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Ipecoside Sale

目录号 : GC38626

Ipecoside 是从 Psychotria 分离的生物碱。

Ipecoside Chemical Structure

Cas No.:15401-60-2

规格 价格 库存 购买数量
1mg
¥1,008.00
现货
5mg
¥3,024.00
现货
10mg
¥5,139.00
现货

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Sample solution is provided at 25 µL, 10mM.

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产品描述

Ipecoside is an alkaloid isolated from Psychotria[1].

[1]. J Biol Chem. 2008 Dec 12;283(50):34650-9. doi: 10.1074/jbc.M806953200. Epub 2008 Oct 16.

Chemical Properties

Cas No. 15401-60-2 SDF
Canonical SMILES O=C(C1=CO[C@@H](O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@H](C=C)[C@@H]1C[C@H]3N(C(C)=O)CCC4=C3C=C(O)C(O)=C4)OC
分子式 C27H35NO12 分子量 565.57
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 1.7681 mL 8.8406 mL 17.6813 mL
5 mM 0.3536 mL 1.7681 mL 3.5363 mL
10 mM 0.1768 mL 0.8841 mL 1.7681 mL
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Research Update

The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha

J Biol Chem 2008 Dec 12;283(50):34650-9.PMID:18927081DOI:10.1074/jbc.M806953200.

Ipecac alkaloids produced in the medicinal plant Psychotria ipecacuanha such as emetine and cephaeline possess a monoterpenoid-tetrahydroisoquinoline skeleton, which is formed by condensation of dopamine and secologanin. Deglucosylation of one of the condensed products N-deacetylisoipecoside (1 alpha(S)-epimer) is considered to be a part of the reactions for emetine biosynthesis, whereas its 1 beta(R)-epimer N-deacetylipecoside is converted to Ipecoside in P. ipecacuanha. Here, we isolated a cDNA clone Ipeglu1 encoding Ipecac alkaloid beta-D-glucosidase from P. ipecacuanha. The deduced protein showed 54 and 48% identities to raucaffricine beta-glucosidase and strictosidine beta-glucosidase, respectively. Recombinant IpeGlu1 enzyme preferentially hydrolyzed glucosidic Ipecac alkaloids except for their lactams, but showed poor or no activity toward other substrates, including terpenoid-indole alkaloid glucosides. Liquid chromatography-tandem mass spectrometry analysis of deglucosylated products of N-deacetylisoipecoside revealed spontaneous transitions of the highly reactive aglycons, one of which was supposed to be the intermediate for emetine biosynthesis. IpeGlu1 activity was extremely poor toward 7-O-methyl and 6,7-O,O-dimethyl derivatives. However, 6-O-methyl derivatives were hydrolyzed as efficiently as non-methylated substrates, suggesting the possibility of 6-O-methylation prior to deglucosylation by IpeGlu1. In contrast to the strictosidine beta-glucosidase that stereospecifically hydrolyzes 3 alpha(S)-epimer in terpenoid-indole alkaloid biosynthesis, IpeGlu1 lacked stereospecificity for its substrates where 1 beta(R)-epimers were preferred to 1 alpha(S)-epimers, although Ipecoside (1 beta(R)) is a major alkaloidal glucoside in P. ipecacuanha, suggesting the compartmentalization of IpeGlu1 from Ipecoside. These facts have significant implications for distinct physiological roles of 1 alpha(S)- and 1 beta(R)-epimers and for the involvement of IpeGlu1 in the metabolic fate of both of them.