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)
KEGG
PubChem CID
UNII
  • 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

Occurence

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]

Related Research Articles

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Helicobacter suis is a species within the Helicobacter genus of Gram-negative bacteria. Helicobacter pylori is by far the best known Helicobacter species, primarily because humans infected with it may develop gastrointestinal tract diseases such as stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers of the nonlymphoma type, and various subtypes of extranodal marginal zone lymphomass, e.g. those of the stomach, small intestines, large intestines, and rectumn. H. pylori is also associated with the development of bile duct cancer and has been associated with a wide range of other diseases although its role in the development of many of these other diseases requires further study. Humans infected with H. suis may develop some of the same gastrointestinal diseases - stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers that are not lymphomas, and extranodal marginal B cell lymphomas of the stomach. Other non-H. pylori Helicobacter species that are known to be associated with these gastrointestinal diseases are Helicobacter bizzozeronii, Helicobacter salomonis, Helicobacter felis, and Helicobacter heilmannii s.s. Because of their disease associations, these four Helicobacter species plus H. suis are often group together and termed Helicobacter heilmannii sensu lato.

Helicobacter heilmannii s.s. is a species within the Helicobacter genus of Gram negative bacteria. Helicobacter pylori is by far the best known Helicobacter species primarily because humans infected with it may develop gastrointestinal tract diseases such as stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers of the non-lymphoma type, and various subtypes of extranodal marginal zone lymphomass, e.g. those of the stomach, small intestines, large intestines, and rectumn. H. pylori is also associated with the development of bile duct cancer and has been associated with a wide range of other diseases although its role in the development of many of these other diseases requires further study. Humans infected with H. heilmannii s.s. may develop some of the same gastrointestinal diseases viz., stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers that are not lymphomas, and extranodal marginal B cell lymphomas of the stomach. Other non-H. pylori Helicobacter species that are known to be associated with these gastrointestinal diseases are Helicobacter bizzozeronii, Helicobacter suis, Helicobacter felis, and Helicobacter salomonis. Because of their disease associations, these four Helicobacter species plus H. heilmannii s.s. are often group together and termed Helicobacter heilmannii sensu lato.

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.