PTEROPODINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24N2O4
Molecular Weight	368.4263
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@]3([H])C(=CO[C@@H](C)[C@]3([H])CN1CC[C@]24C(=O)NC5=CC=CC=C45)C(=O)OC

InChI

InChIKey=JMIAZDVHNCCPDM-QLMFUGSGSA-N

InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14-,18-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H24N2O4
Molecular Weight	368.4263
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19175366 | https://www.ncbi.nlm.nih.gov/pubmed/12191580 | https://www.ncbi.nlm.nih.gov/pubmed/11397448 | https://www.ncbi.nlm.nih.gov/pubmed/16445836

Pteropodine is a heterohimbine-type oxindole alkaloid specifically isolated from ‘Cat’s claw’ (Uncaria tomentosa), a plant that has shown cytostatic, anti-inflammatory and antimutagenic properties and is used in traditional medicine to cure a number of diseases. Pteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte but further studies are necessary to elucidate the exact mechanism by which Pteropodine positively modulates muscarinic M1 and 5-HT2 receptor functions. Pteropodine reduced the sister-chromatid exchanges and micronucleated polychromatic erythrocytes production by doxorubicin in mouse, showing a protective effect on the in vivo DNA damage. Pteropodine exhibited a significant pro-apoptotic effect on Medullary thyroid carcinoma cells. Moreover, anti-proliferative effect of pteropodine was demonstrated on the acute lymphoblastic leukaemia cells and ovarian carcinoma cells.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL3733 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12191580	Activator 1430	9.52 µM [EC50]
Serotonin 2 (5-HT2) receptor 87 Target ID: CHEMBL2096671 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12191580	Activator 1430	13.5 µM [EC50]
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16445836	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
T-cell lymphoblastic leukaemia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16445836	Primary	Basic research	Unknown Approved Use Unknown
Medullary thyroid carcinoma 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20032400	Primary	Basic research	Unknown Approved Use Unknown
Ovarian cancer 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11397448	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Alkaloids and procyanidins of an Uncaria sp. from Peru.	1976 Jul	947783
Bioactive indole alkaloids from the bark of Uncaria guianensis.	1999 Dec	10630124
Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test.	2000 Dec	11197086
Two stereoisomeric pentacyclic oxindole alkaloids from Uncaria tomentosa: uncarine C and uncarine E.	2001 Apr	11313600
Investigation of Uña De Gato I. 7-Deoxyloganic acid and 15N NMR spectroscopic studies on pentacyclic oxindole alkaloids from Uncaria tomentosa.	2001 Jul	11397448
Pteropodine and isopteropodine positively modulate the function of rat muscarinic M(1) and 5-HT(2) receptors expressed in Xenopus oocyte.	2002 May 24	12191580
Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells.	2006 Mar	16445836
Antigenotoxic, antioxidant and lymphocyte induction effects produced by pteropodine.	2009 Mar	19175366
Antiproliferative and pro-apoptotic effects of Uncaria tomentosa in human medullary thyroid carcinoma cells.	2009 Nov	20032400

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 40 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

CEM-C7H2 cells were incubated for 24, 48 and 72 h with increasing concentrations (50–200 uM/l) of pteropodine. Dex, a standard chemotherapeutic agent for T-ALL cells, served as positive control. A dose of 50 uM/l pteropodine increased the sub-G1 population after 24 h by 31% compared with controls.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:15:16 GMT 2023` Edited by `admin` on `Sat Dec 16 11:15:16 GMT 2023`
Record UNII	W24PZJ9QRZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PTEROPODINE

Common Name

English

UNCARINE C

Common Name

English

UNCARIN C

Common Name

English

FORMOSANAN-16-CARBOXYLIC ACID, 19-METHYL-2-OXO-, METHYL ESTER, (19.ALPHA.,20.ALPHA.)

Common Name

English

ALLO-PTEROPODINE

Common Name

English

NSC-113093

Code

English

PTEROPODIN

Common Name

English

PTEROPOIDINE (UNCARINE C) (CONSTITUENT OF CAT'S CLAW) [DSC]

Common Name

English

METHYL (19.ALPHA.,20.ALPHA.)-19-METHYL-2-OXOFORMOSANAN-16-CARBOXYLATE

Systematic Name

English

Code System Code Type Description

CAS

5629-60-7