title: Two new indole alkaloids, 2-(3,3-dimethylprop-1-ene)-costaclavine and 2-(3,3-dimethylprop-1-ene)-epicostaclavine, from the marine-derived fungus Aspergillus fumigatus.
abstract: Two new indole alkaloids, 2-(3,3-dimethylprop-1-ene)-costaclavine (1) and 2-(3,3-dimethylprop-1-ene)-epicostaclavine (2), together with the known compounds costaclavine (3), fumgaclavine A (4) and C (5), were isolated from the marine-derived fungus Aspergillus fumigatus. The planar structures of the two new compounds were elucidated on the basis of chemical and physicochemical evidence including MS, UV, IR and NMR spectra. Their stereochemistry was studied by NOESY, (1)H-(1)H coupling constant and CD spectra. The compounds 1, 2, 3 and 5 showed weak cytotoxicity against a mouse leukemia cell line (P388).
authors.affiliation: Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. zhang-dahai@hotmail.com
authors.forename: Dahai
authors.initials: D
authors.lastname: Zhang
authors.forename: Masayuki
authors.initials: M
authors.lastname: Satake
authors.forename: Seketsu
authors.initials: S
authors.lastname: Fukuzawa
authors.forename: Kohtaro
authors.initials: K
authors.lastname: Sugahara
authors.forename: Ai
authors.initials: A
authors.lastname: Niitsu
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Shirai
authors.forename: Kazuo
authors.initials: K
authors.lastname: Tachibana
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001232:Aspergillus fumigatus / Q000737:chemistry*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002942:Circular Dichroism; D004305:Dose-Response Relationship, Drug; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007938:Leukemia / Q000473:pathology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: C571068:2-(3,3-dimethylprop-1-ene)costaclavine; C571069:2-(3,3-dimethylprop-1-ene)epicostaclavine; D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids