PHYTOLACCAGENINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H48O7
Molecular Weight	532.7086
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@](C)(CC[C@@]1(CC[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)C[C@H](O)[C@H](O)[C@@](C)(CO)[C@]5([H])CC[C@@]34C)C(O)=O)C(=O)OC

InChI

InChIKey=CYJWWQALTIKOAG-FLORRLIPSA-N

InChI=1S/C31H48O7/c1-26(25(37)38-6)11-13-31(24(35)36)14-12-29(4)18(19(31)15-26)7-8-22-27(2)16-20(33)23(34)28(3,17-32)21(27)9-10-30(22,29)5/h7,19-23,32-34H,8-17H2,1-6H3,(H,35,36)/t19-,20-,21+,22+,23-,26-,27-,28-,29+,30+,31-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C31H48O7
Molecular Weight	532.7086
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22006712 | https://www.ncbi.nlm.nih.gov/pubmed/25575173 | https://www.ncbi.nlm.nih.gov/pubmed/20734930

Radix Phytolaccae (the dried root of Phytolacca acinosa Roxb. or Phytolacca americana L.) is widely used in East Asian countries for the treatment of inflammation-related diseases. The active component of Radix Phtolaccae is Phytolcaccagenin a triterpenoid saponin. Phytolcaccagenin has anti-inflammatory activities that exceed those of Esculentoside A and its derivatives regarding suppression of LPS-induced inflammation, and has a lower toxicity profile with less hemolysis. Phytolaccagenin has promising antifungal activity against ATCC standard cultures of Candida albicans and Cryptococcus neoformans, and against clinical isolates of these fungi.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20734930	Inhibitor 8297
Cryptococcus neoformans var. neoformans 2 Target ID: CHEMBL2367317 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20734930	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Candida infections 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20734930	Primary		Basic research	Unknown Approved Use Unknown
Cryptococcosis 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20734930	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antifungal activity of saponin-rich extracts of Phytolacca dioica and of the sapogenins obtained through hydrolysis.	2010 Jul	20734930
Synthesis of novel derivatives of esculentoside A and its aglycone phytolaccagenin, and evaluation of their haemolytic activity and inhibition of lipopolysaccharide-induced nitric oxide production.	2011 Oct	22006712
Development and validation of a HPLC-MS/MS method for the determination of phytolaccagenin in rat plasma and application to a pharmacokinetic study.	2015 Mar 25	25575173

Patents

Sample Use Guides

In Vivo Use Guide

Rats: intravenous bolus injection in male Sprague-Dawley rats (10 mg/kg, i.v.).

Route of Administration: Intravenous

In Vitro Use Guide

Phytolaccagenin inhibited LPS-Induced NO production in macrophages with IC50 value of 18.4 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:09:37 GMT 2023` Edited by `admin` on `Sat Dec 16 09:09:37 GMT 2023`
Record UNII	18YX12Q68B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHYTOLACCAGENINE

Common Name

English

OLEAN-12-ENE-28,30-DIOIC ACID, 2.BETA.,3.BETA.,23-TRIHYDROXY-, 30-METHYL ESTER

Systematic Name

English

JALIGONIC ACID 30-METHYL ESTER

Systematic Name

English

OLEAN-12-ENE-28,29-DIOIC ACID, 2,3,23-TRIHYDROXY-, 29-METHYL ESTER, (2.BETA.,3.BETA.,4.ALPHA.,20.BETA.)-

Systematic Name

English

NSC-116453

Code

English

Code System Code Type Description

NSC

116453