Isolation of a Reduced Form of Cyanidin 3-O-^|^beta;-D-Glucoside from Immature Black Soybean (Glycine max (L.) Merr.) and Its Reducing Properties

Fukami, Hironobu; Yano, Yoshihisa; Iwashita, Takashi

doi:10.5650/jos.62.623

Cited by 9 publications

(12 citation statements)

References 16 publications

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“…Moreover, this linkage was strengthened by the analysis of NOESY spectrum ( Figure S17) through cross-peaks observed between H-6 ( H 6.18) and H-6 ( H 5.88). Additional data from the HMBC spectrum, enabled us to locate C-2 at C 140.0, C-1 at C 120.2 [through correlations between H-6 ( H 6.89) and olefinic carbons at C 140.0 (C-2) and C-1 (120.2), respectively] and C-3 ( C 133.1) involved in a relationship with H-4 ( H 3.18); these data were consistent with a flav-2-en-3-ol type flavonoid (Fukami et al 2013). Consequently, all those various details emphasize the presence of another flavonoid linkage for this molecule.…”

Section: Resultssupporting

confidence: 54%

“…Consequently, all those various details emphasize the presence of another flavonoid linkage for this molecule. It was noted that the flav-2-en-3-ol moiety was found as intermediate in the synthesis of anthocyanin (Fukami et al 2013). In addition, IR spectrum ( Figure S10) at 1595 cm −1 also confirmed the presence of a conjugated olefinic double bond in this molecule (Marković et al 2013).…”

Section: Resultsmentioning

confidence: 99%

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A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

Nyemeck

Bikobo

Zintchem

et al. 2017

Natural Product Research

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Phytochemical investigation of the stem bark of Campylospermum zenkeri led to the isolation of five known compounds: (Z,Z)-9,12-octadecadienoic acid (1), serotobenine (2), agathisflavone (3), lophirone A (4) and lophirone F (5), together with a new derivative of procyanidin B, a catechin dimer named zenkerinol (6). Serotobenine (2) is structurally related to decursivine which shows moderate activity against D6 and W2 strains of Plasmodium falciparum. For a better understanding of structure-activity relationships, three new semisynthetic derivatives of serotobenine (2) have been prepared. These are: serotobenine monopropionate (2a), serotobenine monopivalate (2b) and serotobenine cyclohexyl ether (2c) respectively. Two of them (2a) and (2b), were evaluated for their antiplasmodial activity against P. falciparum 3D7 strain in a parasite lactate-dehydrogenase (pLDH) assay. Compound 2b was more active than compound 2a based on their IC 50 values (36.6 and 123 μM, respectively).

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Section: Resultssupporting

confidence: 54%

Section: Resultsmentioning

confidence: 99%

A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

Nyemeck

Bikobo

Zintchem

et al. 2017

Natural Product Research

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“…Therefore compound 46 was tentatively characterized as 7-O-methyl catechin, and compound 54 was tentatively characterized as 7-O-methyl afzelechin. (Wellmann, Griesser, Schwab, Martens, Eisenreich, Matern, et al, 2006) and have been found in plant materials of soybeans (Fukami, Yano, & Iwashita, 2013).…”

Section: Resultsmentioning

confidence: 94%

Identification and characterization of phenolic compounds in hydromethanolic extracts of sorghum wholegrains by LC-ESI-MSn

et al. 2016

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Hydromethanolic extracts of brown, red, and white sorghum whole grains were analysed by LC-MS(n) in negative ESI mode within the range m/z 150-550amu. Besides the flavonoids already reported in sorghum, a number of flavonoids were also identified in the sorghum grain for the first time, including flavanones, flavonols and flavanonols, and flavan-3-ol derivatives. Various phenylpropane glycerides were also found in the sorghum grain, the majority of them are reported here for the first time, and a few of them were detected with abundant peaks in the extracts, indicating they are another important class of phenolic compounds in sorghum. In addition, phenolamides were also found in sorghum grain, which have not been reported before, and dicaffeoyl spermidine was detected in high abundance in the extracts of all three type sorghum grains. These results confirmed that sorghum is a rich source of various phenolic compounds.

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“…The minor anthocyanins such as catechincyanidin-3- O -glucoside, delphinidin-3- O -galactoside, cyanidin-3- O -galactoside, and peonidin-3- O -glucoside have also been isolated and identified based on the fragmentation patterns of high-performance liquid chromatography–diode array detector–electrospray ionization/mass spectrometry analysis [45,46]. 5,7,3′,4′-Tetrahydroxyflav-2-en-3-ol 3- O - β - d -glucoside have also been isolated from immature BSB [47]. The structure of anthocyanins-rich BSB is depicted in Figure 2.…”

Section: Anthocyanins Rich Bsbmentioning

confidence: 99%

A Critical Review on Polyphenols and Health Benefits of Black Soybeans

2017

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Polyphenols are plant secondary metabolites containing antioxidant properties, which help to protect chronic diseases from free radical damage. Dietary polyphenols are the subject of enhancing scientific interest due to their possible beneficial effects on human health. In the last two decades, there has been more interest in the potential health benefits of dietary polyphenols as antioxidant. Black soybeans (Glycine max L. Merr) are merely a black variety of soybean containing a variety of phytochemicals. These phytochemicals in black soybean (BSB) are potentially effective in human health, including cancer, diabetes, cardiovascular diseases, cerebrovascular diseases, and neurodegenerative diseases. Taking into account exploratory study, the present review aims to provide up-to-date data on health benefit of BSB, which helps to explore their therapeutic values for future clinical settings. All data of in vitro and in vivo studies of BSB and its impact on human health were collected from a library database and electronic search (Science Direct, PubMed, and Google Scholar). The different pharmacological information was gathered and orchestrated in a suitable spot on the paper.

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Isolation of a Reduced Form of Cyanidin 3-O-^|^beta;-D-Glucoside from Immature Black Soybean (Glycine max (L.) Merr.) and Its Reducing Properties

Cited by 9 publications

References 16 publications

A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

Identification and characterization of phenolic compounds in hydromethanolic extracts of sorghum wholegrains by LC-ESI-MSn

A Critical Review on Polyphenols and Health Benefits of Black Soybeans

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