Labdane-Type Diterpenes, Galangalditerpenes A-C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga.
作者： Yoshiaki Manse , Kiyofumi Ninomiya , Ryosuke Nishi , Yoshinori Hashimoto , Saowanee Chaipech
DOI: 10.3390/MOLECULES22122279
关键词: Traditional medicine 、 Structure–activity relationship 、 Arbutin 、 Chemistry 、 Zingiberaceae 、 Biological activity 、 Alpinia galanga 、 IC50 、 Alpinia 、 Labdane
摘要: In our continuing study of biologically active natural products from the fruit Alpinia galanga (Zingiberaceae), we newly isolated three new labdane-type diterpenes, termed galangalditerpenes A–C (1–3), along with four known sesquiterpenes (4–7) and two diterpenes (8 9). The stereostructures 1–3 were elucidated on basis their spectroscopic properties. melanogenesis inhibitory activities in theophylline-stimulated murine B16 melanoma 4A5 cells these isolates, including (1–3, IC50 = 4.4, 8.6, 4.6 μM, respectively), found to be more than 6–87-fold higher that arbutin (174 μM), a commercially available positive control.
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sci-hub.se 参考文章(30)
Costas Demetzos, Konstantinos S. Dimas, Labdane-type diterpenes: Chemistry and biological activity Bioactive Natural Products (Part F). ,vol. 25, pp. 235- 292 ,(2001) , 10.1016/S1572-5995(01)80009-0
Hideji Itokawa, Shinji Yoshimoto, Hiroshi Morita, Diterpenes from the rhizomes of Alpinia formosana Phytochemistry. ,vol. 27, pp. 435- 438 ,(1988) , 10.1016/0031-9422(88)83115-7
Henry HEYMANN, Yasuhiro TEZUKA, Tohru KIKUCHI, Sutardjo SUPRIYATNA, Constituents of Sindora sumatrana MIQ.I. Isolation and NMR Spectral Analysis of Sesquiterpenes from the Dried Pods Chemical & Pharmaceutical Bulletin. ,vol. 42, pp. 138- 146 ,(1994) , 10.1248/CPB.42.138
SEIJI MITSUI, SHINSAKU KOBAYASHI, HITOSHI NAGAHORI, AKIRA OGISO, Constituents from Seeds of Alpinia galanga WILD. and Their Anti-ulcer Activities Chemical & Pharmaceutical Bulletin. ,vol. 24, pp. 2377- 2382 ,(1976) , 10.1248/CPB.24.2377
Hisashi Matsuda, Yutana Pongpiriyadacha, Toshio Morikawa, Momotaro Ochi, Masayuki Yoshikawa, Gastroprotective effects of phenylpropanoids from the rhizomes of Alpinia galanga in rats: structural requirements and mode of action. European Journal of Pharmacology. ,vol. 471, pp. 59- 67 ,(2003) , 10.1016/S0014-2999(03)01785-0
I. Chinou, Labdanes of natural origin-biological activities (1981-2004). Current Medicinal Chemistry. ,vol. 12, pp. 1295- 1317 ,(2005) , 10.2174/0929867054020990
Hiroshi Morita, Hideji Itokawa, Cytotoxic and antifungal diterpenes from the seeds of Alpinia galanga. Planta Medica. ,vol. 54, pp. 117- 120 ,(1988) , 10.1055/S-2006-962365
Hironao Sajiki, Kazuyuki Hattori, Kosaku Hirota, Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF Chemistry - A European Journal. ,vol. 6, pp. 2200- 2204 ,(2000) , 10.1002/1521-3765(20000616)6:12<2200::AID-CHEM2200>3.0.CO;2-3
Qiao-hui Zeng, Chuan-Li Lu, Xue-wu Zhang, Jian-Guo Jiang, Isolation and identification of ingredients inducing cancer cell death from the seeds of Alpinia galanga, a Chinese spice Food & Function. ,vol. 6, pp. 431- 443 ,(2015) , 10.1039/C4FO00709C
Shin Ando, Hisashi Matsuda, Toshio Morikawa, Masayuki Yoshikawa, 1′S-1′-Acetoxychavicol acetate as a new type inhibitor of interferon-β production in lipopolysaccharide-activated mouse peritoneal macrophages Bioorganic & Medicinal Chemistry. ,vol. 13, pp. 3289- 3294 ,(2005) , 10.1016/J.BMC.2005.02.022