Читать книгу Secondary Metabolites of Medicinal Plants - Bharat Singh - Страница 24

Ageratina pichinchensis (Kunth) R. M. King and H. Rob syn. Eupatorium adenophora Spreng (Fam. – Asteraceae) is used for the healing of skin wounds in folk medicine system of Mexico (Monroy and Castillo 2000), an antidiabetic, and a diminution in fibroblast proliferation and increases tissue regeneration (Romero-Cerecero et al. 2014, 2015). The hexane-ethylacetate extracts of A. pichinchensis were used for curing of diabetic foot ulcer rat models (Romero et al. 2013; Romero-Cerecero et al. 2014). The chloroform, methanol, petroleum ether, ethyl acetate, and aqueous extracts of Ageratina adenophora demonstrated antibacterial activity against Staphylococcus aureus, Klebsiella pneumoniae, and Escherichia coli (Harish Kumar et al. 2014). The hexane extract of A. pichinchensis possesses antifungal properties against Trichophyton rubrum (Romero-Cerecero et al. 2006, 2008, 2009) and antibacterial properties against S. aureus and Enterococcus faecalis (Torres et al. 2013), and acetone extract against Aedes aegypti and Culex quinquefasciatus larvae activities (Mohan and Ramaswamy 2007). The methanolic and aqueous extracts of Ageratina jahnii and A. pichinchensis showed antiparasitic effects against Lutzomyia migonei females and Leishmania transmitters in Latin America (Torres et al. 2017). The methanolic extract of leaves of A. adenophora demonstrated antioxidant activity (Lallianrawna et al. 2013; Rajalakshmi et al. 2016). The aqueous extract of A. pichinchensis showed cytotoxic activity of KB (nasopharyngeal carcinoma), UISO (squamous cell carcinoma of the cervix), OVCAR (ovarian carcinoma), and HCT-15 (Romero-Cerecero et al. 2011).

Secondary metabolites such as 5-acetyl-3-angeloyloxy-2-(1-hydroxyisopropyl)-2,3-dihydrobenzofurane, 5-acetyl-3-angeloyloxy-2-(1-hydroxyisopropyl)-6-methoxy-2,3-dihydrobenzofurane, espeletone, encecalinol, O-methylencecalinol, encecalin, sonorol, taraxerol, (+)-β-eudesmol, 8,9-epoxythymyl isobutyrate, germacrene D, thymyl isobutyrate, eupatoriochromene, encecalol, neryl isobutyrate (Torres et al. 2013), and a mixture of β-sitosterol and stigmasterol were isolated from the aerial parts of A. pichinchensis var. bustamenta. Encecalin and sonorol showed antimicrobial effects against T. rubrum, Trichophyton mentagrophytes, Candida albicans, and Aspergillus niger (Aguilar-Guadarrama et al. 2009). Ayarin, casticin, cirsiliol, tomentin, chrysosplenol D, eupalitin, 5,7,4′-trihydroxy-3,6-dimethoxyflavone, 3,5,7,4′-tetrahydroxy-6-methoxyflavone, 5,6,7,4′-tetrahydroxy-3-methoxyflavone, 5,3′,4′-trihydroxy-3,7-dimethoxyflavone, 5,7-dihydroxy-3,3′,4′-trimethoxyflavone, 5,7,4′-trihydroxy-3,3′-dimethoxyflavone, 5,6,4′-trihydroxy-3,7-dimethoxyflavone (Yang et al. 1990), sakuranetin, 7-methoxyaromadendrin, 4′-O-β-D-glucosyl-7-methoxy-eriodictyol, and 4′-O-β-D-glucosylsakuranetin were separated from Ageratina havanensis and showed antiviral activity against rabbit vesivirus and human herpes simplex viruses (Barrio et al. 2011). Eupatorin, 5-hydroxy-6,7,3′,4′-tetramethoxyflavone, and genkwanin from A. pichinchensis showed antioxidant property (Morán-Pinzón et al. 2017). A total of eight flavonoids, viz quercetagetin-7-β-O-glucoside, 6-methoxykaempferol 7-methyl ether 3-β-O-glucoside, quercetagetin 4′-methyl ether 7-β-O-glucoside, 6-hydroxykaempferol-7-β-O-glucoside, 6-methoxy-genkwanin, 5,4′-dihydroxy-3,6-dimethoxy-7-O-β-D-glucopyranoxyflavonone, 5,4′-dihydroxy-6,7-dimethoxy-3-O-β-D-glucopyranoxyflavonone, and 3,5,4′-trihydroxy-6,7-dimethoxyflavonone, were isolated from A. adenophora (Li et al. 1997; Ding et al. 1999). A (4aR,7R,8S,8aR)-1,2,4a,5,6,7,8,8a-octahydro-8-[3-methylenebut-4-alyl]-4,4a,7,8-tetramethylnaphthalen-2(1H)-one novel norditerpene was isolated from the flowers of Eupatorium adenophorum (Wang et al. 2007).

