title: Sesquiterpenoids and diarylheptanoids from Nidus vespae and their inhibitory effects on nitric oxide production.
abstract: Two coriamyrtin-type sesquiterpenes, fengfangin A (1) and tutin (2), and six diarylheptanoids, namely alnusone (3), centrolobol (4), muricarpone B (5), 1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-one (6), (3S)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-ol (7), and (3S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)heptan-3-ol (8), were isolated from the 95% EtOH extract of nidus vespae, the nest of Polistes species. Their structures were identified by spectroscopic methods. Compounds 1 and 8 are new products. The absolute configuration of 1 was determined by single-crystal X-ray diffraction analysis using Flack parameter. The biological tests showed that compounds 5, 6, and 8 could inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells with IC(50) values in the range of 13-17 μM, whereas the sesquiterpenes were inactive in this assay (>25 μM). In addition, the ecological significance of the presence of neurotoxic sesquiterpene lactones in nidus vespae is briefly discussed.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, PR China.
authors.forename: Jiang-Bo
authors.initials: JB
authors.lastname: He
authors.forename: Yong-Ming
authors.initials: YM
authors.lastname: Yan
authors.forename: Xiu-Jing
authors.initials: XJ
authors.lastname: Ma
authors.forename: Qing
authors.initials: Q
authors.lastname: Lu
authors.forename: Xue-Song
authors.initials: XS
authors.lastname: Li
authors.forename: Jia
authors.initials: J
authors.lastname: Su
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.forename: Guang-Ming
authors.initials: GM
authors.lastname: Liu
authors.forename: Yong-Xian
authors.initials: YX
authors.lastname: Cheng
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002460:Cell Line; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D008516:Medicine, Chinese Traditional; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D009569:Nitric Oxide / Q000009:adverse effects*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014863:Wasps / Q000737:chemistry* / Q000254:growth & development
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D036381:Diarylheptanoids; D012717:Sesquiterpenes; D009569:Nitric Oxide