Isolation and identification of metabolites from dihydromyricetin

Zhang, Yansong; Que, Sheng; Yang, Xiu‐Wei; Wang, Bin; Liao, Qiao; Zhao, Yi

doi:10.1002/mrc.2051

Cited by 59 publications

(56 citation statements)

References 7 publications

(7 reference statements)

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“…While both 2 R ,3 S and 2 S ,3 R enantiomers were eliminated based on the coupling constant of the signals for H-2 and H-3. The two proton signals of 1 were double and double peaks: 4.81 (1H, J = 10.45 Hz, 2-H), 4.16 (1H, J = 10.6 Hz, 3-H), whereas in its 2 R ,3 S isomer they were both single peaks, which indicated that 2-H and 3-H are either 2 R ,3 R or 2 S ,3 S enantiomers [27]. The experimental ECD spectrum showed a positive Cotton effect at 197 nm and a negative Cotton effect at 217 nm (Fig.…”

Section: Resultsmentioning

confidence: 99%

Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation

et al. 2015

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Three new compounds, (2S,3S)-5-methyldihydromyricetin (1), (2S,3S)-5-methyldihydromyricetin-3′-O-sulfate (2) and β-D-glucopyranoside, 3-methyl, but-3-en-1-yl 4-O-α-L-rhamnopyranosyl (3) have been isolated from the Limonium caspium, together with dihydromyricetin (4), dihydromyricetin-3′-O-sulfate (5), myricetin-3′-O-sulfate (6), 5-methylmyricetin (7), myricetin (8), myricetin-3-O-β-glucoside (9), as well as phloridzin (10), and tyramine (11). Compounds 5 and 6 were isolated for the first time as acids. This is the first report of all these compounds from this plant. Their structures were established by extensive NMR studies (1H NMR, 13C NMR, DEPT, 1H–1H COSY, HSQC, HMBC) as well as HRESIMS. All isolated compounds were evaluated for their antibacterial, antifungal, antimalarial and antileishmanial activities. Compounds 7, 8 and 9 exhibited good antifungal activity against Candida glabrata with IC50 values of 6.79, 15.37 and 8.53 μg/mL, respectively. Compound 8 displayed significant antimalarial activity against resistant and sensitive strains of Plasmodium falciparum with IC50 values of 1.82 and 1.51 μg/mL, respectively. Compounds 1, 4, 6, 8 and 9 showed excellent activity against Trypanosoma brucei with IC50 values of 6.93, 9.65, 8.52, 7.67 and 6.31 μg/mL, respectively. To date, this is the first report on the phytochemical and biological activity of secondary metabolites from L. caspium.

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Section: Resultsmentioning

confidence: 99%

Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation

et al. 2015

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“…The Dose 1 group received 150 mg/kg of dihydromyricetin every day, and the Dose 2 group received 300 mg/kg of dihydromyricetin every day. At the termination of the study, the mean volumes of the tumors were 1,957 mm 3 for the control group, 1,238 mm 3 for the Dose 1 group, and 834.6 mm 3 for the Dose 2 group (Fig. 3A).…”

Section: Dihydromyricetin Exerts Antitumor Activity In Vivomentioning

confidence: 96%

“…Ampelopsis grossedentata, a vine plant in South China, is a popular and multipurpose traditional Chinese medicinal herb and has a long history of being used as food and medicine (3). Dihydromyricetin, a 2,3-dihydroflavonol compound, is the main bioactive component extracted from Ampelopsis grossedentata, is one kind of flavonoids that has many biologic effects, including antialcohol intoxication, reducing blood pressure, antibacterial, antioxidant, and antitumor properties (4)(5)(6).…”

Section: Introductionmentioning

confidence: 99%

Dihydromyricetin Activates AMP-Activated Protein Kinase and P38MAPK Exerting Antitumor Potential in Osteosarcoma