Essential oils such as torreyol, 2-pentanone, germacrene, bornyl acetate, 1-α-bisabolene, δ-cadinene, α-bisabolol, 1-napthalenol, α-bisabolol, bornyl acetate, β-bisabolene, germacrene D, α-phellandrene, di-epi-α-cedrene, α-phellandrene, camphene, p-cymene, γ-curcumene, 2-carene, 2-pentanone, 4-hydroxy-4-methyl, diacetone alcohol, bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene, 3,3-dimethyl-2-methylenenorbornane, p-mentha-1,4(8)-diene, 1,3-cyclohexadiene, 2-methyl-5-(1-methylethyl)-, p-mentha-1,5-diene, cymol, β-linalool, bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene, 2-norpinene, 2,6-dimethyl-6-(4-methyl-3-pentenyl), δ-cadinene, germacrene D, trans-caryophyllene, β-sesquiphellandrene, androstan-17-one, (6E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol, andrographolide, (−)-spathulenol, caryophyllene oxide, α-cedrol, biphenylene, guaiol, torreyol, and isoledene were isolated and identified from E. adenophorum (Lee et al. 2012; Subba and Kandel 2012). β-caryophyllene, carvacrol, spathulenol, and terpinen-4-ol from Ageratina jocotepecana have repellant properties against termites (Ramirez-Lopez et al. 2016). 16-Hydroxy-3,4β-epoxy-5β, 10β-cis-17α,20α-cleroda-13(14)-en-15,16-olide, 3α,4β,16-trihydroxy-5β,10β-cis-17α,20α-cleroda-13(14)-en-15,16-olide, 3α,4β-dihydroxy-5β,10β-cis-17α,20α-cleroda-13(14)-en-15,16-olide, 3α-methoxy-4β-hydroxy-5β,10β-cis-17α,20α-cleroda-13(14)-en-15,16-olide, 3-oxo-4β-hydroxy-5β,10β-cis-17α,20α-cleroda-13(14)-en-15,16-olide, 2β-hydroxy-3,4β-epoxy-5β,10β-cis-17α,20α-cleroda-13(14)-en-15,16-olide, 2β-hydroxy-5β,10β-cis-17α,20α-cleroda-3,13(14)-diene-15,16-olide, (13Z)-2β-hydroxy-5β,10β-cis-17α,20β-cleroda-3,13(14)-diene-15-oic acid, (13Z)-2-oxo-5β,10β-cis-17α,20β-cleroda-3,13(14)-diene-15-oic acid, 3,4β-epoxy-5β-10β-cis-17α,20α-cleroda-15-oic acid, 16-hydroxy-3,4β-epoxy-5β,10β-cis-17α,20α-cleroda-15-ol, 8β-5′-[5″-hydroxytigloyloxy]-tigloyloxy-3-dehydro-4β,15-dihydrozaluzanin C, 8β-5′-[5″-hydroxytigloyloxy]-tigloyloxy-4β,15-dihydrozaluzanin C, 4′-desoxy-3-desacetoxy-3β-hydroxyprovincialin, 5′-[5″-hydroxytigloyloxy]-5′-hydroxyheliangine, 3β-acetoxyliacylindrolide, 6-eudesmene-4α-ol, 6,15α-epoxy-1β,4β-dihydroxyeudesmane, and 3,4β-epoxy-5β,10β-cis-17α,20α-cleroda-13(14)-en-15,16-olide were identified from Ageratina saltillensis (Yu et al. 1986). The labdane diterpenoids (−)-(5S,9S,10S,13S)-labd-7-en-15-oic acid, methyl (−)-(5S,9S,10S,13S)-labd-7-en-15-oate, (+)-(5S,8R,9R,10S,13R)-8-hydroxylabdan-15-oic acid, and (−)-(5S,9S,10S,13Z)-labda-7,13-dien-15-oic, (+)-(5S,8R,9R,10S,13R)-8-hydroxylabdan-15-oate, methyl (+)-5S,10S,13S)-labd-8-en-15-oate, and methyl (+)-(5S,10S,13R)-labd-8-en-15-oate were separated from A. jocotepecana and showed antibacterial activity against Bacillus subtilis and S. aureus (García-Sánchez et al. 2014). The p-hydroxyacetophenone derivatives and diterpenes including six new ent-clerodanes were afforded from Ageratina ixiocladon (Tamayo-Castillo et al. 1989); β-D-glucopyranosyl ester of (−)-17-(β-glucopiranosyloxyl)-16-hydroxy-kauran-19-oic acid from Ageratina vacciniaefolia (Ding et al. 1991; Wu and Yang 1994; Torrenegra et al. 1999); and 9-oxo-ageraphorone, 9β-hydroxy-ageraphorone, epifriedelinol, stigmasterol, octacosanoic acid, β-daucosterol, O-hydroxy cinnamic acid, ferulic acid, caffeic acid, and 2-isopropenyl-5-acetyl-6-hydroxy benzofuran acetate have been identified from E. adenophorum(Zhengfang et al. 1997).

