The Structure of Davallic Acid

Lin, Yong-Yeng; Kakisawa, Hiroshi; Y, Shiobara; Nakanishi, Koji

doi:10.1248/cpb.13.986

Cited by 14 publications

(11 citation statements)

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“…Fifteen known compounds, including (-)-epicatech-3- O - β - d -allopyranoside ( 6 ) [23], (-)-epicatech-3- O - β - d -(2′′- O -vanillyl)-allopyranoside ( 7 ) [16], (-)-epicatech-3- O - β - d -(3′′- O -vanillyl)-allopyranoside ( 8 ) [16], eriodictyol-8- C - β - d -glucopyranoside ( 9 ) [24], davallioside A ( 10 ) [20], davallioside B ( 11 ) [20], caffeic acid-4- O - β - d -glucopyranoside ( 12 ) [25], p -coumaric acid-4- O - β - d -glucopyranoside ( 13 ) [25], protocatehuic acid ( 14 ) [26], 4-hydroxy-3,5-dimethylbenzoic acid ( 15 ) [27], vanillic acid ( 16 ) [28], 4-hydroxy-3-aminobenzoic acid ( 17 ) [29], (-)-epicatechin ( 18 ) [30], davallic acid ( 19 ) [15], and β -sitosterol ( 20 ) [31], were identified by comparison with values in the literature. Among them, compounds 9 ~ 17 were first isolated from D. formosana .…”

Section: Resultsmentioning

confidence: 99%

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Evaluation of the Antihyperuricemic Activity of Phytochemicals from Davallia formosana by Enzyme Assay and Hyperuricemic Mice Model

Chen

Huang

Tsai

et al. 2014

Evidence-Based Complementary and Alternative Medicine

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Abnormal serum urate levels are recognized as a critical factor in the progression of several chronic diseases. To evaluate the antihyperuricemic effect of Davallia formosana, the inhibitory activities of 15 isolated phytochemicals, including five novel compounds of 6,8-dihydroxychromone-7-C-β-d-glucopyranoside (1), 6,8,3′,4′-tetrahydroxyflavanone-7-C-β-d-glucopyranoside (2), 6,8,4′-trihydroxyflavanone-7-C-β-d-glucopyranoside (3), 8-(2-pyrrolidinone-5-yl)-catechin-3-O-β-d-allopyranoside (4), and epiphyllocoumarin-3-O-β-d-allopyranoside (5), were examined against xanthine oxidase (XOD) and in a potassium oxonate-(PTO-) induced acute hyperuricemic mice model. The results indicated that compounds 3 and 5 significantly inhibited XOD activity in vitro and reduced serum uric acid levels in vivo. This is the first report providing new insights into the antihyperuricemic activities of flavonoid glycosides which can possibly be developed into potential hypouricemic agents.

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Section: Resultsmentioning

confidence: 99%

“…Davallia formosana is a popular herbal medicine used to treat osteoporosis [14]. Several flavan-3-ols, triterpenoids, proanthocyanidins, and mericprocyanidins were isolated from the rhizome of D. formosana [15, 16]. Our preliminary studies revealed that the crude extract of D. formosana rhizomes could inhibit XOD activity.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the Antihyperuricemic Activity of Phytochemicals from Davallia formosana by Enzyme Assay and Hyperuricemic Mice Model

Chen

Huang

Tsai

et al. 2014

Evidence-Based Complementary and Alternative Medicine

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“…Both neohopene (408) (501)(502)(503) and its 181X-epimer (502) are isomerized to the tetrasubstituted olefin (412). The three fernene isomers (409, 413, and 414), all ofwhich arenatural triterpenes, and various functionalized variants thereof, suffer rearrangement in the retro-biogenetic direction to ß 13 (ls>_neohopene (412) (501,(504)(505)(506). Evidently ß 8 -fernene (413) is relatively resistant to the acidic conditions since mixtures of (412) and (413) are often obtained.…”

Section: Filicenementioning

confidence: 99%

Biogenetic-Type Rearrangements of Terpenes

Coates

1976

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Davallia formosana Hayata (Davalliaceae) is also known as Gu-Sui-Bu in the Taiwanese herbal market and the plant contains several bioactive compounds that include davallic acid [8], flavan-3-ol, and proanthocyanidin allosides [9]. …”

Section: Introductionmentioning

confidence: 99%

(−)-Epicatechin-3-O-β-D-allopyranoside from Davallia formosana prevents diabetes and dyslipidemia in streptozotocin-induced diabetic mice

Lin

Jian

et al. 2017

PLoS ONE

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The objective of this study was to evaluate the effects and molecular mechanism of (−)-epicatechin-3-O-β-D-allopyranoside from Davallia formosana (BB) (also known as Gu-Sui-Bu) on type 1 diabetes mellitus and dyslipidemia in streptozotocin (STZ)-induced diabetic mice. This plant was demonstrated to display antioxidant activities and possess polyphenol contents. Diabetic mice were randomly divided into six groups and were given daily oral gavage doses of either BB (at three dosage levels), metformin (Metf) (at 0.3 g/kg body weight), fenofibrate (Feno) (at 0.25 g/kg body weight) or vehicle (distilled water) and a group of control (CON) mice were gavaged with vehicle over a period of 4 weeks. Treatment with BB led to reduced levels of blood glucose, HbA1C, triglycerides and leptin and to increased levels of insulin and adiponectin compared with the vehicle-treated STZ group. The diabetic islets showed retraction from their classic round-shaped as compared with the control islets. The BB-treated groups (at middle and high dosages) showed improvement in islets size and number of Langerhans islet cells. The membrane levels of skeletal muscular glucose transporter 4 (GLUT4) were significantly higher in BB-treated mice. This resulted in a net glucose lowering effect among BB-treated mice. Moreover, BB enhanced the expression of skeletal muscle phospho-AMPK in treated mice. BB-treated mice increased expression of fatty acid oxidation enzymes, including peroxisome proliferator-activated receptor α (PPARα) and mRNA levels of carnitine palmitoyl transferase Ia (CPT1a). These mice also expressed lower levels of lipogenic genes such as fatty acid synthase (FAS), as well as lower mRNA levels of sterol regulatory element binding protein 1c (SREBP1c) and liver adipocyte fatty acid binding protein 2 (aP2). This resulted in a reduction in plasma triglyceride levels. BB-treated mice also expressed lower levels of PPARγ and FAS protein. This led to reduced adipogenesis, fatty acid synthesis and lipid accumulation within adipose tissue, and consequently, to lower triglyceride levels in liver, blood, and adipose tissue. Moreover, BB treatment not only displayed the activation Akt in liver tissue and skeletal muscle, but also in C2C12 myotube to cause an increase in phosphorylation of Akt in the absence of insulin. These results demonstrated that BB act as an activator of AMPK and /or regulation of insulin pathway (Akt), and the antioxidant activity within the pancreas. Therefore, BB treatment ameliorated the diabetic and dyslipidemic state in STZ-induced diabetic mice.

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The Structure of Davallic Acid

Cited by 14 publications

References 0 publications

Evaluation of the Antihyperuricemic Activity of Phytochemicals from Davallia formosana by Enzyme Assay and Hyperuricemic Mice Model

Evaluation of the Antihyperuricemic Activity of Phytochemicals from Davallia formosana by Enzyme Assay and Hyperuricemic Mice Model

Biogenetic-Type Rearrangements of Terpenes

(−)-Epicatechin-3-O-β-D-allopyranoside from Davallia formosana prevents diabetes and dyslipidemia in streptozotocin-induced diabetic mice

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