Plaunotol

Last updated
Plaunotol
Plaunotol.svg
Names
IUPAC name
(2Z,6E)-2-[(3E)-4,8-Dimethylnona-3,7-dienyl]-6-methylocta-2,6-diene-1,8-diol
Other names
18-Hydroxygeranylgeraniol; Kelnac
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C20H34O2/c1-17(2)8-5-9-18(3)10-6-12-20(16-22)13-7-11-19(4)14-15-21/h8,10,13-14,21-22H,5-7,9,11-12,15-16H2,1-4H3/b18-10+,19-14+,20-13-
    Key: SUWYPNNPLSRNPS-UNTSEYQFSA-N
  • CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/CO)/C)C
Properties
C20H34O2
Molar mass 306.490 g·mol−1
Pharmacology
Legal status
  • Rx in Japan
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

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, plaunotol is used as a pharmaceutical drug under the trade name Kelnac for the treatment of gastritis and gastric ulcers. [6]

References

  1. 1 2 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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