Simultaneous quantification of differently glycosylated, acetylated, and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one-conjugated soyasaponins using reversed-phase high-performance liquid chromatography with evaporative light scattering detection

Decroos, Karel; Vincken, Jean‐Paul; Heng, Lynn; Bakker, Richard G.; Gruppen, Harry; Verstraete, Willy

doi:10.1016/j.chroma.2005.03.021

Cited by 46 publications

(45 citation statements)

References 32 publications

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“…DDMP soyasaponins and the acetylated soyasaponins of group A are sometimes considered as the genuine forms of groups A and B in soybeans. Group E soyasaponins are also considered to be phyto-oxidation products of group B soyasaponins (62,67,68). All four groups of soysaponins are glycosides of oleanan triterpene aglycones known as soyasapongenols.…”

Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

“…Group A soysaponins have two sugar chains, separately attached to C-3 and C-22 positions of soyasapogenol A, except for A3 (33), which has only one sugar chain at C-3 ( Table 1). C-3 sugar chain consists of two or three sugar residues, starting with a glucoronyl residue (glcUA) (67). C-22 side chain consists of two sugar residues, starting with an anarabinosyl, and ending with a xylosyl or glycosyl residue (58,63,65,69) (Figure 3).…”

Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

“…DDMP soyasaponins are categorized under B type soyasaponins by some researchers (27). Their structures were characterized as having DDMP group conjugated to group B at C-22 (67,68,73,74) NO. name C-3 sugar chain C-22 sugar chain molecular formula (Figure 4).…”

Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

“…The most abundant soy phytoserol is -sitosterol (64), followed by campesterol (69) (112). These sterols can be divided into four groups based on their backbones, cholesterol (62), cholesta (63), stigmasta (64)(65)(66)(67)(68) and ergosta (69-75) (Figure 6). Compounds 62 and 63 have the same backbone except for the type of bond between C-24 and C-25.…”

Section: Chemical Characteristics Of Triterpenes and Sterolsmentioning

confidence: 99%

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Phytochemicals in Soy and Their Health Effects

Wu¹,

Kang²

2011

Phytochemicals - Bioactivities and Impact on Health

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Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

Section: Chemical Characteristics Of Triterpenes and Sterolsmentioning

confidence: 99%

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Phytochemicals in Soy and Their Health Effects

Wu¹,

Kang²

2011

Phytochemicals - Bioactivities and Impact on Health

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“…일반적으로 soyasaponin 은 A계열 을 Aa, Ab, Ad, Ae, Af로 B계열은 DDMP가 부 착된 αg, βg, βa, γg, γa와 DDMP가 부착되지 않은 Ba, Bb, Bb', Bc로 E계열은 Bd와 Be로 구분하지만 (Decroos et al, 2005), 학자들에 따라 조금씩 다르게 명명되기도 한다 (Kitagawa et al, 1988a(Kitagawa et al, , 1988bYoshikoshi et al, 1996;Shibuya et al, 2010). Soyasaponin은 쓴맛을 나타내기 때 문에 식미를 저하시키나 (Kitagawa et al, 1988a;Taniyama et al, 1988), 혈중 콜레스테롤 감소효과 (Rao & Sung, 1995)를 비롯한 항산화활성 (Yoshikoshi et al, 1996), 항바 이러스 (Shiraiwa et al, 1991;Hayashi et al, 1997), 간독성 물질제거 (Kinjo et al, 1988;Miyao et al, 1988), 항종양활 성 (Berhow et al, 2000;Konoshima et al, 1992), 면역증진 효과 (Koratkar & Rao, 1997;Vlietinck et al, 1998) 등 각 종 생리활성이 밝혀짐에 따라 많은 주목을 받고 있다.…”

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Isolation of Isoflavones and Soyasaponins from the Germ of Soybean

김선림¹,

이재은²,

김율호³

et al. 2013

Korean Journal of Crop Science

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The objective of present study was to simultaneously isolate of isoflavone and soyasaponin compounds from the germ of soybean seeds. Soy germ flours were defatted with hexane for 48h at room temperature, and methanolic extracts were prepared using reflux apparatus at 90℃ for 6h, two times. After extraction, extracts were separated with preparative RP-C 18 packing column (125 Å, 55-105 µm, 40×150mm), and collected 52 fractions were identified with TLC plate (Kieselgel 60 F-254) and HPLC, respectively. Among the identified isoflavone and soyasaponin fractions, isoflavone fractions were re-separated using a recycling HPLC with gel permeation column (Jaigel-W252, 20×500mm). Final fractions were air-dried, and the purified compounds of two isoflavones (ISF-1-1, ISF-1-2) and four soyasaponins (SAP-1, SAP-2, SAP-3, SAP-4) were obtained. Two isoflavone compounds (ISF-1-1, ISF-1-2) were acid-hydrolyzed for the identification of their aglycones, and confirmed by comparing with 12 types of isoflavone isomers. While the four kinds of soyasaponins were identified by using a micro Q-TOF mass spectrometer in the ESI positive mode with capillary voltage of 4.5kV, and dry temperature of 200℃. Base on the obtained results, it was conclude that ISF-1-1 is the mixture isomers of daidzin (43.4%), glycitin (47.0%), and genistin (9.6%), but ISF-1-2 is the single compound of genistin (99.8% <). On the other hand, soyasaponin SAP-1 is the mixture compounds of soyasaponin A-group (Aa,

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Bitterness of saponins and their content in dry peas

et al. 2006

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The bitterness of a saponin mixture (containing saponin B and DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponin in a ratio of 1:4) and saponin B obtained from dry peas were established by a trained panel using line scaling. Both saponins were found to be bitter. However, the saponin mixture, and hence DDMP saponin, was found to be significantly more bitter than saponin B. The bitterness perceived correlated with the saponin concentration. In addition to saponin bitterness, the saponin content and composition of 16 dry pea varieties were also investigated. In two varieties, DDMP saponin was the only saponin present whereas, in the rest of the varieties, DDMP saponin was more abundant than saponin B. The pea varieties investigated differed significantly in saponin content. The amounts of DDMP saponin ranged from 0.7 to 1.5 g kg −1 (dry matter), whereas those of saponin B ranged from 0 to 0.4 g kg −1 . As saponins are bitter, pea varieties with lower saponin contents would be preferred for use in food production.

show abstract

Simultaneous quantification of differently glycosylated, acetylated, and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one-conjugated soyasaponins using reversed-phase high-performance liquid chromatography with evaporative light scattering detection

Cited by 46 publications

References 32 publications

Phytochemicals in Soy and Their Health Effects

Phytochemicals in Soy and Their Health Effects

Isolation of Isoflavones and Soyasaponins from the Germ of Soybean

Bitterness of saponins and their content in dry peas

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