title: Bioactive constituents of Indigofera spicata.
abstract: Four new flavanones, designated as (+)-5″-deacetylpurpurin (1), (+)-5-methoxypurpurin (2), (2S)-2,3-dihydrotephroglabrin (3), and (2S)-2,3-dihydrotephroapollin C (4), together with two known flavanones (5 and 6), three known rotenoids (7-9), and one known chalcone (10) were isolated from a chloroform-soluble partition of a methanol extract from the combined flowers, fruits, leaves, and twigs of Indigofera spicata, collected in Vietnam. The compounds were obtained by bioactivity-guided isolation using the HT-29 human colon cancer, 697 human acute lymphoblastic leukemia, and Raji human Burkitt's lymphoma cell lines. The structures of 1-4 were established by extensive 1D- and 2D-NMR experiments, and the absolute configurations were determined by the measurement of specific rotations and CD spectra. The cytotoxic activities of the isolated compounds were tested against the HT-29, 697, Raji, and CCD-112CoN human normal colon cells. Also, the quinone reductase induction activities of the isolates were determined using the Hepa 1c1c7 murine hepatoma cell line. In addition, cis-(6aβ,12aβ)-hydroxyrotenone (7) was evaluated in an in vivo hollow fiber bioassay using HT-29, MCF-7 human breast cancer, and MDA-MB-435 human melanoma cells.
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, USA.
authors.forename: Lynette
authors.initials: L
authors.lastname: Bueno Pérez
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.forename: Daniel D
authors.initials: DD
authors.lastname: Lantvit
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.forename: Tran Ngoc
authors.initials: TN
authors.lastname: Ninh
authors.forename: Hee-Byung
authors.initials: HB
authors.lastname: Chai
authors.forename: Djaja Djendoel
authors.initials: DD
authors.lastname: Soejarto
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swanson
authors.forename: David M
authors.initials: DM
authors.lastname: Lucas
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005260:Female; D044950:Flavanones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019073:HT29 Cells; D006801:Humans; D029883:Indigofera / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D014744:Vietnam
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D044950:Flavanones
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