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Tie-jun Fu - One of the best experts on this subject based on the ideXlab platform.
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Isolation and identification of steroidal Saponins in total Saponin from Dioscorea nipponica Makino
Acta pharmaceutica Sinica, 2002Co-Authors: Shu-hu Du, Tie-jun FuAbstract:AIM: To investigate the water-soluble steroidal Saponins in total Saponin from Dioscorea nipponica Makino and look for new active compounds. METHODS: The compounds were isolated with silica gel, PTLC and HPLC, and their structures were elucidated by acid hydrolysis, physical and chemical data and spectral analysis (IR, NMR, MS, HMQC, HMBC) as well as chemical correlations. RESULTS: The two steroidal Saponins (water-insoluble Saponin and water-soluble Saponin) were isolated from the total Saponin of Dioscorea nipponica Makino. The structures were elucidated as diosgenin 3-O-[alpha-L-rhamnopy ranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]]-beta-D-glucopyranoside (I), diosgenin 3-O-[alpha-L-rhamnopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside (II). CONCLUSION: Compound II is a new steroidal Saponin and firstly isolated from Dioscorea nipponica Makino. It was named as dioscin Dc.
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Isolation and identification of steroidal Saponins in total Saponin from Dioscorea nipponica Makino
Acta pharmaceutica Sinica, 2002Co-Authors: Shu-hu Du, Tie-jun FuAbstract:AIM: To investigate the water-soluble steroidal Saponins in total Saponin from Dioscorea nipponica Makino and look for new active compounds. METHODS: The compounds were isolated with silica gel, PTLC and HPLC, and their structures were elucidated by acid hydrolysis, physical and chemical data and spectral analysis (IR, NMR, MS, HMQC, HMBC) as well as chemical correlations. RESULTS: The two steroidal Saponins (water-insoluble Saponin and water-soluble Saponin) were isolated from the total Saponin of Dioscorea nipponica Makino. The structures were elucidated as diosgenin 3-O-[alpha-L-rhamnopy ranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]]-beta-D-glucopyranoside (I), diosgenin 3-O-[alpha-L-rhamnopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside (II). CONCLUSION: Compound II is a new steroidal Saponin and firstly isolated from Dioscorea nipponica Makino. It was named as dioscin Dc.
Chigen Tsukamoto - One of the best experts on this subject based on the ideXlab platform.
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mechanism of ddmp Saponin degradation and maltol production in soymilk preparation
Lwt - Food Science and Technology, 2015Co-Authors: Wanida T Chitisankul, Kazuko Shimada, Yohei Omizu, Yuko Uemoto, Warunee Varanyanond, Chigen TsukamotoAbstract:Abstract The degradation mechanism of 2,3-dihydro-2,5-dihydroxy-6-methyl-4 H -pyran-4-one (DDMP) conjugated Saponins into group B, E Saponins, and maltol production during soymilk preparation was studied by using lipoxygenase (LOXs)-deficient soybean variety (‘L-Star’) and purified DDMP-Saponin βg. Experiments were performed under practical soymilk preparation and model reaction system. DDMP-Saponins (DDMPs) degraded by both heat and radical (LOXs, AAPH, and DPPH) treatments but maltol was produced only by heat degradation. DDMPs in raw soymilk prepared from ‘Fukuyutaka’ (common variety) were completely degraded whereas DDMPs in ‘L-Star’ raw soymilk remained. When DDMP-Saponin βg was treated with AAPH radical, a compound that has one oxygen atom attached at DDMP-moiety, which was identified by LC–MS/MS analysis, was detected but gradually degraded into group B Saponin Bb. After treating DDMP-Saponin βg with DPPH-radical, some compounds which seem to be dehydrogenated DDMP-βg, and group E Saponin Be were produced. These results suggest that competitive degradation of DDMPs between heat treatment and LOXs activities affected the combination of group B, E Saponins, and maltol contents during soymilk preparation. Thus, appropriate processing conditions should be considered for controlling the flavor and health promoting characteristics, which are derived from Saponin components of soybean base foods.
