Two glycosides from roots of Asiasarum sieboldi

doi:10.1016/0031-9422(92)83303-G

Phytochemistry

Volume 31, Issue 7, July 1992, Pages 2477-2480

https://doi.org/10.1016/0031-9422(92)83303-G Get rights and content

Abstract

Two new glycosides, 1-O-feruloyl-β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranoside and 1-O-p-coumaroyl-β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranoside together with four known glycosides have been isolated from the roots of Asiasarum sieboldi. The structures of new compounds have been established on the basis of physiochemical and spectral analyses.

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Asarum species have been used in Chinese traditional medicine more than 2000 years for the treatment of colds, headaches, and rheumatism (Liu and Wang, 2022). Phytochemical studies on the genus Asarum revealed the presence of lignans, phenanthrenes (Jing et al., 2017), flavonoids (Iwashina and Kitajima, 2000), and many other metabolites (Hashimoto et al., 1992). Some of these natural products have exhibited antipyretic, analgesic, anti-inflammatory, and anticancer effects (Liu and Wang, 2022).
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Several phenanthrenes (1–5), phenolics (6–8) and steroidal sapogenins (9–11) were isolated for the first time from the aqueous and methanolic extracts of Dioscorea sansibarensis Pax yam collected from Tanzania. Chemical structures of all the isolates (1–11) were determined by using 1D and 2D nuclear magnetic resonance spectral methods. All pure isolates were evaluated for anti-inflammatory activity using in vitro cyclooxygenase enzyme (COX-1 and -2) inhibitory assays. Among the isolates tested, phenanthrenes 3–5 showed the highest COX-1 and -2 enzyme inhibitory activity whereas phenolics (6–8) and steroidal sapogenins (9–11) exhibited moderate inhibition when compared to non-steroidal anti-inflammatory drugs aspirin, ibuprofen and naproxen. Compounds 6–11 were evaluated for antioxidant activity using lipid peroxidation inhibitory (LPO) assay for the first time and exhibited moderate LPO inhibition.
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Nine phenylpropanoid glycosides, lycibarbarphenylpropanoids A–I (1–9), and one coumarin glycoside, lycibarbarcoumarin A (29) were new compounds also isolated. To our knowledge, 22 known compounds [1-O-trans-feruloyl-6-O-β-d-xylopyranosyl-β-d-glucopyranoside (10) (Hashimoto et al., 1992), 6-O-trans-p-coumaroyl-2-O-β-d-glucopyranosyl-α-d-glucopyranoside (11) (Matsufuji, Otsuki, Takeda, Chino, & Takeda, 2003), 6-O-trans-feruloyl-2-O-β-d-glucopyranosyl-α-d-glucopyranoside (12) (Matsufuji et al., 2003), 1-O-trans-feruloyl-β-d-glucopyranoside (13) (Kim, Kwon, Sa, & Kim, 2011), ethyl 4-O-β-d-glucopyranosyl-trans-p-coumarate (14) (Struijs, Vincken, Verhoef, Voragen, & Gruppen, 2008), ethyl 4-O-β-d-glucopyranosyl-trans-ferulate (15) (Struijs et al., 2008), ethyl trans-p-coumarate (16) (Table S10, Supporting Information), ethyl trans-ferulate (17) (Table S11, Supporting Information), trans-sinapinic acid (18) (Table S12, Supporting Information), syringenin (19) (Table S12, Supporting Information), cis-ferulic acid (24) (Salum, Robles, & Erra-Balsells, 2010), phloretic acid (26) (Owen et al., 2003), dihydroferulic acid (27) (Li et al., 2003), ethyl dihydroferulate (28) (Table S15, Supporting Information), medioresinol (34) (Wang et al., 2014), syringaresinol (35) (Takeshi, 1983), 4-O-β-d-glucopyranosyl-syringaresinol (36) (Wang et al., 2014), threo-1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (39) (He et al., 2014), erythro-1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (40) (He et al., 2014), derrone (46) (Shao et al., 2013), alpinumisoflavone (47) (Shao et al., 2013), and auriculasin (48) (Ganapaty et al., 2014)] were obtained from the genus Lycium for the first time. In view of the traditional effects of wolfberry, antioxidant and anti-AD activities of 53 polyphenols were evaluated.
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A new coumaronochromone and phenolic constituents from the leaves of Iris bungei Maxim.
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Fraction 5 was subjected to a silica gel column (3 × 60 cm, 200–300 mesh), eluting with CHCl3–Me2CO to give vanillic acid (7, 3 mg) (Aldrich Chemical Company Inc., 1992b) and p-coumaric acid (8, 6 mg) (Aldrich Chemical Company Inc., 1992c). Fractions 7–13 were purified by a silica gel CC process and recrystallization to get mangiferin (9, 3000 mg) (Fujita and Inoue, 1982) and 3′,5′-dimethoxy-4′-O-β-d-glucopyranosyl-cinnamic acid (10, 30 mg) (Hashimoto et al., 1992). The structures of the known compounds (2–10) were elucidated by comparison of their UV, IR, ESI-MS, 1H NMR and 13C NMR data with the published data.
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Sixteen compounds were isolated from the MeOH extract of leaves of Myoporum bontioides. The five compounds hitherto unknown, were elucidated to be a chlorine-containing iridoid, named myopochlorin, and an iridoid glucoside, an acylated iridoid glucoside, a linear acetogenin glucoside, and an acyclic monoterpene glucoside, named myobontiosides A–D, respectively, by means of spectroscopic analyses.

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^☆: Part 2 in the series ‘The Constituents of Asiasarum sieboldi’. Fort Part 1 see ref. [1].

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Two glycosides from roots of Asiasarum sieboldi☆

Abstract

Phytochemistry

Tetrahedron