Secondary Metabolites of Medicinal Plants. Bharat Singh
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2.6 Ageratina Species
2.6.1 Ethnopharmacological Properties and Phytochemistry
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,