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comparison of Saponin composition and content in wild soybean glycine soja sieb and zucc before and after germination
Bioscience Biotechnology and Biochemistry, 2014Co-Authors: Panneerselvam Krishnamurthy, Chigen Tsukamoto, Yuya Takahashi, Yuji Hongo, R J Singh, Jeongdong Lee, Gyuhwa ChungAbstract:Eight wild soybean accessions with different Saponin phenotypes were used to examine Saponin composition and relative Saponin quantity in various tissues of mature seeds and two-week-old seedlings by LC-PDA/MS/MS. Saponin composition and content were varied according to tissues and accessions. The average total Saponin concentration in 1 g mature dry seeds of wild soybean was 16.08 ± 3.13 μmol. In two-week-old seedlings, produced from 1 g mature seeds, it was 27.94 ± 6.52 μmol. Group A Saponins were highly concentrated in seed hypocotyl (4.04 ± 0.71 μmol). High concentration of DDMP Saponins (7.37 ± 5.22 μmol) and Sg-6 Saponins (2.19 ± 0.59 μmol) was found in cotyledonary leaf. In seedlings, the amounts of group A and Sg-6 Saponins reduced 2.3- and 1.3-folds, respectively, while DDMP + B + E Saponins increased 2.5-fold than those of mature seeds. Our findings show that the group A and Sg-6 Saponins in mature seeds were degraded and/or translocated by germination whereas DDMP Saponins were newly synthesized.
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the sg 6 Saponins new components in wild soybean glycine soja sieb and zucc polymorphism geographical distribution and inheritance
Euphytica, 2014Co-Authors: Panneerselvam Krishnamurthy, Chigen Tsukamoto, R J Singh, Jeongdong Lee, Hongsig Kim, Seung Hwan Yang, Gyuhwa ChungAbstract:Hypocotyl Saponin composition of 1,198 accessions of wild soybean (Glycine soja) collected from China, Korea, Japan and Russia Far East was analyzed by thin-layer chromatography to determine polymorphic variation and geographical distribution. Eight common distinguishable Saponin phenotypes were identified: Aa, Ab, AaBc, AbBc, Aa+α, Ab+α, AaBc+α and AbBc+α. The latter four +α type were new. All eight types were identified in China. Type Ab+α was absent in Korea. Types Ab+α and AbBc+α, and Aa+α and Ab+α were not identified in Japan and Russia far east, respectively. Six new triterpene Saponins were detected in +α type via LC-PDA/MS/MS analyses. They were, tentatively, designated as H-αg, H-αa, I-αg, I-αa, J-αg and J-αa. These Saponins were inherited together by a single dominant allele. A gene symbol Sg-6 was assigned. Hence, the new Saponins were collectively named as Sg-6 Saponins. The frequency of Sg-6 allele was 17.6 % in Chinese, 10.0 % in Korean and 1.0 % in Japanese wild soybean. The wild soybeans having Sg-6 Saponins can be utilized in soybean breeding programs as well as in Saponin biosynthesis studies in soybean.
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inheritance and characterization of a null allele for group a acetyl Saponins found in a mutant soybean glycine max l merrill
Breeding Science, 1999Co-Authors: Akio Kikuchi, Chigen Tsukamoto, Kohseu Tabuchi, Taizan Adachi, Kazuyoshi OkuboAbstract:A total of 801 cultivated soybean accessions and 330 wild soybean accessions were screened for genotypes lacking group A acetyl Saponins in seed hypocotyls using thin layer chromatography and high performance liquid chromatography. Only one accession from the soybean cultivars, A-b(F) Iacked group A acetyl Saponins but it had an unknown Saponin. The inheritance of a null allele for group A acetyl Saponins in soybeans was determined by crosses between A-b(F) and Shirosennari, which had group A acetyl Saponin Aa, and Suzuyutaka, which had group A acetyl Saponin Ab, respectively. All F1 seeds from these crosses had Aa and Ab respectively. F2 seeds resulting from these crosses segregated 3:1 indicating that the absence of group A acetyl Saponins is inherited as a simple recessive. The gene symbol Sg-1 is assigned to the allele coding for the absence of group A acetyl Saponins, Sg-1a for the presence of group A acetyl Saponin Aa and Sg-1b for the presence of group A acetyl Saponin Ab, respectively. Sg-1a and Sg-1b are co-dominant alleles. Through FAB-MS and chemical analyses, the unknown Saponin accumulated in the seed hypocotyls of A-b(F), was assumed to be 3-O-[β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl]-22-O-[α-L-arabino-pyranosyl] soyasapogenol A.
