Secondary Metabolites of Medicinal Plants. Bharat Singh
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The exudates of aloes (A. barbadensis, Aloe ferox, Aloe harlans, and Aloe hildebrandtii) contain several important compounds, viz protocatechuic acid, 3-furanmethanol, dihydrocoumarone, methyl-p-coumarate, pluridone, isoeleutherol, isoeleutherol-5-O-glucoside, 5-OH-3-methylnaphto(2,3-c)-furan-4(1H)-one, 3-methylnaphto(2,3-c)-furan-4(9H)-one, 3-methylnaphto(2,3-c)furan-4,9-dione, feroxidin, feroxidin A, plicataloside, feroxidin B, 7-O-methylaloesin, 7-O-methylaloesinol, 7-O-methylaloeresin A, 8[C-B-D-(2-O-(E)-cinnamoyl]glucopyranolsyl]-2-[(R)-2-hydroxypropyl]-7-methoxy-5-methylchromone, 8-C-glucosyl-noreudenin, 8-C-glucosyl-(2′-O-cinnamoyl)-7-O-methylaloediol, 8-C-glycosyl-7-O-methyl aloediol, 8-C-glycosyl-S-aloesol, and 8-C-glycosyl-7-O-methyl-S-aloesol (Levin et al. 1988; van Wyk and Smith 2008; van Wyk et al. 1995a,b; Veitch et al. 1994; Dagne et al. 2000; Ombito et al. 2015). The γ-coniceine and coniine were identified from Aloe gillilandii and Aloe viguieri (Dring et al. 1984); dihydroisorhamnetin, aloeresin D, aloeresin A (2′-O-p-coumaroylaloesin), aloesol, aloesin, aloesone, 2′-O-tigloylaloesin, isoeleutherol, 10-hydroxyaloin B, N-methyltyramine, O,N-dimethyltyramine, 5-hydroxyaloin A, chrysophanol anthrone, aloe emodin, aloin A/B, aloinoside A/B, naringenin, apigenin, isovitexin, and aloe emodin anthrone from Aloe spp. (Holdsworth 1972; Sigler and Rauwald 1994; Rauwald and Lohse 1992; Rauwald et al. 1989; Manitto et al. 1990; Reynolds 1985; Rauwald and Beil 1993; Nash et al. 1992; Speranza et al. 1986a; Makino et al. 1974; Conner et al. 1990a,b; Hay and Haynes 1956; Horhammer et al. 1964; Dagne et al. 1994, 1996, 1997; Viljoen et al. 1998; Haynes et al. 1970); aloe-emodin-11-O-rhamnoside, rabaichromone, and aloe-emodin-10-C-rhamnoside from Aloe rabaiensis (Conner et al. 1989); 6′-O-coumaroylaloesin from Aloe castanea (van Heerden et al. 2000); neoaloesin A, isorabaichromone, isoaloesin, isoaloeresin D, deacetylaloesin, aloeresin E, 8-C-glucosyl-noreugenin 8-C-glucosyl-(8)-aloesol, 8-C-glucosyl-7-O-methyl-(8)-aloesol, 8-C-glucosyl-7-O-methylaloediol, 8-C-glucosyl-(2′-O-cinnamoyl)-7-O-methyl-aloediol A, 8-C-glucosyl-(2′-O-cinnamoyl)-7-O-methyl-aloediol B, 4′-O-glucosyl-isoaloeresin DI, and 4′-O-glucosyl-isoaloeresin DII from A. vera (van Heerden et al. 1996; Okamura et al. 1996a,b, 1997, 1998; Park et al. 1996); dihydroisocoumarin glucoside from A. hildebrandtii (Veitch et al. 1994); 7-O-methylaloesin from A. rupestris (Bisrat et al. 2000); 7-O-methylaloesinol from Aloe capensis (Park et al. 1997); nataloin A/B, aloenin (Aloecarbonoside), aloenin aglycone, and aloenin-2″-p-O-coumaroyl ester from Aloe nyeriensis (Suga et al. 1974; Conner et al. 1987); and chrysophanol-8-methyl ether, protocatechuic acid, and aloechrysone have been identified from Aloe berhana (Dagne and Alemu 1991; Dagne et al. 1991, 1992). Nataloin and 7-hydroxyaloin have been isolated from latex of Aloe pulcherrima and demonstrated antimalarial activity in a dose-independent manner (Teka et al. 2014, 2016; Bbosa et al. 2013); asphodelin, bianthracene II–IV, aloesaponol IV-8-O-glucoside, aloesaponol III-8-O-glucoside, aloesaponol I-6-O-glucoside, aloesaponol II-6-O-glucoside, aloesaponol I, aloesaponarin I, aloesaponol II–IV, laccaic acid D methyl ester, isoeleutherol-5-O-glucoside, isoxanthorin, helminthosporin, desoxyerythrolaccin, aloesaponarin II, and