MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 597938 | Name: Stylopin (S-isomer)

Description:

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

Stylopin is discontinued (DEA controlled substance). Stylopin is a major component of the leaf of Chelidonium majus L. (Papaveraceae), which has been used for the removal of warts, papillomas and condylomas, as well as the treatment of liver disease, in oriental countries.

Chemical Structure

Stylopin (S-isomer)
Stylopin (S-isomer)
CAS#84-39-9 (S-isomer)

Theoretical Analysis

MedKoo Cat#: 597938

Name: Stylopin (S-isomer)

CAS#: 84-39-9 (S-isomer)

Chemical Formula: C19H17NO4

Exact Mass: 323.1158

Molecular Weight: 323.34

Elemental Analysis: C, 70.58; H, 5.30; N, 4.33; O, 19.79

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
84-39-9 (S-isomer) 4312-32-7 (racemic) 7461-02-1 (racemic)
Synonym
Stylopin; (S)-Stylopin; l-Tetrahydrocoptisine; l-Stylopine; (-)-Tetrahydrocoptisine; (S)-Stylopin
IUPAC/Chemical Name
(S)-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4',5':7,8]isoquinolino[3,2-a][1,3]dioxolo[4,5-g]isoquinoline
InChi Key
UXYJCYXWJGAKQY-HNNXBMFYSA-N
InChi Code
InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m0/s1
SMILES Code
[H][C@@]12CC(C=C3)=C(C4=C3OCO4)CN1CCC5=C2C=C6OCOC6=C5
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 323.34 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: Hori K, Okano S, Sato F. Efficient microbial production of stylopine using a Pichia pastoris expression system. Sci Rep. 2016 Feb 29;6:22201. doi: 10.1038/srep22201. PubMed PMID: 26923560; PubMed Central PMCID: PMC4770593. 2: Jang SI, Kim BH, Lee WY, An SJ, Choi HG, Jeon BH, Chung HT, Rho JR, Kim YJ, Chai KY. Stylopine from Chelidonium majus inhibits LPS-induced inflammatory mediators in RAW 264.7 cells. Arch Pharm Res. 2004 Sep;27(9):923-9. PubMed PMID: 15473662. 3: Ikezawa N, Iwasa K, Sato F. Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica. FEBS J. 2007 Feb;274(4):1019-35. Epub 2007 Jan 22. PubMed PMID: 17250743. 4: Pietra D, Borghini A, Bianucci AM. In vitro studies of antifibrotic and cytoprotective effects elicited by proto-berberine alkaloids in human dermal fibroblasts. Pharmacol Rep. 2015 Dec;67(6):1081-9. doi: 10.1016/j.pharep.2015.04.001. Epub 2015 Apr 16. PubMed PMID: 26481525. 5: Skarydova L, Hofman J, Chlebek J, Havrankova J, Kosanova K, Skarka A, Hostalkova A, Plucha T, Cahlikova L, Wsol V. Isoquinoline alkaloids as a novel type of AKR1C3 inhibitors. J Steroid Biochem Mol Biol. 2014 Sep;143:250-8. doi: 10.1016/j.jsbmb.2014.04.005. Epub 2014 Apr 24. PubMed PMID: 24769118. 6: Lavenir R, Paris RR. [On the alkaloids of the great celandine (Chelidonium majus L.). Distribution in different organs, isolation of stylopine from the fruit]. Ann Pharm Fr. 1965 May;23(5):307-12. French. PubMed PMID: 5891472. 7: Satou T, Koga M, Matsuhashi R, Koike K, Tada I, Nikaido T. Assay of nematocidal activity of isoquinoline alkaloids using third-stage larvae of Strongyloides ratti and S. venezuelensis. Vet Parasitol. 2002 Mar 1;104(2):131-8. PubMed PMID: 11809332. 