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Plaunotol

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Plaunotol
Names
IUPAC name (2Z,6E)-2--6-methylocta-2,6-diene-1,8-diol
Other names 18-Hydroxygeranylgeraniol; Kelnac
Identifiers
CAS Number
3D model (JSmol)
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/CO)/C)C
Properties
Chemical formula C20H34O2
Molar mass 306.490 g·mol
Pharmacology
Legal status
  • Rx in Japan
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Plaunotol (18-hydroxygeranylgeraniol) is a chemical compound with the molecular formula C20H34O2. It is a diterpene that was first isolated from Croton sublyratus.

Occurrence

Plaunotol has been identified as present in Croton sublyratus and Croton stellatopilosus. In plants, the compound is biosynthesized by hydroxylation of geranylgeraniol, a reaction which is catalyzed by the enzyme geranylgeraniol 18-hydroxylase. A laboratory synthesis of plaunotol has been reported.

Pharmacology

Plaunotol has antibacterial activity against Helicobacter pylori, the bacteria that causes gastric ulcers. In Japan, plauntool is used as a pharmaceutical drug under the trade name Kelnac for the treatment of gastritis and gastric ulcers.

References

  1. ^ Ogiso, Akira; Kitazawa, Eiichi; Kurabayashi, Masaaki; Sato, Aiya; Takahashi, Shuji; Noguchi, Hiroshi; Kuwano, Harumitsu; Kobayashi, Shinsaku; Mishima, Hiroshi (1978). "Isolation and structure of antipeptic ulcer diterpene from Thai medicinal plant". Chemical and Pharmaceutical Bulletin. 26 (10): 3117–3123. doi:10.1248/cpb.26.3117. PMID 729109.
  2. Chaotham, Chatchai; Chivapat, Songpol; Chaikitwattana, Anan; De-Eknamkul, Wanchai (2013). "Acute and Chronic Oral Toxicity of a Partially Purified Plaunotol Extract from Croton stellatopilosus Ohba". BioMed Research International. 2013: 1–12. doi:10.1155/2013/303162. PMC 3806312. PMID 24286075.
  3. Tansakul, Pimpimon; De-Eknamkul, Wanchai (1998). "Geranylgeraniol-18-hydroxylase: The last enzyme on the plaunotol biosynthetic pathway in Croton sublyratus". Phytochemistry. 47 (7): 1241–1246. Bibcode:1998PChem..47.1241T. doi:10.1016/S0031-9422(97)00743-7.
  4. Tago, Keiko; Arai, Masami; Kogen, Hiroshi (2000). "A practical total synthesis of plaunotol via highly Z-selective Wittig olefination of α-acetal ketones". Journal of the Chemical Society, Perkin Transactions 1 (13): 2073–2078. doi:10.1039/B001977L.
  5. Koga, Tetsufumi; Kawada, Harumi; Utsui, Yukio; Domon, Haruki; Ishii, Chika; Yasuda, Hiroshi (1996). "In-vitro and in-vivo antibacterial activity of plaunotol, a cytoprotective antiulcer agent, against Helicobacter pylori". Journal of Antimicrobial Chemotherapy. 37 (5): 919–929. doi:10.1093/jac/37.5.919. PMID 8737142.
  6. "Plaunotol". Inxight Drugs. National Center for Advancing Translational Sciences.
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