title: Coicenals A-D, four new diterpenoids with new chemical skeletons from the plant pathogenic fungus Bipolaris coicis.
abstract: Coicenals A-C (1-3) possessing a previously undescribed 10-(sec-butyl)-6-hydroxy-1,7,9-trimethyl-1,6,7,8,9,9a-hexahydro-1,4-methanobenzo[d]oxepin-2(4H)-ylidene)acetaldehyde skeleton and coicenal D (4) with a new 2-(sec-butyl)-5-hydroxy-1,6,8-trimethyl-2,5,6,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-10-ylidene)acetaldehyde skeleton were isolated from the solid culture of the plant pathogenic fungus Bipolaris coicis. The absolute configurations in 1 and 4 were assigned by electronic circular dichroism (ECD) calculations. Compounds 1 and 2 were transformed into 4 and 5 by treatment with acetyl chloride, respectively. Compounds 1-4 showed moderate inhibitory activity against NO release with IC50 values of 16.34 ± 1.12, 23.55 ± 1.37, 10.82 ± 0.83, and 54.20 ± 2.82 μM, respectively.
authors.affiliation: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No. 8 Beiertiao, Zhongguancun, Haidian District, Beijing 100190, PR China.
authors.forename: Quan-xin
authors.initials: QX
authors.lastname: Wang
authors.forename: Qiu-yue
authors.initials: QY
authors.lastname: Qi
authors.forename: Kai
authors.initials: K
authors.lastname: Wang
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.forename: Li
authors.initials: L
authors.lastname: Bao
authors.forename: Jun-jie
authors.initials: JJ
authors.lastname: Han
authors.forename: Miao-miao
authors.initials: MM
authors.lastname: Liu
authors.forename: Li-xin
authors.initials: LX
authors.lastname: Zhang
authors.forename: Lei
authors.initials: L
authors.lastname: Cai
authors.forename: Hong-wei
authors.initials: HW
authors.lastname: Liu
mesh_terms: D000818:Animals; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010802:Phylogeny
chemical_list: D004224:Diterpenes