Hydroxy-β-sanshool
(Synonyms: 羟基-Β-山椒素) 目录号 : GC36280Hydroxy-β-sanshool 是一种烷基酰胺,存在于花椒油和青椒油中。
Cas No.:97465-69-5
Sample solution is provided at 25 µL, 10mM.
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Hydroxy-β-sanshool is an alkylamide exists in Zanthoxylum bungeanum oil and Zanthoxylum schinifolium oil[1].
[1]. Zhao ZF, et al. Characterization and comparison of the pungent components in commercial Zanthoxylum bungeanum oil and Zanthoxylum schinifolium oil. J Food Sci. 2013 Oct;78(10):C1516-C1522.
Cas No. | 97465-69-5 | SDF | |
别名 | 羟基-Β-山椒素 | ||
Canonical SMILES | CC(C)(O)CNC(/C=C/CC/C=C/C=C/C=C/C)=O | ||
分子式 | C16H25NO2 | 分子量 | 263.38 |
溶解度 | DMSO : 50 mg/mL (189.84 mM; ultrasonic and warming and heat to 80°C) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.7968 mL | 18.984 mL | 37.968 mL |
5 mM | 0.7594 mL | 3.7968 mL | 7.5936 mL |
10 mM | 0.3797 mL | 1.8984 mL | 3.7968 mL |
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2.
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Hydroxy-alpha-sanshool activates TRPV1 and TRPA1 in sensory neurons
Eur J Neurosci 2007 Sep;26(5):1139-47.PMID:17767493DOI:10.1111/j.1460-9568.2007.05743.x.
Sanshools are major active ingredients of Zanthoxylum piperitum and are used as food additives in East Asia. Sanshools cause irritant, tingling and sometimes paresthetic sensations on the tongue. However, the molecular mechanism underlying the pungent or tingling sensation induced by sanshools is not known. Because many transient receptor potential (TRP) channels are responsible for the sensations induced by various spices and food additives, we expressed 17 TRP channels in human embryonic kidney (HEK) cells and investigated their activation by hydroxy-alpha-sanshool (HalphaSS) or hydroxy-beta-sanshool (HbetaSS) isolated from Zanthoxylum piperitum. It was found that HalphaSS, but not HbetaSS, depolarized sensory neurons with concomitant firing of action potentials and evoked inward currents. Among 17 TRP channels expressed in HEK cells, HalphaSS caused Ca(2+) influx in cells transfected with TRPV1 or TRPA1, and evoked robust inward currents in cells transfected with TRPV1 or TRPA1. In primary cultured sensory neurons, HalphaSS induced inward currents and Ca(2+) influx in a capsazepine-dependent manner. Moreover, HalphaSS-induced currents and Ca(2+) influx were greatly diminished in TRPV1(-/-) mice. HalphaSS evoked licking behavior when injected into a single hind paw of wild-type mice, but this was much reduced in TRPV1-deficient mice. These results indicate that TRPV1 and TRPA1 are molecular targets of HalphaSS in sensory neurons. We conclude that the activations of TRPV1 and TRPA1 by HalphaSS explain its unique pungent, tingling sensation.
Human acyl-CoA: cholesterol acyltransferase inhibitory activities of aliphatic acid amides from Zanthoxylum piperitum DC
Biol Pharm Bull 2007 Jan;30(1):205-7.PMID:17202689DOI:10.1248/bpb.30.205.
Acyl-CoA: cholesterol acyltransferase (ACAT) plays an important role in the esterification of cholesterol with its substrates, cholesterol and fatty acyl coenzyme A, to facilitate both intracellular storage and intercellular transport. ACAT-1 is more involved in macrophage foam cell formation and ACAT-2 plays a critical role in the cholesterol absorption process in intestinal enterocytes. Three aliphatic acid amides, beta-sanshool (1), gamma-sanshool (2), and hydroxy-beta-sanshool (3), were isolated by bioassay-guided fractionation of the ethanolic extracts of Zanthoxylum piperitum DC. Compounds 1 and 2 inhibited human ACAT-1 and -2 activities with IC50 values of 39.0 and 79.7 microM for 1 and of 12.0 and 82.6 microM for 2, respectively. However, the hACAT-1 and -2 inhibitory activities of compound 3 having hydroxyl group were relatively less than those of compounds 1 and 2. A semi-synthetic compound 4, which has acetyl residue at 2'-OH of compound 3, exhibited the increased hACAT-1 and -2 inhibitory activities with IC50 values of 28.1 and 87.5 microM, respectively.
Characterization of the pungent principles and the essential oil of Zanthoxylum schinifolium pericarp
Pharmazie 2007 May;62(5):396-400.PMID:17557752doi
The pungent principles and the essential oil from the pericarp of Zanthoxylum schinifolium (Rutaceae) have been investigated and compared to those of Z. bungeanum, the primary source of the traditional Chinese drug Huajiao (Pericarpium Zanthoxyli). HPLC-MS and HPLC-NMR analyses revealed an alkylamide profile highly similar to that of Z. bungeanum, with hydroxy-alpha-sanshool and hydroxy-beta-sanshool being in both plants the major constituents of the alkylamide fraction. GC-FID and GC-MS analyses of the essential oil showed that limonene was, like in Z. bungeanum, the main component (21%), followed by 4-terpineol, gamma-terpinene, alpha-terpineol acetate, beta-pinene, alpha-terpineol and beta-linalool.