Gypsogenic Acid Research Articles

Cytotoxicity of Triterpenes Isolated from Aceriphyllum rossii

Bioassay-guided fractionation of a MeOH extract of the whole plant of Aceriphyllum rossii (Saxifragaceae) led to the isolation of two new triterpenes, 3alpha,23-isopropylidenedioxyolean-12-en-27-oic acid (1) and 23-hydroxy-3-oxoolean-12-en-27-oic acid (2), together with six known triterpenes, 3-oxoolean-12-en-27-oic acid (3), 3alpha-hydroxyolean-12-en-27-oic acid (4), beta-peltoboykinolic acid (5), aceriphyllic acid A (6), oleanolic acid (7), and gypsogenic acid (8). The structures of these compounds were elucidated on the basis of physicochemical and spectroscopic analyses. These compounds were evaluated for in vitro cytotoxicity against the K562 and HL-60 cell lines. Olean-12-en-27-oic acid derivatives (1-6) exhibited considerable cytotoxicity against K562 and HL-60 cell lines with IC(50) values ranging from 12.2 to 28.7 microM and from 12.1 to 25.8 microM, respectively.

Triterpenoid Saponins from the Fruits of Caryocar glabrum

Twenty-one new triterpenoid saponins, named caryocarosides (1-21), glycosides of 2beta-hydroxyoleanolic acid, hederagenin, bayogenin, and gypsogenic acid, have been isolated from the fruits of Caryocar glabrum along with nine known triterpenoid saponins (22-30) that are described for the first time from a plant in the Caryocaraceae. Their structures were established by 1D and 2D NMR techniques ((13)C, COSY, TOCSY, HSQC, HMBC, and ROESY experiments), ESIMS, and acid hydrolysis. The isolated compounds could be classified into two series: glucosides (1-8, 22, 27, and 30) derived from the 3-O-monoglucoside and glucuronides (9-21, 23-26, 28, and 29) derived from the 3-O-monoglucuronide. In 22 of the saponins (1-8, 12-22, and 24-26), a galactose moiety was linked to C-3 of a glucuronic acid or a glucose moiety. The galactose was substituted in position 3 by a second galactose unit (6, 7, 20, and 21) or by a xylose unit (8). Seven saponins (4, 5, 16-19, and 26) were found to be bidesmosides with one glucose unit linked to C-28 of the aglycon. The hemolytic activity of the major saponins (2, 3, 5, 12-15, 17, 24, and 28) was measured on sheep erythrocytes in order to establish structure-activity relationships based on the type of sugar attached to the aglycon and on the structure of this aglycon.

New Oleanene Glycosides from the Leaves of Acanthopanax japonicus

The structures of 6 new oleanene glycosides (1--6) isolated from the leaves of Acanthopanax japonicus FRANCH et. SAVART (Araliaceae) were elucidated by mass, 1D, and 2D NMR spectroscopy. The structures of 1--6 were established as 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester of 3beta,23-dihydroxy-olean-12-en-28,29-dioic acid, 3beta,30-dihydroxy-olean-12-en-23,28-dioic acid, 3beta,29-dihydroxy-olean-12-en-23,28-dioic acid (=dianic aicd), 3beta-dihydroxy-olean-12-en-23,28-dioic acid (=gypsogenic acid), 3beta,29-dihydroxy-23-oxo-olean-12-en-28-oic acid, and 3beta-hydroxy-23-oxo-olean-12-en-28,29-dioic acid, designated acanjaposide D (1), E (2), F (3), G (4), H (5), and I (6), respectively.

Molluscicidal saponins from Swartzia simplex

One monodesmosidic saponin and six bidesmosidic saponins have been isolated from the methanolic extract of the leaves of Swartzia simplex. They were shown to be glucuronides of oleanolic acid, gypsogenin and gypsogenic acid by chemical and spectral means. The monodesmosidic saponins exhibit various molluscicidal activities against the schistosomiasis-transmitting snail Biomphalaria glabrata.

Phytochemical study onMelandrium firmum

The aglycones of saponins isolated fromMelandrium firmum were identified as gypsogenin, gypsogenic acid and quillaic acid.

Analgesic and antihepatotoxic actions of dianosides, triterpenoid saponins of Dianthus superbus var. longicalycinus herbs.

The triterpenoid saponins isolated from the herbs of DIANTHUS SUPERBUS var. LONGICALYCINUS have been evaluated for analgesic and antihepatotoxic activities. The saponins of the gypsogenic acid series were more intensely analgesic than those of the dianic acid series. The efficacy of substances in the former series was potentiated by increased hydrophilic character. On the other hand, the aglycones elicited antihepatotoxic activity in a CCl 4 -induced cytotoxicity assay, and this activity decreased as the number of hydroxyl groups increased. However, they mediated no appreciable antihepatotoxic activity in a GalN-induced cytotoxicity assay. This was probably due to concomitant cytotoxic activity caused by the substances themselves. No definite structure-activity relationship was found in the antihepatotoxic actions of the saponins.

Triterpene glycosides ofClimacoptera transoxana. IV. Structures of copterosides G and H

From the epigeal part of the plantClimacoptera transoxana (Iljin) Botsch. have been isolated new triterpene glycosides — copterosides G and H, which are bisdesmosidic glycosides. On the basis of chemical transformations and spectral characteristics, copteroside G has been assigned the structure of gypsogenic acid 28-O-β-D-glucopyranoside 3-O-β-D-glucuronopyranoside, while copteroside H is gypsogenic acid 28-O-β-D-glucopyranoside 3-O-[O-β-D-xylopyranosyl-(1 → 2)-β-glucuronopyranoside].

Saponin and sapogenol. XXXI. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (1). Triterpenoidal sapogenols and 3-furanmethanol .BETA.-D-glucopyranoside.

3-Furanmethanol β-D-glucopyranoside (1) and (+)-catechin 7-O-β-D-glucopyranoside (3) were isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae) and their structures were substantiated. The saponin mixture designated as total azukisaponin was also isolated from azuki beans. By means of enzymatic hydrolysis, acidic hydrolysis, and photochemical degradation, four genuine sapogenols, which included three known sapogenols, sophoradiol (7), soyasapogenol B (8), gypsogenic acid (9), and a new sapogenol named azukisapogenol (10), were isolated from total azukisaponin and the structure of 10 was elucidated. As one of the artifact sapogenols which were liberated by acidic hydrolysis of total azukisaponin, a new sapogenol named anhydrosophoradiol (5) was isolated and its structure was elucidated.

Formation of gypsogenic acid on the hydrolysis of gypsogenin glycosides

Formation of gypsogenic acid on the hydrolysis of gypsogenin glycosides

Synthesis of glycosides of gypsogenin and of gypsogenic acid by the orthoester method

1. Gypsogenin 3-β-D-glucopyranoside has been obtained for the first time. 2. The natural 3-(β-D-xylopyranoside) of gypsogenic acid (saponaroside) has been synthesized.

Triterpene glycosides of Dianthus deltoides. I

FromDianthus deltoides L. we have isolated three new triterpene glycosides: dianthosides A, B, and C. It has been shown that dianthoside A is the 3-O-β-glucopyranoside and dianthoside B the 3-O-[O-β-D-glucopyranosyl-(1 → 6)-β-glucopyranoside] of gypsogenic acid. Some information on the structure of dianthoside C — a new glycoside of gypsogenin — has been obtained.

Triterpene glycosides fromSaponaria officinalis

The roots ofSaponaria officinalis L. have yielded the known triterpene glycoside gypsoside and the first glycoside of gypsogenic acid, which has been named saponaroside. Saponaroside is the 3-β-D-xylopyranoside of gypsogenic acid.

Gypsogenic acid from the roots ofAcanthophyllum subglabrum andA. gypsophiloides

Gypsogenic acid, previously obtained by the oxidation of gypsogenin and hederagenin, has been found for the first time inA. subglabrum andA. gypsophiloides.