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Open AccessArticle

Lignans from the Twigs of Litsea cubeba and Their Bioactivities

1
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China
2
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
3
Beijing Key Laboratory of Bioactive Substances and Functional Foods, Beijing Union University, Beijing 100023, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Muhammad Ilias
Molecules 2019, 24(2), 306; https://doi.org/10.3390/molecules24020306
Received: 18 December 2018 / Revised: 30 December 2018 / Accepted: 4 January 2019 / Published: 16 January 2019
Litsea cubeba, an important medicinal plant, is widely used as a traditional Chinese medicine and spice. Using cytotoxicity-guided fractionation, nine new lignans 19 and ten known analogues 1019 were obtained from the EtOH extract of the twigs of L. cubeba. Their structures were assigned by extensive 1D- and 2D-NMR experiments, and the absolute configurations were resolved by specific rotation and a combination of experimental and theoretically calculated electronic circular dichroism (ECD) spectra. In the cytotoxicity assay, 7′,9-epoxylignans with feruloyl or cinnamoyl groups (compounds 79, 13 and 14) were selectively cytotoxic against NCI-H1650 cell line, while the dibenzylbutyrolactone lignans 1719 exerted cytotoxicities against HCT-116 and A2780 cell lines. The results highlighted the structure-activity relationship importance of a feruloyl or a cinnamoyl moiety at C-9′ or/and C-7 ketone in 7′,9-epoxylignans. Furthermore, compound 11 was moderate active toward protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 13.5 μM, and compounds 46, 11 and 12 displayed inhibitory activity against LPS-induced NO production in RAW264.7 macrophages, with IC50 values of 46.8, 50.1, 58.6, 47.5, and 66.5 μM, respectively. View Full-Text
Keywords: Litsea cubeba; cytotoxicity; isolation and elucidation; lignans Litsea cubeba; cytotoxicity; isolation and elucidation; lignans
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MDPI and ACS Style

Li, X.; Xia, H.; Wang, L.; Xia, G.; Qu, Y.; Shang, X.; Lin, S. Lignans from the Twigs of Litsea cubeba and Their Bioactivities. Molecules 2019, 24, 306.

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