title: Revised stereochemistry of ficifolidione and its biological activities against insects and cells.
abstract: Ficifolidione (1), a moderately active insecticidal compound from two species of Myrtaceae, and its derivatives were synthesized to evaluate their insecticidal activity. X-ray crystallographic analyses and specific rotation values of ficifolidione and its C-4 (2) demonstrated that the structure of ficifolidione differs from the reported absolute structure; that is, the C-4 configuration of ficifolidione should have an S configuration. The reported insecticidal activity of ficifolidione (1) and its C-4 epimer (2) against adult houseflies (Musca domestica), mosquito larvae (Culex pipiens), and cutworms (Spodoptera litura) was not observed. The cytotoxicities of ficifolidione and its derivatives (1-4) against four cell lines, Sf9, Colon26, HL60, and Vero, were also measured because ficifolidione has a phloroglucinol-derived moiety, a motif that is often present in the structure of cytotoxic chemicals. Compound 1 exhibited IC50 values of ca. 32, 9, 3, and 12 μM for Sf9, Colon26, HL60, and Vero cells, respectively, indicating that ficifolidione possesses selective cytotoxicity against the four cell lines. In HL60 cells treated with 1, DNA fragmentation and the activation of procaspase 3 were observed, suggesting that the cytotoxicity is induced by apoptosis.
authors.affiliation: Faculty of Agriculture, Ehime University , 3-5-7 Tarumi, Matsuyama, 790-8566 Ehime, Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Nishiwaki
authors.forename: Satomi
authors.initials: S
authors.lastname: Fujiwara
authors.forename: Tuti
authors.initials: T
authors.lastname: Wukirsari
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Iwamoto
authors.forename: Shigeki
authors.initials: S
authors.lastname: Mori
authors.forename: Kosuke
authors.initials: K
authors.lastname: Nishi
authors.forename: Takuya
authors.initials: T
authors.lastname: Sugahara
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Shuto
mesh_terms: D000818:Animals; D002522:Chlorocebus aethiops; D003465:Culex / Q000187:drug effects; D018922:HL-60 Cells; D006793:Houseflies / Q000187:drug effects; D006801:Humans; D007313:Insecta / Q000187:drug effects; D007306:Insecticides / Q000737:chemistry* / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D018411:Spodoptera / Q000187:drug effects; D014709:Vero Cells
chemical_list: D007306:Insecticides; C000595953:ficifolidione; D010696:Phloroglucinol