Triterpene saponins from fruit of Ilex crenata

doi:10.1016/0031-9422(92)83636-D

Phytochemistry

Volume 31, Issue 8, August 1992, Pages 2809-2812

https://doi.org/10.1016/0031-9422(92)83636-D Get rights and content

Abstract

From the fresh fruits of Ilex crenata have been isolated six new saponins named ilexosides III–VIII, respectively, along with the known saponin, ilexoside II. Their structures were established on the basis of spectral and chemical evidence.

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Cited by (16)

Triterpenoids with antiplatelet aggregation activity from Ilex rotunda
2018, Phytochemistry
Citation Excerpt :
Thus, the structure of compound 7 was concluded to be 19α,23-dihydroxy oleanolic acid 3β-O-β-D-glucuronopyranoside-6-O-methyl ester. The known triterpenoids were identified as 3β,23-dihydroxy-20-epi-urs-12,18-dien-28-oic acid (8) (Li et al., 2015), rotundioic acid (9) (Amimoto et al., 1992), mateside (10) (Taketa et al., 2004), 19α,23-dihydroxyurs-12-en-28-oic acid 3β-O-β-D-glucuronopyranoside-6′O-methyl ester (11) (Li et al., 2014), ilexside II (12) (Nakanishi et al., 1982), pomolic acid (13) (Kakuno et al., 1992), 28-O-β-D-glucopyranosyl pomolic acid (14) (Amimoto et al., 1992), 9-anhydro-4-epirotungenic acid (15) (Nakatani et al., 1989), 3β,23-dihydroxyursa-12,18 (19)-dien-28-oic acid 28-β-D-glucopyranosyl ester (16) (Wu et al., 2007), ilexosapogenin B (17) (Amimoto et al., 1993b), ilemaminoside A (18) (Che et al., 2012), pedunculoside (19) (Amimoto et al., 1993a), hedergenin 3-O-β-D-glucuronopyranoside-6′O-methyl ester (20) (Kizu et al., 1985), oleanolin acid 3-O-β-D-glucuronopyranoside-6′O-methyl ester (21) (Kizu et al., 1985), gardeniside B (22) (Wang et al., 2012) and 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid (23) (Liu et al., 2005) by means of spectroscopic analysis as well as comparison with literature data. Several triterpenoids isolated from this genus were reported to exhibit antiplatelet aggregation activity (Fan et al., 2015; Yang et al., 2015).
Phytochemical studies on the barks of Ilex rotunda Thunb. had resulted in the isolation of seven previously undescribed triterpenoids, rotundinosides E-K, along with sixteen known ones. The structures of previously undescribed compounds were elucidated on the basis of extensive spectroscopic analysis and the sugar moieties were further identified by HPLC and GC after acid hydrolysis. Among the isolates, rotundinoside F featured a rare triterpene-phenylpropanoid hybrid structure and rotundinoside H was an uncommon triterpene saponin with α-linked glucopyranosyl moiety at C-3. The antiplatelet aggregation of all compounds were evaluated against ADP induced rat platelet aggregation in vitro, and five compounds exhibited moderate inhibitory effects with IC₅₀ values ranging from 22.4 to 32.8 μM.
Mazusaponins I-IV, triterpene saponins from Mazus miquelii
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From whole plants of Mazus miquelii, four new saponins designated as mazusaponins I–IV and a known saponin, ilexoside VIII, were isolated and the structures of the new compounds elucidated as 3-O-α-l-arabinopyranosyl siaresinolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, 3-O-α-l-arabinopyranosyl pomolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, 3-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl siaresinolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester and 3-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl pomolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, respectively, by spectroscopic data and chemical evidence.
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2011, Quimica Nova

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^☆: Part 3 in the series ‘Saponins from Ilex spp.’, for Part 2 see ref. [1].

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Triterpene saponins from fruit of Ilex crenata☆

Abstract

Tetrahedron

Tetrahedron Letters

Phytochemistry