Andirolides W-Y from the flower oil of andiroba (Carapa guianensis, Meliaceae)

Asami Sakamoto; Yuji Tanaka; Takeshi Yamada; Takashi Kikuchi; Osamu Muraoka; Kiyofumi Ninomiya; Toshio Morikawa; Reiko Tanaka

doi:10.1016/j.fitote.2014.09.003

Andirolides W-Y from the flower oil of andiroba (Carapa guianensis, Meliaceae)

Fitoterapia. 2015 Jan:100:81-7. doi: 10.1016/j.fitote.2014.09.003. Epub 2014 Sep 6.

Authors

Asami Sakamoto¹, Yuji Tanaka¹, Takeshi Yamada¹, Takashi Kikuchi¹, Osamu Muraoka², Kiyofumi Ninomiya³, Toshio Morikawa⁴, Reiko Tanaka⁵

Affiliations

¹ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
² Laboratory of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
³ Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
⁴ Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Electronic address: morikawa@kindai.ac.jp.
⁵ Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. Electronic address: tanakar@gly.oups.ac.jp.

PMID: 25200371
DOI: 10.1016/j.fitote.2014.09.003

Abstract

Three new limonoids, andirolides W-Y (1-3), were isolated from the flower oil of Carapa guianasis AUBLET (Meliaceae). Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Seven known limonoids: 7-deacetoxy-7-oxogedunin (4), 6α-acetoxygedunin (5), methylangolensate (6), 6α-hydroxygedunin (7), 6α-acetoxy-7α-deacetoxy-7α-hydroxygedunin (8), gedunin (9), and 7-deacetoxy-7-hydroxygedunin (10) from this flower oil were evaluated for the effects on the production of NO in LPS-activated mouse peritoneal macrophages.

Keywords: Andirolides W–Y; Carapa guianensis; Flower; Limonoid; Meliaceae; NO production.

MeSH terms

Animals
Flowers / chemistry
Limonins / chemistry*
Limonins / isolation & purification
Macrophages, Peritoneal / drug effects*
Male
Meliaceae / chemistry*
Mice
Molecular Structure
Nitric Oxide / biosynthesis
Plant Oils / chemistry*

Substances

Limonins
Plant Oils
andirolide W
andirolide X
andirolide Y
Nitric Oxide