High-yield synthesis of monoglyceride by mono- and diacylglycerol lipase from Penicillium camembertii U-150

Yamaguchi, Shotaro; Mase, Tamio

doi:10.1016/0922-338x(91)90210-8

Cited by 74 publications

(25 citation statements)

References 18 publications

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“…14) Briefly, a mixture of 9.23 mol glycerol (purity > 99%; Wako Pure Chem. Ind., Osaka, Japan), 0.71 mol oleic acid (purity > 60%, Wako) and 65,000 unit lipase G (Amano Enzymes, Aichi, Japan) in 6 mL of water was shaken at 40 C for 4 d. The reactants were extracted with n-hexane.…”

Section: Methodsmentioning

confidence: 99%

TRPV1 Agonist Monoacylglycerol Increases UCP1 Content in Brown Adipose Tissue and Suppresses Accumulation of Visceral Fat in Mice Fed a High-Fat and High-Sucrose Diet

Iwasaki

Tamura

Inayoshi

et al. 2011

Bioscience, Biotechnology, and Biochemistry

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The administration of such a transient receptor potential vanilloid 1 (TRPV1) agonist as capsaicin, which is a pungent ingredient of red pepper, promotes energy metabolism and suppresses visceral fat accumulation. We have recently identified monoacylglycerols (MGs) having an unsaturated long-chain fatty acid as the novel TRPV1 agonist in foods. We investigated in this present study the effects of dietary MGs on uncoupling protein 1 (UCP1) expression in interscapular brown adipose tissue (IBAT) and on fat accumulation in mice fed with a high-fat, high-sucrose diet. The MG30 diet that substituted 30% of all lipids for MGs (a mixture of 1-oleoylglycerol, 1-linoleoylglycerol and 1-linolenoylglycerol) significantly increased the UCP1 content of IBAT and decreased the weight of epididymal white adipose tissue, and the serum glucose, total cholesterol and free fatty acid levels. The diet containing only 1-oleoylglycerol as MG also increased UCP1 expression in IBAT. MGs that activated TRPV1 also therefore induced the expression of UCP 1 and prevented visceral fat accumulation as well as capsaicin.Key words: monoacylglycerol; transient receptor potential vaniloid 1 (TRPV1); uncoupling protein 1; obesity; capsaicin Obesity is a risk factor for hyperglycemia, hyperlipidemia and hypertension. It is important for preventing obesity to decrease the energy intake and increase the energy expenditure. It has been reported that capsaicin (CAP), a pungent ingredient of red pepper, is the functional ingredient for increasing energy expenditure. CAP promotes energy metabolism (oxygen consumption) by increasing adrenaline secreted from the adrenal medulla and upregulating uncoupling protein 1 (UCP1) in interscapular brown adipose tissue (IBAT) by activating the sympathetic nerve. 1-4) Since CAP has the effect of increasing energy expenditure, the ingestion of CAP could suppress the accumulation of visceral fat in rats fed with a high-fat diet. 5) The CAP receptor was identified as vanilloid receptor subtype 1 in 1997, 6) and has recently been called transient receptor potential vanilloid 1 (TRPV1). TRPV1 is mainly expressed in the primary afferent nerve. 6) Recent studies have indicated that stimulating the sensory nerve by activating TRPV1 was essential to CAP-induced energy expenditure. CAP-induced adrenaline secretion was completely dissipated in rats in which the CAP-sensitive sensory nerve had been denervated by an excess CAP treatment, 7) suggesting that the TRPV1-expressing sensory nerve was indispensable for CAPinduced adrenaline secretion. The effects of suppressing an accumulation of visceral fat, increasing oxygen consumption and promoting thermogenesis by CAP were canceled in TRPV1 knockout mice. 8,9) We searched in our previous study for the food compound which would activate TRPV1 as the functional compound increasing energy expenditure, and identified 1-or 2-monoacylglycerols (MGs) having oleic, linoleic, and -linolenic acids from wheat flour, onion (Allium cepa) and myoga (Zingiber mioga) as TRPV1 agonists. 10) The po...

