic acid; 3β-hydroxyurs-11-ene-23(13)-lactone; 3α,13β-dihydroxyurs-11-ene-28-oic acid; oleanolic acid; 3-β-d-glucopyranosyl-β-sitosterol and 3β,6β-dihydroxyolean-12-ene-28-oic acid[405]
Hedyotis diffusa Iridoid glycosides: dunnisinoside; E-6-O-p-methoxycinnamoyl scandoside methyl ester; Z-6-O-p-methoxycinnamoyl scandoside methyl ester; E-6-O-p-feruloyl scandoside methyl ester; E-6-O-p-coumaroyl scandoside methyl ester; Z-6-O-p-coumaroyl scandoside methyl ester[406]
Iridoid glucosides: diffusosides A–B[407]
Anthraquinones: 2-methyl-3-methoxyanthraquinone; 2-methyl-3-hydroxyanthraquinone; 2-methyl-3-hydroxy-4-methoxyanthraquinone; 2,3-dimethoxy-6-methylanthraquinone[398]
Flavonoids: quercetin; quercetin 3-O-glucopyranoside; quercetin 3-O-sambubioside; quercetin 3-O-sophoroside; quercetin 3-O-rutinoside
Hedyotis dichotomaAnthraquinones:1,4-dihydroxy-2,3-dimethoxyanthraquinone; 1,4-dihydroxy-2-hydroxy-methylanthraquinone; 2,3-dimethoxy-9-hydroxy-1,4-anthraquinone; 2-hydroxymethyl-10-hydroxy-1,4-anthraquinone
Flavonoids: isovitexin
[398]
Hedyotis intricataTriterpene: lupeol; oleanolic acid
Iridoid: asperuloside
[408]
Hedyotis hedyotideaIridoids: deacetylasperulosidic acid ethyl ester; hedyotoside; asperulosidic acid; asperuloside; deacetylasperuloside[409]
Hedyotis herbaceaFlavonoids: kaempferol 3-O-rutinoside; rutin; kaempferol 3-O-glucoside; kaempferol 3-O-arabinopyranoside; kaempferol-3-O-arabino pyranoside; quercetin 3-O-galactoside[398,410] [410]
Hedyotis nudicaulisTriterpene glycosides: nudicaucins A–C; guaiacin D[411]
Hedyotis pinifoliaAnthraquinones:1,6-dihydroxy-7-methoxy-2-methylanthraquinone; 1,6-dihydroxy-2-methylanthraquinone; 3,6-dihydroxy-2-methylanthraquinon; 1,3,6-trihydroxy-2-methylanthraquinone[412]
Hedyotis tenellifloraIridoids: teneoside B[413]
Hedyotis verticillataFlavonoids: kaempferitrin[398]
Hedyotis vestitaStereoid: phytol
Flavonoids: rutine; isohrametin 3-O-rutinoside; vomifoliol 9-O-β-d-glucopyranoside; auricularin
Iridoid: 6α-methoxygenyposide;
Phenolic compound: sodium (1S,4aR,5R,7aR)-7-hydroxymethyl-5-methoxy-1-β-d-glucopyranosyloxy-1,4α,5,7α-tetrahydrocyclopenta[c]pyran-4-carboxylate
[414]
Mitracarpus frigidusPyranonaphthoquinone: psychorubrin[415]
Mitracarpus scaber Pentalongin hydroquinone diglycoside: harounoside[416]
Phenolic compounds: pentadecanoic; (Z)-octadec-9-enoic; tetradecanoic; (Z,Z)-octadeca-9,12-dienoic; (Z)-hexadec-9-enoic; octadecanoic; dodecanoic acid[417]
Mitracarpus villosusTriterpenes: methyl ursalate; ursolic acid[418]
Oldenlandia corymbosaIridoid glycosides: geniposidic acid; scandoside; feretoside; 10-O-benzoylscandoside methyl ester; odenlandoside III; asperulosidic acid; deacetylasperulosidic acid[419]
Oldenlandia difusaTriterpenes: ursolic acid[420]
