Analysis of balenine in muscle extract of opah &lt;i&gt;Lampris guttatus&lt;/i&gt; with automatic amino acid analyzer

Omura, Yuji; Kimiya, Takashi; Matsuda, Takashi; Kuniyoshi, Michiko; Maegawa, Takahiro; Kawabata, Yasunosuke; Adachi, Syungo; Amitani, Yuya

doi:10.2331/suisan.18-00010

Cited by 12 publications

(4 citation statements)

References 17 publications

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“…Harris and Milne (1987) suggested that BAL was distributed, albeit at a low level, in the skeletal muscles of a number of common mammals, including humans, rats, and rabbits. Recently, Omura et al (2018) reported that the muscle in opah (Lampris guttatus) showed a remarkably high BAL level of 2561 ± 436 mg/100 g, which is much higher than that recorded in baleen whales (1889 mg/100 g). Meanwhile, a number of studies on BAL bioactivity and function have been carried out since 2000.…”

Section: Introductionmentioning

confidence: 81%

Ability of Three Kind of Imidazole Dipeptides, Carnosine, Anserine, and Balenine, to Interact with Unsaturated Fatty Acid-Derived Aldehydes and Carbohydrate-Derived Aldehydes

Mori

Hatate

Tanaka

2019

Int J Pept Res Ther

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Imidazole dipeptides (IDPs) such as carnosine (CAR), anserine (ANS), and balenine (BAL) are widely distributed in the skeletal muscle of vertebrates. Recently, several studies have revealed that CAR plays an important role in the detoxification of cytotoxic aldehydes arising from the peroxide of unsaturated fatty acids and carbohydrate metabolite. Although intensive studies on the detoxification of aldehydes by CAR have been performed, few studies have focused on the effects of detoxification by ANS and BAL. To determine the potential of minor IDPs such as ANS and BAL to react with cytotoxic aldehydes, the present study was established to investigate the consumption of IDP after co-incubation with cytotoxic aldehydes using high-performance liquid chromatography (HPLC). In the case of unsaturated fatty acid-derived aldehydes such as 4-hydroxy-2-trans-nonenal (from n-6 fatty acid) and 4-hydroxy-2-trans-hexenal (from n-3 fatty acid), ANS and CAR decreased considerably after co-incubation, but BAL did not. In the case of 3-deoxyglucosone and methylglyoxal as carbohydrate metabolites, no IDPs decreased after co-incubation; however, the absorbance at 336 nm of the CAR and BAL mixtures increased dramatically in a time-dependent manner. In the case of glyceraldehyde, which is also a carbohydrate metabolite, all IDPs, especially BAL, decreased after co-incubation and a new peak, surmised to represent an IDP-glyceraldehyde adduct, appeared on the HPLC chromatogram. These results can help explain the unique function and behavior of ANS and BAL in specific species.

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Section: Introductionmentioning

confidence: 81%

Ability of Three Kind of Imidazole Dipeptides, Carnosine, Anserine, and Balenine, to Interact with Unsaturated Fatty Acid-Derived Aldehydes and Carbohydrate-Derived Aldehydes

Mori

Hatate

Tanaka

2019

Int J Pept Res Ther

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“…The biological origin of N τ-methylhistidine has been documented in more detail. N τ-methylation is a common modification of proteins such as the skeletal muscle proteins actin and myosin − or the β-alanyl- N τ - methylhistidine dipeptide balenine. − Consistent with an animal origin, the concentration of N τ-methylhistidine in human urine strictly correlated with dietary meat intake. − Accordingly, several Clostridia species that are common members of the gastrointestinal microbiome contain N τ-methylhistidine degrading enzymes (Table S5). However, most species with this activity are saprophytic soil-dwelling bacteria.…”

Section: Biogenic Origin Of N-methylformamide and Nτ-methylhistidinementioning

confidence: 97%

Bacterial Degradation of Nτ-Methylhistidine

2022

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The first three enzymatic steps by which organisms degrade histidine are universally conserved. A histidine ammonia-lyase (EC 4.3.1.3) catalyzes 1,2-elimination of the α-amino group from L-histidine; a urocanate hydratase (EC 4.2.1.49) converts urocanate to 4-imidazolone-5-propionate, and this intermediate is hydrolyzed to N-formimino-Lglutamate by an imidazolonepropionase (EC 3.5.2.7). Surprisingly, despite broad distribution in many species from all kingdoms of life, this pathway has rarely served as a template for the evolution of other metabolic processes. The only other known pathway with a similar logic is that of ergothioneine degradation. In this report, we describe a new addition to this exclusive collection. We show that the firmicute Bacillus terra and other soil-dwelling bacteria contain enzymes for the degradation of Nτ-methylhistidine to L-glutamate and N-methylformamide. Our results indicate that in some environments, Nτ-methylhistidine can accumulate to concentrations that make its efficient degradation a competitive skill. In addition, this process describes the first biogenic source of N-methylformamide.

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“…However, because of its distribution in inedible animal muscles, the health functionalities of Bal as a food material have not been fully studied in human trials. Very recently, Bal was detected in the muscles of opah (Lampris guttatus), a mesopelagic and regionally endothermic fish, in high concentrations [ 22 ]. Omura et al detected 18.89 and 25.61 g/kg wet weight of Bal in minke whale and opah, respectively, but none in bigeye tuna and albacore.…”

Section: Introductionmentioning

confidence: 99%

Detection of Balenine in Mouse Plasma after Administration of Opah-Derived Balenine by HPLC with PITC Pre-Column Derivatization

Shigemura

Iwasaki

Satō

et al. 2022

Foods

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We examined the absorption of balenine (Bal) in mouse blood after the administration of a high-purity Bal prepared from opah muscle. Using HPLC with phenyl isothiocyanate pre-column derivatization, we successfully isolated imidazole peptides and their constituents. We detected Bal and 3-methylhistidine (3-Me-His) in mouse blood 1 h after the administration of opah-derived Bal. The concentrations of Bal and 3-Me-His significantly increased to 128.27 and 69.09 nmol/mL in plasma, respectively, but were undetectable in control and carnosine (Car)-administrated mice. In contrast, β-alanine and histidine did not increase in mouse plasma 1 h after the administration of Car and opah-derived Bal. The present study is the first report on the absorption of food-derived Bal in mouse blood and serves as a pilot study for future clinical trials.

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Analysis of balenine in muscle extract of opah <i>Lampris guttatus</i> with automatic amino acid analyzer

Cited by 12 publications

References 17 publications

Ability of Three Kind of Imidazole Dipeptides, Carnosine, Anserine, and Balenine, to Interact with Unsaturated Fatty Acid-Derived Aldehydes and Carbohydrate-Derived Aldehydes

Ability of Three Kind of Imidazole Dipeptides, Carnosine, Anserine, and Balenine, to Interact with Unsaturated Fatty Acid-Derived Aldehydes and Carbohydrate-Derived Aldehydes

Bacterial Degradation of Nτ-Methylhistidine

Detection of Balenine in Mouse Plasma after Administration of Opah-Derived Balenine by HPLC with PITC Pre-Column Derivatization

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