Carapanolides T-X from Carapa guianensis (Andiroba) Seeds

Teppei Miyake; Sari Ishimoto; Naoko Ishimatsu; Keiichiro Higuchi; Katsuhiko Minoura; Takashi Kikuchi; Takeshi Yamada; Osamu Muraoka; Reiko Tanaka

doi:10.3390/molecules201119737

Carapanolides T-X from Carapa guianensis (Andiroba) Seeds

Molecules. 2015 Nov 24;20(11):20955-66. doi: 10.3390/molecules201119737.

Authors

Teppei Miyake¹, Sari Ishimoto², Naoko Ishimatsu³, Keiichiro Higuchi⁴, Katsuhiko Minoura⁵, Takashi Kikuchi⁶, Takeshi Yamada⁷, Osamu Muraoka⁸, Reiko Tanaka⁹

Affiliations

¹ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. teppei-727@ezweb.ne.jp.
² Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. saridon55@yahoo.co.jp.
³ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. mini-mini.naoko@hotmail.co.jp.
⁴ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. rikiaifuni815@yahoo.co.jp.
⁵ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. minoura@gly.oups.ac.jp.
⁶ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. t.kikuchi@gly.oups.ac.jp.
⁷ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. yamada@gly.oups.ac.jp.
⁸ Laboratory of Pharmaceutical Organic Chemistry, Faculty of Pharmacy Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. muraoka@phar.kindai.ac.jp.
⁹ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@gly.oups.ac.jp.

Abstract

Two new mexicanolide-type limonoids, carapanolides T-U (1-2), and three new phragmalin-type limonoids, carapanolides V-X (3-5), were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D- and 2D-NMR spectroscopy.

Keywords: Carapa guianensis; Meliaceae; NO production; andiroba; limonoid; mexicanolide; phragmalin; seeds.

MeSH terms

Animals
Cell Line
Cell Survival / drug effects
Inhibitory Concentration 50
Limonins / chemistry*
Limonins / isolation & purification
Magnetic Resonance Spectroscopy
Meliaceae / chemistry*
Mice
Molecular Structure
Nitric Oxide / biosynthesis
Seeds / chemistry*

Substances

Limonins
Nitric Oxide