Saponin and sapogenol. XLIX: On the constituents of the roots of Glycyrrhiza inflata BATALIN from Xinjiang, China. Characterization of two sweet oleanane-type triterpene oligoglycosides, apioglycyrrhizin and araboglycyrrhizin

Two sweet oleanane-type triterpene oligoglycosides named apioglycyrrhizin and araboglycyrrhizin were isolated from the air-dried roots of Glycyrrhiza inflata Batalin, collected in Xinjiang province (Shinkyo-Kanzo in Japanese), together with glycyrrhizin (3), licorice-saponins A3 (8), G2 (10), and H2...

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Published inChemical & pharmaceutical bulletin Vol. 41; no. 8; pp. 1350 - 1357
Main Authors KITAGAWA, I, HORI, K, SAKAGAMI, M, HASHIUCHI, F, YOSHIKAWA, M, JIALI REN
Format Journal Article
LanguageEnglish
Published Tokyo Maruzen 1993
Subjects
Biological and medical sciences
China
General pharmacology
Glycyrrhetinic Acid - analogs & derivatives
Glycyrrhetinic Acid - analysis
Glycyrrhiza - chemistry
Medical sciences
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plants, Medicinal
Saponins - analysis
Asia
China
Terpenoid
Sweet product
Medicinal plant
Saponin
Leguminosae
Folk medicine
Structure activity relation
Dicotyledones
Angiospermae
Plant origin
Triterpene
Isolation
Spermatophyta
Sweetener
Glycoside
Structural analysis
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Summary:Two sweet oleanane-type triterpene oligoglycosides named apioglycyrrhizin and araboglycyrrhizin were isolated from the air-dried roots of Glycyrrhiza inflata Batalin, collected in Xinjiang province (Shinkyo-Kanzo in Japanese), together with glycyrrhizin (3), licorice-saponins A3 (8), G2 (10), and H2 (11) and known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of apioglycyrrhizin and araboglycyrrhizin have been determined to be expressed as 3-O-[beta-D-apiofuranosyl(1-->2)-beta-D- glucuronopyranosyl]glycyrrhetic acid (1) and 3-O-[alpha-L- arabinopyranosyl(1-->2)-beta-D-glucuronopyranosyl]glycyrrhet ic acid (2), respectively. During the course of these studies, it has been found that the hydroxyl groups in the oligosaccharide moiety of the glucuronide saponins may be partially methylated by prolonged treatment with diazomethane in methanol. The sweetness of the saponins hitherto isolated from various Glycyrrhizae Radix has been examined and a structure-sweetness relationship, as compared with glycyrrhizin, has been found.
Bibliography:ObjectType-Article-1
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.41.1350