Читать книгу Secondary Metabolites of Medicinal Plants - Bharat Singh - Страница 33

Allium cepa L. (Fam. – Amaryllidaceae) is considered as the largest genus of monocots (Li et al. 2010), known to be carminative and expectorant. The corms are used for treatment of diabetes, arthritis, colds and flu, stress, fever, coughs, headache, hemorrhoids, asthma, and arteriosclerosis in Iranian system of medicine (Jellin et al. 2000). The corms of Allium hirtifolium are used as remedy for rheumatic and inflammatory disorders (Jafarian et al. 2003); bulbs and pounded leaves are applied as paste on the head to treat cold, headache, and fever; the whole plant parts are used against stomachache and tuberculosis. The boiled leaves and crushed bulbs are applied to heal wounds and combat skin infections (Keusgen et al. 2006). Allium ascalonicum, Allium fistulosum, and Allium sativum showed hypoglycemic and antiseptic properties to heal wounds and anti-influenza A effects (Essman 1984; Jalal et al. 2007; Lee et al. 2012). The steroids of Allium chinense are cardioprotective (Ren et al. 2010), the A. cepa bulb is anthelmintic (Bidkar et al. 2012), and the methanolic extract of leaves of Allium stracheyi showed analgesic activities (Ranjan et al. 2010). 3,4-Dihydro-3-vinyl-1,2-dithiin, produced by a thermochemical reaction of allyl 2-propenethiosulfinate, exhibited the highest antioxidative activity (Higuchi et al. 2003). The hypolipidemic, antihypertensive, anti-diabetic, antithrombotic, anti-hyperhomocysteinemia effects, and to possess many other biological activities including antimicrobial, antioxidant, anticarcinogenic, antimutagenic, anti-asthmatic, immunomodulatory, and prebiotic activities (Corzo-Martínez et al. 2007; Ye et al. 2013; Siddiq et al. 2013). The hypoglycemic and hypolipidemic effects of A. cepa were associated with antioxidant activity, because it reduced superoxide dismutase activity in experimental rats (Campos et al. 2003).

Linolenic acid, linoleic acid, palmitic acid, palmitoleic acid, stearic acid, and oleic acid (Ebrahimi et al. 2009; Asgarpanah and Ghanizadeh 2012); hirtifoliosides A1/A2, B, C1/C2, and D; alliogenin 3-O-β-D-glucopyranoside; gitogenin 3-O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranoside; agapanthagenin; 3-O-β-D-glucopyranoside; kaempferol 3-O-β-D-rhamnopyranosyl-(1→2)-glucopyranoside; kaempferol 3-O-β-D-glucopyranosyl-(1→4)-glucopyranoside; kaempferol 3-O-glucopyranoside; and kaempferol-7-O-glucopyranoside have been isolated from A. hirtifolium flowers (Barile et al. 2005). Quercetin-O-glucoside, kaempferol-O-glucoside, quercetin-O-rhamnoside, isorhamnetin-O-hexoside, N-γ-glutamyl-S-allylcysteine, N-γ-glutamylisoleucine, N-γ-glutamyl-S-allylthiocysteine, N-γ-glutamylphenylalanine, and 40-O-glucoside were extracted from A. cepa and A. sativum (Mimaki et al. 1994; Lee and Mitchell 2011; Farag et al. 2017). The tuberoside J, (25R)-5α-spirostan-2α,3β,27-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside; tuberoside K, (25R)-5α-spirostan-2α,3β,27-triol 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside; and tuberoside L, 27-O-β-D-glucopyranosyl-(25R)-5α-spirostan-2α,3β,27-triol 3-O-α-D-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside, and tuberoside M, (2α,3β,5α,25S)-2,3,27-trihydroxyspirostane 3-O-α-L-rhamnopyranoyl-(1→2)-O-[α-L-rhamnopyranoyl-(1→4)]-β-D-glucopyranoside were identified from Allium tuberosum (Zou et al. 2001; Sang et al. 2001, 2002), while proto-eruboside B, proto-iso-eruboside B, eruboside B, and iso-eruboside B from A. sativum (Matsuura et al. 1988). Sativoside-B1, proto-desgalactotigonin, (25R)-26-O-β-D-glucopyranosyl-22-hydroxy-5α-furostane-3β, 6β, 26-triol 3-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside, sativoside-R1, sativoside-R2, (25R)-26-O-β-D-glucopyranosyl-22-hydroxy-5α-furostane-3β, 26-diol 3-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside, desgalactotigonin, and F-gitonin were identified from roots and leaves of A. sativum (Matsuura et al. 1988). Ascalonicoside A1/A2 and ascalonicoside B, furost-5(6)-en-3β,22α-diol 1β-O-β-D-galactopyranosyl-26-O-[α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside], its epimer at position 22, and furost-5(6),20(22)-dien-3β-ol-1β-O-β-D-galactopyranosyl-26-O-[α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside], quercetin, isorhamnetin, and their glycosides were also isolated from A. ascalonicum (Fattorusso et al. 2002).

