Potent Antioxidative Isoflavones Isolated from Soybeans Fermented with<i>Aspergillus saitoi</i>

Esaki, Hideo; Onozaki, Hiromichi; Morimitsu, Yasujiro; Kawakishi, Shunrô; Osawa, Toshihiko

doi:10.1271/bbb.62.740

Cited by 82 publications

(63 citation statements)

References 8 publications

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“…A ring-opened and lactonized product with increased polarity should diffuse more slowly into fungal cells and, therefore, show decreased toxicity. Converting plant defense compounds to more polar products has been shown to be a successful detoxification strategy for other plant pathogens (Weltring and Barz, 1980;Esaki et al, 1998). A more recent study (Sobolev et al, 2006) reported the appearance of a novel stilbene phytoalexin in peanut (Arachis hypogaea) kernels infected by Aspergillus species.…”

Section: Discussionmentioning

confidence: 99%

A Common Fungal Associate of the Spruce Bark Beetle Metabolizes the Stilbene Defenses of Norway Spruce

et al. 2013

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Norway spruce (Picea abies) forests suffer periodic fatal attacks by the bark beetle Ips typographus and its fungal associate, Ceratocystis polonica. Norway spruce protects itself against fungal and bark beetle invasion by the production of terpenoid resins, but it is unclear whether resins or other defenses are effective against the fungus. We investigated stilbenes, a group of phenolic compounds found in Norway spruce bark with a diaryl-ethene skeleton with known antifungal properties. During C. polonica infection, stilbene biosynthesis was up-regulated, as evidenced by elevated transcript levels of stilbene synthase genes. However, stilbene concentrations actually declined during infection, and this was due to fungal metabolism. C. polonica converted stilbenes to ring-opened, deglycosylated, and dimeric products. Chromatographic separation of C. polonica protein extracts confirmed that these metabolites arose from specific fungal enzyme activities. Comparison of C. polonica strains showed that rapid conversion of host phenolics is associated with higher virulence. C. polonica is so well adapted to its host’s chemical defenses that it is even able to use host phenolic compounds as its sole carbon source.

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Section: Discussionmentioning

confidence: 99%

A Common Fungal Associate of the Spruce Bark Beetle Metabolizes the Stilbene Defenses of Norway Spruce

et al. 2013

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“…A composição química da soja, em 100g de amostra em base seca, constitui-se de 40g de proteínas, 30g de glicídios, 20g de lipídios, 226mg de cálcio, 546mg de fósforo e 8,8mg de ferro [23,27]. Além da proteína, a soja fornece os ácidos graxos essenciais, linoléico e linolênico [19], algumas vitaminas [14] e compostos fitoquímicos, como as isoflavonas, que apresentam importantes propriedades biológicas, tais como atividade antioxidante [9,10,24], atividade antifúngica [18], propriedades estrogênicas e atividade anticancerígena (câncer de mama e próstata) [5,7,20]. Produtos de soja tradicionalmente consumidos no Japão, tais como miso, natto e tempeh são ativos contra a peroxidação lipídica, pois apresentam atividade antioxidante, além de atividade contra tumores pediátricos [22], câncer de próstata [1,20], câncer de cólon [25] e inibição de neovascularização, ou angiogênese [13].…”

Section: -Introduçãounclassified

Conversão de malonil-beta-glicosil isoflavonas em isoflavonas glicosadas presentes em alguns cultivares de soja brasileira

Park¹,

Aguiar²,

Alencar³

et al. 2002

Ciênc. Tecnol. Aliment.

