Demethoxycapillarisin

Distinct Fractions of an Artemisia scoparia Extract Contain Compounds With Novel Adipogenic Bioactivity.[Pubmed:30906741]

Front Nutr. 2019 Mar 8;6:18.

Adipocytes are important players in metabolic health and disease, and disruption of adipocyte development or function contributes to metabolic dysregulation. Hence, adipocytes are significant targets for therapeutic intervention in obesity and metabolic syndrome. Plants have long been sources for bioactive compounds and drugs. In previous studies, we screened botanical extracts for effects on adipogenesis in vitro and discovered that an ethanolic extract of Artemisia scoparia (SCO) could promote adipocyte differentiation. To follow up on these studies, we have used various separation methods to identify the compound(s) responsible for SCO's adipogenic properties. Fractions and subfractions of SCO were tested for effects on lipid accumulation and adipogenic gene expression in differentiating 3T3-L1 adipocytes. Fractions were also analyzed by Ultra Performance Liquid Chromatography- Mass Spectrometry (UPLC-MS), and resulting peaks were putatively identified through high resolution, high mass accuracy mass spectrometry, literature data, and available natural products databases. The inactive fractions contained mostly quercetin derivatives and chlorogenates, including chlorogenic acid and 3,5-dicaffeoylquinic acid, which had no effects on adipogenesis when tested individually, thus ruling them out as pro-adipogenic bioactives in SCO. Based on these studies we have putatively identified the principal constituents in SCO fractions and subfractions that promoted adipocyte development and fat cell gene expression as prenylated coumaric acids, coumarin monoterpene ethers, 6-Demethoxycapillarisin and two polymethoxyflavones.

Qualitative variation of anti-diabetic compounds in different tarragon (Artemisia dracunculus L.) cytotypes.[Pubmed:21798321]

Fitoterapia. 2011 Oct;82(7):1062-74.

Ethanolic extracts of diploid Artemisia dracunculus L. (wild tarragon) from populations in the U.S., and polyploid tarragon from a variety of sources, were screened for the anti-diabetic compounds davidigenin; sakuranetin; 2',4'-dihydroxy-4-methoxydihydrochalcone; 4,5-di-O-caffeoylquinic acid; 5-O-caffeoylquinic acid and 6-Demethoxycapillarisin using LC-MS. Only decaploid plants contained all six target compounds and were the only plants that contained davidigenin and 2,4-dihydroxy-4-methoxydihydrochalcone. These results exhibit the importance of germplasm selection and provenance when studying plants for medicinal activity. Relying only on the "right species" for consistent medicinal activities may not be sufficient, as intraspecific variation may be highly significant.

Polyphenolic compounds from Artemisia dracunculus L. inhibit PEPCK gene expression and gluconeogenesis in an H4IIE hepatoma cell line.[Pubmed:17848630]

Am J Physiol Endocrinol Metab. 2007 Dec;293(6):E1503-10.

An ethanolic extract of Russian tarragon, Artemisia dracunculus L., with antihyperglycemic activity in animal models was reported to decrease phosphoenolpyruvate carboxykinase (PEPCK) mRNA expression in STZ-induced diabetic rats. A quantitative polymerase chain reaction (qPCR) assay was developed for the bioactivity-guided purification of the compounds within the extract that decrease PEPCK expression. The assay was based on the inhibition of dexamethasone-stimulated PEPCK upregulation in an H4IIE hepatoma cell line. Two polyphenolic compounds that inhibited PEPCK mRNA levels were isolated and identified as 6-Demethoxycapillarisin and 2',4'-dihydroxy-4-methoxydihydrochalcone with IC(50) values of 43 and 61 muM, respectively. The phosphoinositide-3 kinase (PI3K) inhibitor LY-294002 showed that 6-Demethoxycapillarisin exerts its effect through the activation of the PI3K pathway, similarly to insulin. The effect of 2',4'-dihydroxy-4-methoxydihydrochalcone is not regulated by PI3K and dependent on activation of AMPK pathway. These results indicate that the isolated compounds may be responsible for much of the glucose-lowering activity of the Artemisia dracunculus extract.

Bioassay-guided isolation of aldose reductase inhibitors from Artemisia dracunculus.[Pubmed:16806328]

Phytochemistry. 2006 Jul;67(14):1539-46.

An ethanolic extract of Artemisia dracunculus L. having antidiabetic activity was examined as a possible aldose reductase (ALR2) inhibitor, a key enzyme involved in diabetic complications. At 3.75 microg/mL, the total extract inhibited ALR2 activity by 40%, while quercitrin, a known ALR2 inhibitor, inhibited its activity by 54%. Bioactivity guided fractionation and isolation of the compounds that inhibit ALR2 activity was carried out with the total ethanolic extract yielding four bioactive compounds with ALR2 inhibitory activity ranging from 58% to 77% at 3.75 microg/mL. Using LC/MS, (1)H NMR, (13)C NMR and 2D NMR spectroscopic analyses, the four compounds were identified as 4,5-di-O-caffeoylquinic acid, davidigenin, 6-Demethoxycapillarisin and 2',4'-dihydroxy-4-methoxydihydrochalcone. This is the first report on their isolation from A. dracunculus and the ALR2 inhibitory activity of 4,5-di-O-caffeoylquinic acid, 6-Demethoxycapillarisin and 2',4'-dihydroxy-4-methoxydihydrochalcone. These results suggest a use of the extract of A. dracunculus for ameliorating diabetic complications.

Tenuiflorins A-C: new 2-phenoxychromones from the leaves of Mimosa tenuiflora.[Pubmed:15229805]

Planta Med. 2004 Jun;70(6):536-9.

Five 2-phenoxychromones, the new tenuiflorin A [5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenoxy)-6-methoxychromone], tenuiflorin B [5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenoxy)-6-methoxychromone] and tenuiflorin C [5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenoxy)chromone], along with the known 6-Demethoxycapillarisin and 6-demethoxy-4'- O-methylcapillarisin were isolated from leaves of Mimosa tenuiflora. Structures of these compounds were established by analysis of their spectroscopic data. A single-crystal diffraction analysis of 6-demethoxy-4'- O-methylcapillarisin was performed in order to confirm the proposed structures.