Diterpenoids from the stem bark of Croton megalocarpoides Friis & M. G. Gilbert

[Display omitted] •Ent-clerodane with a rare bicyclo[5.4.0]undecane skeleton was isolated from stembark of C. megalocarpoides Friis & Gilbert.•The ent-clerodane with a rare bicyclo[5.4.0]undecane skeleton was determined using logic for structural determination.•Four unreported ent-clerodanes wer...

Full description

Saved in:

Bibliographic Details
Published in:	Phytochemistry letters Vol. 39; pp. 1 - 7
Main Authors:	Langat, Moses K., Ndunda, Beth M., Salter, Caitlin, Odusina, Babatope O., Isyaka, Sani M., Mas-Claret, Eduard, Onocha, Patricia A., Midiwo, Jacob O., Nuzillard, Jean-Marc, Mulholland, Dulcie A.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 01-10-2020 Elsevier
Subjects:	1-trans-p-hydroxycoumaroyl–geranylgerani-1-ol 12-epi-crotonzambefuran A Analytical chemistry Chemical Sciences Croton megalocarpoides Friis & M. G. Gilbert Euphorbiaceae Logic for structure determination Megalocarpoidolide I Megalocarpoidolide J Megalocarpoidolide K Organic chemistry Megalocarpoidolide J Megalocarpoidolide K 1-trans-p-hydroxycoumaroyl–geranylgerani-1-ol Megalocarpoidolide I 12-epi-crotonzambefuran A Euphorbiaceae Croton megalocarpoides Friis & M. G. Gilbert Logic for structure determination
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	[Display omitted] •Ent-clerodane with a rare bicyclo[5.4.0]undecane skeleton was isolated from stembark of C. megalocarpoides Friis & Gilbert.•The ent-clerodane with a rare bicyclo[5.4.0]undecane skeleton was determined using logic for structural determination.•Four unreported ent-clerodanes were isolated from the stem bark of Croton megalocarpoides Friis & Gilbert.•A 1-trans-p-hydroxycoumaroyl–geranylgerani-1-ol was isolated from the stem bark of Croton megalocarpoides Friis & Gilbert.•Three ent-clerodanes were evaluated against the NCI60 panel of human tumour cell lines at 10μM but found to be inactive. Five previously undescribed compounds, megalocarpoidolide I (1), megalocarpoidolide J (3), 12-epi-crotonzambefuran A (4), megalocarpoidolide K (5), 1-trans-p-hydroxycoumaroyl–geranylgerani-1-ol (6) were isolated from the stem bark of Croton megalocarpoides Friis & M. G. Gilbert. The known ent-trachyloban-18-ol, megalocarpoidolide B, megalocarpoidolide C (2), megalocarpoidolide H, crotocorylifuran, 7,8-dehydrocrotocorylifuran, 1,2-dehydrocrotocorylifuran-2-one, acetyl aleuritolic acid, lupeol, N-trans-p-coumaroyl-3′,4′-dihydroxyphenylethylamine, dodecyl trans-ferulate and lignoceryl trans-ferulate were also isolated. The structures of the compounds were determined using NMR, IR spectroscopy and HRMS. The structure of compound 1 was determined using Logic for Structural Determination (LSD). Compounds 1, 2 and 3 that were selected for screening based on their ability to add diversity to the NCI small molecule compound collection, were evaluated against the NCI60 panel of human tumour cell lines at 10μM level but found to be inactive.
ISSN:	1874-3900 1876-7486
DOI:	10.1016/j.phytol.2020.07.003