• Natural Product Sciences
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• 제8권2호
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• pp.35-43
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• 2002

Glycosides of herbal medicines, such as glycyrrhizin, ginsenosides, kalopanaxsaponins, rutin and ponicirin, were studied regarding their metabolic fates and pharmacological actions in relation to intestinal bacteria using germ-free, gnotobiotic and conventional animals. When glycyrrhizin (GL) was orally administered, $18{\beta}-glycyrrhetinic\;acid\;(GA)$, not GL, was detected in plasma and intestinal contents of gnotobiotic and conventional rats. However, GA could not be detected in germ-free rats. When GL was incubated with human intestinal bacteria, it was directly metabolized to GA (>95%) or via $18{\beta}-glycyrrhetinic\;acid-3-{\beta}-D-glucuronide$(>5%). Orally administered GL was effective in gnotobiotic and conventional rats for liver injury induced by carbon tetrachloride, but was not effective in germ-free rats. When ginseng saponins were orally administered to human beings, compound K in the plasma was detected, but the other protopanxadiol saponins were not detected. The compound K was active for tumor metastasis and allergy. When kalopanaxsaponins were incubated with human intestinal microflora, they were metabolized to kalopanaxsaponin A, kalopanaxsaponin I and hederagenin. These metabolites were active for rheumatoid arthritis and diabetic mellitus while the other kalopanxsaponins were not. When flavonoid glycosides were orally administered to animals, aglycones and/or phenolic acids were detected in the urine. The metabolic pathways proceeded by intestinal bacteria rather than by liver or blood enzymes. These metabolites, aglycones and phenolic acids, showed antitumor, antiinflammatory and antiplatelet aggregation activities. These findings suggest that glycosides of herbal medicines are prodrugs.

• Journal of Microbiology and Biotechnology
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• 제33권11호
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• pp.1475-1483
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• 2023

This study aimed to evaluate the cholesterol-lowering and antioxidant activities of soymilk fermented with probiotic Lactobacillaceae strains and to investigate the production of related bioactive compounds. Lactiplantibacillus plantarum KML06 (KML06) was selected for the fermentation of soymilk because it has the highest antioxidant, cholesterol-lowering, and β-glucosidase activities among the 10 Lactobacillaceae strains isolated from kimchi. The genomic information of strain KML06 was analyzed. Moreover, soymilk fermented with KML06 was evaluated for growth kinetics, metabolism, and functional characteristics during the fermentation period. The number of viable cells, which was similar to the results of radical scavenging activities and cholesterol assimilation, as well as the amount of soy isoflavone aglycones, daidzein, and genistein, was the highest at 12 h of fermentation. These results indicate that soymilk fermented with KML06 can prevent oxidative stress and cholesterol-related problems through the production of soy isoflavone aglycones.

• 한국환경농학회지
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• 제15권2호
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• pp.167-178
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• 1996

전보에서 대두(大豆)와 벼의 현탁배양세포(懸濁培養細胞)에서 생성된 PCP의 주요 수용성대사물은 PCP를 비롯한 여러 종류의 염화페놀과 glucose간 ${\beta}-linkage$로 연결된 ${\beta}-glucoside$ 구조를 가질 것으로 추정한 바 있다. 본 연구에서는 conjugates를 가수분해시키지 않는 조건에서 기기적인 방법으로 그 구조를 확인하고자 하였다. Acetyl화(化) 한 glucose conjugates는 aglycones 분석에서 예상한 대로 3종류 이상이 존재하는 것으로 확인할 수 있었으며, 충분히 정제한 각각의 acetyl화(化) 대사물을 FAB-MS로 분석한 결과 분자량과 aglycones part와 관련된 특징적 spectral data 등 conjugates 구조 확인에 필수적인 정보를 얻을 수 있었다. 이러한 구조적 정보와 지금까지의 연구 결과, 즉 현탁배양초기에 생성된 PCP의 glucose conjugates는 ${\beta}-glucosidase$에 의해 특징적으로 가수분해되고, aglycones이 PCP 외에도 tetrachlorophenol 및 tetrachlorocatechol 등이라는 사실을 종합할 때 현탁배양에서 생성된 conjugates는 주로 pentachlorophenyl ${\beta}-D-glucopyranoside$, tetrachlorophenyl ${\beta}-D-gluco$ pyranoside 및 2-hydroxy-3,4,5,6-tetrachlorophenyl ${\beta}-D-glucopyranoside$인 것으로 확인할 수 있었다.

