Development of Semisynthetic Soyasaponin Derivatives

doi:10.7506/spkx1002-6630-201322025

Abstract

Abstract:

The natural structure of saponins may not stay in the best active state. To enlarge its application and gain intensive
insight into the relationship between structure and function, modification of sugar chains in soyasaponins is required.
Derivatives of soyasaponin Ab were prepared by adding either dodecylamine or phenylethylamine in the presence of carbodiimide.
The semi-synthesized derivatives of soyasaponin Ab with weak polarity were identified by IR, EMI-MS, and
NMR. The derivatives can be used for further exploration of the relationship between immunostimulating adjuvant/haemolytic
activities and molecular structure of soyasaponins and their derivatives.

Key words: soyasaponin Ab, dodecylamine, phenylethylamine, derivatives

CLC Number:

TS207.3

GUO Wen-xiu，YAN Xin-bin，ZHAO Da-yun. Development of Semisynthetic Soyasaponin Derivatives[J]. FOOD SCIENCE, 2013, 34(22): 123-127.

References

[1] Lee S.O., Simons A.L., Murphy P.A. et.al. Soyasaponins Lowered Plasma Cholesterol and Increased Fecal Bile Acids in Female Golden Syrian Hamsters[J].Experimental Biology and Medcine,2005,230(7):472-478.

[2] Rao A.V.,Sung M.K..Saponins as anticarcinogens[J].Journal of Nutrition,1995,125:717-724.

[3] Nakashima H.,Okubo.K.,Honda Y.et.al.Inhibitory effect of glycosides like saponins from soybean on the infectivity of HIV in vitro[J].AIDS,1989,3(10):655-658.

[4] Ohminami H.,Kimura Y.,Okuda H.etal. Effect of soyasaponins on liver injury induced by highly peroxidized fat in rats[J].Planta Medica,1984,50(5):440-441.

[5] Dante J. Marciani, Brimingham,Ala. Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof. America[P],U.S.6080725A,2000-07-27.

[6] Voutquenne L, Lavaud C, Massiot G, et al. Structure-Activity relationships of haemolytic saponins[J],Pharmaceutical Biology(Formerly International Journal of Pharmacognosy),2002,40(4): :253-263.

[7] D.J.Marciani, J.B.Press, R.c.Reynolds, et al. Development of semisynthetic triterpenoid saponin derivatives with immune stimulating activity[J].Vaccine 2000,18:3141-3151.

[8] Gui Liu, Christine Anderson, Heidi Scaltreto, et al.QS-21 structure/function studies: effect of acylation on adjuvant activity[J],vaccine 2002,20:2808-2815.

[9 ] Pham, Hoang L., Ross, Benjamin P., McGeary, Ross P., et al. Synthesis of cationic derivatives of Quil A and the preparation of cationic immune-stimulating complexes (ISCOMs). International Journal of Pharmaceutics, 2009, 376(1-2): 123-133.

[10] K Decroos,JP vincken,L Heng,et al.Simultaneous quantification of differently glycosylated, acetylated, and 2,3-dihydro-2,5-dihydroxy-6-methy1-4 H-pyran-4-one-conjugated soyasaponins using reversed-phase high-performance liquid chromatography with evaporative light scattering detection[J].J chromatogra,2005,1072(1):185-193.

[11] 翁诗甫，傅里叶变换红外光谱分析[M]，化学工业出版社，2010.

[12] 胡皆汉，郑学仿，实用红外光谱学[M]，科学出版社，2010,300-323.

[13] 庾石山，三萜化学[M]，化学工业出版社，2008,121-128.

[14] 庾石山，张东明，浮光苗，实用天然产物手册-皂苷[M]，化学工业出版社，2005，8-21

[15] Gurfinker D.M., Reynolds W.F., Rao A.V.. The isolation of soyasaponins by fractional precipitation, solid phase extraction, and low pressure liquid chromatography[J].International Journal of Food and Nurtition,2005,56(7):501-509.

[16] 徐龙权，翟滨，田晶，金凤燮，大豆皂甙酶解的研究[J].大连轻工业学院学报,2011,20(3):37-40.

[17] Seo-Young Changa, Myung Joo Hana, et al. Liquid chromatography/mass spectrometry-based structural analysis of soyasaponin Ab metabolites by human fecal micro?ora[J]. Journal of Pharmaceutical and Biomedical Analysis 2010,(52) :752–756.

