Carapanolides J-L from the seeds of Carapa guianensis (Andiroba) and their effects on LPS-activated NO production

Yuuki Matsui; Takashi Kikuchi; Takanobu Inoue; Osamu Muraoka; Takeshi Yamada; Reiko Tanaka

doi:10.3390/molecules191117130

Carapanolides J-L from the seeds of Carapa guianensis (Andiroba) and their effects on LPS-activated NO production

Molecules. 2014 Oct 24;19(11):17130-40. doi: 10.3390/molecules191117130.

Authors

Yuuki Matsui¹, Takashi Kikuchi¹, Takanobu Inoue¹, Osamu Muraoka², Takeshi Yamada¹, Reiko Tanaka³

Affiliations

¹ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
² Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashiosaka, Osaka 577-8502, Japan.
³ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@gly.oups.ac.jp.

Abstract

A novel gedunin and two novel phragmalin-type limonoids, named carapanolides J-L (compounds 1-3) as well as a known gedunin-type limonoid 4 were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D and 2D NMR spectroscopy and HRFABMS. Compounds 1-4 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages.

MeSH terms

Animals
Cell Line
Limonins / chemistry*
Limonins / pharmacology
Lipopolysaccharides / pharmacology
Macrophages / drug effects
Macrophages / metabolism
Magnetic Resonance Spectroscopy / methods
Meliaceae / chemistry*
Mice
Nitric Oxide / metabolism*
Seeds / adverse effects*

Substances

Limonins
Lipopolysaccharides
gedunin
Nitric Oxide