DEMISSIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H45NO
Molecular Weight	399.6523
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC[C@H](C)CN1[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[C@@H]2C

InChI

InChIKey=JALVTHFTYRPDMB-HRRTYWNUSA-N

InChI=1S/C27H45NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h16-25,29H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15137822 | https://www.ncbi.nlm.nih.gov/pubmed/18833031 | https://www.ncbi.nlm.nih.gov/pubmed/9491766 | https://www.ncbi.nlm.nih.gov/pubmed/27232858

Demissidine was isolated from several potato species including Solanum demissum, Solanum acaule and Solanum tuberosum. Demissidine was synthesized from the related steroidal alkaloid dihydrotomatidine. Demissidine is an alkaloid that inhibits the growth of human colon and liver cancer cells in culture, though less actively than glycoalkaloid dehydrocommersonine. Demissidine is a growth inhibitor of Trypanosoma cruzi.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15137822	Primary		Basic research	Unknown Approved Use Unknown
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15137822	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts.	2001 Jul 13	11486878
Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.	2004 May 19	15137822
Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids.	2005 Mar	15365763
Compartmentalization of oxidative stress and antioxidant defense in the larval gut of Spodoptera littoralis.	2006 Sep	16921519
Alkaloids induce programmed cell death in bloodstream forms of trypanosomes (Trypanosoma b. brucei).	2008 Oct 3	18833031
Elucidation of the mass fragmentation pathways of potato glycoalkaloids and aglycons using Orbitrap mass spectrometry.	2010 Sep	20641001

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Alkaloid demissidine induced apoptosis at a concentration of 100 uM in Trypanosoma brucei. EC50 value was 14 uM.

Name

Type

Language

DEMISSIDINE

Common Name

English

(22R,25S)-5.ALPHA.-SOLANIDAN-3.BETA.-OL

Common Name

English

NSC-409074

Code

English

SOLANINE D

Common Name

English

DIHYDROSOLANIDINE

Common Name

English

SOLANIDAN-3-OL, (3.BETA.,5.ALPHA.)-

Common Name

English

Code System Code Type Description

FDA UNII

VG66W0726Y