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

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 establishe...

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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
id 2-s2.0-85071887359
spelling 2-s2.0-85071887359
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.
Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
2019
Journal of Natural Products
82
9
10.1021/acs.jnatprod.8b01067
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.
American Chemical Society
1633864
English
Article

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.
spellingShingle 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.
Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
author_facet 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.
author_sort 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.
title Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
title_short Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
title_full Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
title_fullStr Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
title_full_unstemmed Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
title_sort Goniolanceolatins A-H, Cytotoxic Bis-styryllactones from Goniothalamus lanceolatus
publishDate 2019
container_title Journal of Natural Products
container_volume 82
container_issue 9
doi_str_mv 10.1021/acs.jnatprod.8b01067
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85071887359&doi=10.1021%2facs.jnatprod.8b01067&partnerID=40&md5=f24aead5a42422f067a84aa8d3354a86
description 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.
publisher American Chemical Society
issn 1633864
language English
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