Methysticin - CAS 20697-20-5
Catalog number: 20697-20-5
Category: Inhibitor
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Molecular Formula:
C15H14O5
Molecular Weight:
274.27
COA:
Inquire
Targets:
NF-κB
Description:
Methysticin, the first Kava-pyrone isolated from the active constituents of rhizome extracts from Piper methysticum-a shrub indigenous to South Pacific islands, has an anticonvulsant effect and potently inhibits non-toxic NF-κB .
Appearance:
Solid powder
Synonyms:
(2S)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one methysticin methysticin, ((E)-(+-))-isomer
Solubility:
Soluble in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -57℃ for long term (months to years).
MSDS:
Inquire
Shelf Life:
2 years
Boiling Point:
496.5±45.0 °C | Condition: Press: 760 Torr
Melting Point:
129-131 °C
Density:
1.31±0.1 g/cm3
InChIKey:
GTEXBOVBADJOQH-JRBALWBOSA-N
InChI:
1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m1/s1
Canonical SMILES:
COC1=CC(=O)OC(C1)C=CC2=CC3=C(C=C2)OCO3
1.Kavalactones, a novel class of protein glycation and lipid peroxidation inhibitors.
Upadhyay A1, Tuenter E1, Ahmad R1, Amin A1, Exarchou V1, Apers S1, Hermans N1, Pieters L1. Planta Med. 2014 Aug;80(12):1001-8. doi: 10.1055/s-0034-1382949. Epub 2014 Aug 6.
Both advanced glycation endproducts and advanced lipoxidation endproducts are implicated in many age-related chronic diseases and in protein ageing. In this study, kawain, methysticin, and dihydromethysticin, all belonging to the group of kavalactones, were identified as advanced glycation endproduct inhibitors. With IC50 values of 43.5 ± 1.2 µM and 45.0 ± 1.3 µM for kawain and methysticin, respectively, the compounds inhibited the in vitro protein glycation significantly better than aminoguanidine (IC50 = 231.0 ± 11.5 µM; p = 0.01), an established reference compound. Kawain and methysticin also inhibited the formation of dicarbonyl compounds, which are intermediates in the process of advanced glycation endproduct formation. Similarly, kawain and aminoguanidine prevented the formation of thiobarbituric reactive substances in both low-density lipoprotein and linoleic acid oxidation. Moreover, kawain and aminoguanidine prevented advanced glycation endproduct formation by chelating Fe(3+) and Cu(2+) two to three times better than aminoguanidine.
2.Herbal bioactivation, molecular targets and the toxicity relevance.
Chen XW1, Serag ES, Sneed KB, Zhou SF. Chem Biol Interact. 2011 Jul 15;192(3):161-76. doi: 10.1016/j.cbi.2011.03.016. Epub 2011 Apr 1.
There have been increasing reports on the adverse reactions associated with herbal consumption. For many of these adverse reactions, the underlying biochemical mechanisms are unknown, but bioactivation of herbal compounds to generate reactive intermediates have been implicated. This minireview updates our knowledge on metabolic activation of herbal compounds, molecular targets and the toxicity relevance. A number of studies have documented that some herbal compounds can be converted to toxic or even carcinogenic metabolites by Phase I [e.g. cytochrome P450s (CYPs)] and less frequently by Phase II enzymes. For example, aristolochic acids (AAs) in Aristolochia spp, which undergo reduction of the nitro group by hepatic CYP1A1/2 or peroxidases in extrahepatic tissues to generate highly reactive cyclic nitrenium ions. The latter can react with macromolecules (DNA and protein), resulting in activation of H-ras and myc oncogenes and gene mutation in renal cells and finally carcinogenesis of the kidneys.
3.Phototoxicity of kava - formation of reactive oxygen species leading to lipid peroxidation and DNA damage.
Xia Q1, Chiang HM, Zhou YT, Yin JJ, Liu F, Wang C, Guo L, Fu PP. Am J Chin Med. 2012;40(6):1271-88. doi: 10.1142/S0192415X12500942.
Kava is one of the most widely sold herbal dietary supplements in the United States. It has been reported that, besides exhibiting hepatotoxicity, kava also possesses photosensitivity and induces dermopathy in humans. In this study, we determined that UVA irradiation of kava in the presence of a lipid, methyl linoleate, generated lipid peroxidation which was mediated by singlet oxygen generated during photoirradiation. The six major kavalactones(yangonin, 7,8-dihydrokawa in, kawain, 7,8-dihydromethysticin, methysticin, and 5,6-dehydrokawain) were also studied in parallel; only 5,6-dehydrokawain and yangonin-induced a low level of lipid peroxidation. UVA irradiation of kava in human HaCaT skin keratinocytes induced cytotoxicity which was mediated by oxidative stress, led to DNA strand cleavage, and produced 8-hydroxy-2'-deoxyguanosine (8-OHdG) adduct. Study by the electron spin resonance (ESR) method revealed that UVA irradiation of kava produced singlet oxygen and carbon-centered radicals.
4.Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in mice.
Li X1, Liu Z, Xu X, Blair CA, Sun Z, Xie J, Lilly MB, Zi X. PLoS One. 2012;7(2):e31213. doi: 10.1371/journal.pone.0031213. Epub 2012 Feb 9.
Men living in Fiji and drinking kava have low incidence of prostate cancer (PCa). However, the PCa incidence among Fijian men who had migrated to Australia, increased by 5.1-fold. We therefore examined the potential effects of kava root extracts and its active components (kavalactones and flavokawains) on PCa growth and androgen receptor (AR) expression. PCa cell lines (LNCaP, LAPC-4, 22Rv1, C4-2B, DU145 and PC-3) with different AR expression, and a transformed prostate myofibroblast cell line (WPMY-1), were treated with a commercial kava extract, kavalactones (kawain, 5'6'-dehydrokawain, yangonin, methysticin) and flavokawain B. Expression of AR and its target genes (PSA and TMPRSS2) was examined. Two novel patient-derived PCa xenograft models from high grade PCa specimens were established by implanting the specimens into nude mice and passing tumor pieces through subcutaneous injection in nude mice, and then treated with kava extract and flavokawain B to examine their effects on tumor growth, AR expression and serum PSA levels.
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CAS 20697-20-5 Methysticin

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