Journal of the science of food and agriculture · 2024
Qingqianliutianosides A-E: five new sweet dammarane triterpenoid glycosides derived from the leaves of Cyclocarya paliurus - identification, characterization and interactions with T1R2/T1R3 sweet taste receptors.
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Guo Tingsi, Yang Yong, Liang Ling, Huang Qin, Hu Qiqi, Xie Qingling, Yuan Hanwen, Chen Guangyu, Wang Wei, Jian Yuqing
Аннотация
BACKGROUND: Cyclocarya paliurus, as a new food resource, is utilized extensively in human and animal diets due to its bioactive compounds, health benefits, and its highly prized sweet flavor. This study aimed to investigate the sweet-taste ingredient of C. paliurus leaves.
RESULTS: Five new dammarane triterpenoid glycosides were isolated and identified as qingqianliutianosides A-E (1-5) by comprehensive spectroscopic data analysis and a single crystal X-ray diffraction experiment. Qingqianliutianoside A (1) and qingqianliutianoside C (3), present in relatively high quantities in the plant, were shown to exhibit sweetness by sensory evaluation and electronic tongue analysis. Further monitoring was conducted on the content changes in 3 in leaves at different growth stages, indicating that 3 reached its peak content in April and then showed a decreasing trend. Molecular docking studies revealed that T1R2/T1R3 receptors Ser212, Ser105, Thr239, Asn380, Thr305, and Val381 may play critical roles, demonstrating that hydrogen bonding and hydrophobic interactions were the dominant interaction forces between all of the identified compounds and the active sites in the Venus flytrap module of the T1R2/T1R3 receptors.
CONCLUSION: Qingqianliutianosides A-E are promising natural source sugar substitutes for use in functional foods and beverages. © 2024 Society of Chemical Industry.
RESULTS: Five new dammarane triterpenoid glycosides were isolated and identified as qingqianliutianosides A-E (1-5) by comprehensive spectroscopic data analysis and a single crystal X-ray diffraction experiment. Qingqianliutianoside A (1) and qingqianliutianoside C (3), present in relatively high quantities in the plant, were shown to exhibit sweetness by sensory evaluation and electronic tongue analysis. Further monitoring was conducted on the content changes in 3 in leaves at different growth stages, indicating that 3 reached its peak content in April and then showed a decreasing trend. Molecular docking studies revealed that T1R2/T1R3 receptors Ser212, Ser105, Thr239, Asn380, Thr305, and Val381 may play critical roles, demonstrating that hydrogen bonding and hydrophobic interactions were the dominant interaction forces between all of the identified compounds and the active sites in the Venus flytrap module of the T1R2/T1R3 receptors.
CONCLUSION: Qingqianliutianosides A-E are promising natural source sugar substitutes for use in functional foods and beverages. © 2024 Society of Chemical Industry.