Sphenostylisins A-K: bioactive modified isoflavonoid constituents of the root bark of Sphenostylis marginata ssp. erectaShow others and affiliations
2013 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 78, no 20, p. 10166-10177Article in journal (Refereed) Published
Sustainable development
SDG 3: Ensure healthy lives and promote well-being for all at all ages
Abstract [en]
Sphenostylisins A-C (1-3), three complex dimeric compounds representing two novel carbon skeletons, along with an additional eight new compounds, sphenostylisins D-K (4-11), were isolated from the active chloroform-soluble extract of the root bark of Sphenostylis marginata ssp. erecta using a bioactivity-guided isolation approach. The structures were elucidated by means of detailed spectroscopic analysis, including NMR and HRESIMS analysis, and tandem MS fragmentation was utilized to further support the structures of 1-3. The absolute configuration of sphenostylisin C (3) was established by electronic circular dichroism analysis. Plausible biogenetic relationships between the modified isoflavonoids 1-11 are proposed, and a cyclization reaction of 9 was conducted to support one of the biogenetic proposals made. All of these pure isolates were evaluated against a panel of in vitro bioassays, and among the results obtained, sphenostylisin A (1) was found to be a very potent NF-κB inhibitor (IC50 = 6 nM).
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2013. Vol. 78, no 20, p. 10166-10177
Keywords [en]
NF-κB, drug discovery
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-101823DOI: 10.1021/jo401573hPubMedID: 24044416Scopus ID: 2-s2.0-84886405795OAI: oai:DiVA.org:lnu-101823DiVA, id: diva2:1540903
2021-03-302021-03-302021-04-28Bibliographically approved