title: A new diterpene from Litsea cubeba fruits: structure elucidation and capability to induce apoptosis in HeLa cells.
abstract: A new diterpene, identified as (+)-6-(4-hydroxy-4-methyl-2-pentenoyl)-4,6-dimethyl-5-(3-methyl-2-butenyl)-1,3-cyclohexadienecarbaldehyde (1, cubelin), was isolated from a methanol extract of Litsea cubeba fruits by normal phase column chromatography and purified by preparative HPLC. The structure elucidation was conducted by spectroscopic methods (UV, IR, ESI-TOF-MS, 1-D and 2-D NMR). Cubelin exhibited activity against HeLa cell viability and proliferation. The cells also exhibited changes in nuclear morphology which are hallmarks of apoptotic cell death. The presence of cleaved caspase-3/-7, caspase-8 and caspase-9 in the cubelin treated population indicated the potential of the compound to induce apoptosis in HeLa cells via both intrinsic and extrinsic pathways.
authors.affiliation: The United Graduate School of Agricultural Science (UGAS), Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime Prefecture 790-8566, Japan. pyp.trisonthi@gmail.com.
authors.forename: Piyapat
authors.initials: P
authors.lastname: Trisonthi
authors.affiliation: The United Graduate School of Agricultural Science (UGAS), Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime Prefecture 790-8566, Japan.
authors.forename: Akihiko
authors.initials: A
authors.lastname: Sato
authors.affiliation: The United Graduate School of Agricultural Science (UGAS), Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime Prefecture 790-8566, Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Nishiwaki
authors.affiliation: The United Graduate School of Agricultural Science (UGAS), Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime Prefecture 790-8566, Japan. tamura@ag.kagawa-u.ac.jp.
authors.forename: Hirotoshi
authors.initials: H
authors.lastname: Tamura
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000506:poisoning*; D017209:Apoptosis / Q000187:drug effects; D053148:Caspase 3 / Q000378:metabolism; D053181:Caspase 8 / Q000378:metabolism; D053453:Caspase 9 / Q000378:metabolism; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004224:Diterpenes / Q000737:chemistry* / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D032862:Litsea / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: C000597863:6-(4-hydroxy-4-methyl-2-pentenoyl)-4,6-dimethyl-5-(3-methyl-2-butenyl)-1,3-cyclohexadienecarbaldehyde; D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D053148:Caspase 3; D053181:Caspase 8; D053453:Caspase 9