New Acylated Triterpene Saponins from Silene fortunei that Modulate Lymphocyte Proliferation

Gaidi, Ghezala; Miyamoto, Tomofumi; Laurens, Véronique; Lacaille‐Dubois, Marie‐Aleth

doi:10.1021/np020105a

Cited by 48 publications

(36 citation statements)

References 18 publications

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“…The saponins, jenisseensosides C and D and their deacylated derivatives stimulated the proliferation of the Jurkat tumor cell lines (human T-cell leukaemia) at low concentrations (1 nM to 5 μM). At high concentrations (>10 μM), they inhibited the proliferation of the cells probably due to the induction of apoptosis [28]. These authors [49] reported that the trans-and cis-p-methoxycinnamoyl triterpene saponins jenisseensosides A to D (from S. jenisseensis and S. fortunei) increased the accumulation and cytotoxicity of the anticancer agent cisplatin in HT 29 (human colon tumor) cells.…”

Section: Antitumor Activitymentioning

confidence: 99%

Diversity of Secondary Metabolites in the Genus Silene L. (Caryophyllaceae)—Structures, Distribution, and Biological Properties

2014

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Abstract:The genus Silene (family Caryophyllaceae) comprises more than 700 species, which are widely distributed in temperate zones of the Northern Hemisphere, but are also present in Africa and have been introduced in other continents. Silene produces a high diversity of secondary metabolites and many of them show interesting biological and pharmacological activities. More than 450 compounds have been isolated; important classes include phytoecdysteroids (which mimic insect molting hormones), triterpene saponins (with detergent properties), volatiles, other terpenoids and phenolics. This review focusses on the phytochemical diversity, distribution of Silene secondary metabolites and their biological activities.

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Section: Antitumor Activitymentioning

confidence: 99%

Diversity of Secondary Metabolites in the Genus Silene L. (Caryophyllaceae)—Structures, Distribution, and Biological Properties

2014

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“…Since some saponins from plants in the Caryophyllaceae have been reported to exert immunomodulant activities, 13,14) compounds 1 and 2 were tested in an in vitro lymphocyte proliferation test system according to a reported procedure, 15,16) and in the in vitro T cell activation assay according to the reported method. 17) Only 1 showed an immunomodulatory effect dependent on concentration.…”

Section: Xylopyranosyl-(1→4)]-a -L-rhamnopyranosyl-(1→2)-b -D-fucopyrmentioning

confidence: 99%

Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Luo

Kong

Takaya

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Gypsophila oldhamiana MIQ. (Caryophyllaceae) is widely distributed in Shanxi and Shandong province in China. The roots of this plant have been used as an alternative remedy to the most common traditional Chinese medicine Yin-Chai-Hu (roots of Stellria dichotoma var. Lanceolata Bge) and utilized to treat heat due to yin deficiency, hectic and tidal fever, and infantile malnutrition syndrome in China.1) Previous chemical investigation on the roots of this species led to the isolation of saponins, sterols, and fatty acid.2-5) As a part of our search for bioactive saponins from traditional Chinese medicine, we present in this report the isolation and structural elucidation of two new saponins (1, 2) from the roots of G. oldhamiana. In addition, their immunologic properties were investigated. Results and DiscussionThe 70% EtOH extract of the roots of G. oldhamiana was partitioned with water and CHCl 3 . The water layer was chromatographed successively over marcoporous resin D101, silica gel, and ODS-C 18 to yield compounds 1 and 2, which were identified as quillaic acid, a-L-arabinopyranosyl- (2) (Fig. 1).Compound 1 was obtained as a white amorphous powder. Its molecular formula was assigned as C 57 H 90 O 25 determined from its pseudomolecular ion peak at m/z 1175.5833 [MϩH] ϩ (Calcd 1175.5849) in the HR-FAB-MS. The IR spectrum showed absorption at 3600-3300 cm Ϫ1 (-OH) and 1724 cm Ϫ1 (ester carbonyl). The alkaline hydrolysis of 1 yielded quillaic acid identified by TLC in comparison with an authentic sample 6) and an oligosaccharide. Acid hydrolysis of 1 afforded quillaic acid and monosaccharides, D-fucose, L-rhamnose, D-xylose, and L-arabinose identified by gas chromatography in comparison with standard monosaccharides.6) The proton and carbon signals (Tables 1, 2) were assigned by a combination analysis of 1D and 2D NMR (HSQC and HMBC). The aglycone moiety was further identified by comparison with literature data.2) The chemical shifts of C-3 (d 71.7) and C-28 (d 176.3) indicated that 1 was a monodesmosidic glycoside in which the sugar moiety was connected at C-28. units were determined from their 3 J H1,H2 coupling constants (7-8 Hz) and 13 C-NMR data.8) The a-anomeric configuration of rhamnose was judged by its C 5 (d 68.3).9) The sequence of the oligosaccharide chains in 1 was determined from the HMBC spectrum. Two new monodesmosidic triterpene saponins were isolated from the roots of Gypsophila oldhamiana (Caryophyllaceae). Their structures were elucidated on the basis of spectral data to be quillaic acid, a a-L-arabinopyranosyl- (

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“…Silene species possess mainly triterpene saponins and ecdysteroids [4,5]. Ecdysteroids have been found in more than 120 species and subspecies of Silene from 155 species so far tested [6].…”

Section: Introductionmentioning

confidence: 99%

“…Ecdysteroids have been found in more than 120 species and subspecies of Silene from 155 species so far tested [6]. The steroid-containing fractions of some Silene species are immunosuppressive, potentially antiinflammatory [6], inhibit the proliferation of cancer cells by inducing apoptosis [5], and show in vivo anticancer activity in mice [7]. On the other hand, several studies are devoted to the fatty acid and essential oil composition of various Silene species [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents, Cytotoxic, Antioxidant and Cholinesterases Inhibitory Activities of Silene Compacta (Fischer) Extracts

Boğa¹

2017

Marmara Pharmaceutical Journal

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In Turkey, Silene species have been used as infusion in urinary bladder and biliary tract diseases in traditional medicine. Silene species have been also consumed as food in Anatolia and Europe. In this study, the phenolic, fatty acid and essential oil profiles and the cytotoxic, antioxidant and cholinesterases inhibitory activities, and total phenolic-flavonoid content of Silene compacta Fischer (SC) were studied. The essential oil and fatty acid compositions of S. compacta were determined by using GC/MS in the current study. The chemical composition of the methanol extract was determined using LC-MS/MS for quantitative and qualitative purposes. The major components of the essential oil and fatty acid were identified as α-selinene (12.4%) and palmitic acid (26.3%), respectively. The methanol extract (SCM: S. compacta methanol extract) which possessed the best activity in four tested antioxidant methods among the tested extracts exhibited very strong cholinesterases inhibitory activities. Additionaly, this extract indicated the highest cytotoxic effect against A549 cells. In the SCM extract, hesperidin and rutin, quinic and malic acids were quantified by LC-MS/MS as major contituents.

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New Acylated Triterpene Saponins from Silene fortunei that Modulate Lymphocyte Proliferation

Cited by 48 publications

References 18 publications

Diversity of Secondary Metabolites in the Genus Silene L. (Caryophyllaceae)—Structures, Distribution, and Biological Properties

Diversity of Secondary Metabolites in the Genus Silene L. (Caryophyllaceae)—Structures, Distribution, and Biological Properties

Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Chemical Constituents, Cytotoxic, Antioxidant and Cholinesterases Inhibitory Activities of Silene Compacta (Fischer) Extracts

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