SENECIPHYLLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23NO5
Molecular Weight	333.3789
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12[C@H]3CCN1CC=C2COC(=O)[C@](C)(O)C(=C)C\C(=C\C)C(=O)O3

InChI

InChIKey=FCEVNJIUIMLVML-QPSVUOIXSA-N

InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15-,18-/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22188914 | https://www.ncbi.nlm.nih.gov/pubmed/25518325

Seneciphylline, a pyrrolizidine alkaloid, the one of the main component of Chinese medicine herb Tusanqi, which is a reason of the hepatic sinusoidal obstruction syndrome (HSOS). In addition, experiments on rats have shown that seneciphylline had adverse effects on the development and organic morphodifferentiation of embryos, thus the pregnant people exposed to Hebra may get potential risk on the fetus.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Seneciphylline.	1976	791805
Covalent binding of two pyrrolizidine alkaloids, senecionine and seneciphylline, to hepatic macromolecules and their distribution, excretion, and transfer into milk of lactating mice.	1982 May-Jun	6179729
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides.	2015 Apr	25666399

Patents

Sample Use Guides

In Vivo Use Guide

seneciphylline is a part of Chinese medicinal herb Tusanqi

Route of Administration: Oral

In Vitro Use Guide

It was evaluated the embryotoxicity of alkaloids in Senecionis Scandentis Hebra on in vitro cultured mouse embryos. Post-implantation (8.5 d) mouse embryos were isolated from their mothers, and cultured in the medium of immediately centrifuged serum (ICS) with different concentrations of seneciphylline (target concentrations were 100, 50, 25 and 12.5 μg x mL(-1)) for 48 h. Treatment with seneciphylline had adverse effects on the development and organic morphodifferentiation of embryos.

Name

Type

Language

SENECIPHYLLINE

Common Name

English

NSC-30622

Code

English

ALPHA-LONGILOBINE

Common Name

English

JACODINE

Common Name

English

13,19-DIDEHYDRO-12-HYDROXYSENECIONAN-11,16-DIONE

Common Name

English

.ALPHA.-LONGILOBINE

Common Name

English

SENECIPHYLLINE [HSDB]

Common Name

English

(3Z,6R,14AR,14BR)-3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-6-METHYL-5-METHYLENE(1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE

Common Name

English

SENECIPHYLLINE [IARC]

Common Name

English

SENECIPHYLLINE [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

5281750