Four triterpenoid saponins from dried roots of Gypsophila species

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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“…with the literature data for similarly linked sugar moieties, 12) which was confirmed by HMQC, HMBC, and NOESY experiments (Fig. 2).…”

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confidence: 88%

Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Luo

Kong

Takaya

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…2). The structural fragement deduced above had been reported, 6) whose molecular weight was 1542, referring to the quasi-molecular ion mass …”

Section: Resultsmentioning

confidence: 99%

Triterpenoid Saponins from Gypsophila altissima L.

Chen

Luo

Kong

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In the course of our studies on the bioactive constituents of medicinal foodstuffs, 1,4) we have also characterized many triterpene glycosides from the fruit of M. charantia originated in Japan, Thailand, Indonesia, India, and Sri Lanka. In this paper, we present the isolation and structure elucidation of goyaglycosides-a (1), -b (2), -c (3), -d (4), -e (5), -f (6), -g (7), and -h (8) and goyasaponins I (9), II (10), and III (11) from the fresh fruit of Japanese M. charantia, which is commonly called "nigauri" or "goya".…”

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confidence: 99%

“…The aqueous phase was extracted with 1-butanol to furnish a 1-butanol extract and an aqueous extract. The 1-butanol extract was subjected to normal-and reversed-phase silica gel column chromatography and finally HPLC to give goyaglycosides-a (1), -b (2), -c (3), -d (4), -e (5), -f (6), -g (7), and -h (8), goyasaponins I (9), II (10), and III (11), and momordicosides A 3a) (12), C 3b) (13), F 1 3c) (14), I 3c) (15), and K 3d) (16). Structures of Cucurbitane-Type Triterpene Glycosides (1-8) Goyaglycoside-a (1) was obtained as a white pow-der with negative optical rotation ([a] D 26 Ϫ101.4°).…”

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confidence: 99%

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Medicinal Foodstuffs. XXI. Structures of New Cucurbitane-Type Triterpene Glycosides, Goyaglycosides-a, -b, -c, -d, -e, -f, -g, and -h, and New Oleanane-Type Triterpene Saponins, Goyasaponins I, II, and III, from the Fresh Fruit of Japanese Momordica charantia L.

et al. 2001

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The Cucurbitaceae plant Momordica (M.) charantia L. (Japanese name "Tsurureishi") is cultivated as a vegetable in Asian countries. In Chinese, Indian Ayurvedic, and Indonesian Jamu traditional medicines, the fruit of this plant has been used as a bitter stomachic, a laxative, an antidiabetic, and an anthelmintic for children. Recently, the alcoholic extract from the fruit of M. charantia originated in Sri Lanka was reported to inhibit the increase of serum glucose in glucose-loaded rats.2) As chemical constituents of the fruit, many cucurbitane-type triterpene glycosides were reported, 3) but the constituents responsible for the inhibition of glucose absorption have not been identified. In the course of our studies on the bioactive constituents of medicinal foodstuffs, 1,4) we have also characterized many triterpene glycosides from the fruit of M. charantia originated in Japan, Thailand, Indonesia, India, and Sri Lanka. In this paper, we present the isolation and structure elucidation of goyaglycosides-a (1), -b (2), -c (3), -d (4), -e (5), -f (6), -g (7), and -h (8) and goyasaponins I (9), II (10), and III (11) from the fresh fruit of Japanese M. charantia, which is commonly called "nigauri" or "goya".The cucurbitane-and oleanene-type triterpene glycosides of the fresh fruit of Japanese M. charantia were separated by the procedures shown in Chart 1. The methanolic extract obtained from the fresh fruit of M. charantia was partitioned into an ethyl acetate and a water mixture to give an ethyl acetate extract and an aqueous phase. The aqueous phase was extracted with 1-butanol to furnish a 1-butanol extract and an aqueous extract. The 1-butanol extract was subjected to normal-and reversed-phase silica gel column chromatography and finally HPLC to give goyaglycosides-a

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Four triterpenoid saponins from dried roots of Gypsophila species

Cited by 64 publications

References 3 publications

Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Triterpenoid Saponins from Gypsophila altissima L.

Medicinal Foodstuffs. XXI. Structures of New Cucurbitane-Type Triterpene Glycosides, Goyaglycosides-a, -b, -c, -d, -e, -f, -g, and -h, and New Oleanane-Type Triterpene Saponins, Goyasaponins I, II, and III, from the Fresh Fruit of Japanese Momordica charantia L.

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