(R,S)-Stylopine - CAS 4312-32-7
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
(R,S)-Stylopine
Catalog Number:
4312-32-7
Synonyms:
Tetrahydrocoptisine; 7,12b,13,14-Tetrahydro-6H-[1,3]dioxolo[4,5-g][1,3]dioxolo[6,7]isoquinolino[2,1-a]quinoline;
CAS Number:
4312-32-7
Description:
Extract from the plant of Argemone mexicana acts as an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as Sanguinarine.
Molecular Weight:
323.34
Molecular Formula:
C19H17NO4
Quantity:
Milligrams-Grams
Quality Standard:
Enterprise Standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
c1c2c(cc3c1OCO3)N4CCc5cc6c(cc5C4CC2)OCO6
InChI:
1S/C19H17NO4/c1-2-14-13-7-18-16(21-9-23-18)5-11(13)3-4-20(14)15-8-19-17(6-12(1)15)22-10-24-19/h5-8,14H,1-4,9-10H2
InChIKey:
YHNPPTYQEPECRU-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 4312-32-7 (R,S)-Stylopine

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Reference Reading


1.Isoquinoline alkaloids as a novel type of AKR1C3 inhibitors.
Skarydova L1, Hofman J1, Chlebek J2, Havrankova J1, Kosanova K1, Skarka A1, Hostalkova A2, Plucha T1, Cahlikova L2, Wsol V3. J Steroid Biochem Mol Biol. 2014 Sep;143:250-8. doi: 10.1016/j.jsbmb.2014.04.005. Epub 2014 Apr 24.
AKR1C3 is an important human enzyme that participates in the reduction of steroids and prostaglandins, which leads to proliferative signalling. In addition, this enzyme also participates in the biotransformation of xenobiotics, such as drugs and procarcinogens. AKR1C3 is involved in the development of both hormone-dependent and hormone-independent cancers and was recently demonstrated to confer cell resistance to anthracyclines. Because AKR1C3 is frequently upregulated in various cancers, this enzyme has been suggested as a therapeutic target for the treatment of these pathological conditions. In this study, nineteen isoquinoline alkaloids were examined for their ability to inhibit a recombinant AKR1C3 enzyme. As a result, stylopine was demonstrated to be the most potent inhibitor among the tested compounds and exhibited moderate selectivity towards AKR1C3. In the follow-up cellular studies, stylopine significantly inhibited the AKR1C3-mediated reduction of daunorubicin in intact cells without considerable cytotoxic effects.
2.Efficient microbial production of stylopine using a Pichia pastoris expression system.
Hori K1, Okano S1, Sato F1. Sci Rep. 2016 Feb 29;6:22201. doi: 10.1038/srep22201.
Stylopine is a protoberberine-type alkaloid that has potential biological activities. Based on the successful microbial production of (S)-reticuline, we attempted to produce stylopine from (S)-reticuline by the reaction of berberine bridge enzyme, cheilanthifoline synthase (CYP719A5), and stylopine synthase (CYP719A2). Biosynthetic enzyme expression was examined in a methanol-utilizing yeast (Pichia pastoris), and both a "consolidated" system with all genes expressed in one cell and a "co-culture" system with three cell lines that each express a single gene were examined. Although both systems efficiently converted reticuline to stylopine, the consolidated system was more rapid and efficient than the co-culture system. However, substrate-feeding experiments revealed a decrease in the conversion efficiency in the consolidated system during successive cultures, whereas the conversion efficiency in the co-culture system remained constant. Thus, the final amount of stylopine produced from reticuline after successive feedings in the co-culture system was more than 150 nmoles from 750 nmoles of (R, S)-reticuline (375 nmoles of (S)-reticuline).
3.Investigation of the composition and antibacterial activity of Ukrain™ drug using liquid chromatography techniques.
Jesionek W1, Fornal E2, Majer-Dziedzic B3, Móricz ÁM4, Nowicky W5, Choma IM6. J Chromatogr A. 2016 Jan 15;1429:340-7. doi: 10.1016/j.chroma.2015.12.015. Epub 2015 Dec 8.
The greater celandine (Chelidonium majus L.) has been known for the centuries as a medicinal plant. One of the therapeutic agents based on C. majus is anticancer drug Ukrain™ known as a semi-synthetic C. majus alkaloid derivative. Although there are no doubts about antitumor properties of the drug, there is still controversy about its composition. In this study, Ukrain™ was subjected to TLC and LC-MS/MS analyses to compare it with C. majus alkaloid root extract and to determine its composition. Moreover, microbiological activity of both Ukrain™ and the alkaloid extract were tested against Bacillus subtilis strains using TLC-direct bioautography. Sanguinarine, chelidonine, α-homochelidonie and chelerythrine were found to have antibacterial properties. Besides chelidonine, sanguinarine, chelerythrine, protopine, allocryptopine, homochelidonie, berberine and coptisine reported earlier in literature, the presence of stylopine, norchelidonine, dihydrochelidonine and hydroberberine in Ukrain™ was detected, and here they have been reported for the first time.
4.Engineering strategies for the fermentative production of plant alkaloids in yeast.
Trenchard IJ1, Smolke CD2. Metab Eng. 2015 Jul;30:96-104. doi: 10.1016/j.ymben.2015.05.001. Epub 2015 May 14.
Microbial hosts engineered for the biosynthesis of plant natural products offer enormous potential as powerful discovery and production platforms. However, the reconstruction of these complex biosynthetic schemes faces numerous challenges due to the number of enzymatic steps and challenging enzyme classes associated with these pathways, which can lead to issues in metabolic load, pathway specificity, and maintaining flux to desired products. Cytochrome P450 enzymes are prevalent in plant specialized metabolism and are particularly difficult to express heterologously. Here, we describe the reconstruction of the sanguinarine branch of the benzylisoquinoline alkaloid pathway in Saccharomyces cerevisiae, resulting in microbial biosynthesis of protoberberine, protopine, and benzophenanthridine alkaloids through to the end-product sanguinarine, which we demonstrate can be efficiently produced in yeast in the absence of the associated biosynthetic enzyme.