Reserpiline
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| Category | Enzyme inhibitors |
| Catalog number | BBF-05256 |
| CAS | 131-02-2 |
| Molecular Weight | 412.48 |
| Molecular Formula | C23H28N2O5 |
| Purity | >95% by HPLC |
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Description
Reserpiline is an indole alkaloid that has been found in R. tetraphylla. It is an antipsychotic, antiparasitic and hypotensive agent.
Specification
| Synonyms | Methyl (3beta,19alpha,20alpha)-16,17-didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylate; Elliptamine; Reserpilin; (-)-Reserpiline; (4S,4aS,13bR,14aS)-4a,5,7,8,13,13b,14,14a-octahydro-10,11-dimethoxy-4-methyl-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylic acid, methyl ester; methyl (4S,4aS,13bR,14aS)-10,11-dimethoxy-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate |
| Storage | Store at -20°C |
| IUPAC Name | methyl (1R,15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate |
| Canonical SMILES | CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC(=C(C=C45)OC)OC |
| InChI | InChI=1S/C23H28N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h8-9,11-12,14,16,19,24H,5-7,10H2,1-4H3/t12-,14-,16-,19+/m0/s1 |
| InChI Key | FGWJRZQNNZVCHR-BCRCDCHUSA-N |
Properties
| Appearance | Solid |
| Boiling Point | 569.9±50.0°C at 760 mmHg |
| Density | 1.31±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO, Methanol |
Reference Reading
1. New bioactive monoterpene indole alkaloid from Rinorea yaundensis Engl
Bushra Khatoon, Sadia Zikr Ur Rehman, Sammar Yousuf, Mehreen Lateef, Martial Flora Adjapmoh Essombo, Alain Francois Kamdem Waffo, Muhammad Shaiq Ali Nat Prod Res. 2022 Feb;36(4):942-951. doi: 10.1080/14786419.2020.1855160. Epub 2020 Dec 12.
Extraction of the aerial part of Rinorea yaundensis has led to the isolation of a new monoterpene indole alkaloid (1) along with 10 known compounds (2-11) for the first time from this plant. Their structures were determined by HRMS and NMR spectroscopic analyses as yaundentine hydrochloride (1), Nb-oxide of iso-reserpiline (2), iso-reserpiline (3), iso-carapanaubine (4), lichenxanthone (5), stigmastane-3,6-dione (6), methyl β-orcinol carboxylate (7), β-sitosterol-3-O-β-D-glucoside (8), betulinic acid (9), ursolic acid (10) and benzoic acid (11) while the stereochemistry and absolute configuration of 1 was confirmed by single crystal x-ray crystallography and circular dichroism CD spectrum. Yaundentine hydrochloride (1) exhibited pronounced antioxidant, urease and lipoxygenase inhibitory activities with IC50 values of 35.6 ± 0.23, 20.3 ± 0.58 and 29.6 ± 0.77 µM, respectively. Compound 1 also showed good antimicrobial activity against some Gram positive and negative bacteria.
2. Drug design of cyclin-dependent kinase 2 inhibitor for melanoma from traditional Chinese medicine
Hsin-Chieh Tang, Calvin Yu-Chian Chen Biomed Res Int. 2014;2014:798742. doi: 10.1155/2014/798742. Epub 2014 Jun 19.
One has found an important cell cycle controller. This guard can decide the cell cycle toward proliferation or quiescence. Cyclin-dependent kinase 2 (CDK2) is a unique target among the CDK family in melanoma therapy. We attempted to find out TCM compounds from TCM Database@Taiwan that have the ability to inhibit the activity of CDK2 by systems biology. We selected Tetrahydropalmatine, Reserpiline, and (+)-Corydaline as the candidates by docking and screening results for further survey. We utilized support vector machine (SVM), multiple linear regression (MLR) models and Bayesian network for validation of predicted activity. By overall analysis of docking results, predicted activity, and molecular dynamics (MD) simulation, we could conclude that Tetrahydropalmatine, Reserpiline, and (+)-Corydaline had better binding affinity than the control. All of them had the ability to inhibit the activity of CDK2 and might have the opportunity to be applied in melanoma therapy.
3. Synergy Potential of Indole Alkaloids and Its Derivative against Drug-resistant Escherichia coli
Gaurav Raj Dwivedi, Shikha Gupta, Anupam Maurya, Shubhandra Tripathi, Ashok Sharma, Mahendra P Darokar, Santosh K Srivastava Chem Biol Drug Des. 2015 Dec;86(6):1471-81. doi: 10.1111/cbdd.12613. Epub 2015 Aug 21.
Antibacterial and synergy potential of naturally occurring indole alkaloids (IA): 10-methoxy tetrahydroalstonine (1), isoreserpiline (2), 10 and 11 demethoxyreserpiline (3), reserpiline (4), serpentine (5), ajmaline (6), ajmalicine (7), yohimbine (8), and α-yohimbine (9) was evaluated using microbroth dilution assay. Further, α-yohimbine (9) was chemically transformed into six semisynthetic derivatives (9A-9F), and their antibacterial and synergy potential in combination with nalidixic acid (NAL) against E. coli strains CA8000 and DH5α were also evaluated. The IA 1, 2, 4, 5, 9 and the derivative 9F showed eightfold reduction in the MIC of NAL against the DH5α and four- to eightfold reduction against CA8000. These alkaloids also reduced MIC of another antibiotic, tetracycline up to 8folds, against the MDREC-KG4, a multidrug-resistant clinical isolate of E. coli. Mode of action study of these alkaloids showed efflux pumps inhibitory potential, which was supported by their in silico binding affinity and downregulation of efflux pump genes. These results may be of great help in the development of cost-effective antibacterial combinations for treating patients infected with multidrug-resistant Gram-negative infections.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
