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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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WGK Germany 
3

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Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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

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

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