title: Bioactive flavaglines and other constituents isolated from Aglaia perviridis.
abstract: Eight new compounds, including two cyclopenta[b]benzopyran derivatives (1, 2), two cyclopenta[b]benzofuran derivatives (3, 4), three cycloartane triterpenoids (5-7), and an apocarotenoid (8), together with 16 known compounds, were isolated from the chloroform-soluble partitions of separate methanol extracts of a combination of the fruits, leaves, and twigs and of the roots of Aglaia perviridis collected in Vietnam. Isolation work was monitored using human colon cancer cells (HT-29) and facilitated with an LC/MS dereplication procedure. The structures of the new compounds (1-8) were determined on the basis of spectroscopic data interpretation. The Mosher ester method was employed to determine the absolute configurations of 5-7, and the absolute configuration of the 9,10-diol unit of compound 8 was established by a dimolybdenum tetraacetate [Mo2(AcO)4] induced circular dichroism procedure. Seven known rocaglate derivatives (9-15) exhibited significant cytotoxicity against the HT-29 cell line, with rocaglaol (9) being the most potent (ED50 0.0007 μM). The new compounds 2-4 were also active against this cell line, with ED50 values ranging from 0.46 to 4.7 μM. The cytotoxic compounds were evaluated against a normal colon cell line, CCD-112CoN. In addition, the new compound perviridicin B (2), three known rocaglate derivatives (9, 11, 12), and a known sesquiterpene, 2-oxaisodauc-5-en-12-al (17), showed significant NF-κB (p65) inhibitory activity in an ELISA assay.
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, USA.
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.forename: Ulyana Muñoz
authors.initials: UM
authors.lastname: Acuña
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.forename: Nivedita
authors.initials: N
authors.lastname: Jena
authors.forename: Tran Ngoc
authors.initials: TN
authors.lastname: Ninh
authors.forename: Caroline M
authors.initials: CM
authors.lastname: Pannell
authors.forename: Heebyung
authors.initials: H
authors.lastname: Chai
authors.forename: James R
authors.initials: JR
authors.lastname: Fuchs
authors.forename: Esperanza J
authors.initials: EJ
authors.lastname: Carcache de Blanco
authors.forename: Djaja D
authors.initials: DD
authors.lastname: Soejarto
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D031602:Aglaia / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology*; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006801:Humans; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors*; D019906:Nuclear Magnetic Resonance, Biomolecular; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014744:Vietnam
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D001572:Benzofurans; D001578:Benzopyrans; D016328:NF-kappa B; D014315:Triterpenes; C510144:rocaglaol