Carvacrol, ageraborniol, β-sitosterol, stigmasterol, 5-acethyl-3β-angeloxy-2,3-dihydro-2β-(1-hydroxy-isopropyl)-1-benzofuran, 2,2-dimethyl-7-methoxy-2H-1-chromene, 3-O-β-D-galactopyranosyl-5,4′-dihydroxy-6,7-dimethoxy flavones (Bohlmann and Fiedler 1978; Tamayo-Castillo et al. 1989; Herz 2003), 8-β-hydroxy-13-epi-ent-labdan-15-oic acid, 16-α-hydroxy-ent-kauran-19-oic acid, 5-hydroxy-6-7-4′-trimethoxy flavone, 5-hydroxy-3,7,4′-trimethoxy flavone (Morales and Rosquete 1988; Morales and Rosquete 1990), hardwickiic acid, tremetone and the other benzofuran ketones, jhanol, and jhanidiol have been identified from A. jahnii (Lee et al. 2010; Davis et al. 2015). Epifriedelinol, stigmasterol, stigmasterol acetate, octamethylpicen-3-ol, octacosanoic acid, 8-daucosterol, 2-isopropenyl-5-acetyl-6-hydroxy benzofuran acetate, O-hydroxy einnamic acid (Zhu et al. 1995; Ma et al. 2015), α-dotriacontane, β-sitosterol, stigmasterol and taraxasteryl palmitate, taraxasteryl acetate (Xu et al. 1988; Xie et al. 2010), and 5,6-dihydroxycadinan-3-ene-2,7-dione from E. adenophorum Spreng exhibited antinemic activity (Kundu et al. 2016).

9β-Hydroxy-ageraphorone, fenvalerate, 9-oxo-ageraphorone, 9-oxo-10,11-dehydro-ageraphorone, 5-O-trans-o-coumaroylquinic acid methyl ester, chlorogenic acid methyl ester, macranthoin F, and macranthoin G were separated from A. adenophora and possess insecticidal property (Zhang et al. 2013). Thymol derivatives such as hydroxypiperitol glucoside, germacranolides, 7,9-di-isobutyryloxy-8-ethoxythymol, 7-acetoxy-8-methoxy-9-isobutyryloxythymol, 7,9-di-isobutyryloxy-8-methoxythymol, 9-oxoageraphorone, (−)-isochaminic acid and (1α,6α)-10-hydroxycar-3-ene-2-one, and provincialin were identified from Ageratina anisochroma (Tamayo-Castillo et al. 1988; Tori et al. 2001; Dong et al. 2017). Phenolic compounds such as 7-hydroxy-8,9-dehydrothymol 9-O-trans-ferulate, 7-hydroxythymol 9-O-trans-ferulate, 7,8-dihydroxythymol 9-O-trans-ferulate, 7,8-dihydroxythymol 9-O-cis-ferulate, methyl (7R)-3-deoxy-4,5-epoxy-D-manno-2-octulosonate 8-O-trans-p-coumarate, methyl (7R)-3-deoxy-4,5-epoxy-D-manno-2-octulosonate 8-O-cis-p-coumarate, and 3-(2-hydroxyphenyl)propyl methyl malonate were isolated from ethanolic extract of the roots of A. adenophora (Zhou et al. 2013).