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MedKoo Cat#: 413524 | Name: Demissidine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Demissidine
Demissidine
CAS#474-08-8

Theoretical Analysis

MedKoo Cat#: 413524

Name: Demissidine

CAS#: 474-08-8

Chemical Formula: C27H45NO

Exact Mass: 399.3501

Molecular Weight: 399.66

Elemental Analysis: C, 81.14; H, 11.35; N, 3.50; O, 4.00

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Synonym
Demissidine; Demissidin; Dihydrosolanidine; Solanin D; Solanine D; NSC409074; NSC-409074; NSC 409074
IUPAC/Chemical Name
(2aS,4S,6aS,6bS,8aS,8bR,9S,9aR,12S,14aS,15aS,15bR)-6a,8a,9,12-tetramethyldocosahydro-1H-naphtho[2',1':4,5]indeno[1,2-b]indolizin-4-ol
InChi Key
JALVTHFTYRPDMB-HRRTYWNUSA-N
InChi Code
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
SMILES Code
C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@H]4[C@@H]5CC[C@H]6C[C@H](CC[C@@]6([C@H]5CC[C@]34C)C)O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM
Solubility
To be determined 0.0 0.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 399.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Rivas-Loaiza JA, Baj A, López Y, Witkowski S, Wojtkielewicz A, Morzycki JW. Synthesis of Solanum Alkaloid Demissidine Stereoisomers and Analogues. J Org Chem. 2021 Jan 15;86(2):1575-1582. doi: 10.1021/acs.joc.0c02410. Epub 2021 Jan 4. PMID: 33393776. 2: Wojtkielewicz A, Kiełczewska U, Baj A, Morzycki JW. Synthesis of Demissidine Analogues from Tigogenin via Imine Intermediates. Int J Mol Sci. 2021 Oct 8;22(19):10879. doi: 10.3390/ijms221910879. PMID: 34639219; PMCID: PMC8509427. 3: Zhang ZD, Shi Y, Wu JJ, Lin JR, Tian WS. Synthesis of Demissidine and Solanidine. Org Lett. 2016 Jun 17;18(12):3038-40. doi: 10.1021/acs.orglett.6b01320. Epub 2016 May 27. PMID: 27232858. 4: Baj A, Kaewnok N, Rivas-Loaiza JA, Szymańska M, Witkowski S, Wojtkielewicz A, Morzycki JW. A Simple Four-Step Synthesis of the Potato Alkaloid Demissidine from the Common Sapogenin Tigogenin. Chemistry. 2023 Apr 6;29(20):e202203314. doi: 10.1002/chem.202203314. Epub 2023 Mar 13. PMID: 36720039. 5: Zhang Z, Giampa GM, Draghici C, Huang Q, Brewer M. Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach. Org Lett. 2013 May 3;15(9):2100-3. doi: 10.1021/ol4004993. Epub 2013 Apr 15. PMID: 23586838; PMCID: PMC3671602. 6: SCHREIBER K, ROENSCH H. [Synthesis of solanidine from demissidine]. Experientia. 1961 Nov 15;17:491-2. German. doi: 10.1007/BF02158613. PMID: 13909258. 7: Hossain MB, Tiwari BK, Gangopadhyay N, O'Donnell CP, Brunton NP, Rai DK. Ultrasonic extraction of steroidal alkaloids from potato peel waste. Ultrason Sonochem. 2014 Jul;21(4):1470-6. doi: 10.1016/j.ultsonch.2014.01.023. Epub 2014 Feb 15. PMID: 24582305. 8: Hossain MB, Rawson A, Aguiló-Aguayo I, Brunton NP, Rai DK. Recovery of steroidal alkaloids from potato peels using pressurized liquid extraction. Molecules. 2015 May 13;20(5):8560-73. doi: 10.3390/molecules20058560. PMID: 25985357; PMCID: PMC6272683. 9: Osman SF, Sinden SL. Analysis of mixtures of solanidine and demissidine glycoalkaloids containing identical carbohydrate units. J Agric Food Chem. 1977 Jul-Aug;25(4):955-7. doi: 10.1021/jf60212a002. PMID: 881520. 10: Chataing B, Concepción JL, Lobatón R, Usubillaga A. Inhibition of Trypanosoma cruzi growth in vitro by Solanum alkaloids: a comparison with ketoconazole. Planta Med. 1998 Feb;64(1):31-6. doi: 10.1055/s-2006-957361. PMID: 9491766. 11: Krishnan N, Sehnal F. Compartmentalization of oxidative stress and antioxidant defense in the larval gut of Spodoptera littoralis. Arch Insect Biochem Physiol. 2006 Sep;63(1):1-10. doi: 10.1002/arch.20135. PMID: 16921519. 12: Kozukue N, Yoon KS, Byun GI, Misoo S, Levin CE, Friedman M. Distribution of glycoalkaloids in potato tubers of 59 accessions of two wild and five cultivated Solanum species. J Agric Food Chem. 2008 Dec 24;56(24):11920-8. doi: 10.1021/jf802631t. PMID: 19053181. 13: Rosenkranz V, Wink M. Alkaloids induce programmed cell death in bloodstream forms of trypanosomes (Trypanosoma b. brucei). Molecules. 2008 Oct 3;13(10):2462-73. doi: 10.3390/molecules13102462. PMID: 18833031; PMCID: PMC6244846. 14: Cahill MG, Caprioli G, Vittori S, James KJ. Elucidation of the mass fragmentation pathways of potato glycoalkaloids and aglycons using Orbitrap mass spectrometry. J Mass Spectrom. 2010 Sep;45(9):1019-25. doi: 10.1002/jms.1785. PMID: 20641001. 15: Paczkowski C, Kalinowska M, Wojciechowski ZA. UDP-glucose:solasodine glucosyltransferase from eggplant (Solanum melongena L.) leaves: partial purification and characterization. Acta Biochim Pol. 1997;44(1):43-53. PMID: 9241353. 16: Hossain MB, Rai DK, Brunton NP. Optimisation and validation of ultra-high performance liquid chromatographic-tandem mass spectrometry method for qualitative and quantitative analysis of potato steroidal alkaloids. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Aug 1;997:110-5. doi: 10.1016/j.jchromb.2015.05.033. Epub 2015 Jun 9. PMID: 26102635. 17: Lee KR, Kozukue N, Han JS, Park JH, Chang EY, Baek EJ, Chang JS, Friedman M. Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. J Agric Food Chem. 2004 May 19;52(10):2832-9. doi: 10.1021/jf030526d. PMID: 15137822. 18: Saleem A, Engström M, Wurster S, Savola JM, Pihlaja K. Interaction of folk medicinal plant extracts with human alpha2-adrenoceptor subtypes. Z Naturforsch C J Biosci. 2002 Mar-Apr;57(3-4):332-8. doi: 10.1515/znc-2002-3-423. PMID: 12064736. 19: Friedman M, Rayburn JR, Bantle JA. Developmental toxicology of potato alkaloids in the frog embryo teratogenesis assay--Xenopus (FETAX). Food Chem Toxicol. 1991 Aug;29(8):537-47. doi: 10.1016/0278-6915(91)90046-a. PMID: 1894220. 20: Claeys M, Van den Heuvel H, Chen S, Derrick PJ, Mellon FA, Price KR. Comparison of high- and low-energy collision-induced dissociation tandem mass spectrometry in the analysis of glycoalkaloids and their aglycons. J Am Soc Mass Spectrom. 1996 Feb;7(2):173-81. doi: 10.1016/1044-0305(95)00636-2. PMID: 24203239.

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