Sphenostylisins A-K: bioactive modified isoflavonoid constituents of the root bark of Sphenostylis marginata ssp. erecta

Sphenostylisins A-K : bioactive modified isoflavonoid constituents of the root bark of Sphenostylis marginata ssp. erecta

Soejarto, Djaja D (author): University of Illinois at Chicago, USA;Field Museum of Natural History, USA

(creator_code:org_t)

2013-10-03
2013
English.
In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 78:20, s. 10166-10177

Related links:: https://europepmc.or...; show more...; https://urn.kb.se/re...; https://doi.org/10.1...; show less...

Abstract Subject headings

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).

By the author/editor: Li, Jie; Pan, Li; Deng, Ye; Acuña, Ulyana Mu ...; Yuan, Chunhua; Lai, Hongshan; show more...; Chai, Heebyung; Chagwedera, Tang ...; Farnsworth, Norm ...; Carcache de Blan ...; Li, Chenglong; Soejarto, Djaja ...; Kinghorn, A Doug ...; show less...

About the subject

NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

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