Four New Metabolites of Aspergillus terreus.

Kaji, Akira; Iwata, Tomoki; Kiriyama, Noriki; Wakusawa, Shinya; Miyamoto, Ken‐ichi

doi:10.1248/cpb.42.1682

Cited by 36 publications

(16 citation statements)

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“…The asterriquinones (105) exhibit a wide spectrum of biological activities including antitumor properties, and are inhibitors of HIV reverse transcriptase [111]. Thus, the electrochemical oxidation of catechol (1) has been studied in the presence of indole (7) as the nucleophile in a water/acetonitrile (50:50) mixture using cyclic voltammetry and controlled-potential coulometry.…”

Section: Ececece Mechanismmentioning

confidence: 99%

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Nematollahi

Rafiee

Fotouhi

2009

JICS

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The electrochemical oxidation of catechols was described and has shown that these compounds can be oxidized to related obenzoquinones. The electrochemically generated o-benzoquinones are quite reactive and can be attacked by a variety of nucleophiles under various mechanistic disciplines such as CE, EC, EC ' , ECE, ECEC, ECEC 2 , ECECE, ECECEC, ECECECE and trimerization, in which E represents an electron transfer at the electrode surface, and C represents a homogeneous chemical reaction. The mechanistic pathways and final products are depending on some parameters such as electron withdrawing or donating properties of nucleophile, electrolysis medium (solvent, acidity or pH) and nature of catechol.

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Section: Ececece Mechanismmentioning

confidence: 99%

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Nematollahi

Rafiee

Fotouhi

2009

JICS

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“…The asterriquinones ( Fig. 1) and demethylasterriquinones exhibit a wide spectrum of biological activities including antitumor properties and are inhibitors of HIV reverse transcriptase [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical oxidation of some dihydroxybenzene derivatives in the presence of indole

Nematollahi

Dehdashtian

Ниази

2008

Journal of Electroanalytical Chemistry

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“…In 1999, demethylasterriquinone-B1 (DAQ-B1) was identified as a small, cell-permeable activator of the insulin receptor. This compound was isolated from the fungus Pseudomassaria (Zhang et al, 1999) and is closely related to a large family of Aspergillus terreus natural products (Arai and Yamamoto, 1990;Kaji et al, 1994). These compounds have an unusual tripartite bis-indolyl-dihydroxybenzoquinone structure.…”

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confidence: 99%

Identification of Novel Orally Available Small Molecule Insulin Mimetics

Lin

Li²,

Park³

et al. 2007

J Pharmacol Exp Ther

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Oral hypoglycemic agents have great potential for the treatment of both type 1 and type 2 diabetes. Here we report the identification of novel, small-molecule, insulin mimetics that activate the insulin receptor (IR) in vivo and in vitro, stimulate the Akt and extracellular signal-regulated kinase pathways downstream of the IR, and mimic the ability of insulin to stimulate glucose uptake, glycogen synthesis, and lipid synthesis in 3T3-L1 adipocytes. However, the compounds do not mimic the mitogenic effect of insulin. In animals, these compounds have oral hypoglycemic effects in both normal C57BL6 mice and diabetic db/db mice. Quantitative structure activity relationship modeling on data from a library of 60 compounds has highlighted structural features that are important for IR agonist activity that can be used to guide design of second and third generation compounds with greater potency and specificity.Orally available insulin analogs would be an enormous benefit to the millions of diabetics who rely on painful regimens of daily insulin injections. In 1999, demethylasterriquinone-B1 (DAQ-B1) was identified as a small, cell-permeable activator of the insulin receptor. This compound was isolated from the fungus Pseudomassaria (Zhang et al., 1999) and is closely related to a large family of Aspergillus terreus natural products (Arai and Yamamoto, 1990;Kaji et al., 1994). These compounds have an unusual tripartite bis-indolyl-dihydroxybenzoquinone structure. DAQ-B1 does not compete with insulin binding but acts directly on the intracellular tyrosine kinase domain of the receptor and furthermore can activate the recombinant IR kinase domain in vitro. Although selective for the IR, DAQ-B1 also activates the insulin-like growth factor-1 receptor (IGF-IR), the nerve growth factor receptor, or epidermal growth factor receptor (EGFR) at 3 to 10-fold higher concentrations (Liu et al., 2000;Wilkie et al., 2001). It stimulates glucose uptake in rat adipocytes and mouse soleus muscle and shows oral antidiabetic activity in ob/ob and db/db mice. Interestingly, DAQ-B1 does not have a mitogenic effect on vascular smooth muscle cells (Weber et al., 2000). DAQ-B1 suppresses neuropeptide Y and stimulates pro-opiomelanocortin gene expression in rats and reduces 24-h food intake and body weight, without causing taste aversion (Air et al., 2002;Obici et al., 2002).A second generation IR activator (Cpd.2) was subsequently identified with slightly greater potency and higher specificity (Liu et al., 2000;Wood et al., 2000). This compound has good pharmacokinetics in preclinical studies in rats, dogs, and monkeys. The addition of Cpd.2 to food prevents increased food intake and weight gain when normal mice are placed on a high fat diet for 7 weeks (Air et al., 2002;Strowski et al., 2004). No toxic effects were observed in treated mice, and

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Four New Metabolites of Aspergillus terreus.

Cited by 36 publications

References 0 publications

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Electrochemical oxidation of some dihydroxybenzene derivatives in the presence of indole

Identification of Novel Orally Available Small Molecule Insulin Mimetics

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