Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Three New Resin Glycosides and a New Tetrahydropyran Derivative from the Seeds of Quamoclit pennata
Masateru Ono, Yoshinari Takaki, Masamitsu Takatsuji, Kousuke Akiyama, Masafumi Okawa, Junei Kinjo, Hiroyuki Miyashita, Hitoshi Yoshimitsu, Toshihiro Nohara
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Keywords: Quamoclit pennata, resin glycoside, jalapin, tetrahydropyran derivative, Convolvulaceae
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2012 Volume 60 Issue 8 Pages 1083-1087

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Abstract

Three new resin glycosides, quamoclins V (1), VI (2), and VII (3) and a new tetrahydropyran derivative, quamopyran (4), were isolated from the seeds of Quamoclit pennata BOJER (Convolvulaceae). The chemical structures of these compounds were determined primarily on the basis of spectroscopic data. The carboxyl group of the aglycone, 11S-convolvulinolic acid, of 1 and 2 was linked intermoleculary with a hydroxy group of the sugar moiety to form a macrocyclic ester structure, as in already known jalapins, and 3 was an acylated glycosidic acid methyl ester. All of the sugar moieties of 1–3 were acylated by one 2S-methylbutyric acid. Compound 4 was a diketone having a tetrahydropyran ring.

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© 2012 The Pharmaceutical Society of Japan
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