High performance liquid chromatography (HPLC) determination of A. cepa and A. ascalonicum showed the presence of rutin, isoquercitrin, quercitrin, quercetin and kaempferol, quercetin-3-O-rhamnoside, quercetin-3-O-glucoside, kaempferol-3-O-glucoside, isorhamnetin-3-O-glucoside, kaempferol-3,4′-O-diglucoside, isorhamnetin-3,4′-O-diglucoside, and isolated compounds that demonstrated antioxidant as well as cytotoxic activities (Beesk et al. 2010; Mogren et al. 2006; Olayeriju et al. 2015; Pobłocka-Olech et al. 2016; Fredotović et al. 2017). Quercetin-3,4′-O-diglucoside and quercetin-4′-O-monoglucoside from A. cepa demonstrated antioxidant effects against free radical scavenging activity (FRSA) and hydrogen peroxide (H₂O₂) models (Stajner et al. 2004; Nencini et al. 2007; Jaiswal and Rizvi 2012) as well as antifungal activity (Pârvu et al. 2010). The N-feruloyltyrosine and N-feruloyl-tyramine were isolated from A. sativum and Allium porrum and exhibited antifungal activity against Fusarium culmorum as well as anticancer effects against prostate cancer, ovarian cancer, and renal cell cancer (Fattorusso et al. 1999; Galeone et al. 2006; Mahmoudabadi and Nasery 2009; Pârvu et al. 2009). Quercetin 3,4′-di-O-glucoside, and quercetin 4′-glucoside were identified from A. cepa and showed antioxidant activity (Pudzianowska et al. 2012).

Phenolic acids such as caftaric acid, rutoside, gentisic acid, myricetin, caffeic acid, chlorogenic acid, quercitrin, p-coumaric acid, quercetol, ferulic acid, patuletin, sinapic acid, luteolin, chicoric acid, kaempferol, hyperoside, apigenin, isoquercitrin, and steroids such as ergosterol, brassicasterol, stigmasterol, campesterol, β-sitosterol, alliin, and allicin were identified from Allium obliquum (Vlase et al. 2013; Alpsoy et al. 2013).

The (25R and S)-5α-spirostane-2α,3β,6β-triol 3-O-(O-β-D-glucopyranosyl-(1→2)-O-[3-O-acetyl-β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside); (25R)-2-O-[(S)-3-hydroxy-3-methylglutaroyl]-5-α-spirostane-2α,3β,6β-triol 3-O-(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside); (22S)-cholest-5-ene-1β,3β,16β,22-tetraol 1-O-α-L-rhamnopyranoside 16-O-(O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranoside); 1β,3β,16β-trihydroxycholest-5-en-22-one 1-O-α-L-rhamnopyranoside 16-O-(O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranoside); 1β,3β,16β-trihydroxy-α-cholestan-22-one 1-O-α-L-rhamnopyranoside 16-O-(O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranoside); and (22S)-cholest-5-ene-1β,3β,16β,22-tetraol 16-O-(O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside) have been identified from Allium albopilosum, Allium ostrowskianum and Allium karataviense (Mimaki et al. 1993, 1994). Alliogenin 2-O-β-D-glucopyranoside; (25R)-3-O-acetyl-5α-spirostane-2α,3β,5,6β-tetrol-2-O-β-D-glucopyranoside; (25R)-3-O-benzoyl-5α-spirostane-2α,3β,5,6β-tetrol 2-O-β-D-glucopyranoside; (25R)-spirost-5-ene-2α,3β-diol 3-O-{O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}; alliogenin 3-O{O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}; and minutoside A, minutoside B, and minutoside C have been isolated from A. albopilosum, A. ostrowskianum, and A. karataviense (Mimaki et al. 1999; Barile et al. 2007).

Tropeoside A1/A2 and tropeoside B1/B2 along with 22-O-methyl derivatives from A. cepa var. Tropea, ascalonicoside A1/A2 and ascalonicoside B were isolated from Allium asacalonicum; quercetin, quercetin 4I-glucoside, taxifolin, taxifolin 7-glucoside, and phenylalanine were from A. cepa and possess antispasmodic activity (Corea et al. 2005). Similarly, the 26-O-β-D-glucopyranosyl-5α-furost-25 (27)-ene-3β,12β,22,26-tetraol-3-O-β-D-glucopyranosyl-(1→2) [β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside and 26-O-β-D-glucopyranosyl-5β-furost-20 (22)-25 (27)-dien-3β,12β,26-triol-3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside were separated from Allium macrostemon and exhibited cytotoxic activity against SF-268, while 26-O-β-D-glucopyranosyl-5β-furost-20 (22)-25 (27)-dien-3β,12β,26-triol-3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside showed cytotoxicity against NCI-H460 and SF-268 cell lines (Chen et al. 2009). Yayoisaponin C, eruboside B, aginoside, (25R)-5α-spirostane-3β,6β-diol-3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1→ 4)-β-D-galactopyranoside, leucospiroside A, (25R)-5α-spirostane-2α,3β,6β-triol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside, (25R)-5α-spirostane-3β,6β-diol 3-O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside isolated from Allium leucanthum and showed cytotoxic activity (Mskhiladze et al. 2008). Alliogenin and alliogenin 3-β-D-glucopyranoside have been isolated from the bulbs of Allium giganteum Rgl (Gorovits et al. 1971). Elburzensoside A1/A2, B1/B2, C1/C2, and D1/D2; furost-2α,3β,5α,6β,22α-pentol 3-O-β-D-glucopyranosyl-26-O-β-D-glucopyranoside; furost-2α,3β,5α,6β,22α-pentol 3-O-[β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl]-26-O-β-D-glucopyranoside; furost-2α,3β,5α,22α-tetrol 3-O-β-D-glucopyranosyl-26-O-β-D-glucopyranoside; and furost-2α,3β,5α,22α-tetrol 3-O-[β-D-xylopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→ 4)-O-β-D-galactopyranosyl]-26-O-β-D-glucopyranoside were reported from Allium elburzense (Barile et al. 2004; Zolfaghari et al. 2012), while alliogenin, alliogenin β-D-glucopyranoside, diosgenin, yuccagenin, and karatavigenin were identified from A. karataviense (Gorovits et al. 1973).