• Natural Product Sciences
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• 제15권3호
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• pp.121-124
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• 2009

Phytochemical investigation of the aerial parts of Lonicera etrusca resulted in the isolation of three iridoids including two aglycones, loganin aglycone (log-1) (1) and lonicerin (log-2) (2), and the known common glycoside loganin (4). The study also afforded a coumarin derivative, 7-hydroxycoumarin (3), and a flavonoid glycoside, luteolin-7-O-$\beta$-D-glucoside (5). The structures were determined utilizing physical, chemical and spectral methods.

• Archives of Pharmacal Research
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• 제11권2호
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• pp.166-168
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• 1988

The effects of aglycones moring and quercetin and their corresponding glycosides quercitrin and rutin were studied on the blood glucose levels of rats. Quercetin and quercetrin caused hypoglycaemia in rats while rutin and morin showed almost no difference. Quercetin, which showed 50% pronounced hypoglycaemic effects, reduced significantly the blood glucose level of alloxan diabetic rats.

• Archives of Pharmacal Research
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• 제16권1호
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• pp.18-24
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• 1993

In this inverstigation, the various flavonoid aglycones were evaluated for their inhibitory activities against croton-oil or arachidonic acid induced mouse ear edema by oral or topical administration. The compounds tested were thirteen derivatives of flavan-3-ol(catechin and epicatechin), flavanone (flavanone and naringenin), flavone (flavone, chrysin and apigenin), flavonol(favonol, galangin, quercetin and morin) and isoflavone (biochanin A and 2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone), along with hydrocortisone, indomethacin, 4-bormophenacyl bromide, nordihydroguaiaretic acid and phenidone as positive controls. A(isoflavone) were found to show broad inhibitoty activities (14-52%) against croton-oil or arachidonic acid induced ear edema by oral or topical application at the dose of 2 mg/mouse, although they showed less activity than hydrocortisone (26-88%) or indomethacin (36-80%). Flavonoid agtlycones tested showed higher activity when aplied topically than by the oral administration. It was also found that they inhibited arachidonic acid induced edema more profoundly than croton-oil induced edema by topical application. In arachidonic acid induced edema when applied topically, flavone derivatives such as flavone, chrysin and apigenin were revealed to be the good inhibitory agents in addition to flavonols and isoflavones. When quercetin and biochanin. A were selected for evaluating in carrageenan induced rat pleurisy and biochanin both flavonoids showed antiinflammatory activity at the dose of 70 mg/kg by the oral adminis-tration. All of these results revealed that flavonoid aglycones, especially 5,7-dihydroxy-flavonols having hydroxyl group(s) in B-ring and biochanin A (isoflavone) possessed in vivo antiinflammatory activity.

• 한국식품과학회지
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• 제39권3호
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• pp.231-236
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• 2007

천연소재인 아몬드 첨가에 의한 대두 이소플라본의 특성 변화를 연구하였다. 대두를 침지처리 및 oven-drying 공정을 통해 ${\beta}-glucosides$ 함량을 증가시킨 후 아몬드 2.5%첨가 12시간 반응으로 ${\beta}-glucosides$로부터 비배당체를 전환시켜 비배당체의 함량을 날콩에 비해 17.5배 이상 증가시킬 수 있었다. 아몬드 첨가에 의한 genistin 분해 속도 및 genistein 생성속도는 각각의 daidzin 분해 속도 및 daidzein 생성속도보다 높았다.