[1]	XIANG Ting, XIA Chen, LIU Jianhua, WANG Chaoran, SHEN Jianfu. Separation, Structural Identification and Anti-tumor Effects of New Compounds from Cordyceps militaris [J]. FOOD SCIENCE, 2021, 42(8): 235-242.
[2]	ZHANG Xingya, YANG Bo, LI Yalei, LUO Ruiming, RUAN Zhentian, SA Miaomiao, ZHAO Junyi. Proteomics Studies on Myoglobin Content and Its Transformation into Derivatives in Muscle of Qinchuan Cattle during Postmortem Storage [J]. FOOD SCIENCE, 2021, 42(7): 226-231.
[3]	LIU Na, CAO Qiang, XIAO Yushi, HUANG Rong, CHENG Lei, LIU Huan, HAN Gang, LI Jincheng, LI Menglong, WU Lidong. Recent Progress of Sensors Based on Dopamine and Its Derivatives in Food Safety Rapid Detection [J]. FOOD SCIENCE, 2021, 42(5): 332-339.
[4]	YUE Cuinan, WANG Zhihui, SHI Xuping, JIANG Xinfeng, LI Yansheng, YANG Puxiang. Effects of Light Quality on Aroma Metabolites in Tea: A Review of Recent Literature [J]. FOOD SCIENCE, 2020, 41(5): 299-305.
[5]	GONG Lei, HAN Zhi, CHENG Hui, LIU Jie, PENG Qingzhi. Determination and Contamination Pattern of Deoxynivalenol and Derivatives in Cereals and Their Products [J]. FOOD SCIENCE, 2020, 41(4): 307-312.
[6]	ZHANG Bo, HAN Shunyu, MA Tengzhen, ZHU Xia, LI Min. Progress in Understanding Structures of Anthocyanins Derivatives in Red Wines [J]. FOOD SCIENCE, 2018, 39(5): 284-295.
[7]	Lü Haipeng, WANG Mengqi, ZHANG Yue, ZHU Yin, LIN Zhi. Recent Advances in Research on Biotransformation of Polypheonls during Pu-erh Tea Pile Fermentation [J]. FOOD SCIENCE, 2018, 39(23): 306-312.
[8]	LI Shujing, ZHOU Ziruo, ZHOU Wei, WANG Xinrui, YUAN Li. Preparation and Properties of Inclusion Complexes of β-Cyclodextrin Derivatives with Phloretin [J]. FOOD SCIENCE, 2017, 38(7): 11-16.
[9]	SONG Xiaoqing, REN Yamei, ZHANG Yanyi, SHI Junling, FAN Mingtao. Mechanism of Chlorophyll Degradation and Effect of 1-MCP Treatment on Chlorophyll Metabolism in Postharvest Kiwifruit [J]. FOOD SCIENCE, 2017, 38(17): 260-265.
[10]	DUAN Zhifang, FAN Meishan, LIANG Qili. Synthesis and Antioxidant Activities of Three Classes of New Chalcone Derivatives [J]. FOOD SCIENCE, 2016, 37(23): 38-44.
[11]	WU Nao, WANG Jingyi, ZHANG Qian, GUO Ying, LI Shuyi, HE Yi, ZHU Zhenzhou, HE Jingren. Optimized Preparation of New Anthocyanin Derivative Oxovitisin A and Its Antiproliferation Effect on Cancer Cells in vitro [J]. FOOD SCIENCE, 2016, 37(16): 1-7.
[12]	WANG Zhihua, JIANG Yangyang, YU Xiaohua, YAN Yongbin, QIN Caiqin. Effect of Chitosan and Its Water-Soluble Derivatives on Immune Function in Mice [J]. FOOD SCIENCE, 2016, 37(1): 198-202.
[13]	HE Jingren1,2, KUANG Minjie1, QI Minyu1, LIU Gang1,2, LI Shuyi1, WU Nao1, ZHU Zhenzhou1, GUO Ying1, LIANG Zheng1. Recent Progress in Research on Pyranoanthocyanins Derivatives [J]. FOOD SCIENCE, 2015, 36(7): 228-234.
[14]	LIU Fei, XIONG Zhengwei, LI Chunhua, ZHANG Juan, WANG Xiaoping, TANG Xiaobo, WANG Yun. Progress in Molecular Modification and Anticancer Activity of (–)-Epigallocatechin-3-gallate (EGCG) [J]. FOOD SCIENCE, 2015, 36(23): 321-328.
[15]	ZHONG Ci-ping 1，QIAN Yu2，SHU Chang1，SUO Hua-yi1，LI Lin1,*. Research Progress in Antimicrobial Effects of Berberine and Its Derivatives [J]. FOOD SCIENCE, 2013, 34(7): 321-325.