Termitomenins F and G, Two New Lignan Glucosides from Terminalia chebula var. tomentella (Kurz) C. B. Clarke

doi:10.1007/s13659-021-00314-z

Natural Products and Bioprospecting ›› 2021, Vol. 11 ›› Issue (5): 565-572.DOI: 10.1007/s13659-021-00314-z

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Termitomenins F and G, Two New Lignan Glucosides from Terminalia chebula var. tomentella (Kurz) C. B. Clarke

Jun Yin^1,2, Hong-Tao Zhu¹, Man Zhang¹, Dong Wang¹, Chong-Ren Yang¹, Ying-Jun Zhang^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3 Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

Received:2021-04-30 Online:2021-09-27 Published:2021-10-24
Contact: Ying-Jun Zhang
Supported by:
This research was supported by the National Natural Science Foundation of China (82074124) and the Key Project of Basic Research Plan of Yunnan Province, China (202001AS070017). The authors are grateful to the staffs of the analytical and bioactivity screening groups at the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, for measuring the spectroscopic data and α-glucosidase inhibitory activity.

Termitomenins F and G, Two New Lignan Glucosides from Terminalia chebula var. tomentella (Kurz) C. B. Clarke

Jun Yin^1,2, Hong-Tao Zhu¹, Man Zhang¹, Dong Wang¹, Chong-Ren Yang¹, Ying-Jun Zhang^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3 Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

通讯作者: Ying-Jun Zhang
基金资助:
This research was supported by the National Natural Science Foundation of China (82074124) and the Key Project of Basic Research Plan of Yunnan Province, China (202001AS070017). The authors are grateful to the staffs of the analytical and bioactivity screening groups at the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, for measuring the spectroscopic data and α-glucosidase inhibitory activity.

Abstract

Abstract: The extensive chemical investigation on the branches and leaves of Terminalia chebula var. tomentella (Combretaceae) led to the isolation of two new lignan glucosides with a furofuran skeleton, termitomenins F (1) and G (2). In addition, 19 known compounds including five lignan glucosides (3-7), six hydrolyzable tannins (8-13) and eight simple phenolics (14-21) were also identified. Their structures were determined by comprehensive spectroscopic analyses. It is noted that 8 and 9 were C-glycosidic hydrolyzable tannins with one hexahydroxydiphenoyl and one gallagyl group linked to an open-chain glucosyl C-1/O-2/O-3 and O-4/O-6, respectively, which were rarely found in plants. Nine known compounds, 6-9, 13, and 18-21, were procured from the titled plant for the first time, while 3-5, 10-12 and 14-17 were also found in the fruits. Notably, the known hydrolyzable tannins 8-13 exhibited stronger α-glucosidase inhibitory activities with IC₅₀ values ranging from 0.10 to 3.12 μM, than the positive control, quercetin (IC₅₀=9.38 ±0.33 μM).

Key words: Terminalia chebula var. tomentella, Lignan glucosides, Hydrolyzable tannins, α-Glucosidase inhibitory activity, Calculated ECD

摘要： The extensive chemical investigation on the branches and leaves of Terminalia chebula var. tomentella (Combretaceae) led to the isolation of two new lignan glucosides with a furofuran skeleton, termitomenins F (1) and G (2). In addition, 19 known compounds including five lignan glucosides (3-7), six hydrolyzable tannins (8-13) and eight simple phenolics (14-21) were also identified. Their structures were determined by comprehensive spectroscopic analyses. It is noted that 8 and 9 were C-glycosidic hydrolyzable tannins with one hexahydroxydiphenoyl and one gallagyl group linked to an open-chain glucosyl C-1/O-2/O-3 and O-4/O-6, respectively, which were rarely found in plants. Nine known compounds, 6-9, 13, and 18-21, were procured from the titled plant for the first time, while 3-5, 10-12 and 14-17 were also found in the fruits. Notably, the known hydrolyzable tannins 8-13 exhibited stronger α-glucosidase inhibitory activities with IC₅₀ values ranging from 0.10 to 3.12 μM, than the positive control, quercetin (IC₅₀=9.38 ±0.33 μM).

关键词: Terminalia chebula var. tomentella, Lignan glucosides, Hydrolyzable tannins, α-Glucosidase inhibitory activity, Calculated ECD

Jun Yin, Hong-Tao Zhu, Man Zhang, Dong Wang, Chong-Ren Yang, Ying-Jun Zhang. Termitomenins F and G, Two New Lignan Glucosides from Terminalia chebula var. tomentella (Kurz) C. B. Clarke[J]. Natural Products and Bioprospecting, 2021, 11(5): 565-572.

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Termitomenins F and G, Two New Lignan Glucosides from Terminalia chebula var. tomentella (Kurz) C. B. Clarke

Termitomenins F and G, Two New Lignan Glucosides from Terminalia chebula var. tomentella (Kurz) C. B. Clarke

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