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Isoreserpiline Sale

(Synonyms: 3-Isoreserpilinic Acid, methyl ester, Neoreserpiline) 目录号 : GC48554

An indole alkaloid with diverse biological activities

Isoreserpiline Chemical Structure

Cas No.:572-67-8

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产品描述

Isoreserpiline is an indole alkaloid that has been found in R. tetraphylla and has diverse biological activities.1,2 It has a synergistic effect on the antibacterial activity induced by nalidixic acid in nalidixic acid-sensitive and -resistant strains of E. coli.2 It also reduces amphetamine-induced hyperactivity in mice when administered at a dose of 25 mg/kg.1

1.Gupta, S., Khanna, V.K., Maurya, A., et al.Bioactivity guided isolation of antipsychotic constituents from the leaves of Rauwolfia tetraphylla L.Fitoterapia83(6)1092-1099(2012) 2.Dwivedi, G.R., Gupta, S., Maurya, A., et al.Synergy potential of indole alkaloids and its derivative against drug-resistant Escherichia coliChem. Biol. Drug Des.86(6)1471-1481(2015)

Chemical Properties

Cas No. 572-67-8 SDF
别名 3-Isoreserpilinic Acid, methyl ester, Neoreserpiline
Canonical SMILES COC1=CC(N2)=C(C=C1OC)C3=C2[C@@]4([H])N(CC3)C[C@@]5([H])[C@H](C)OC=C(C(OC)=O)[C@@]5([H])C4
分子式 C23H28N2O5 分子量 412.5
溶解度 储存条件 -20°C
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1 mM 2.4242 mL 12.1212 mL 24.2424 mL
5 mM 0.4848 mL 2.4242 mL 4.8485 mL
10 mM 0.2424 mL 1.2121 mL 2.4242 mL
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Research Update

Synergy Potential of Indole Alkaloids and Its Derivative against Drug-resistant Escherichia coli

Chem Biol Drug Des 2015 Dec;86(6):1471-81.PMID:26132412DOI:10.1111/cbdd.12613.

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.

Oppositinines A and B: new vasorelaxant beta-carboline alkaloids from Neisosperma oppositifolia

Chem Pharm Bull (Tokyo) 2010 Aug;58(8):1085-7.PMID:20686264DOI:10.1248/cpb.58.1085.

A phytochemical study on the bark of Neisosperma oppositifolia (Apocynaceae) yielded two new beta-carboline indole alkaloids, oppositinines A (1) and B (2), together with five known alkaloids, Isoreserpiline, isocarapanaubine, vobasine, 10-methoxydihydrocorynantheol-N-oxide, and ochropposinine oxindole. Structural elucidation of 1 and 2 was performed using 2D NMR methods. Oppositinines A (1) and B (2) showed potent vasorelaxant effects on the rat aorta.

Application of pH-zone-refining countercurrent chromatography for the separation of indole alkaloids from Aspidosperma rigidum Rusby

J Chromatogr A 2013 Dec 6;1319:166-71.PMID:24192149DOI:10.1016/j.chroma.2013.10.044.

Species of Aspidosperma (Apocynaceae) are characterized by the occurrence of indole alkaloids, but few recent reports on Aspidosperma rigidum Rusby chemical constituents were found. The present work shows the application of pH-zone refining countercurrent chromatography on the separation of alkaloids from the barks of A. rigidum. In this study, the dichloromethane extract was fractionated with the solvent system composed of methyl-tert-butyl ether and water with different concentrations of the retainer triethylamine in the organic stationary phase and formic or hydrochloric acids as eluters in the aqueous mobile phase, in order to evaluate the most suitable condition. In each experiment, from circa 200mg of the dichloromethane extract of A. rigidum, three major alkaloids were isolated and identified as 3α-aricine (circa 17mg), Isoreserpiline (ca. 22mg) and 3β-reserpiline (ca. 40mg), with relative purity of 79%, 89% and 82% respectively, in a one-step separation of 2h. Two of them - 3α-aricine and Isoreserpiline - were isolated and identified for the first time in this species.

Bioactivity guided isolation of antipsychotic constituents from the leaves of Rauwolfia tetraphylla L

Fitoterapia 2012 Sep;83(6):1092-9.PMID:22579842DOI:10.1016/j.fitote.2012.04.029.

This study was undertaken to ascertain the antipsychotic properties of Rauwolfia tetraphylla L. leaves and to isolate and characterize the antipsychotic constituents. Among the MeOH extract and some alkaloidal fractions at different pHs, the alkaloidal CHCl(3) fraction at pH-9 (2C) showed the highest antipsychotic activity against dopaminergic (DA-D(2)) and serotonergic (5-HT(2A)) receptors in-vitro and amphetamine induced hyperactive mouse model in-vivo. The activity guided isolation of CHCl(3) fraction (2C) afforded six indole alkaloids: 10-methoxytetrahydroalstonine (1), Isoreserpiline (2), an isomeric mixture of 11-demethoxyreserpiline (3) and 10-demethoxyreserpiline (4), α-yohimbine (5) and reserpiline (6). Given orally, alkaloids 3-6 showed significant antipsychotic activity in a dose dependent manner. None of the extract, alkaloidal fractions or alkaloids showed any extra pyramidal symptoms at the tested doses. It was also observed that MeOH extract was behaving similar to other clinically used novel atypical antipsychotics in having 5-HT(2A) occupancy greater than the DA-D(2) receptor at the tested doses. Further toxicity and safety evaluation studies of MeOH extracts of R. tetraphylla leaves at different doses (10, 100, 300 and 2000 mg/kg) on female Swiss albino mice showed that MeOH extract is non toxic. The isolated alkaloids, 3-6 could serve as a promising lead structure for drug development of treating psychotic conditions in human.

Large-scale separation of antipsychotic alkaloids from Rauwolfia tetraphylla L. by pH-zone-refining fast centrifugal partition chromatography

J Sep Sci 2013 Jan;36(2):407-13.PMID:23335460DOI:10.1002/jssc.201200273.

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.