chrysophanol from Aloe saponaria (Yagi et al. 1974, 1977a,b, 1978, 1983; Snider and Zhang 1993), 2′-p-O-methylcoumaroylaloesin, and 1,5-dihydroxy-3-hydroxymethylanthraquinone from Aloe excelsa (Mebe 1987); 7-hydroxyaloin-6′-O-monoacetate A/B, 7-hydroxyaloe-emodin, 7-hydroxyaloin-4′,6′-O-diacetate A/B from Aloe succotrina (Sigler and Rauwald 1994; Rauwald and Diemer 1986); nataloe-emodin and nataloe-emodin-2-O-glucoside from A. nyeriensis (Conner et al. 1987); nataloe-emodin-8-methyl ether from Aloe speciosa (Thomson 1987); campesterol, cholesterol, lupeol, bisbenzopyran, 8-[C-β-D-[2-O-(E)-cinnamoyl]glucopyranosyl]-2-[(R)-2-hydroxypropyl]-7-methoxy-5-methylchromone, 6′-O-p-coumaroyl-7-hydroxylaloin A/B, 7-hydroxyaloin A/B, 6′-O-cinnamoyl-8-O-methyl-7-hydroxylaloin A/B, 8-O-methyl-7-hydroxylaloin A/B, aloesaponol IV-4-O-glucoside, aloe barbendol, aloesaponol IV, 7″-deoxyaloeresin D, O-demethyl,4-O-glucoside and aloesaponol IV- O-demethyl, 4-O-glucoside from A. barbadensis (Rauwald 1990; Yagi et al. 1998; Saleem et al. 1997a,b; Rauwald and Voetig 1982; Haynes et al. 1960; Hutter et al. 1996; Saleem et al. 1997a,b); prechrysophanol from Aloe graminicola (Yenesew et al. 1993); eigonicardine (elgonica-dimers A and B) from Aloe elgonica (Conner et al. 1990b); 7-O-methylaloeresin A and 5-hydroxyaloin A 6′-O-acetate from A. marlothii (Bisrat et al. 2000); microstigmin A from A. microstigma (Dagne et al. 1997); 10-hydroxyaloin B 6′-O-acetate from A. claviflora (Dagne et al. 1998a,b); littoraloside, littoraloin, and deacetyllittoraloin from Aloe littoralis (Dagne et al. 1996, 1998b; Viljoen et al. 1996); (E)-2-acetonyl-8-(2′-O-cinnamoyl)-β-D-glucopyranosyl-7-methoxy-5-methylchromone, (E)-2-acetonyl-8-(2′-O-caffeoyl)-β-D-glucopyranosyl-7-methoxy-5-methylchromone, and 6′-O-cinnamoyl-5-hydroxyaloin A from Aloe broomii (Holzapfel et al. 1997); microdontin A/B from Aloe microdonta (Farah et al. 1992); homonataloin A/B from Aloe jacksonii (Conner et al. 1990a; Haynes et al. 1960); homonataloside B from Aloe lutescens (van Heerden et al. 2000; Viljoen et al. 2002); 2-(carboxyethenyl)-5,7-dihydroxychromone from Aloe cremnophila (Conner et al. 1990a); aloenin B, isoaloeresin A, aloeresin C, 2-acetonyl-7-hydroxy-8-(3-hydroxyacetonyl)-5-methylchromone, 2-acetonyl-8-(2-furoylmethyl)-7-hydroxy-5-methylchromone, CA-14 [benzo(f)chroman-3-one (process product)], feralolide, 7-hydroxy-2,5-dimethylchromone, CA-12 (1,1-diphenylethane derivative), and feroxin A and B from Cape and Kenya aloe (Speranza et al. 1985, 1986b, 1988, 1990, 1993a,b, 1994, 1996, 1997); β-sitosterol,4″,6″-ethylidene-aloenin, aloenin acetal, 3-furanmethanol, 2′-O-feruloylaloesin, and dihydrocoumarone (2,3-dihydrobenzofuran) from A. arborescens (Woo et al. 1994; Makino et al. 1974; Yamamoto et al. 1991); plicataloside from Aloe plicatilis (Wessels et al. 1996); pluridone from Aloe pluridens (Confalone et al. 1983); aloeresin E and aloeresin F from Aloe peglerae (van Heerden et al. 1996); (E)-2-acetonyl-8-(2′,6′-di-O,O-coumaroyl)-β-D-glucopyranosyl-7-hydroxy-5-methylchromone from A. speciosa (Holzapfel et al. 1997); (E)-2-acetonyl-8-(2′-O-feruloyl)-β-D-glucopyranosyl-7-methoxy-5-methylchromone from Aloe africana (Holzapfel et al. 1997); methyl-p-coumarate, feroxidin, 5-OH-3-methylnaphto[2,3-c]furan-4(1H)-one, 5-OH-3-methylnaphto[2,3-c]furan-4(9H)-one, and 5-OH-3-methylnaphto[2,3-c]furan-4,9-dione from A. ferox (Speranza et al. 1990; Koyama et al. 1994).
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