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SML0295 Sigma

Dihydromyricetin

≥98% (HPLC)

Synonym: (2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one, Ampelopsin, DHM

  • CAS Number 27200-12-0

  • Empirical Formula (Hill Notation) C15H12O8

  • Molecular Weight 320.25

  •  MDL number MFCD00189451

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Properties

Related Categories Antioxidants and Cytoprotectants, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
assay   ≥98% (HPLC)
form   powder
storage condition   protect from light
color   white to beige
solubility   DMSO: ≥5 mg/mL (warmed)
storage temp.   −20°C

Description

Biochem/physiol Actions

Dihydromyricetin (Ampelopsin) is a flavanonol with antioxidant and anti-cancer activity, found to have anti-alcohol intoxication effects. Its anti-alcohol effects appear to be by its actions as a positive modulator of GABA-A receptors at the benzodiazepine site.

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Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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Ampelopsin sodium exhibits antitumor effects against bladder carcinoma in orthotopic xenograft models. Zhang, B., et al. Anticancer Drugs Jan. 10, (2012)

Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: glucosylation enhancing physicochemical properties. Woo HJ, Kang HK, Nguyen TT, et al. Enzyme Microb. Technol. 51(6-7), 311-8, (2012)

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Dihydromyricetin as a novel anti-alcohol intoxication medication. Shen, Y., et al. J. Neurosci. 32, 390-401, (2012)

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Organic chemistry: Triumph for unnatural synthesis. Quideau S Nature 474(7352), 459-60, (2011)

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[Reversal effect and its mechanism of ampelopsin on multidrug resistance in K562/ADR cells]. Ye J, Zheng Y, and Liu D Zhongguo Zhong Yao Za Zhi 34(6), 761-5, (2009)

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[Study on preparation of ampelopsin liposomes]. He ZF, Liu DY, Zeng S, et al. Zhongguo Zhong Yao Za Zhi 33(1), 27-30, (2008)

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[Optimizing the extracting technique of ampelopsin from Ampelopsis cantoniensis Planch by a uniform design method]. He ZF, Zeng S, Hou JJ, et al. Zhong Yao Cai 29(7), 718-20, (2006)

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[The chemotaxis effect of ampelopsin on the immunocytes]. Zeng S, Luo GQ, and Liu DY Zhong Yao Cai 29(3), 260-2, (2006)

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[Inhibitory effects of ampelopsin on angiogenesis]. Luo GQ, Zeng S, and Liu DY Zhong Yao Cai 29(2), 146-50, (2006)

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[Anti-tumor effects of ampelopsin on human lung cancer GLC-82 implanted in nude mice]. Zeng S, Liu D, Ye Y, et al. Zhong Yao Cai 27(11), 842-5, (2004)

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[Effects of ampelopsin on invasion and metastasis of B16 mouse melanoma in vivo and in vitro]. Liu DY, Zheng HQ, and Luo GQ Zhongguo Zhong Yao Za Zhi 28(10), 957-61, (2003)

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[Anti-invasive and anti-metastatic effect of ampelopsin on melanoma]. Zheng HQ and Liu DY Ai Zheng 22(4), 363-7, (2003)

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[Study on inhibitory effect of ampelopsin on melanoma by serologic pharmacological method]. Liu D and Luo M Zhong Yao Cai 24(5), 348-50, (2001)

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[Determination of ampelopsin in the different parts of Ampelopsis grossedentata in different seasons by RP-HPLC]. Wang Y, Zhou L, Li R, et al. Zhong Yao Cai 25(1), 23-4, (2002)

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[Studies on the chemical constituents from Ampelopsis grossedentata]. Wang Y, Zhou L, Li R, et al. Zhong Yao Cai 25(4), 254-6, (2002)

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Regioselective reactions for programmable resveratrol oligomer synthesis. Snyder SA, Gollner A, and Chiriac MI Nature 474(7352), 461-6, (2011)

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Ampelopsin reduces endotoxic inflammation via repressing ROS-mediated activation of PI3K/Akt/NF-κB signaling pathways. Qi S, Xin Y, Guo Y, et al. Int. Immunopharmacol. 12(1), 278-87, (2012)

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Flavonoid ampelopsin inhibits the growth and metastasis of prostate cancer in vitro and in mice. Ni F, Gong Y, Li L, et al. PLoS ONE 7(6), e38802, (2012)

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Improving the solubility of ampelopsin by solid dispersions and inclusion complexes. Ruan LP, Yu BY, Fu GM, et al. J. Pharm. Biomed. Anal. 38(3), 457-64, (2005)

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Spectroscopic studies on the interaction between an anticancer drug ampelopsin and bovine serum albumin. Shi Y, Liu H, Xu M, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 87, 251-7, (2012)

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Ampelopsin, a small molecule inhibitor of HIV-1 infection targeting HIV entry. Liu DY, Ye JT, Yang WH, et al. Biomed. Environ. Sci. 17(2), 153-64, (2004)

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Development and application of high-performance liquid chromatography for the study of ampelopsin pharmacokinetics in rat plasma using cloud-point extraction. Zhou J, Zeng P, Tu HH, et al. J. Sep. Sci. 34(2), 160-8, (2011)

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Ampelopsin prevents apoptosis induced by H2O2 in MT-4 lymphocytes. Ye J, Guan Y, Zeng S, et al. Planta Med. 74(3), 252-7, (2008)

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Ampelopsin inhibits H₂O₂-induced apoptosis by ERK and Akt signaling pathways and up-regulation of heme oxygenase-1. Kou X, Shen K, An Y, et al. Phytother Res. 26(7), 988-94, (2012)

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Ampelopsin sodium exhibits antitumor effects against bladder carcinoma in orthotopic xenograft models. Zhang B, Dong S, Cen X, et al. Anticancer Drugs 23(6), 590-6, (2012)

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Synthesis and biological evaluation of new 5-fluorouracil-substituted ampelopsin derivatives. Zhou WM, He RR, Ye JT, et al. Molecules 15(4), 2114-23, (2010)

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cis-Ampelopsin E, a stilbene isolated from the seeds of Paeonia suffruticosa, inhibits lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages via blockade of nuclear factor-kappa B signaling pathway. Cai T and Cai Y Biol. Pharm. Bull. 34(9), 1501-7, (2011)

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