title: Phenanthrene derivatives from Cymbidium Great Flower Marie Laurencin and their biological activities.
abstract: A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), were isolated from the roots of Cymbidium Great Flower Marie Laurencin, along with six known phenanthrenes, 5-10. The structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 μM. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC(50) 2.8 μM) against HL-60 cells. Compounds 4-9 also showed weak cytotoxic activity against the HL-60 cell line with IC(50) values of 19.3-52.4 μM.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, 770-8514, Japan. yosikawa@ph.bunri-u.ac.jp
authors.forename: Kazuko
authors.initials: K
authors.lastname: Yoshikawa
authors.forename: Takuya
authors.initials: T
authors.lastname: Ito
authors.forename: Kanako
authors.initials: K
authors.lastname: Iseki
authors.forename: Chihiro
authors.initials: C
authors.lastname: Baba
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Imagawa
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Yagi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Morita
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Asakawa
authors.forename: Sachiko
authors.initials: S
authors.lastname: Kawano
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Hashimoto
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D007564:Japan; D008968:Molecular Conformation; D015394:Molecular Structure; D029595:Orchidaceae / Q000737:chemistry*; D010616:Phenanthrenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D010616:Phenanthrenes; C573519:ephemeranthoquinone B