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(S)-Laudanosine

(Synonyms: (+)-Laudanosine, L-Laudanosine, L-(+)-Laudanosine, NSC 35045) 目录号 : GC40145

The (S) enantiomer of laudanosine

(S)-Laudanosine Chemical Structure

Cas No.:2688-77-9

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1mg
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5mg
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产品描述

(S)-Laudanosine is the (S) enantiomer of laudanosine, a metabolite of the neuromuscular blocking agents atracurium and cisatracurium . (S)-Laudanosine is also an alkaloid that has been found in the prickly poppy A. platyceras. It inhibits prolyl endopeptidase with an IC50 value of 341 μM. (S)-Laudanosine (100 μM) inhibits both arachidonic acid- and collagen-induced aggregation in washed rabbit platelets.

Chemical Properties

Cas No. 2688-77-9 SDF
别名 (+)-Laudanosine, L-Laudanosine, L-(+)-Laudanosine, NSC 35045
Canonical SMILES COC1=C(OC)C=C(CCN(C)[C@H]2CC3=CC=C(OC)C(OC)=C3)C2=C1
分子式 C21H27NO4 分子量 357.4
溶解度 Chloroform: slightly soluble,Ethanol: slightly soluble,Methanol: slightly soluble 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.798 mL 13.9899 mL 27.9799 mL
5 mM 0.5596 mL 2.798 mL 5.596 mL
10 mM 0.2798 mL 1.399 mL 2.798 mL
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Research Update

Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy

Plant Physiol 2012 Jun;159(2):618-31.PMID:22535422DOI:PMC3375929

Noscapine is a benzylisoquinoline alkaloid produced in opium poppy (Papaver somniferum) and other members of the Papaveraceae. It has been used as a cough suppressant and more recently was shown to possess anticancer activity. However, the biosynthesis of noscapine in opium poppy has not been established. A proposed pathway leading from (S)-reticuline to noscapine includes (S)-scoulerine, (S)-canadine, and (S)-N-methylcanadine as intermediates. Stem cDNA libraries and latex extracts of eight opium poppy cultivars displaying different alkaloid profiles were subjected to massively parallel pyrosequencing and liquid chromatography-tandem mass spectrometry, respectively. Comparative transcript and metabolite profiling revealed the occurrence of three cDNAs encoding O-methyltransferases designated as SOMT1, SOMT2, and SOMT3 that correlated with the accumulation of noscapine in the eight cultivars. SOMT transcripts were detected in all opium poppy organs but were most abundant in aerial organs, where noscapine primarily accumulates. SOMT2 and SOMT3 showed strict substrate specificity and regiospecificity as 9-O-methyltransferases targeting (S)-scoulerine. In contrast, SOMT1 was able to sequentially 9- and 2-O-methylate (S)-scoulerine, yielding (S)-tetrahydropalmatine. SOMT1 also sequentially 3'- and 7-O-methylated both (S)-norreticuline and (S)-reticuline with relatively high substrate affinity, yielding (S)-tetrahydropapaverine and (S)-Laudanosine, respectively. The metabolic functions of SOMT1, SOMT2, and SOMT3 were investigated in planta using virus-induced gene silencing. Reduction of SOMT1 or SOMT2 transcript levels resulted in a significant decrease in noscapine accumulation. Reduced SOMT1 transcript levels also caused a decrease in papaverine accumulation, confirming the selective roles for these enzymes in the biosynthesis of both alkaloids in opium poppy.