title: Neolignans and other metabolites from Ocotea cymosa from the Madagascar rain forest and their biological activities.
abstract: Ten new neolignans including the 6'-oxo-8.1'-lignans cymosalignans A (1a), B (2), and C (3), an 8.O.6'-neolignan (4a), ococymosin (5a), didymochlaenone C (6a), and the bicyclo[3.2.1]octanoids 7-10 were isolated along with the known compounds 3,4,5,3',5'-pentamethoxy-1'-allyl-8.O.4'-neolignan, 3,4,5,3'-tetramethoxy-1'-allyl-8.O.4'-neolignan, didymochlaenone B, virologin B, ocobullenone, and the unusual 2'-oxo-8.1'-lignan sibyllenone from the stems or bark of the Madagascan plant Ocotea cymosa. The new 8.O.6'-neolignan 4a, dihydrobenzofuranoid 5a, and the bicyclo[3.2.1]octanoid 7a had in vitro activity against Aedes aegypti, while the new compounds 5a, 7a, 8, and 10a and the known virolongin B (4b) and ocobullenone (10b) had antiplasmodial activity. We report herein the structure elucidation of the new compounds on the basis of spectroscopic evidence, including 1D and 2D NMR spectra, electronic circular dichroism, and mass spectrometry, and the biological activities of the new and known compounds.
authors: †Department of Chemistry and Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg, Virginia 24061, United States.
authors: L Harinantenaina
authors: LH
authors: Rakotondraibe
authors: ‡Discovery Research, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States.
authors: Paul R
authors: PR
authors: Graupner
authors: ‡Discovery Research, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States.
authors: Quanbo
authors: Q
authors: Xiong
authors: ‡Discovery Research, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States.
authors: Monica
authors: M
authors: Olson
authors: §Department of Biochemistry and Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, Virginia 24061, United States.
authors: Jessica D
authors: JD
authors: Wiley
authors: §Department of Biochemistry and Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, Virginia 24061, United States.
authors: Priscilla
authors: P
authors: Krai
authors: †Department of Chemistry and Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg, Virginia 24061, United States.
authors: Peggy J
authors: PJ
authors: Brodie
authors: ⊥Missouri Botanical Garden, B.P 3391, Antananarivo 101, Madagascar.
authors: Martin W
authors: MW
authors: Callmander
authors: ∥Centre National d'Application des Recherches Pharmaceutiques, B.P 702, Antananarivo 101, Madagascar.
authors: Etienne
authors: E
authors: Rakotobe
authors: ⊥Missouri Botanical Garden, B.P 3391, Antananarivo 101, Madagascar.
authors: Fidy
authors: F
authors: Ratovoson
authors: ∥Centre National d'Application des Recherches Pharmaceutiques, B.P 702, Antananarivo 101, Madagascar.
authors: Vincent E
authors: VE
authors: Rasamison
authors: §Department of Biochemistry and Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, Virginia 24061, United States.
authors: Maria B
authors: MB
authors: Cassera
authors: ‡Discovery Research, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States.
authors: Donald R
authors: DR
authors: Hahn
authors: †Department of Chemistry and Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg, Virginia 24061, United States.
authors: David G I
authors: DG
authors: Kingston
authors: ‡Discovery Research, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States.
authors: Serge
authors: S
authors: Fotso
mesh_terms: D000818:Animals; D004354:Drug Screening Assays, Antitumor; D005260:Female; D065928:Forests; D006801:Humans; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008270:Madagascar; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D027444:Ocotea / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D018411:Spodoptera / Q000187:drug effects
chemical_list: D007306:Insecticides; D017705:Lignans; C508834:didymochlaenone B
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