Tetrahydroisoquinoline alkaloids and 2-deoxyribonolactones from Aristolochia arcuata

Francisco, Maurı́cio C; Nasser, Ana Lúcia Martiniano; Lopes, Lucia Maria Xavier

doi:10.1016/s0031-9422(02)00655-6

Cited by 27 publications

(19 citation statements)

References 12 publications

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“…In the NOESY spectrum, the absence of a NOE correlation between H-3 and H-4 suggested that H-3 and H-4 existed in a trans formation. Enzymatic hydrolysis of 3 gave the known compound 2-hydroxymethyl-D-ribono-γ-lactone (4) which was identified by comparison of its NMR data and optical rotation with those reported [2,3]. Acid hydrolysis of 3 afforded D-glucose.…”

Section: Resultsmentioning

confidence: 95%

“…Literature studies revealed that no phytochemical work has been done so far on the plant. Chemical investigations resulted in the isolation and elucidation of a new phenolic glycoside (1) and a new D-ribono-γ -lactone derivative (3), together with thirteen known compounds, syringin (2) [1], 2-hydroxymethyl-D-ribono-γ-lactone (4) [2,3], (+)-pinoresinol-4-O-β -D-glucopyranoside (5) [4,5], (+)-lariciresinol-4-O-β -D-glucopyranoside (6) [5], (+)-lariciresinol-4 -O-β -D-glucopyranoside (7) [6 -8], 5,6,7,8,4 -pentamethoxyflavone (tangeretin) (8) [9], isoliquiritigenin (9) [10], 3,7,4 -trihydroxyflavone (10) [11], luteolin (11) [12], puerarin (12) [13], magnoline (13) [14], protocatechuic acid (14) [15], and n-dotriacontane acid (15) [16] (Fig. 1).…”

Section: Clematis Hexapetala Pall (Family Ranunculaceae)mentioning

confidence: 99%

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Chemical Constituents From The Roots And Rhizomes Of Clematis Hexapetala Pall.

Dong

Shi

Ke-si

et al. 2007

Zeitschrift Für Naturforschung B

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A new phenolic glycoside, 2,6-dimethoxy-4-(3-hydroxy-propen-1-yl)phenyl-4-O-α-L-rhamnopyranosyl-(1 → 6)-β -D-glucopyranoside (1) and a new D-ribono-γ -lactone derivative, 3-O-β -D-glucopyranosyl-2-hydroxymethyl-D-ribono-γ-lactone (3), together with thirteen known compounds have been isolated from the roots and rhizomes of Clematis hexapetala Pall. The characterization of these compounds was achieved by various chromatographic and spectroscopic methods.

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Section: Resultsmentioning

confidence: 95%

Section: Clematis Hexapetala Pall (Family Ranunculaceae)mentioning

confidence: 99%

Chemical Constituents From The Roots And Rhizomes Of Clematis Hexapetala Pall.

Dong

Shi

Ke-si

et al. 2007

Zeitschrift Für Naturforschung B

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“…Lack of these important information limits our ability to use herbal therapies to treat diabetes. In this work, we have identified sequoyitol, a natural compound present in many plants (e.g., Amentotaxus yunnanensis, Aristolochia arcuata, and Crossostephium Chinese) (12,24,43), as a novel antidiabetic small molecule (molecular weight: 194).…”

Section: Discussionmentioning

confidence: 99%

Herbal constituent sequoyitol improves hyperglycemia and glucose intolerance by targeting hepatocytes, adipocytes, and β-cells

Shen

Shao

Cho

et al. 2012

American Journal of Physiology-Endocrinology and Metabolism

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prevalence of insulin resistance and type 2 diabetes increases rapidly; however, treatments are limited. Various herbal extracts have been reported to reduce blood glucose in animals with either genetic or dietary type 2 diabetes; however, plant extracts are extremely complex, and leading compounds remain largely unknown. Here we show that 5-O-methyl-myo-inositol (also called sequoyitol), a herbal constituent, exerts antidiabetic effects in mice. Sequoyitol was chronically administrated into ob/ob mice either orally or subcutaneously. Both oral and subcutaneous administrations of sequoyitol decreased blood glucose, improved glucose intolerance, and enhanced insulin signaling in ob/ob mice. Sequoyitol directly enhanced insulin signaling, including phosphorylation of insulin receptor substrate-1 and Akt, in both HepG2 cells (derived from human hepatocytes) and 3T3-L1 adipocytes. In agreement, sequoyitol increased the ability of insulin to suppress glucose production in primary hepatocytes and to stimulate glucose uptake into primary adipocytes. Furthermore, sequoyitol improved insulin signaling in INS-1 cells (a rat ␤-cell line) and protected INS-1 cells from streptozotocin-or H2O2-induced injury. In mice with streptozotocin-induced ␤-cell deficiency, sequoyitol treatments increased plasma insulin levels and decreased hyperglycemia and glucose intolerance. These results indicate that sequoyitol, a natural, water-soluble small molecule, ameliorates hyperglycemia and glucose intolerance by increasing both insulin sensitivity and insulin secretion. Sequoyitol appears to directly target hepatocytes, adipocytes, and ␤-cells. Therefore, sequoyitol may serve as a new oral diabetes medication. insulin resistance; diabetes; hyperglycemia GLUCOSE IS A PRIMARY METABOLIC fuel. Blood glucose levels are maintained within a narrow range through the action of insulin and other metabolic hormones (18, 34). Insulin decreases blood glucose by stimulating glucose uptake into adipose tissue and skeletal muscle and by suppressing hepatic glucose production (34). Insulin resistance is the primary risk factor for type 2 diabetes (42). Additionally, pancreatic ␤-cell function is also impaired in type 2 diabetes and unable to secrete sufficient insulin to compensate for insulin resistance (26). Relative insulin deficiency, due to a combination of insulin resistance and impaired pancreatic ␤-cell function, contributes to hyperglycemia and glucose intolerance in type 2 diabetes. Small molecules with the capability to improve insulin sensitivity and/or ␤-cell function have a great therapeutic potential for the treatment of type 2 diabetes.Growing evidence indicate that herbal constituents hold a great promise for the treatment of type 2 diabetes, and extracts of numerous plants have been reported to reduce blood glucose (6,8,17,22,41). In search for small compounds with an anti-diabetic property, we examined natural compounds in plant extracts, focusing on inositol derivatives. Inositols consist of nine isomeric forms (myo-, scyllo-, epi-, al...

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“…Species belonging to the Aristolochiaceae family have been used in Brazilian traditional medicine as stomachic, antiophidian, antiinflammatory, antiasthmatic, and abortifacient agents (Lopes et al, 2001), and more recently, in slimming therapy as a substitute for, or in addition to, medicinal plants (Francisco et al, 2003). Flavonols, dihydroflavonols, and isoflavonols have also been isolated from these species (Lopes et al, 2001).…”

Section: Introductionmentioning

confidence: 99%