Shu-hu Du - One of the best experts on this subject based on the ideXlab platform.
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Isolation and identification of steroidal Saponins in total Saponin from Dioscorea nipponica Makino
Acta pharmaceutica Sinica, 2002Co-Authors: Shu-hu Du, Tie-jun FuAbstract:AIM: To investigate the water-soluble steroidal Saponins in total Saponin from Dioscorea nipponica Makino and look for new active compounds. METHODS: The compounds were isolated with silica gel, PTLC and HPLC, and their structures were elucidated by acid hydrolysis, physical and chemical data and spectral analysis (IR, NMR, MS, HMQC, HMBC) as well as chemical correlations. RESULTS: The two steroidal Saponins (water-insoluble Saponin and water-soluble Saponin) were isolated from the total Saponin of Dioscorea nipponica Makino. The structures were elucidated as diosgenin 3-O-[alpha-L-rhamnopy ranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]]-beta-D-glucopyranoside (I), diosgenin 3-O-[alpha-L-rhamnopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside (II). CONCLUSION: Compound II is a new steroidal Saponin and firstly isolated from Dioscorea nipponica Makino. It was named as dioscin Dc.
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Isolation and identification of steroidal Saponins in total Saponin from Dioscorea nipponica Makino
Acta pharmaceutica Sinica, 2002Co-Authors: Shu-hu Du, Tie-jun FuAbstract:AIM: To investigate the water-soluble steroidal Saponins in total Saponin from Dioscorea nipponica Makino and look for new active compounds. METHODS: The compounds were isolated with silica gel, PTLC and HPLC, and their structures were elucidated by acid hydrolysis, physical and chemical data and spectral analysis (IR, NMR, MS, HMQC, HMBC) as well as chemical correlations. RESULTS: The two steroidal Saponins (water-insoluble Saponin and water-soluble Saponin) were isolated from the total Saponin of Dioscorea nipponica Makino. The structures were elucidated as diosgenin 3-O-[alpha-L-rhamnopy ranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]]-beta-D-glucopyranoside (I), diosgenin 3-O-[alpha-L-rhamnopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside (II). CONCLUSION: Compound II is a new steroidal Saponin and firstly isolated from Dioscorea nipponica Makino. It was named as dioscin Dc.
W A Oleszek - One of the best experts on this subject based on the ideXlab platform.
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chromatographic determination of plant Saponins an update 2002 2005
Journal of Chromatography A, 2006Co-Authors: W A Oleszek, Zbigniew BialyAbstract:Abstract The developments during 2002–2005 in the methods used for Saponin analyses in plant material are presented. There were number of papers published on isolation and identification of new Saponins by chromatographic techniques. Some new developments can be found in separation techniques or solid and mobiles phases used. Separation of individual Saponins is still complicated and time consuming. This is due to the fact that in most of the plant species Saponins occur as a multi-component mixture of compounds of very similar polarities. Thus, to isolate single compound for structure elucidation or biological activity testing, a combination of different chromatographic techniques has to be used, e.g. first separation of the mixture to simpler sub-fractions on reversed phase C18 has to be followed by further purification on normal phase Silica gel column. Especially difficult is determination of Saponins in plant material as these compounds do not posses chromophores and their profiles cannot be registered in UV. Most HPLC methods apply not only specific registration at 200–210 nm, but these methods are not applicable for determination of many Saponins in plant material at levels lower than 200–300 mg/kg. Some new or improved techniques for quantification of Saponins in plant material were published in reviewed period. These include further progress in the application of evaporative light scattering detection (ELSD) for Saponin profiling and quantification, which is also not only specific but also more sensitive in comparison to 200–210 nm detection. Some progress in development of new applications for liquid chromatography-electrospray mass spectrometry (LC/ESI/MS) for Saponin determination has also been done. This method gives highest sensitivity and on line identification of separated Saponins and should be recommended for specialized analyses of extracts and pharmaceutical formulas like the validation of a new assay. From non-chromatographic techniques for Saponin determination, a sensitive and compound specific ELISA tests for some Saponins were developed.
