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A cytotoxic decahydronaphthalenylpropenal derivative and tetrahydrofuran lignans from the stems of Cameraria latifolia.

ABSTRACT: A new decahydronaphthalenylpropenal derivative, (+)-camerarialdehyde (1), a new tetrahydrofuran lignan, (-)-diepiolivil (2), and two known lignans were isolated from a methanol-soluble extract of the stems of Cameraria latifolia, which was obtained from a repository donated to IHVR by Merck Research Laboratories. The structures of compounds 1 and 2 were determined by interpretation of their spectroscopic data, with the absolute configuration of 1 being established by analysis of its CD spectrum. The absolute configuration of the 1,3-diol moiety of 2 was proposed from the CD spectrum induced with dimolybdenum tetraacetate in DMSO solution. All compounds isolated were evaluated against HT-29 human colon cancer cells, and compound 1 was found to show cytotoxicity toward this cell line.

SUBMITTER: Ren Y

PROVIDER: S-EPMC3755466 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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A cytotoxic decahydronaphthalenylpropenal derivative and tetrahydrofuran lignans from the stems of Cameraria latifolia.

Ren Yulin Y Chai Heebyung H Goetz Michael M Kinghorn A Douglas AD

Tetrahedron letters 20130901 36

A new decahydronaphthalenylpropenal derivative, (+)-camerarialdehyde (1), a new tetrahydrofuran lignan, (-)-diepiolivil (2), and two known lignans were isolated from a methanol-soluble extract of the stems of Cameraria latifolia, which was obtained from a repository donated to IHVR by Merck Research Laboratories. The structures of compounds 1 and 2 were determined by interpretation of their spectroscopic data, with the absolute configuration of 1 being e ...[more]

PMID: 23997317

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Project description:The genus Wikstroemia has about 70 species, but only a limited number of species have been studied chemically. Wikstroemia indica has long been used as a traditional crude drug in China. However, there is no report about the bioactivity of Wikstroemia scytophylla.This paper reports the chemical investigation and biological evaluation of the W. scytophylla.The EtOAc extraction of W. scytophylla was isolated using chromatographic methods, and the compounds were analyzed by spectroscopic methods. The in vitro antitumor activities against five human cancer cell lines were performed according to the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide method.The chemical investigation of the stems of W. scytophylla resulted in the isolation of 12 compounds mainly including one biflavone (1), five flavones (2-6) compounds, and six lignans (7-12), in which compound 8 was a new natural product. Compounds 1 and 7-12 were evaluated for their antitumor activities while these compounds showed weak cytotoxicity with the half maximal inhibitory (IC50) values more than 40 μM.All of these compounds were isolated from this plant for the first time, and compounds 2-12 were first reported from genus Wikstroemia, in which compound 8 was a new natural product. Compounds 1 and 7-12 exhibited weak antitumor activities (IC50>40 μM). The chemotaxonomic significance of all the isolations was summarized.The chemical investigation of the stems of W. scytophylla resulted in the isolation of 12 compoundsThe 12 compounds including six lignans (7-12), in which compound 8 was a new natural productThe isolated compounds 1 and 7-12 were evaluated for their antitumor activitiesThe chemotaxonomic significance of all the isolations was summarized. Abbreviations used: MTT: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide; IC50: Half maximal inhibitory; HL-60: Human leukemia cell line; SMMC-7721: Human hepatocellular carcinoma cell line; A549: Human lung tumor cell line; MCF-7: Human breast cancer cell line; SW480: Human colon cancer cell line; MS: Mass spectrometry; NMR: Nuclear Magnetic Resonance.

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A cytotoxic decahydronaphthalenylpropenal derivative and tetrahydrofuran lignans from the stems of Cameraria latifolia.

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A cytotoxic decahydronaphthalenylpropenal derivative and tetrahydrofuran lignans from the stems of <i>Cameraria latifolia.</i>

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