Anthrone and oxanthrone C,O-diglycosides from Picramnia teapensis

• Published in: Phytochemistry (Oxford) Vol. 55; no. 7; pp. 837 - 841
• Main Authors: Rodriguez-Gamboa, T, Victor, Fernandes, JB, Fo, ER, da Silva, MFGF, Vieira, PC, Pagnocca, FC, Bueno, OC, Hebling, MJA, Castro, O
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 01.12.2000
• Subjects: Biochemistry & Molecular Biology; Biological and medical sciences; Chemical constitution; Chromatography, High Pressure Liquid; Fundamental and applied biological sciences. Psychology; Glycosides - chemistry; Glycosides - isolation & purification; Life Sciences & Biomedicine; Molecular Structure; Plant physiology and development; Plant Sciences; Rosales - chemistry; Science & Technology; Spectrum Analysis; anthrone glycoside; Simaroubaceae; anthraquinone glycosides; oxanthrone glycoside; ANTIDESMA; Picramnia teapensis; picramnioside; mayoside; antifungal activity; Bioassay; Pesticides; Bark; Biological activity; Fungicide; Stem; Anthraquinone; Ketophenols; Dicotyledones; Angiospermae; Isolation; Lignan; Spermatophyta; Glycoside
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(00)00323-X

Two C,O-diglycosylated compounds, the anthrone picramnioside F, and the oxanthrone mayoside C, were isolated from the stem bark of Picramnia teapensis, along with the previously reported anthraquinones, 1-O-beta -D- and 8-O-beta -D-glucopyranosyl emodin. The compounds were separated by recycling-HPLC, and their structures were determined on the basis of spectroscopic analysis. CD measurements were used to establish the absolute configuration of the anthrone and oxanthrone. The antifungal activity of 1-O-beta -D- and 8-O--D-glucopyranosyl emodin against Leucoagaricus gongilophorus was shown to be similar to that of the lignan sesamin. (C) 2000 Elsevier Science Ltd. All rights reserved.