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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology*
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Butylene Glycols / chemistry
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Butylene Glycols / isolation & purification
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Cardenolides / chemistry
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Cardenolides / isolation & purification*
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Cardenolides / pharmacology*
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Chromones / chemistry
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Chromones / isolation & purification*
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Chromones / pharmacology*
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Drug Screening Assays, Antitumor
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Female
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Furans / chemistry
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Furans / isolation & purification
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Glycosides / chemistry
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Glycosides / isolation & purification*
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Glycosides / pharmacology*
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HT29 Cells
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Humans
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Hypoxia-Inducible Factor 1, alpha Subunit / antagonists & inhibitors*
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Hypoxia-Inducible Factor 1, alpha Subunit / drug effects
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Lignans / chemistry
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Lignans / isolation & purification
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Magnoliopsida / chemistry*
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Mexico
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Plants, Medicinal / chemistry*
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Structure-Activity Relationship
Substances
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3beta-((O-beta-D-glucopyranosyl-(1-3)-4,6-dideoxy-2-O-methyl-beta-D-glucopyranosyl))-5beta,14beta-dihydroxy-19-oxocard-20(22)enolide
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5-hydroxy-2-methylchromone-7-O-rutinoside
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5-hydroxy-6-methoxy-2-methylchromone-7-O-rutinoside
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Antineoplastic Agents, Phytogenic
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Butylene Glycols
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Cardenolides
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Chromones
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Furans
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Glycosides
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Hypoxia-Inducible Factor 1, alpha Subunit
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Lignans
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matairesinol
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secoisolariciresinol