Issue 45, 2020
From the journal:

Organic & Biomolecular Chemistry

Carapanins A–C: new limonoids from andiroba (Carapa guianensis) fruit oil†

Takashi Kikuchi, ORCID logo *a   Keiko Akita,a   Hiroki Koike,a   Yasuko In, ORCID logo a   Takeshi Yamada ORCID logo a  and  Reiko Tanakaa  

* Corresponding authors

a Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
E-mail: t.kikuchi@gly.oups.ac.jp

Abstract

Carapanins A–C (1–3) were isolated from the fruit oil of Carapa guianensis. Compounds 1 and 2 are limonoids with unique structures. Namely, compound 1 is an andirobin-type limonoid with a C-15/C-30 γ-lactone instead of the δ-lactone of the D-ring, and compound 2 is a mexicanolide-type limonoid with a C-16/C-30 δ-lactone ring. The absolute structures of 1 and 2 were determined using X-ray crystallography, whereas the structure of 3 was established mainly via NMR and mass spectroscopy. The inhibitory effects of 1–3 on nitric oxide production were evaluated, and it was revealed that 2 and 3 were potent nitric oxide inhibitors.

Graphical abstract: Carapanins A–C: new limonoids from andiroba (Carapa guianensis) fruit oil

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D0OB01872D
Article type
Paper
Submitted
10 Sep 2020
Accepted
28 Oct 2020
First published
06 Nov 2020

Org. Biomol. Chem., 2020,18, 9268-9274

Permissions

Request permissions

Carapanins A–C: new limonoids from andiroba (Carapa guianensis) fruit oil

T. Kikuchi, K. Akita, H. Koike, Y. In, T. Yamada and R. Tanaka, Org. Biomol. Chem., 2020, 18, 9268 DOI: 10.1039/D0OB01872D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements