Separation and characterization of the immunostimulatory components in unpolished rice black vinegar (kurozu)

Hashimoto, Masahito; Obara, Kyoko; Ozono, Mami; Furuyashiki, Maiko; Ikeda, Tsuyoshi; Suda, Yasuo; Fukase, Koichi; Fujimoto, Yukari; Shigehisa, Hiroshi

doi:10.1016/j.jbiosc.2013.05.029

“…Kurozu is used in Japan as a healthy drink to relieve hypertension, prevent cancer and improve the symptoms of allergies. Many of these effects have been shown in scientific studies (Shimoji et al, 2002;Fukuyama et al, 2007;Hashimoto et al, 2013;Miyoshi et al, 2014. ).…”

Section: Functional Properties Of Vinegarmentioning

confidence: 86%

“…White rice vinegar may have antiglycemic function (Salbe et al, 2009;Gu et al, 2012), brown rice vinegar (kurosu) has benefits across the immune system (Hashimoto et al, 2013) and antitumor effect, for example (Fukuyama et al, 2007). Gu et al (2012) found that the consumption of Chinese white rice vinegar helped in controlling blood glucose; Fan et al (2011) obtained similar results, verifying inhibitory activity of α-glucosidase, which can be useful for diabetics.…”

Section: Functional Properties Of Vinegarmentioning

confidence: 94%

“…Gu et al (2012) found that the consumption of Chinese white rice vinegar helped in controlling blood glucose; Fan et al (2011) obtained similar results, verifying inhibitory activity of α-glucosidase, which can be useful for diabetics. Other studies have demonstrated benefits across the immune system (Hashimoto et al, 2013) and anti-hypertensive effect (Kondo et al, 2001).…”

Section: Functional Properties Of Vinegarmentioning

confidence: 98%

“…The process of fermentation lasts 6 months, followed by a year, at least, of aging. During this process, the majority of micro-organisms associated with fermentation loses its activity, and it is expected the presence of microbial components responsible for some of the functional properties of the vinegar (Hashimoto et al, 2013).…”

Section: Functional Properties Of Vinegarmentioning

confidence: 99%

“…According to Hashimoto et al (2013), many microbial components have antitumor effect. Therefore, it is believed that microbial components of kurosu can help in preventing cancer and relieve allergies.…”

Section: Antitumor Effectmentioning

confidence: 99%

See 3 more Smart Citations

Vinegar: functional aspects

Pazuch¹,

Siepmann²,

Canan³

et al. 2015

View full text Add to dashboard Cite

Chemical Synthesis of Acetobacter pasteurianus Lipid A with a Unique Tetrasaccharide Backbone and Evaluation of Its Immunological Functions

Yamaura,

Shimoyama,

Hosomi

et al. 2024

Angewandte Chemie

Self Cite

0

View full text Add to dashboard Cite

Lipopolysaccharide (LPS), a cell surface component of Gram‐negative bacteria, activates innate immunity. Its active principle is the terminal glycolipid lipid A. Acetobacter pasteurianus is a Gram‐negative bacterium used in the fermentation of traditional Japanese black rice vinegar (kurozu). In this study, we focused on A. pasteurianus lipid A, which is a potential immunostimulatory component of kurozu. The active principle structure of A. pasteurianus lipid A has not yet been identified. Herein, we first systematically synthesized three types of A. pasteurianus lipid As containing a common and unique tetrasaccharide backbone. We developed an efficient method for constructing the 2‐trehalosamine skeleton utilizing borinic acid‐catalyzed glycosylation to afford 1,1’‐α,α‐glycoside in high yield and stereoselectivity. A common tetrasaccharide intermediate with an orthogonal protecting group pattern was constructed via [2+2] glycosylation. After introducing various fatty acids, all protecting groups were removed to achieve the first chemical synthesis of three distinct types of A. pasteurianus lipid As. After evaluating their immunological function using both human and murine cell lines, we identified the active principles of A. pasteurianus LPS. We also found the unique anomeric structure of A. pasteurianus lipid A contributes to its high chemical stability.

show abstract

Chemical Synthesis of Acetobacter pasteurianus Lipid A with a Unique Tetrasaccharide Backbone and Evaluation of Its Immunological Functions

Yamaura,

Shimoyama,

Hosomi

et al. 2024

Angew Chem Int Ed

Self Cite

0

View full text Add to dashboard Cite

Lipopolysaccharide (LPS), a cell surface component of Gram‐negative bacteria, activates innate immunity. Its active principle is the terminal glycolipid lipid A. Acetobacter pasteurianus is a Gram‐negative bacterium used in the fermentation of traditional Japanese black rice vinegar (kurozu). In this study, we focused on A. pasteurianus lipid A, which is a potential immunostimulatory component of kurozu. The active principle structure of A. pasteurianus lipid A has not yet been identified. Herein, we first systematically synthesized three types of A. pasteurianus lipid As containing a common and unique tetrasaccharide backbone. We developed an efficient method for constructing the 2‐trehalosamine skeleton utilizing borinic acid‐catalyzed glycosylation to afford 1,1’‐α,α‐glycoside in high yield and stereoselectivity. A common tetrasaccharide intermediate with an orthogonal protecting group pattern was constructed via [2+2] glycosylation. After introducing various fatty acids, all protecting groups were removed to achieve the first chemical synthesis of three distinct types of A. pasteurianus lipid As. After evaluating their immunological function using both human and murine cell lines, we identified the active principles of A. pasteurianus LPS. We also found the unique anomeric structure of A. pasteurianus lipid A contributes to its high chemical stability.

show abstract

Separation and characterization of the immunostimulatory components in unpolished rice black vinegar (kurozu)

Cited by 22 publications

References 46 publications

Vinegar: functional aspects

Vinegar: functional aspects

Chemical Synthesis of Acetobacter pasteurianus Lipid A with a Unique Tetrasaccharide Backbone and Evaluation of Its Immunological Functions

Chemical Synthesis of Acetobacter pasteurianus Lipid A with a Unique Tetrasaccharide Backbone and Evaluation of Its Immunological Functions

Contact Info

Product

Resources

About