title: Sphenostylisins A-K: bioactive modified isoflavonoid constituents of the root bark of Sphenostylis marginata ssp. erecta.
abstract: 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).
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University , 500 West 12th Avenue, Columbus, Ohio 43210, United States.
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.forename: Ye
authors.initials: Y
authors.lastname: Deng
authors.forename: Ulyana
authors.initials: U
authors.lastname: Muñoz-Acuña
authors.forename: Chunhua
authors.initials: C
authors.lastname: Yuan
authors.forename: Hongshan
authors.initials: H
authors.lastname: Lai
authors.forename: Heebyung
authors.initials: H
authors.lastname: Chai
authors.forename: Tangai E
authors.initials: TE
authors.lastname: Chagwedera
authors.forename: Norman R
authors.initials: NR
authors.lastname: Farnsworth
authors.forename: Esperanza J
authors.initials: EJ
authors.lastname: Carcache de Blanco
authors.forename: Chenglong
authors.initials: C
authors.lastname: Li
authors.forename: Djaja D
authors.initials: DD
authors.lastname: Soejarto
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D002942:Circular Dichroism; D007529:Isoflavones / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D031303:Sphenostylis / Q000737:chemistry*
chemical_list: D007529:Isoflavones; D010936:Plant Extracts; C000588940:sphenostylisin-A
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