Zhao

Yin

et al. 2014

Cancer Prevention Research

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Numerous patients with osteosarcoma either are not sensitive to chemotherapy or develop drug resistance to current chemotherapy regimens. Therefore, it is necessary to develop several potentially useful therapeutic agents. Dihydromyricetin is the major flavonoid component derived from Ampelopsis grossedentata, which has a long history of use in food and medicine. The present study examined the antitumor activity both in vitro and in vivo without noticeable side effects and the underlying mechanism of action of dihydromyricetin in osteosarcoma cells. We found that dihydromyricetin induced increased p21 expression and G 2 -M cellcycle arrest, caused DNA damage, activated ATM-CHK2-H2AX signaling pathways, and induced apoptosis in osteosarcoma cells as well as decreasing the sphere formation capability by downregulating Sox2 expression. Mechanistic analysis showed that the antitumor potential of dihydromyricetin may be due to the activation of AMPKa and p38 MAPK , as the activating AMPKa led to the inactivation of GSK3b in osteosarcoma cells. Moreover, GSK3b deletion or GSK3b inhibition by LiCl treatment resulted in increased p21 expression and reduced Sox2 expression in osteosarcoma cells. Taken together, our results strongly indicate that the antitumor potential of dihydromyricetin is correlated with P38 MAPK and the AMPKaGSK3b-Sox2 signaling pathway. Finally, immunohistochemical analysis indicated that some patients had a lower p-AMPK expression after chemotherapy, which supports that the combination of dihydromyricetin and chemotherapy drug will be beneficial for patients with osteosarcoma. In conclusion, our results are the first to suggest that dihydromyricetin may be a therapeutic candidate for the treatment of osteosarcoma. Cancer Prev Res; 7(9); 927-38. Ó2014 AACR.

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“…Dihydromyricetin (DHM) is a kind of bioactive flavonoids and identified as the benefit constituent in the tender stems and leaves of Ampelopsis grossendentata (Zhang et al, 2007a). Pharmacokinetic studies of dihydromyricetin and myricetin in rat plasma by High Performance Liquid Chromatography with Diode Array Detector (HPLC-DAD) also have been assessed after oral administration of Ampelopsis grossedentata (Zhang et al, 2007b).…”

Section: Introductionmentioning

confidence: 99%

Total flavonoids from Ampelopsis megalophylla suppress proliferation of vascular smooth muscle cells in vivo and in vitro

Qiu

Zhou

et al. 2018

Braz. J. Pharm. Sci.

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Various benefits of flavonoids for ameliorating cardiovascular diseases have been demonstrated. However, the lowering effects on blood pressure caused by antiproliferative potentials of flavonoids in vascular smooth muscle cells are rare. In this study, the antihypertensive effects of total flavonoids from Ampelopsis megalophylla were investigated. The dynamic pressure values and the rate of media thickness versus lumen diameter were measured by the tail-cuff system and H&E staining in vivo, respectively. The mRNA expressions of ACE, Ang II, eNOS, c-Myc, cyclin D1 and p27Kip1 in thoracic aorta or A7r5 cells were measured by qPCR, respectively. The protein expressions of c-Myc, Cyclin D1, p27Kip1 and β-catenin in tissues or A7r5 cells were measured by Western blot assay. Total flavonoids of A. megalophylla (TFAM) reduced the expressions of ACE and Ang II, and elevated the content of eNOS in thoracic aorta cells of SHRs. Furthermore, TFAM decreased the mRNA and protein expressions of c-Myc and cyclin D1 by repressing the Wnt/β-catenin-mediated TCF/LEF transcriptional activation both in vivo and in vitro, which is synergetic with the up-regulation of p27Kip1 expression. Our study provided evidence for developing flavonoids from A. megalophylla as herbal supplements to prevent against cardiovascular diseases by suppressing vascular remodeling.

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Isolation and identification of metabolites from dihydromyricetin

Cited by 59 publications

References 7 publications

Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation

Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation

Dihydromyricetin Activates AMP-Activated Protein Kinase and P38MAPK Exerting Antitumor Potential in Osteosarcoma

Total flavonoids from Ampelopsis megalophylla suppress proliferation of vascular smooth muscle cells in vivo and in vitro

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