Dihydromethysticin
Dihydromethysticin is a kavalactone originally found in Piper methysticum (kava plant) that exhibits antifungal, antiepileptic/anticonvulsant, neuroprotective, anticancer, and chemopreventive activities. This compound displays antimicrobial efficacy against species of Fusarium, Trichoderma, and Colletotrichum. Dihydromethysticin also binds receptor site 2 and inhibits voltage-gated Na+ channels; it inhibits L-type voltage-gated Ca2+ channels as well. In vivo, dihydromethysticin inhibits the formation of NNK-induced tumors and, separately, protects against cerebral ischemia-induced damage.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18871880
| Cas No. |
19902-91-1 |
|---|---|
| Purity |
≥98% |
| Formula |
C15H16O5 |
| Formula Wt. |
276.28 |
| IUPAC Name |
(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one |
| Synonym |
2H-Pyran-2-one,6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-, (S)-; 7,8-Dihydromethysticin |
| Appearance |
White crystalline powder |
Narayanapillai SC, Balbo S, Leitzman P, et al. Dihydromethysticin (DHM) from kava blocks tobacco carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis and differentially reduces DNA damage in A/J mice. Carcinogenesis. 2014 Jul 22. [Epub ahead of print]. PMID: 25053626.
Xuan TD, Elzaawely AA, Fukuta M, et al. Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum). J Agric Food Chem. 2006 Feb 8;54(3):720-5. PMID: 16448174.
Friese J, Gleitz J. Kavain, dihydrokavain, and dihydromethysticin non-competitively inhibit the specific binding of [3H]-batrachotoxinin-A 20-alpha-benzoate to receptor site 2 of voltage-gated Na+ channels. Planta Med. 1998 Jun;64(5):458-9. PMID: 9690349.
Backhauss C, Krieglstein J. Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents. Eur J Pharmacol. 1992 May 14;215(2-3):265-9. PMID: 1396990.
