Guianolides A and B, new carbon skeletal limonoids from the seeds of Carapa guianensis

Takanobu Inoue; Yuuki Matsui; Takashi Kikuchi; Yasuko In; Takeshi Yamada; Osamu Muraoka; Shunyo Matsunaga; Reiko Tanaka

doi:10.1021/ol400924u

Guianolides A and B, new carbon skeletal limonoids from the seeds of Carapa guianensis

Org Lett. 2013 Jun 21;15(12):3018-21. doi: 10.1021/ol400924u. Epub 2013 Jun 4.

Authors

Takanobu Inoue¹, Yuuki Matsui, Takashi Kikuchi, Yasuko In, Takeshi Yamada, Osamu Muraoka, Shunyo Matsunaga, Reiko Tanaka

Affiliation

¹ Osaka University of Pharmaceutical Sciences , 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan, and Faculty of Pharmaceutical Sciences, Kinki University , 3-4-1 Kowakae, Higashiosaka, Osaka 577-8502, Japan.

PMID: 23734934
DOI: 10.1021/ol400924u

Abstract

Two novel limonoids, named guianolides A (1) and B (2), were isolated from the seeds of Carapa guianensis AUBLET (Meliaceae). Their structures were established by spectroscopic analyses and X-ray crystallography. Guianolides A (1) and B (2) featured an unprecedented carbon skeleton via the formation of a C-11-C-21 bond.

MeSH terms

Carbon / chemistry*
Crystallography, X-Ray
Limonins / chemistry*
Limonins / isolation & purification
Molecular Structure

Substances

Limonins
guianolide A
guianolide B
Carbon