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chromatographic determination of plant Saponins
Journal of Chromatography A, 2002Co-Authors: W A OleszekAbstract:Abstract The methods used for Saponin determination in plant materials are presented. It is emphasised that the biological and spectrophotomeric methods still being used for Saponin determination provide, to some extent, valuable results on Saponin concentrations in plant material. However, since they are sensitive to the structural variation of individual Saponins they should be standardized with Saponin mixtures isolated from the plant species in which the concentration is measured. However, one plant species may contain some Saponins which can be determined with a biological test and others which cannot. That is why biological and colorimetric determinations do not provide accurate data and have to be recognized as approximate. Thin-layer chromatography on normal and reversed-phases (TLC, HPTLC, 2D-TLC) provides excellent qualitative information and in combination with on-line coupling of a computer with dual-wavelength flying-spot scanner and two-dimensional analytical software can be used for routine determination of Saponins in plant material. The densitometry of Saponins has been very sensitive, however, to plate quality, spraying technique and the heating time and therefore appropriate Saponin standards have to be run in parallel with the sample. Gas–liquid chromatography has limited application for determination since Saponins are quite big molecules and are not volatile compounds. Thus, there are only few applications of GC for determination of intact Saponins. The method has been used for determination of TMS, acetyl or methyl derivatives of an aglycones released during Saponin hydrolysis. However, structurally different Saponins show different rates of hydrolysis and precise optimisation of hydrolysis conditions is essential. Besides, during hydrolysis a number of artefacts can be formed which can influence the final results. High performance liquid chromatography on reversed-phase columns remains the best technique for Saponin determination and is the most-widely used method for this group of compounds. However, the lack of chromophores allowing detection in UV, limits the choice of gradient and detection method. The pre-column derivatisation with benzoyl chloride, coumarin or 4-bromophenacyl bromide has been used successfully in some cases allowing UV detection of separation. Standardisation and identification of the peaks in HPLC chromatograms has been based on comparison of the retention times with those observed for authentic standards. But new hyphenated techniques, combining HPLC with mass spectrometry and nuclear magnetic resonance are developing rapidly and allow on-line identification of separated Saponins. Capillary electrophoresis has been applied for Saponin determination only in a limited number of cases and this method is still being developed.
Shuying Liu - One of the best experts on this subject based on the ideXlab platform.
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application of electrospray ionization mass spectrometry combined with sequential tandem mass spectrometry techniques for the profiling of steroidal Saponin mixture extracted from tribulus terrestris
Planta Medica, 1999Co-Authors: Shiping Fang, Chunyan Hao, Zhiqiang Liu, Fengrui Song, Shuying LiuAbstract:Using electrospray ionization mass spectrometry combined with sequential tandem mass spectrometry (ESI-MS (n)), the steroidal Saponin mixture extracted from TRIBULUS TERRESTRIS was studied. The structures of five known steroidal Saponins and two unknown steroidal Saponins in the Saponin mixture were investigated by sequential tandem mass spectrometry experiments. All of the steroidal Saponins displayed similar fragmentation behavior in ESI-MS (n), and the characteristic cross ring cleavage pattern could be used as a fingerprint for the identification of steroidal Saponins. The methodology has been established as a powerful tool for the profiling of mixtures, especially of crude plant extracts, and the structural elucidation of compounds.
