Cycloalliin, a cyclic sulfur imino acid, reduces serum triacylglycerol in rats

Yanagita, Teruyoshi; Han, Sang Hoon; Wang, Yuming; Tsuruta, Yumi; Anno, Takahiko

doi:10.1016/s0899-9007(02)00857-2

Cited by 46 publications

(32 citation statements)

References 31 publications

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“…Contents of cycloalliin and deoxyalliin in Allium vegetables Cycloalliin and deoxyalliin (S-allyl-L-cysteine), which do not contribute to flavor as they lack alliinase sensitivity, are considered to be bioactive compounds for human health (Lawson, 1996). Cycloalliin has a lipid-lowering effect (Agarwal et al, 1977;Yanagita et al, 2003); it is converted from isoalliin when heated (Ueda et al, 1994). Although no remarkable difference in cycloalliin content (0.1 -0.4 g/ 100 g dry wt) was noted among the seven Allium vegetables, onion, Welsh onion, asatsuki, and leek are presumed to have high cycloalliin contents when heated, based on their isoalliin contents (2.1 -4.9 g/100 g dry wt).…”

Section: Contents Of Sacso In Allium Vegetablesmentioning

confidence: 99%

Distribution of Eleven Flavor Precursors, S-Alk(en)yl-L-Cysteine Derivatives, in Seven Allium Vegetables

Yamazaki

Iwasaki

Mikami

et al. 2010

FSTR

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Using high-performance liquid chromatography, 11 sulfur-containing flavor precursors were determined quantitatively in seven Allium vegetables: garlic (Allium sativum), onion (A. cepa), Welsh onion (A. fistulosum), Chinese chive (A. tuberosum Rotter), rakkyo (A. chinense G. Don), 'asatsuki' (A. schoenoprasum), and leek (A. porrum). Keywords: alliin, Alliums, flavor precursor, glutamyl peptide, high-performance liquid chromatography, isoalliin, S-alk(en) yl-L-cysteine *To whom correspondence should be addressed. E-mail: yoshihisa_yamazaki@aomori-itc.or.jp The determinants were S-alk(en)yl-L-cysteine derivatives, methiin, alliin, isoalliin, cycloalliin, deoxyalliin, N-(γ-glutamyl)-S-methyl-L-cysteine, N-(γ-glutamyl)-S-(2-propenyl)-L-cysteine, N-(γ-glutamyl)-S-(E-1-propenyl)-L-cysteine (Glu-PEC), N-(γ-glutamyl)-S-(2-propenyl)-Lcysteine sulfoxide, N-(γ-glutamyl)-S-(E-1-propenyl)-L-cysteine sulfoxide (Glu-PECSO) and S-(2-carboxy IntroductionAllium vegetables, such as garlic (A. sativum L.) and onion (A. cepa L.), have been used as seasoning vegetables worldwide (Block, 1992(Block, , 2010. Allium vegetables contain large amounts of S-alk(en)yl-L-cysteine derivatives (SACs, Fig. 1) (Kubec et al., 2000). When these vegetables are cut or crushed, S-alk(en)yl-L-cysteine sulfoxides (SACSOs), i.e., methiin, alliin, isoalliin, are cleaved by alliinase (cysteine sulfoxide lyase: EC 4.4.1.4) to give the corresponding alk(en) yl sulfenic acids (Stoll and Seebeck, 1951). The sulfenic acids are transformed via continuous reactions to thiosulfinates (e.g., diallyl thiosulfinate (allicine)) and other organosulfur volatile compounds (e.g., diallyl disulfide) to produce characteristic flavors . These organosulfur volatile compounds have been reported as flavor compounds of food, in addition to bioactive compounds (Block, 1994), or causal compounds of processed food discoloration (Kubec et al., 2004;Imai et al., 2006).The degrees of the respective contributions of these organosulfur volatile compounds to flavor, bioactivity, and food discoloration depend on their alkyl moieties: they are dominated by the kinds and quantities of SACSO as substrates of alliinase in Allium vegetables. Allium vegetables also contain γ-glutamyl peptides of S-alk(en)yl-L-cysteine (Glu-SAC) corresponding to SACSOs that are storage compounds during dormancy (Tuboi et al., 1989;Lancaster and Shaw, 1991;Lawson et al., 1991;Ichikawa et al., 2006b). These SACSOs as well as Glu-SAC in Allium vegetables should be evaluated as Glu-SAC is metabolized to SACSO depending on the storage conditions.Comparing the contents of SACs in individual Allium ical Industries Ltd. (Osaka, Japan). Water purified using a Milli-Q instrument (Millipore Corp., MA, USA) was used for all sample preparations and mobile phases. Reference compounds, and N-(γ-glutamyl)-S-(2-propenyl)-L-cysteine sulfoxide (Glu-ALCSO) (98%) were isolated from garlic cloves. Isoalliin (99%), N-(γ-glutamyl)-S-(E-1-propenyl)-L-cysteine sulfoxide (Glu-PECSO) (96%), and S-2-carboxy propyl gluthathion (2CPGTH) (98%) ...