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Isoflavonas em soja brasileira, Park et al. Alimentos, Laboratório de Bioquímica, Caixa Postal, 6177, CEP. 13083-970, Campinas/SP, Brasil. E-mail: ykpark@fea.unicamp.br 3 Inatituto Agornômico de Campinas, Centro de Plantas Graníferas, Caixa Postal, 28, CEP. 13001-970, Campinas/SP, Brasil. * A quem a correspondência deve ser enviada. -INTRODUÇÃODesde sua primeira menção nas estatísticas brasileiras em 1941, a soja (Glycine max L.), tem se destacado por fornecer diferentes produtos de grande importância no mercado internacional. Entre estes produtos estão: o óleo, o farelo, a lecitina, além de outros metabólitos secundários como, as saponinas e as isoflavonas. Inúmeros estudos têm destacado o potencial destes fitoquímicos no controle de diferentes enfermidades. Por outro lado, o Brasil é o segundo maior exportador de grãos de soja e o principal exportador de farelo de soja, com 32% do mercado mundial, o que representa 75% da produção brasileira [21]. A composição química da soja, em 100g de amostra em base seca, constitui-se de 40g de proteínas, 30g de glicídios, 20g de lipídios, 226mg de cálcio, 546mg de fósforo e 8,8mg de ferro [23,27] [5,7,20]. Produtos de soja tradicionalmente consumidos no Japão, tais como miso, natto e tempeh são ativos contra a peroxidação lipídica, pois apresentam atividade antioxidante, além de atividade contra tumores pediátricos [22], câncer de próstata [1,20], câncer de cólon [25] e inibição de neovascularização, ou angiogênese [13]. Japão entre outros países orientais, já utilizam há muitos anos a soja fermentada na alimentação e, atualmente, tem-se percebido um crescente consumo desta leguminosa e de seus derivados em países europeus e nos Estados Unidos, como alimento funcional. Nos Estados Unidos, para este ano, a produção de alimentos funcionais, como a soja, será de 20 bilhões de dólares, contudo estima-se que haverá um crescimento exponencial e, no ano 2010, atingirá a cifra de quase 60 bilhões de dólares [16]. Atualmente existem muitos produtos comerciais à base de soja, como bolos, chocolates, biscoitos, cápsulas enriquecidas com farinha de soja, que possuem na sua composição isoflavonas glicosiladas [5,26] ou na forma de acetila e malonil-β-glicosil isoflavonas. Isoflavonas são os maiores componentes fenólicos em soja, sendo encontradas em concentrações que vão de 0,1 a 5mg/g [5], e esta variação está ligada à fatores genéticos, locais de plantio e condições climáticas [2,4]. O grão de soja contém basicamente três tipos de isoflavonas que se apresentam normalmente em quatro diferentes formas, ou seja, glicosiladas (daidzina, genistina e glicitina); formas acetilglicosiladas (acetildaidzina, acetilgenistina e acetilglicitina); formas malonilglicosiladas (malonildaidzina, malonilgenistina e malonilglicitina) [17] e na forma estrutural não conjugada, aglicona (daidzeína, genisteína e gliciteína). Soja e farinha desengordurada de soja contêm principalmente malonil-glicosil isoflavonas, com menores quantidades das formas β-glicosiladas e somente traços de acetil-glicosil conj...

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“…A fermented soybean product, tempeh has been known to be very stable to rancidity development, and the antioxidative 6,7,4¢-trihydroxyisoflavone was isolated and identified. Two potent antioxidative isoflavones, 8-hydroxydaidzein and 8-hydroxygenistein, were isolated from soybeans fermented with Aspergillus saitoi (Esaki et al, 1998). These isoflavones, which have an o-dihydroxy structure between the 7-and 8-position, exhibited significantly stronger antioxidative activity than daidzein and genistein in both oil and lipid/aqueous systems; they are also the principal antioxidants in potent antioxidative soybeans fermented with A. saitoi.…”

Section: Discussionmentioning

confidence: 99%

Anti-Atherogenic Effects of Fermented Fresh Coffee Bean, Soybean and Rice Bran Extracts

Naito¹,

Lin

et al. 2003

FSTR

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Fermented fresh coffee bean, soybean and rice bran extracts (FCSRE, Guardox TM) is a mixture of aqueous extract of fresh coffee beans, rice bran, and soybeans fermented with Bacillus subtilis Natto. Superoxide anion and hydroxy radical were effectively trapped by FCSRE, as shown by electron spin resonance experiments. Thiobarbituric acid reacting substance (TBARS) formation in human low-density lipoprotein (LDL) induced by copper ion was inhibited by adding FCSRE (0.1 mg/dl) in vitro. Male New Zealand white rabbits were assigned to two groups, control rabbits (n‫)8؍‬ were fed a diet containing 1% cholesterol for 12 weeks, and experimental rabbits (n‫)8؍‬ were fed a 1% cholesterol diet with added 5% FCSRE (2 g/kg body weight/day). Although plasma cholesterol levels rapidly increased after initiation of the high cholesterol diet, no statistical difference was observed between the control and experimental groups. After 12 weeks, sera were sampled, rabbits were sacrificed, and aortas were removed. TBARS formation in LDL induced by copper ion was significantly lower in the experimental group compared with the control group. Lag time of LDL oxidation was also significantly longer in the experimental group. FCSRE administration significantly inhibited the TBARS formation in the aorta compared with the control animals. There was a significant difference in the aortic area covered with atherosclerotic lesions between the experimental and the control groups (53.7؎16.3 % vs. 36.2؎8.18%, pϽ Ͻ0.05). These results suggest that FCSRE may be a promising material for the prevention of atherosclerosis.

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Potent Antioxidative Isoflavones Isolated from Soybeans Fermented withAspergillus saitoi

Cited by 82 publications

References 8 publications

A Common Fungal Associate of the Spruce Bark Beetle Metabolizes the Stilbene Defenses of Norway Spruce

A Common Fungal Associate of the Spruce Bark Beetle Metabolizes the Stilbene Defenses of Norway Spruce

Conversão de malonil-beta-glicosil isoflavonas em isoflavonas glicosadas presentes em alguns cultivares de soja brasileira

Anti-Atherogenic Effects of Fermented Fresh Coffee Bean, Soybean and Rice Bran Extracts

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