8: Bribi N, Algieri F, Rodriguez-Nogales A, Vezza T, Garrido-Mesa J, Utrilla MP, Del Mar Contreras M, Maiza F, Segura-Carretero A, Rodriguez-Cabezas ME, Gálvez J. Intestinal anti-inflammatory effects of total alkaloid extract from Fumaria capreolata in the DNBS model of mice colitis and intestinal epithelial CMT93 cells. Phytomedicine. 2016 Aug 15;23(9):901-13. doi: 10.1016/j.phymed.2016.05.003. Epub 2016 May 12. PubMed PMID: 27387398. 9: Narcross L, Bourgeois L, Fossati E, Burton E, Martin VJ. Mining Enzyme Diversity of Transcriptome Libraries through DNA Synthesis for Benzylisoquinoline Alkaloid Pathway Optimization in Yeast. ACS Synth Biol. 2016 Dec 16;5(12):1505-1518. Epub 2016 Aug 2. PubMed PMID: 27442619. 10: Díaz Chávez ML, Rolf M, Gesell A, Kutchan TM. Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana. Arch Biochem Biophys. 2011 Mar 1;507(1):186-93. doi: 10.1016/j.abb.2010.11.016. Epub 2010 Nov 20. PubMed PMID: 21094631. 11: Bozhadze AD, Vachnadze VIu, Dzhokhadze MS, Berashvili DT, Bakuridze AD. [Study on the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia]. Georgian Med News. 2013 Apr;(217):61-5. Russian. PubMed PMID: 23676491. 12: Liscombe DK, Facchini PJ. Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy. J Biol Chem. 2007 May 18;282(20):14741-51. Epub 2007 Mar 27. PubMed PMID: 17389594. 13: Li W, Huang H, Niu X, Fan T, Hu H, Li Y, Yao H, Li H, Mu Q. Tetrahydrocoptisine protects rats from LPS-induced acute lung injury. Inflammation. 2014 Dec;37(6):2106-15. doi: 10.1007/s10753-014-9945-7. PubMed PMID: 24928630. 14: Yahyazadeh M, Ratmoyo P, Bittner F, Sato F, Selmar D. Cloning and Characterization of Cheilanthifoline and Stylopine Synthase Genes from Chelidonium majus. Plant Cell Physiol. 2017 Aug 1;58(8):1421-1430. doi: 10.1093/pcp/pcx077. PubMed PMID: 28633475. 15: Wangchuk P, Keller PA, Pyne SG, Sastraruji T, Taweechotipatr M, Rattanajak R, Tonsomboon A, Kamchonwongpaisan S. Phytochemical and biological activity studies of the Bhutanese medicinal plant Corydalis crispa. Nat Prod Commun. 2012 May;7(5):575-80. PubMed PMID: 22799079. 16: Popova ME, Simánek V, Dolejs L, Smysl B, Preininger V. Alkaloids from Fumaria parviflora and F. kralikii. Planta Med. 1982 Jun;45(2):120-2. PubMed PMID: 17396798. 17: Kiryakov HG, Iskrenova E, Kuzmanov B, Evstatieva L. Alkaloids from Corydalis marschalliana. Planta Med. 1981 Mar;41(3):298-302. PubMed PMID: 17401850. 18: Zhou JY, Tong XJ, Lian WY, Fang QC. Chemical Study on the Alkaloids of Corydalis hsuchowensis. Planta Med. 1991 Apr;57(2):156-8. PubMed PMID: 17226140. 19: Jesionek W, Fornal E, Majer-Dziedzic B, Móricz ÁM, Nowicky W, Choma IM. Investigation of the composition and antibacterial activity of Ukrain™ drug using liquid chromatography techniques. J Chromatogr A. 2016 Jan 15;1429:340-7. doi: 10.1016/j.chroma.2015.12.015. Epub 2015 Dec 8. PubMed PMID: 26718183. 20: Kulp M, Bragina O, Kogerman P, Kaljurand M. Capillary electrophoresis with LED-induced native fluorescence detection for determination of isoquinoline alkaloids and their cytotoxicity in extracts of Chelidonium majus L. J Chromatogr A. 2011 Aug 5;1218(31):5298-304. doi: 10.1016/j.chroma.2011.06.016. Epub 2011 Jun 17. PubMed PMID: 21726876.

View History

LEO-29102

LEO-29102