白花丹素

化合物

白花丹素Plumbagin5-hydroxy-2-methyl-1,4-naphthoquinone)為萘醌衍生物,為黃色染料。[1]其得名於植物白花丹Plumbago[2]白花丹素常見於茅膏菜豬籠草體內。[3]

白花丹素
IUPAC名
5-hydroxy-2-methyl-naphthalene-1,4-dione
識別
CAS號 481-42-5  checkY
PubChem 10205
ChemSpider 9790
SMILES
 
  • O=C\2c1c(O)cccc1C(=O)/C(=C/2)C
InChI
 
  • 1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
InChIKey VCMMXZQDRFWYSE-UHFFFAOYAB
ChEBI 8273
KEGG C10387
性質
化學式 C11H8O3
摩爾質量 188.17942 g/mol g·mol⁻¹
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

藥理性質

各種細胞和動物模型試驗中得出了以下藥理學特性:

參考文獻

  1. ^ Black Walnut頁面存檔備份,存於互聯網檔案館). 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. ^ Itoigawa, M., K. Takeya & H. Furukawa 1991. Cardiotonic action of plumbagin on guinea-pig papillary muscle. Planta Medica 57(4): 317–319.
  11. ^ 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.
  12. ^ Bhargava, S.K. 1984. Effects of plumbagin on reproductive function of male dog. Indian Journal of Experimental Biology 22(3): 153–156.
  13. ^ 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.
  14. ^ 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.