title: Cytotoxic and HIF-1alpha inhibitory compounds from Crossosoma bigelovii.
abstract: Cytotoxicity-guided fractionation of an organic solvent extract of the plant Crossosoma bigelovii led to the discovery of a new strophanthidin glycoside (1) and two new 2-methylchromone glycosides (2 and 3). Also isolated were the known chromones eugenin and noreugenin, the indole alkaloid ajmalicine, the dibenzylbutane lignan secoisolariciresinol, the dibenzylbutyrolactone lignan matairesinol, and the furanone 5-tetradec-5-enyldihydrofuran-2-one. Further investigation into the biological properties of strophanthidin glycosides revealed a connection between inhibition of HIF-1 activation and the glycosylation of the genin. This work is the first published study of the bioactive phytochemicals of the family Crossosomataceae.
authors.affiliation: Natural Products Support Group, SAIC-Frederick, Inc, NCI-Frederick, Frederick, Maryland 21702, USA.
authors.forename: Paul
authors.initials: P
authors.lastname: Klausmeyer
authors.forename: Qin
authors.initials: Q
authors.lastname: Zhou
authors.forename: Dominic A
authors.initials: DA
authors.lastname: Scudiero
authors.forename: Badarch
authors.initials: B
authors.lastname: Uranchimeg
authors.forename: Giovanni
authors.initials: G
authors.lastname: Melillo
authors.forename: John H
authors.initials: JH
authors.lastname: Cardellina
authors.forename: Robert H
authors.initials: RH
authors.lastname: Shoemaker
authors.forename: Ching-Jer
authors.initials: CJ
authors.lastname: Chang
authors.forename: Thomas G
authors.initials: TG
authors.lastname: McCloud
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002072:Butylene Glycols / Q000737:chemistry / Q000302:isolation & purification; D002298:Cardenolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019073:HT29 Cells; D006801:Humans; D051795:Hypoxia-Inducible Factor 1, alpha Subunit / Q000037:antagonists & inhibitors* / Q000187:drug effects; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification; D019684:Magnoliopsida / Q000737:chemistry*; D008800:Mexico; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: C550782:3beta-((O-beta-D-glucopyranosyl-(1-3)-4,6-dideoxy-2-O-methyl-beta-D-glucopyranosyl))-5beta,14beta-dihydroxy-19-oxocard-20(22)enolide; C550780:5-hydroxy-2-methylchromone-7-O-rutinoside; C550781:5-hydroxy-6-methoxy-2-methylchromone-7-O-rutinoside; D000972:Antineoplastic Agents, Phytogenic; D002072:Butylene Glycols; D002298:Cardenolides; D002867:Chromones; D005663:Furans; D006027:Glycosides; D051795:Hypoxia-Inducible Factor 1, alpha Subunit; D017705:Lignans; C068935:matairesinol; C060283:secoisolariciresinol