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(Z)-Akuammidine Sale

(Synonyms: 钩吻素丁,19-(Z)-Akuammidine; (Z)-Rhazine) 目录号 : GC60010

(Z)-Akuammidine((Z)-Rhazine)分离于Gelsemiumelegans。

(Z)-Akuammidine Chemical Structure

Cas No.:113973-31-2

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5mg
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产品描述

(Z)-Akuammidine ((Z)-Rhazine) is isolated from Gelsemium elegans[1].

[1]. Zhang Q, Zhang B, Chou G, Wang Z. Zhongguo Zhong Yao Za Zhi. 2011;36(10):1305-1310

Chemical Properties

Cas No. 113973-31-2 SDF
别名 钩吻素丁,19-(Z)-Akuammidine; (Z)-Rhazine
Canonical SMILES O=C([C@@]1([C@@](CC2=C3NC4=CC=CC=C24)([H])[N@@](C/5)[C@H]3C[C@H]1C5=C\C)CO)OC
分子式 C21H24N2O3 分子量 352.43
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1 mM 2.8374 mL 14.1872 mL 28.3744 mL
5 mM 0.5675 mL 2.8374 mL 5.6749 mL
10 mM 0.2837 mL 1.4187 mL 2.8374 mL
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Research Update

Microfractionation bioactivity-based ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry for the identification of nuclear factor-κB inhibitors and β2 adrenergic receptor agonists in an alkaloidal extract of the folk herb Alstonia scholaris

J Chromatogr B Analyt Technol Biomed Life Sci 2012 Nov 1;908:98-104.PMID:23122407DOI:10.1016/j.jchromb.2012.10.004.

Traditional Chinese medicines (TCMs) are generally considered complementary or alternative remedies in most Western countries. The constituents of TCMs are hard to define, and their efficacy is difficult to appraise. Thus, the development of suitable methods for evaluating the relationship between bioactivity and the chemical makeup of complex TCM mixtures remains a great challenge. In the present work, the bioactivity-integrated fingerprints of alkaloidal leaf extracts of Alstonia scholaris, a folk medicinal herb for chronic respiratory diseases, were established by ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC-Q/TOF). This method was coupled with two dual-luciferase reporter assay systems to show nuclear factor-κB (NF-κB) inhibition and β(2) adrenergic receptor (β(2)AR) activation. Using UPLC-Q/TOF, 18 potential candidates were identified according to unique mass spectrometric fragmentation. After in vitro biological evaluation, several indole alkaloids with anti-inflammatory and anti-asthmatic properties were found, including akuammidine, (E)-alstoscholarine, and (Z)-alstoscholarine. Compared with conventional fingerprints, the microfractionation based bioactivity-integrated fingerprints that contain both chemical and bioactivity details offer a more comprehensive understanding of the chemical makeup of plant materials. This strategy clearly demonstrated that dual bioactivity-integrated fingerprinting is a powerful tool for the improved screening and identification of potential dual-target lead compounds in complex herbal medicines.

[Chemical constituents of aerial parts of Gelsemium elegans]

Zhongguo Zhong Yao Za Zhi 2011 May;36(10):1305-10.PMID:21837971doi

Objective: To study the chemical constituents from the aerial parts of Gelsemium elegans. Method: Compounds were isolated and purified by repeated column chromatography, as well as semiprep arative HPLC, and their structures were identified by physicochemical properties and spectroscopic methods, such as NMR and MS. Result: Sixteen compounds were obtained and identified from G. elegans, including nine alkaloids: koumine (1), gelsenicine (2), 19-(Z)-Akuammidine (3), gelsemoxonine(4), gelsemin (5), gelsevirine (6), humantenine (7), 11-methoxygelsemamide (8) and gelegamine D (9). Three megastigmane glycosides: (3R, 5S, 6S, 7E, 9R)-megastigman-7-ene-3, 5, 6, 9-tetrol-9-O-beta-D-glucopyranoside (10), (6R, 7E, 9R)-9-hydroxy-4, 7-megastigmadien-3-one-9-O-[alpha-L-arabinopyranosyl-(1 --> 6)-beta-D-glucopyranoside] (11) and (6S, 7E, 9R) -6, 9-dihydroxy-4, 7-megastigmadien-3-one-9-O-[alpha-L-arabinopyranosyl-(1 --> 6) -beta-D-glucopyranoside] (12). Two flavone C-glycosides: orientin (13) and isorientin (14); one iridoid glycoside, sweroside (15) and one fructoside, n-butyl-alpha-D-fructofuranoside (16). Conclusion: Compounds 10-16 were isolated from the genus Gelsemium for the first time.

Comparative metabolomics analysis reveals alkaloid repertoires in young and mature Mitragyna speciosa (Korth.) Havil. Leaves

PLoS One 2023 Mar 21;18(3):e0283147.PMID:36943850DOI:10.1371/journal.pone.0283147.

The fresh leaves of Mitragyna speciosa (Korth.) Havil. have been traditionally consumed for centuries in Southeast Asia for its healing properties. Although the alkaloids of M. speciosa have been studied since the 1920s, comparative and systematic studies of metabolite composition based on different leaf maturity levels are still lacking. This study assessed the secondary metabolite composition in two different leaf stages (young and mature) of M. speciosa, using an untargeted liquid chromatography-electrospray ionisation-time-of-flight-mass spectrometry (LC-ESI-TOF-MS) metabolite profiling. The results revealed 86 putatively annotated metabolite features (RT:m/Z value) comprising 63 alkaloids, 10 flavonoids, 6 terpenoids, 3 phenylpropanoids, and 1 of each carboxylic acid, glucoside, phenol, and phenolic aldehyde. The alkaloid features were further categorised into 14 subclasses, i.e., the most abundant class of secondary metabolites identified. As per previous reports, indole alkaloids are the most abundant alkaloid subclass in M. speciosa. The result of multivariate analysis (MVA) using principal component analysis (PCA) showed a clear separation of 92.8% between the young and mature leaf samples, indicating a high variance in metabolite levels between them. Akuammidine, alstonine, tryptamine, and yohimbine were tentatively identified among the many new alkaloids reported in this study, depicting the diverse biological activities of M. speciosa. Besides delving into the knowledge of metabolite distribution in different leaf stages, these findings have extended the current alkaloid repository of M. speciosa for a better understanding of its pharmaceutical potential.