Isoreserpiline
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| Category | Others |
| Catalog number | BBF-04737 |
| CAS | 572-67-8 |
| Molecular Weight | 412.48 |
| Molecular Formula | C23H28N2O5 |
| Purity | >95% by HPLC |
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Description
Isoreserpiline is an indole alkaloid isolated from Rhodiola crassifolia and has a variety of biological activities. Isoergophylline has antihypertensive and antipsychotic activities.
Specification
| Synonyms | 3-Isoreserpiline |
| Storage | Store at -20°C |
| IUPAC Name | methyl (1S,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-HAHWVIBASA-N |
Properties
| Solubility | Soluble in methanol, DMSO |
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. 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.
3. Large-scale separation of antipsychotic alkaloids from Rauwolfia tetraphylla L. by pH-zone-refining fast centrifugal partition chromatography
Anupam Maurya, Shikha Gupta, Santosh K Srivastava J Sep Sci. 2013 Jan;36(2):407-13. doi: 10.1002/jssc.201200273. Epub 2012 Nov 29.
pH-zone-refining centrifugal partition chromatography was successively applied in the large-scale separation of close R(f) antipsychotic indole alkaloids directly from CHCl(3) fraction of Rauwolfia tetraphylla leaves. Two experiments with increasing mass from 500 mg to 3 g of crude alkaloid extracts (1C) of R. tetraphylla were carried out in normal-displacement mode using a two-phase solvent system composed of methyl tert-butyl ether/ACN/water (4:1:5, v/v/v) where HCl (12 mM) was added to the lower aqueous stationary phase as a retainer and triethylamine (5 mM) to the organic mobile phase as an eluter. The two centrifugal partition chromatography separations afforded a total of 162.6 mg of 10-methoxytetrahydroalstonine (1) and 296.5 mg of isoreserpiline (2) in 97% and 95.5% purity, respectively, along with a 400.9 mg mixture of α-yohimbine and reserpiline (3 and 4). Further, this mixture was resolved over medium pressure LC using TLC grade silica gel H (average particle size 10 μm), which afforded 160.4 mg of α-yohimbine (3) and 150.2 mg of reserpiline (4) in >95% purities. The purity of the isolated antipsychotic alkaloids was analyzed by high-performance LC and their structures were characterized on the basis of their 1D, 2D NMR and electrospray ionization-mass spectroscopic data.
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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 ╳
