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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Dehydrobruceine C, A New Quassinoid from the Seeds of Brucea javanica

Author(s): Jun Li, Dayong Zheng, Yukun Sun, Yunfeng Sun, Li Liu, Ying Fan* and Lide Zhang*

Volume 14, Issue 5, 2017

Page: [368 - 371] Pages: 4

DOI: 10.2174/1570178614666170420182036

Price: $65

Abstract

Background: The seeds of Brucea javanica are known to be an abundant source of quassinoids, which have a structurally diverse and wide spectrum of biological effects, such as potential antiinflammatory, antitumor, antimalarial, antiamebic, and cytotoxic activities. However, only several dehydro-quassinoids were isolated and identified in this plant.

Methods: The EtOAc extract of the seeds of B. javanica was submitted to silica gel CC, ODS, Sephadex LH-20, and RP-HPLC to get four compounds. Their chemical structures were elucidated by spectroscopic methods including UV, IR, 1D-NMR, 2D-NMR, and HR-MS. The inhibitory effects of 1-4 on nitric oxide (NO) production in lipopolysaccharide-activated macrophages were also evaluated.

Results: A new dehydro-quassinoid namely, dehydrobruceine C (1), along with bruceine B (2), bruceine C (3), and bruceantinol (4) were separated from the EtOAc extract of the seeds of B. javanica. Compounds 1-4 displayed different intensity inhibitory effects on NO production, and their IC50 values were 33.11, 26.83, 9.08 and 8.25 μM, respectively, compared to indomethacin.

Conclusion: B. javanica has been proven to contain structurally diverse and biologically active quassinoids. This is the first report on the isolation and chemical structure identification of dehydrobruceine C (1), this new quassinoid compound exhibited moderate anti-inflammatory activities in vitro.

Keywords: Brucea javanica, dehydrobruceine C, nitric-oxide production, quassinoid, simaroubaceae.

Graphical Abstract

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