Triterpene glycosides of Chenopodium ambrosioides

Abstract

We have investigated the roots of Chenopodium ambrosioides L., collected in 1969 in the Moscow oblast [Introduction Laboratory of the All-Union Scientific-Research Institute for Medicinal Plants (VILR)]. The combined saponins isolated by the extraction of the roots with methanol and subsequent twice-repeated reprecipitation in acetone consisted, according to thin-layer chromatography, of two glycosides which we have called in order of increasing polarity chenopodiosides A and B. When the combined triterpene glycosides were chromatographed on a column of KSK silica gel, chenopodioside B was isolated, with the composition C52H82022 ,mp 213-216°C [~]~-50 ° (c 0.5; ethanol), tool. wt, 1071 (spectrophotometrically) [1]. The complete acid hydrolysis of chenopodioside B gave us echinocystic acid with mp 304-306°C (methanol), [~]~+47.6 ° (c 0.3; ethanol). Literature data: mp 305-306°C, [~]~+33 ° (c 1.5; chloroform) [2]. The acetate of this echinocystic acid, with mp 260-264°C (methanol), had physicochemical constants which agreed with those of an authentic sample kindly given to us by V. Ya. Chirva (Kishinev). According to paper chromatography, the carbohydrate part of chenopodioside B contains glucuronic acid, rhamnose, xylose, and arabinose. The alkaline hydrolysis of chenopodioside B formed a less polar glycoside with mp 285-287°C (methanol) giving on acid hydrolysis glucuronic acid and rhamnose, while xylose and arabinose were found inthe aqueous fraction from the alkaline hydrolyzate. The stepwise acid hydrolysis of chenopodioside B gave a glucuronide of echinocystic acid with mp 182-185°C (methanol), [~]~-34.3 ° (c 0.5; ethanol). Thus, in the glycoside studied glucuronic acid and rhamnose are attached to the hydroxy group of echinocystic acid and xylose and arabinose to the carboxy group. LITERATURE CITED

Biological activities and chemistry of saponins from Chenopodium quinoa Willd.

“…Several chemical investigations concerns C. ambrosioides (Bogacheva et al 1974), C. anthelminticum (Chirva et al 1971), C. album (Lavaud et al 2000), C. ficifolium (Gohar et al 2002), and C. pallidicaule (Rastrelli et al 1996). Earlier reviews (Ahamed et al 1998) covered nutritional composition of the seeds and the leaves but did not focus on biological activities and chemistry of triterpene saponins.…”

“…1 Different oxidation steps occurring in the oleanolic acid and serjanic acid aglycones from the bamyrin leading to hederagenin, 3b-hydroxy-23-oxo-12-en-28-oic acid, serjanic acid, phytolaccagenic acid, and 3b, 23a, 30b-Trihydroxy-12-en-28-oic acid as a common feature. Some Chenopodium species such as C. ambrosioides (Bogacheva et al 1974) and C. anthelminticum (Chirva et al 1971) have a carbohydrate chain attached at C22.…”