title: Isolation and total syntheses of cytotoxic cryptolactones A1, A2, B1, and B2: α,β-unsaturated δ-lactones from a Cryptomyzus sp. aphid.
abstract: The cryptolactones A1, A2, B1, and B2, which are α,β-unsaturated δ-lactones, were isolated from a Cryptomyzus sp. aphid. The structures were established by 1-D and 2-D NMR spectra and CI-HRMS. Their absolute configurations were determined with the Kusumi-Mosher method, combined with asymmetric total syntheses. The syntheses were accomplished with the Mukaiyama aldol reaction and olefin metathesis, which utilized the second-generation Grubbs catalyst for the key steps. These compounds exhibited cytotoxic activity against human promyelocytic leukemia HL-60 cells with IC50 values of 0.97-5.3 μM.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University , Tokushima 770-8514, Japan.
authors.forename: Mitsuyo
authors.initials: M
authors.lastname: Horikawa
authors.forename: Makoto
authors.initials: M
authors.lastname: Inai
authors.forename: Yuki
authors.initials: Y
authors.lastname: Oguri
authors.forename: Eri
authors.initials: E
authors.lastname: Kuroda
authors.forename: Masami
authors.initials: M
authors.lastname: Tanaka
authors.forename: Shinya
authors.initials: S
authors.lastname: Suzuki
authors.forename: Takuya
authors.initials: T
authors.lastname: Ito
authors.forename: Shigeru
authors.initials: S
authors.lastname: Takahashi
authors.forename: Hiroto
authors.initials: H
authors.lastname: Kaku
authors.forename: Tetsuto
authors.initials: T
authors.lastname: Tsunoda
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001042:Aphids; D002384:Catalysis; D018922:HL-60 Cells; D006801:Humans; D007564:Japan; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000970:Antineoplastic Agents; D007783:Lactones; C116609:3-hydroxybutanal