Triterpenes: 2,6-dihydroxy-1-methoxy-3-methylanthraquinone; 2-hydroxy-1-methoxy-3-methylanthraquinone; 2-hydroxy-3-methylanthraquinone; quercetin-3-O-[2-O-(6-O-E-sinapoyl)-β-d-glucopyranosyl]-β-glucopyranoside; quercetina-3-O-[2-O-(6-O-E-feruloyl)-β-d-glucopyranosyl]-β-glucopyranoside; kaempferol-3-O-[2-O-(6-O-E-feruloyl)-β-d-glucopyranosyl]-β-galactopyranoside; quercetin-3-O-(2-O-β-d-glucopyranosyl)-β-d-glucopyranoside; rutin; quercertin[421]
Oldenlandia umbellataAnthraquinones: 1,2,3-trimethoxyanthraquinone; 1,3-dimethoxy-2-hydroxy-anthraquinone; 1,2-dimethoxyanthraquinone; 1-methoxy-2-hydroxyanthraquinone; 1,2-dihydroxyanthraquinone[422]
Richardia grandifloraPhenolic compounds: o-hydroxybenzoic acid; m-methoxy-p-hydroxybenzoic acid[423]
Saprosma fragransAnthraquinones: 4-dihydroxy-1-methoxyanthraquinone-2-corboxaldehyde; damnacanthal[424]
Saprosma hainanenseAlkaloids: saprosmine A; saprosmine B; marcanine A; quinolone; cleistopholine; 4-methoxycarbonyl-5; 10-benzogquinolinequinone; liriodenine[425]
Saprosma scortechiniiIridoid: 6-O-epi-acetylscandoside[426]
Iridoids: 10-O-benzoyl deacetylasperulosidic acid; 3,4-dihydro-3α-methoxy-paederoside; saprosmosides A–H[426]
Bis-iridoid glucosides: saprosmosides A–F
Iridoid glucosides: 3,4-dihydro-3-methoxypaederoside; 10-O-benzoyldeacetylasperulosidic acid; deacetylasperuloside; asperuloside; paederoside; deacetylasperulosidic acid; scandoside; asperulosidic acid; 10-acetylscandoside; paederosidic acid; 6-epi-paederosidic acid; methylpaederosidate; monotropein
[427]
Saprosma ternatumAlkaloid: vittadinoside
Coumarins: scopoletin
Iridoid glycosides: epiasperuloside; epipaederosidic acid; epipaederosi
Triterpenes: betulinic acid; betulinaldehyde
[428]
Spermacoce verticillataTriterpenes: morolic acid; oleanolic acid; ursolic acid; 3,5-dioxofriedelane
Flavonoids: 3-O-α-l-rhamnopyranosyl quercetin; quercetin
Anthraquinones: 2-hydroxy-3-methylanthraquinone
[429]
RUBAsperula maximowicziiIridoids: asperuloides A–C[430]
Crucianella graecaCoumarins: daphnin; daphnetin; daphnetin glucoside
Iridoids: deacetylasperulosidic acid; scandoside; asperuloside; asperulosidic acid; methyl ester of deacetylasperulosidic acid; dafiloside; geniposidic acid; 10-hydroxyloganin; deacetylasperuloside
[431]
Crucianella maritimaIridoid: deacetylasperulosidic acid 6'-glucoside sodium salt;
Anthraquinones: 1-hydroxy-2-carbomethoxyanthraquinone; 6-methylanthragallol-2-methyl ether; 6-methylanthragallol-2,3-dimethyl ether; 6-methoxy-2-methylquinizarin; 1-hydroxy-2-methyl-6-methoxyanthraquinone
[432]
Iridoids: asperuloside; asperulosidic acid; deacetylasperulosidic acid[433]
Cruciata glabraCoumarins: daphnin; daphnetin; daphnetin glucoside
Iridoids: scandoside
[431]
Cruciata laevipesCoumarins: daphnin; daphnetin glucoside
Iridoids: scandoside; asperuloside; asperulosidic acid; methyl ester of deacetylasperulosidic acid; daphylloside
Cruciata pedemontanaCoumarins: daphnin; daphnetin glucoside
Iridoids: scandoside; asperuloside; asperulosidic acid; methyl ester of deacetylasperulosidic acid; daphylloside
Cruciata tauricaMonoterpenoid glycosides: cruciaside A (2,5-O-β-d-diglucopyranosyl-3-hydroxy-p-cymene); cruciaside B (5-O-β-d-glucopyranosyl-2,3-dihydroxy-p-cymene)[434]
Coumarin glucosides: daphnin; daphnetin glucoside; 7-O-(6′-acetoxy-β-d-glucopyranosyl)-8-hydroxycoumarin; 7-O-[6′-O-(3′′,4′′-dihydroxycinnamoyl)-β-d-glucopyranosyl]-8-hydroxycoumarin[435]
Crucianella graecaIridoids: deacetylasperulosidic acid; scandoside; asperuloside; asperulosidic acid; geniposidic acid; 10-hydroxyloganin; deacetylasperuloside; iridoid V3[431]
Galium albumIridoid glycosides: secogalioside; asperuloside; deacetyl asperulosidic acid; scandoside; monotropein; asperulosidic acid; geniposidic acid; 10-hydroxyloganin; 10-hydroxymorroniside (isomers 7α e7β); daphylloside[436]
Galium aparineAnthraquinone aldehyde: nordamnacanthal[437]
Galium lovcenseIridoid glycosides: secogalioside; asperuloside; deacetyl asperulosidic acid; scandoside; monotropein; asperulosidic acid; geniposidic acid; 10-hydroxyloganin; 10-hydroxymorroniside (isomers 7α e7β); daphylloside; 7-β-hydroxy-11-methyl forsythide; 7-O-acetyl-10-acetoxyloganin[436]
Galium rivaleIridoid glycosides: monotropein; scandoside; eacetylasperulosidic acid; geniposidic acid; asperulosidic acid
Triterpene glycosides: rivalosides A–E e momordin II
[438]
Galium macedonicumIridoid: macedonine[439]
Galium sinaicumAnthraquinones: 6,7-dimethoxyxanthopurpurin; 6-hydroxy-7-methoxyrubiadin; 5-hydroxy-6-hydroxymethyl anthragallol 1,3-dimethyl ether; 7-carboxyanthragallol 1,3-dimethyl ether; anthragallol
l-methyl ether 3-O-β-d-glucopyranoside; anthragallol l-methyl ether 3-O-rutinoside; anthragallol 3-O-rutinoside; alizarin 1-methyl ether 2-O-primeveroside
[440]
Galium spuriumFlavonoids: asperulosidic acid ester ; asperuloside; caffeic acid; kaempferol-3-O-l-rhamnopyranoside; quercetin-3-O-[α-l-rhamnopyranosyl(1→6)-β-d-glucopyranoside]; isorhamnetin-3-O-glucopyranoside; quercetin-3-O-α-l-rhamnopyranoside; kaempferol-3-O-[α-l-rhamnopyranosyl(1→6)-β-d-glucopyranoside]; quercetin[441]
Galium verumAnthraquinones: 1,3-dihydroxy-2 methoxy methyl; 1,3-dimethoxy-2-hydroxy; 1,3-dihydroxy-2-acetoxy; 1-hydroxy-2-hydroxy-methyl; 1,3-dihydroxy-2-methyl; 1-methoxy-2-hydroxy; 1,3-dihydroxy-2-hydroxy-methyl-6-methoxy; 1,6-dihydroxy-2-methyl anthraquinones[442]
Galium verum var. asiaticumIridoid glycoside: 10-p-dihydrocoumaroyl-6-α-hydroxygeniposide; 10-p-dihydrocoumaroyl deacetylasperuloside; asperulosidic acid methyl ester; asperuloside; asperulosidic acid; deacetylasperuloside; scandoside[443]
Rubia akaneAnthraquinones: 1,3-dihydroxyanthraquinone-2-al; lucidin-3-O-primeveroside[437]
Rubia cordifoliaNaphtoquinones: dihydromollugin; 2-carbomethoxy-3-(3'-hydroxy)-isopentyl-1,4-naphthohydroquinone 1,4-O-di-β-glucoside; 2-carbomethoxy-3-(3'-hydroxy) isopentyl-1,4-naphthohydroquinona 4-O-β-glucoside
