Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus

• Published in: Journal of Natural Products
• Main Author: Bihud N.V.; Rasol N.E.; Imran S.; Awang K.; Ahmad F.B.; Mai C.-W.; Leong C.-O.; Cordell G.A.; Ismail N.H.
• Format: Article
• Language: English
• Published: American Chemical Society 2019
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85071887359&doi=10.1021%2facs.jnatprod.8b01067&partnerID=40&md5=f24aead5a42422f067a84aa8d3354a86

Eight new bis-styryllactones, goniolanceolatins A-H (1-8), possessing a rare α,β-unsaturated Î-lactone moiety with a (6S)-configuration, were isolated from the CH2Cl2 extract of the stembark and roots of Goniothalamus lanceolatus Miq., a plant endemic to Malaysia. Absolute structures were established through extensive 1D-A nd 2D-NMR data analysis, in combination with electronic dichroism (ECD) data. All of the isolates were evaluated for their cytotoxicity against human lung and colorectal cancer cell lines. Compounds 2 and 4 showed cytotoxicity, with IC50 values ranging from 2.3 to 4.2 μM, and were inactive toward human noncancerous lung and colorectal cells. Compounds 1, 3, 6, 7, and 8 showed moderate to weak cytotoxicity. Docking studies of compounds 2 and 4 showed that they bind with EGFR tyrosine kinase and cyclin-dependent kinase 2 through hydrogen bonding interactions with the important amino acids, including Lys721, Met769, Asn818, Arg157, Ile10, and Glu12. Copyright © 2019 American Chemical Society and American Society of Pharmacognosy.