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Section: Methodsmentioning

confidence: 99%

TRPV1 Agonist Monoacylglycerol Increases UCP1 Content in Brown Adipose Tissue and Suppresses Accumulation of Visceral Fat in Mice Fed a High-Fat and High-Sucrose Diet

Iwasaki

Tamura

Inayoshi

et al. 2011

Bioscience, Biotechnology, and Biochemistry

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“…The reaction systems used are microemulsions, waterorganic biphasic systems and organic solvents . The product is often a mixture of MAG with different fatty acid residues and sometimes small amounts of 2-MAG (McNeil et al, 1990;Akoh, 1993;Holmberg et al, 1989;Chang et al, 1991, Yamagushi andMase, 1991). In the present work an attempt has been made to compare different strategies for monoglycerides production using the lipase from Pseudomonas cepacia.…”

Section: Introductionmentioning

confidence: 99%

A comparison of different strategies for lipase-catalyzed synthesis of partial glycerides

et al. 1994

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Four different approaches for the synthesis of monolaurylglycerol (MLG) by non specific Pseudomonas cepacia lipase in a crude and purified form have been studied: a. The direct esterification of glycerol by lauric acid in bis-(2-ethylhexyl)sulfosuccinate sodium salt (AOT)/isooctane microemulsion systems; b. the transesterification of glycerol by vinyl laurate in the presence or not of any solvent; c. solid-phase glycerolysis of trilaurin; and, d. transesterification of protected glycerol, 1,2-O-isopropylidene glycerol, by vinyl laurate, in the presence or not of any solvent. It was found that in the two latter cases (d and c) the formation of pure MLG was occurred, while in the first two cases (a and b) apart of MLG the formation of DLG was also observed.

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“…he addressed During the last decade, enzymatic synthesis of MG by various lipase catalysts has received a lot of attention due to lower energy requirements and selectivity of the catalyst (7)(8)(9)(10). Although enzyrnatic synthesis of MG offers perhaps the greatest potential for future production of MG, cursent industrial processes are based on the physicochemical glycerolysis of fats and oils.…”

Section: *To Whom Correspondence S H O~~l Dmentioning

confidence: 99%

“…9. The effect of the initial presence ot methyl esters on the overall conversion in )methyl esters and fat glycerolyiir: (Cl!, vacuum distillation; (A;: pure glycerol.…”

Section: Molar Ratio (Methyl Asters/glyceral)mentioning

confidence: 99%

Glycerolysis of fats and methyl esters

Noureddini

Medikonduru

1997

J Americ Oil Chem Soc

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The glycerolysis of methyl esters and triglycerides with crude glycerol, a coproduct from the transesterification of triglycerides, was studied. Three procedures were followed for this conversion. The first procedure was a one‐step glycerolysis with methyl esters. The second procedure was a two‐step process. This procedure involved an initial partial glycerolysis with methyl esters, followed by fat glycerolysis. The third procedure was a simultaneous glycerolysis with methyl esters and triglycerides. In the glycerolysis with methyl esters, the removal of methanol is vital to the production of mono‐ and diglycerides. Methanol was removed either by drawing vacuum on the reactor or by stripping methanol out by means of an inert carrier gas (nitrogen). Different molar ratios of methyl esters to glycerol were tested in the first two processes. At low concentration of methyl esters, total conversion of methyl esters to mono‐ and diglycerides was achieved. As the concentration of methyl esters was increased, the conversion of methyl esters to mono‐ and diglycerides was decreased. Furthermore, the ratio of mono‐ to diglycerides was also higher at lower concentrations of methyl esters. The conversion of triglycerides in the two‐step process with crude glycerol was similar to a one‐step fat glycerolysis with pure glycerol. The composition of different components and the ratio of mono‐ to diglycerides were also comparable.

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High-yield synthesis of monoglyceride by mono- and diacylglycerol lipase from Penicillium camembertii U-150

Cited by 74 publications

References 18 publications

TRPV1 Agonist Monoacylglycerol Increases UCP1 Content in Brown Adipose Tissue and Suppresses Accumulation of Visceral Fat in Mice Fed a High-Fat and High-Sucrose Diet

TRPV1 Agonist Monoacylglycerol Increases UCP1 Content in Brown Adipose Tissue and Suppresses Accumulation of Visceral Fat in Mice Fed a High-Fat and High-Sucrose Diet

A comparison of different strategies for lipase-catalyzed synthesis of partial glycerides

Glycerolysis of fats and methyl esters

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