プルンバギン(plumbagin)または5-ヒドロキシ-2-メチル-1,4-ナフトキノン(5-hydroxy-2-methyl-1,4-naphthoquinone)は、化学式がC11H8O3有機化合物。生物毒と見なされる[1]

プルンバギン
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識別情報
CAS登録番号 481-42-5 ×
PubChem 10205
ChemSpider 9790 チェック
KEGG C10387 チェック
ChEBI
ChEMBL CHEMBL295316 チェック
特性
化学式 C11H8O3
モル質量 188.17942 g/mol
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

概要編集

プルンバギンは黄色の染料[1]、形式的にナフトキノンから誘導される。

物質名の由来はルリマツリPlumbago)から初めて単離されたことから[2]。この他、食虫植物モウセンゴケ属ウツボカズラ科の植物でも普遍的に見られる[3]

薬理学的利用編集

出典編集

[脚注の使い方]
  1. ^ a b Black Walnut. Drugs.com.
  2. ^ Van der Vijver, L.M. 1972. Distribution of plumbagin in the Plumbaginaceae. Phytochemistry 11: 3247–3248.
  3. ^ Wang, W., X. Luo, & H. Li 2010. Terahertz and infrared spectra of plumbagin, juglone, and menadione. Carnivorous Plant Newsletter 39(3): 82–88.
  4. ^ Didry, N., L. Dubrevil & M. Pinkas 1994. Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Die Pharmazie 49(9): 681–683.
  5. ^ Paiva, S.R.d., M.R. Figueiredo, T. V. Aragão, M.A.C. Kaplan 2003. Antimicrobial Activity in Vitro of Plumbagin Isolated from Plumbago Species. (PDF, 511 KiB) Mem Inst Oswaldo Cruz 98(7): 959–961.
  6. ^ Likhitwitayawuid, K., R. Kaewamatawong, N. Ruangrungsi & J. Krungkrai 1998. Antimalarial naphthoquinones from Nepenthes thorelii. Planta Medica 64(3): 237–241.
  7. ^ Checker R., Sharma D., Sandur S.K., Subrahmanyam G., Krishnan S., Poduval T.B., Sainis K.B. "Plumbagin inhibits proliferative and inflammatory responses of T cells independent of ROS generation but by modulating intracellular thiols" Journal of Cellular Biochemistry 2010 110:5 (1082-1093)
  8. ^ Parimala, R. & P. Sachdanandam 1993. Effect of plumbagin on some glucose metabolizing enzymes studied in rats in experimental hepatoma. Molecular and Cellular Biochemistry 12(1): 59–63.
  9. ^ Hsu, Y.-L., C.-Y. Cho, P.-L. Kuo, Y.-T. Huang & C.-C. Lin 2006. Plumbagin (5-Hydroxy-2-methyl-1,4-naphthoquinone) Induces Apoptosis and Cell Cycle Arrest in A549 Cells through p53 Accumulation via c-Jun NH2-Terminal Kinase-Mediated Phosphorylation at Serine 15 in Vitro and in Vivo. Journal of Pharmacology and Experimental Therapeutics 318(2): 484–494. doi:10.1124/jpet.105.098863 PMID 16632641
  10. ^ Navarro, Alfons; Subramaniya, Bharathi Raja; Srinivasan, Gayathri; Mohammed Sadullah, Sakeena Sadullah; Davis, Nimitha; Baddi Reddi Subhadara, Lakshmi; Halagowder, Devaraj; Sivasitambaram, Niranjali Devaraj (2011). “Apoptosis Inducing Effect of Plumbagin on Colonic Cancer Cells Depends on Expression of COX-2”. PLoS ONE 6 (4): e18695. doi:10.1371/journal.pone.0018695. ISSN 1932-6203. 
  11. ^ Itoigawa, M., K. Takeya & H. Furukawa 1991. Cardiotonic action of plumbagin on guinea-pig papillary muscle. Planta Medica 57(4): 317–319.
  12. ^ McKallip, Robert J. Lombard, Catherine. Sun, Jingping. Ramakrishnan, Rupal. "Plumbagin-induced apoptosis in lymphocytes is mediated through increased reactive oxygen species production, upregulation of Fas, and activation of the caspase cascade."Toxicology & Applied Pharmacology. 247(1):41-52, 2010 Aug 15.
  13. ^ Bhargava, S.K. 1984. Effects of plumbagin on reproductive function of male dog. Indian Journal of Experimental Biology 22(3): 153–156.
  14. ^ Son TG. Camandola S. Arumugam TV. Cutler RG. Telljohann RS. Mughal MR. Moore TA. Luo W. Yu QS. Johnson DA. Johnson JA. Greig NH. Mattson MP. Plumbagin, a novel Nrf2/ARE activator, protects against cerebral ischemia.
  15. ^ Ding, Y., Z.-J. Chen, S. Liu, D. Che, M. Vetter, C.-H. Chang 2005. Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone. Journal of Pharmacy and Pharmacology 57(1): 111.