• Journal of Microbiology and Biotechnology
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• 제12권1호
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• pp.8-13
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• 2002

The isoflavone glycosides are hydrolyzed by ${\beta}$-glucosidase from gut microbes to the bioactive aglycones. However, the specific bacteria from the human intestinal tract that are involved in the metabolism of these compounds are not known. This study was undertaken to develop a fermented soymilk which converts isoflavones to the more bioactive aglycones form using a Bifidobacterium strain. The ${\beta}$-glucosidase activity of 15 Bifidobacterium strains were measured during cell growth. Among them, Bifidobacterium sp. Int-57 was selected for this study, because it has the highest ${\beta}$-glucosidase activity. Growth, acid development, ${\beta}$-glucosidase activity, and the hydrolysis of daidzin and genistin were investigated in four soymilks inoculated with Bifidobacterium sp. Int-57. After 12 h of fermentation, the counts of viable Bifidobacterium sp. Int-57 in all the soymilks reached a level of more than $10^8$ cfu/ml, which was then maintained. The pH of soymilks started to decrease rapidly after 6 h of fermentation and leveled off after 18 h. The titratable acidity of BL# 1 soymilk, BL#2 soymilk, and JP#l soymilk increased from 0.18 to 1.21, 1.15, and $1.08\%$ over the fermentation period, respectively. After 24 h of fermentation, the $\beta$-glucosidase activity in BL#1 soymilk, BL#2 soymilk, JP#l soymilk, and JP#2 soymilk increased to 59.528, 40.643, 70.844, and 56.962 mU/ml, respectively. The isoflavone glycosides, daidzin and genistin, in soymilks were hydrolyzed completely in the relatively short fermentation time of 18 h. These results show that Bifidobacterium sp. Int-57 can be used as a potential starter culture for developing fermented soymilk which has completely hydrolyzed isoflavone glycosides.

• Journal of Microbiology and Biotechnology
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• 제27권11호
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• pp.1952-1960
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• 2017

Recently, soybean isoflavone aglycones (i.e., daidzein and genistein) and ${\gamma}-aminobutyric$ acid (GABA) have begun to receive considerable consumer attention owing to their potential as nutraceuticals. To produce these ingredients, multiple microorganisms and their enzymes are commonly used for catalysis in the nutraceutical industry. In this work, we introduce a novel fermentation process that uses whole-cell biocatalysis to accelerate GABA and isoflavone aglycone production in doenjang (a traditional Korean soybean paste). Microbial enzymes transform soybean isoflavone glycosides (i.e., daidzin and genistin) and monosodium glutamate into soybean isoflavone aglycones and GABA. Lactobacillus brevis GABA 100 and Aspergillus oryzae KACC 40250 significantly reduced the production time with the aid of a protease. The resulting levels of GABA and daidzein were higher, and genistein production resembled the levels in traditional doenjang fermented for over a year. Concentrations of GABA, daidzein, and genistein were measured as 7,162, 60, and $59{\mu}g/g$, respectively on the seventh day of fermentation. Our results demonstrate that the administration of whole-cell L. brevis GABA 100 and A. oryzae KACC 40250 paired with a protease treatment is an effective method to accelerate GABA, daidzein, and genistein production in doenjang.

• Applied Biological Chemistry
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• 제40권6호
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• pp.577-582
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• 1997

감귤류에 포함되어있는 성분중, 생리활성물질로 거론되어지고 있는 citrus flavonoid 즉, hesperidin, hesperetin, naringin 및 naringenin 4종류를 가지고 간장triglyceride합성의 율속효소로 알려져 있는 phosphatidate phosphohydrolase 활성에 대하여 in vitro계에 미치는 영향과 이들 flavonoid가 HepG2 세포의 생존율 및 증식에 미치는 영향에 대해서도 함께 검토하였다. 그 결과 본 실험에 사용된 모든 flavonoid 는 $10{-4}M$ 농도까지는 세포생존율 및 증식이 최고에 도달하였으나, $10{-3}M$ 농도에서 aglycone flavonoid는 현저한 저해효과를 나타냈다. naringin 및 hesperidin의 glycoside flavonoid는 첨가한 모든 농도에서 PAP활성을 촉진시키는 경향을 나타내었다. 그러나, aglycone flavonoid인 hesperetin은 PAP활성을 농도 의존적으로 저해하였으며, naringenin은 $10{-2}M$ 농도에서 강한 저해효과를 나타내었다. 이러한 결과로 미루어 볼 때 aglycone flavonoid가 생체내에서 세포 생존율, 증식 및 지질대사에 강한 영향을 미칠 것으로 생각되어진다.