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Section: Contents Of Sacso In Allium Vegetablesmentioning

confidence: 99%

Distribution of Eleven Flavor Precursors, S-Alk(en)yl-L-Cysteine Derivatives, in Seven Allium Vegetables

Yamazaki

Iwasaki

Mikami

et al. 2010

FSTR

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“…Previous studies of the effects on triacylglycerol level in the plasma have reported the suppressive effect of a garlic extract on the fatty acid synthase activity, 14) but cycloalliin, a cyclic sulfur compound in onion, had no effect on triacylglycerol synthesis. 15) We need further studies to examine the mechanism for the lipid-lowering effects of green Welsh onion.…”

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confidence: 99%

Welsh Onion Attenuates Hyperlipidemia in Rats Fed on High-Fat High-Sucrose Diet

Yamamoto

Yasuoka

2010

Bioscience, Biotechnology, and Biochemistry

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“…Cycloalliin reportedly lowers blood pressure and reduces serum triglycerol levels in rats (Agarwal et al, 1977;Yanagita et al, 2003). Therefore, the use of warm storage to prevent greening, as described in this report, presumably also enhances the bio-activity of treated garlic (Yamazaki, 2005).…”

Section: Effect Of Warm Storage Of Cold Stored Bulbs On S-alk(en) Yl-mentioning

confidence: 77%

Causes and Remedies for Green Discoloration of Processed Garlic Puree: Effects of Storage Conditions on Ingredient Bulbs

Yamazaki

Yamamoto

Okuno

2012

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Storage experiments on garlic (Allium sativum L.) bulbs were conducted to elucidate the causes and prevention of green discoloration (greening) of garlic puree, a severe problem in garlic processing. Greening of the pureed bulbs increased with the accumulation of S-(E-1-propenyl)-l-cysteine sulfoxide (isoalliin), which is metabolized from N-(γ-glutamyl)-S-(E-1-propenyl)-l-cysteine (Glu-PEC) during cold storage (3℃). Greening was reduced by warm storage ( > 25℃) of the cold pre-stored bulbs, with an accompanying decrease in isoalliin. Accumulated isoalliin in the garlic bulbs during cold storage was converted to 5-methyl thiomorpholine-3-carboxylic acid sulfoxide (cycloalliin) with warm storage ( > 25℃). The relationship between warm storage conditions (temperature, duration) and decreases in isoalliin content were presumed to be applicable to a first order-Arrhenius equation. Two-week storage of the ingredient garlic bulbs at 40℃, after cold pre-storage at 3℃ for 12 weeks, sufficiently reduced greening of the processed puree to maintain the commercial quality of the bulbs.

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Cycloalliin, a cyclic sulfur imino acid, reduces serum triacylglycerol in rats

Cited by 46 publications

References 31 publications

Distribution of Eleven Flavor Precursors, S-Alk(en)yl-L-Cysteine Derivatives, in Seven Allium Vegetables

Distribution of Eleven Flavor Precursors, S-Alk(en)yl-L-Cysteine Derivatives, in Seven Allium Vegetables

Welsh Onion Attenuates Hyperlipidemia in Rats Fed on High-Fat High-Sucrose Diet

Causes and Remedies for Green Discoloration of Processed Garlic Puree: Effects of Storage Conditions on Ingredient Bulbs

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