Two New Biologically Active Triterpene Saponins from <i>Acanthophyllum squarrosum</i>

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

doi:10.1021/np000212+

Cited by 28 publications

(42 citation statements)

References 19 publications

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“…Mass spectra were obtained on a MS Agilent 1100 Series LC/MSD Trap Mass spectrometer (ESI-MS), and a JEOL-HX-110 spectrometer (HR-FAB-MS) using m-nitrobenzyl alcohol as a matrix. 1D and 2D NMR spectra were recorded in C 5 D 5 N at 300 K on Bruker ACF-500 NMR ( 1 H: 500 MHz, 13 C: 125 MHz) spectrometers, with tetramethylsilane (TMS) as an internal standard, in which coupling constants were given in Hz. Gas chromatography was done on a GC-14B Gas Chromatograph (Shimadzu), with an SE30 capillary column (12 m, 0.22 mm i.d.…”

Section: Methodsmentioning

confidence: 99%

“…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%

“…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).…”

mentioning

confidence: 99%

“…Base upon the above information, the aglycone moiety of 2 was established to be 3b, 4a-dihydroxy-23-norolean-12-en-28-oic acid, a nortriterpenoid sapogenin called vaccaric acid, which has been only isolated as an aglycone of saponins from Vaccaria segetalis (NECK) GARCKE (Caryophyllaceae). 11) In addition to the signals of the aglycone, the 13 …”

mentioning

confidence: 99%

“…2). Therefore the structure of 2 was determined to be vaccaric acid, a) The assignments were based upon 1 H-NMR, 13 C-NMR, HSQC, and HMBC spectra. b) 13 C chemical shifts of substituted residues are underlined.…”

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confidence: 99%

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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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Section: Methodsmentioning

confidence: 99%

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

confidence: 99%

“…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).…”

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Luo

Kong

Takaya

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Chubak (Acanthophyllum glandulosum) Root Gum

Karazhiyan

2019

Emerging Natural Hydrocolloids

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Naturally Occurring Triterpenoid Saponins

Dinda

Debnath²,

Mohanta

et al. 2010

Chemistry & Biodiversity

140

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Naturally occurring new triterpenoid saponins reported from mid-1996 to March, 2007 are reviewed including their physical constants and plant sources, and are compiled in Table 1. New saponins are arranged in Table 1 on the basis of the skeletal structures of their aglycones, e.g., oleanane type, ursane type, lupane type, hopane type, taraxastane type, cycloartane type, lanostane type, tirucallane type, dammarane type, cucurbitane type, and holostane type. The known triterpenoid saponins and prosapogenins of the new saponins, the biological and pharmacological activities of which were published during 1996-2007, are also reviewed together with their plant sources listed in Table 2 according to the skeletal structures of their aglycones in the same fashion as in Table 1. The plant and animal sources of both new and known bioactive triterpenoid saponins are collected in Table 3 in alphabetical order. The biological and pharmacological activities such as antiallergic, antiatherosclerosis and antiplatelet, antibacterial, anticomplementary, antidiabetic, contraceptive, antifungal, anti-inflammatory, antileishmanial, antimalarial/antiplasmodial, anti-obesity, anti-proliferative, antipsoriatic, antispasmodic, antisweet, antiviral, cytotoxic/antitumor, detoxication, gastroprotective, haemolytic, hepatoprotective, immunomodulatory, anti-enzyme, anti-osteoporotic, insecticidal, insulin-like, membrane-porosity, molluscicidal, neuropharmacological, anti-endothelial dysfunction, snake venom antidote, and sweet activities of these saponins or derived prosapogenins are discussed briefly after Table 3.

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Two New Biologically Active Triterpene Saponins from Acanthophyllum squarrosum

Cited by 28 publications

References 19 publications

Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Chubak (Acanthophyllum glandulosum) Root Gum

Naturally Occurring Triterpenoid Saponins

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