Plaunotol Explained

Plaunotol (18-hydroxygeranylgeraniol) is a chemical compound with the molecular formula C20H34O2. It is a diterpene that was first isolated from Croton sublyratus.[1]

Occurrence

Plaunotol has been identified as present in Croton sublyratus[1] and Croton stellatopilosus.[2] In plants, the compound is biosynthesized by hydroxylation of geranylgeraniol, a reaction which is catalyzed by the enzyme geranylgeraniol 18-hydroxylase.[3] A laboratory synthesis of plaunotol has been reported.[4]

Pharmacology

Plaunotol has antibacterial activity against Helicobacter pylori, the bacteria that causes gastric ulcers.[5] In Japan, plauntool is used as a pharmaceutical drug under the trade name Kelnac for the treatment of gastritis and gastric ulcers.[6]

Notes and References

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

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