PLAUNOTOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H34O2
Molecular Weight	306.4828
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCC\C(C)=C\CC\C(CO)=C\CC\C(C)=C\CO

InChI

InChIKey=SUWYPNNPLSRNPS-UNTSEYQFSA-N

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-

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Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/18845620
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/16253229 http://www.ncbi.nlm.nih.gov/pubmed/8889714

Plaunotol [(2E, 6Z, 10E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10, 14-hexadecatetraen-1-ol)] is an acyclic diterpene alcohol originally isolated from the plant Croton sublyratus, which is native to southeast Asia. Plaunotol has been used to treat gastritis and gastric ulcers in Japan. Plaunotol increases the prostaglandin production in the gastric mucosa and accelerates ulcer healing. The precise mechanisms underlying the gastroprotective actions by plaunotol are not known. On the other hand, cyclooxygenase (COX)-2 is a key enzyme in PGE(2) production and its induction is thought to have an important role in ulcer healing. Plaunotol induced COX-2 expression and increased PGE(2) production in serum-starved RGM1 cells via activation of the NF-kappaB and CRE sites of Cox-2 gene promoters. In vitro studies showed bactericidal action against H. pylori by increasing membrane fluidity, leading to autolysis and deterioration of cell structure

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial cell membrane 5 Target ID: bacterial cell membrane Sources: http://www.ncbi.nlm.nih.gov/pubmed/8889714	Interacts 323

Conditions

Condition	Modality	Highest Phase	Product
Gastric ulcer 67 Sources: http://www.ncbi.nlm.nih.gov/pubmed/18845620	Curative	Approved 8429	Unknown Approved Use Unknown
Gastritis 45 Sources: http://www.ncbi.nlm.nih.gov/pubmed/18845620	Curative	Approved 8429	Unknown Approved Use Unknown
Helicobacter infection 3 Sources: http://www.ncbi.nlm.nih.gov/pubmed/8889714	Preventing	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Plaunotol prevents indomethacin-induced gastric mucosal injury in rats by inhibiting neutrophil activation.	1999 Apr	10215738

Patents

Sample Use Guides

In Vivo Use Guide

Five male and five female ICR mice were treated with either water for the control group or purified plaunotol extract (PPE) at 2.5, 5, 10, and 20 g/kg for each treatment group.

Route of Administration: Oral

In Vitro Use Guide

10 and 1 μg/ml (33 and 3.3 μmol/l) plaunotol induced toxicity in human gingival fibroblasts (HGFs) and human oral keratinocytes (HOKs), respectively. However, 0.1 μg/ml (0.33 μmol/l) plaunotol promoted HGF proliferation and wound healing in monolayer and FPCL models. In contrast, 0.1 μg/ml plaunotol could not induce HOK proliferation nor in vitro wound healing using monolayer culture, but it induced wound healing in a modified FPCL model.

Name

Type

Language

PLAUNOTOL

Official Name

English

Plaunotol [WHO-DD]

Common Name

English

PLAUNOTOL [JAN]

Common Name

English

PLAUNOTOL [MI]

Common Name

English

PLAUNOTOL [MART.]

Common Name

English

plaunotol [INN]

Common Name

English

KELNAC

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29701