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Trichiliasinenoids A-C, three novel 6,7-secomexicanolide limonoid | 41063
Organic Chemistry: Current Research

Organic Chemistry: Current Research
Open Access

ISSN: 2161-0401

Trichiliasinenoids A-C, three novel 6,7-secomexicanolide limonoids with a 7, 29-linkage from Trichilia sinensis


4th European Organic Chemistry Congress

March 01-03, 2018 | London, UK

Donghua Cao

Xishuangbanna Tropical Botanical Garden-CAS, China

Posters & Accepted Abstracts: Organic Chem Curr Res

Abstract :

Meliaceous limonoids, characteristic chemical markers of the Meliaceae family, are natural products with both fascinating structures and potential bioactivities that have attracted interest from both natural products chemists and synthetic chemists in the past half century. As part of a continuing search for structurally interesting and biologically important limonoids from the Meliaceae family, the leaves and twigs of Trichilia sinensis collected from Xishuangbanna, Yunnan province of China were investigated. Trichilia sinensis Bentv, a shrub, is native to the south of China and Vietnam, and has traditional applications for the treatment of several diseases such as abdominal pain caused by Ascaris lumbricoides, chronic osteomyelitis, scabies, and eczema in folk medicine. The three novel rearranged mexicanolide-type limonoids (Trichiliasinenoids A-C) with an unprecedented C-29-C-7 connecting carbon skeleton formed by migration of C-7 from C-6 to C-29 of a mexicanolide-type limonoid precursor were isolated from the leaves and twigs of Trichilia sinensis. Their structures were assigned by spectroscopic analysis, and the absolute configurations were determined by X-ray crystallography and CD calculation. A possible biosynthetic pathway of Trichiliasinenoids A was also proposed. The three new limonoids were evaluated for their cytotoxic activity against human myeloid leukaemia (HL-60), hepatocellular carcinoma (SMMC-7721), lung cancer (A-549), breast cancer (MCF-7), and colon cancer (SW480) cell lines by MTS assay. Trichiliasinenoid B showed cytotoxicity against HL-60 cells, SMMC-7721 with an IC50 value of 5.2 �?µM and 30.6 �?µM, respectively, whereas other limonoids were inactive and comparable to the cisplatin positive control (IC50: 1.1â�?�?17.3 �?µM). caodonghua@xtbg.ac.cn

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