Anthraquinones: xanthopurpurin; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-β-glucoside; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone; 2-methyl-1-hydroxy-9,10-anthraquinone; 3-O-α-rhamnosyl(1→2)-β-glucoside; 3-O-(6'-O-acetyl)-α-rhamnosyl (1→2)-β-glucoside; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-(4′,6′-O-diacetyl)-α-rhamnosyl (1→2)-β-glucoside; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-(3′,6′-O-diacetyl)-α-rhamnosyl (1→2)-β-glucoside
[444]
Iridoids glycoside: 6-methoxygeniposidic acid; 6-methoxygeniposidic acid methyl ester
Triterpene: oleanolic aldehyde acetate
Fenolic compound: furomollugin
[445]
Rubia peregrinaAnthocyanins: cyanidin 3-O-glucoside; delphinidin 3-O-glucoside; cyanidin 3-O-arabinoside[446]
Rubia schumannianaAnthraquinones glycosides: 1,3,6-trihydroxy-2-methyl anthraquinone; (2-methyl-1,3,6-trihydroxy-9,10-anthraquinone-3-O-α-L-rhamnopyranosyl (1→2)-β-d-glucopyranoside); 1-hydroxy-2-hydroxy-methylene-9,10-anthraquinone-11-O-β-d-glucopyranosyl (1→6)-β-d-glucopyranoside; digiferruginol glycoside[447]
Triterpenes: 3β-hydroxy-urs-30-p-Z-hydroxycinnamoyl-12-en-28-oic-acid; 3β-hydroxy-olean-30-p-E-hydroxycinnamoyl-12-en-28-oic-acid; 3β,6α-dihydroxy-urs-14-en-12-one[448]
Cyclopeptides: rubischumanins A–C; C-6β-oxy-RA IV; RA-IV; O-seco-RA-V[448]
Rubia yunnanensisTriterpene: rubiarbonol K[449]
Rubia tinctorumAnthraquinones: alizarin; lucidin; mollugin; xanthopurpurin; rubiadin[450]
Anthraquinones: 1-hydroxy-2-hydroxymethylanthraquinone 3-glucoside 2-hydroxymethyl-anthraquinone 3-glucoside; 3,8-dihydroxymethylanthraquinone 3-glucoside
Anthraquinone glycosides: alizarin; lucidian-ω-ethyl ether; lucidin primeveroside
Iridoid: asperuloside
[451]
Anthraquinones: pseudopurpurin; lucidin; alizarin; purpurin; alizarin-2-methylether; lucidin-ω-ethylether; nordamnacanthal; munjistin ethyl ester; lucidin primeveroside; ruberithric acid[452,453]
Rubia yunnanensisCyclic hexapeptides: rubiyunnanins A–B[454]
Triterpenes: rubiarbonones D–F; rubiarbosides F–G; rubiarbonone A; rubiarbonol A–B; rubiarbonone B; rubiarbonol A; rubiarbonol B; rubiarbonol F; rubiarbonol G; rubiarboside A[455]
***Luculia pincianaTriterpene: luculiaoic acid A[456]
Triterpenes: vogeloside; epi-vogeloside; loganoside; loganin; cincholic acid 28-O-β-d-glucopyranosyl ester; cincholic acid-3-O-β-d-glucopyranoside, 28-O-β-d-glucopyranosyl ester; cincholic acid-3-O-β-d-glucopyranoside[457]
ALB: Alberteae; ARG: Argostemmateae; CHI: Chiococceae; CIN: Cinchoneae; COF: Coffeeae; CON: Condamineeae; COU: Coussareeae; GAR: Gardenieae; GUE: Guettardeae; HAM: Hamelieae; HIL: Hillieae; HYM: Hymenodictyeae; ISE: Isertieae; IXO: Ixoreae; KNO: Knoxieae; LAS: Lasiantheae; MOR: Morindeae; MUS: Mussaendeae; NAU: Naucleeae; OCT: Octotropideae; OPH: Ophiorrhizeae; PAE: Paederieae; PAV: Pavetteae; POS: Posoquerieae; PRI: Prismatomerideae; PSY: Psychotrieae; PUT: Putorieae; RUB: Rubieae; SAB: Sabiceeae; SPE: Spermacoceae; VAN: Vanguerieae. * Genera not allocated to any tribe. ** Genera unclassified to subfamily.
Figure 3. Chemical diversity and major secondary metabolites distribution among Rubiaceae subfamilies observed in this revision. IXO: Ixoroideae, CIN: Cinchonoideae, RUB: Rubioideae.
Figure 3. Chemical diversity and major secondary metabolites distribution among Rubiaceae subfamilies observed in this revision. IXO: Ixoroideae, CIN: Cinchonoideae, RUB: Rubioideae.
Molecules 20 13422 g003
This survey found Rubioideae subfamily has the highest chemical diversity in Rubiaceae subfamily. Among the described tribes, the most chemically studied are: Naucleeae (44), Gardenieae (39), Psycotrieae (34), Spermacoceae (35), Rubieae (25) and Ophiorrhizeae (14); other tribes have around five to six studied species. In general, the species with the largest number of phytochemical studies recorded from 1990 to 2014 belong to the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. Plants from the Psycotrieae tribe were shown to be the major producers of alkaloids, since all phytochemical studies with genera belonging to this tribe (Camptotheca, Carapichea, Cephaelis, Chassalia, Margaritopsis, Palicourea and Psychotria) resulted in the isolation of alkaloids. In the Gardenieae tribe, the presence of iridoids was observed, not only in this survey, but also in other studies [59,60,61,62,64]. Studies showed Rubia, Galium and Morinda genera (subfamily Rubioideae) as important sources of anthraquinones, such as aglycone and rarely glycosides [56].
However, studies establishing a chemotaxonomic classification of plants are quite complex, since there are different types of secondary metabolites that can be distinct in correlated species. These differences in the production of secondary metabolites can be attributed to a number of factors such as genetic mutation, blocking of a biosynthetic pathway and changes in the metabolism due to infection. Soil and climatic variations such as altitude, soil type, macronutrients, micronutrients and water availability, plant age, ultraviolet radiation, rainfall, seasonality and circadian rhythm, also have great influence on the production of metabolites. Besides the fact that the chemical composition can be variable in accordance with the plant organ, it is necessary to study the plant as a whole, to be able to infer a degree of similarity [59,60,61,62,63,64].
Considering the chemical profile of the Rubiaceae family and the metabolic pathways used to produce it, Rubioideae is the most ancient subfamily from an evolutive point of view [16], then it was subdivided into Ixoroideae and finally into Cinchonoideae. The chemical biosynthetic pathway now supports this botanical conclusion. In Rubioideae, anthraquinones are the main metabolites and the pathways are not so specific, being iridoids and indole alkaloids produced also in a large amount. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it is the one that produces indole alkaloids together with other alkaloids.

6. Conclusions

This review has encompassed phytochemical studies of Rubiaceae species for the past 24 years. These substances have been isolated mainly from Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda genera. From the Rubioideae subfamily, 139 species were studied; 80 from the Ixoroideae, and 74 from the Cinchonoideae. Some correlations between iridoids, triterpenes, alkaloids and anthraquinones occurrence and distribution between tribes and subfamilies could be observed, providing chemotaxonomic clues. From an evolutionary point of view, the Rubioideae is the most ancient subfamily [16], then it was subdivided into the Ixoroideae and finally into the Cinchonoideae.

Acknowledgments

The authors are thankful to the Brazilian Agencies CNPq, CAPES and FAPEAM for the financial support.

Conflicts of Interest

The authors declare no conflict of interest.

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