Enantiomeric diarylheptanoids from Ottelia acuminata var. acuminata and their α-glucosidase inhibitory activity

doi:10.1007/s13659-025-00515-w

Natural Products and Bioprospecting ›› 2025, Vol. 15 ›› Issue (4): 33-33.DOI: 10.1007/s13659-025-00515-w

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Enantiomeric diarylheptanoids from Ottelia acuminata var. acuminata and their α-glucosidase inhibitory activity

Jia-Ru Zhou^1,2, Xin-Yue Hu^1,2, Hong-Xing Liu¹, Yu Zhou^1,2, Fei-Fei Xiong^1,2, Jian-Jun Zhao¹, Xing-Ren Li¹, Gang Xu¹

1. State Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China;
2. University of Chinese Academy of Sciences, Beijing, 100049, China

Received:2025-03-10 Accepted:2025-04-20 Online:2025-05-16 Published:2025-08-23
Supported by:
This study was supported financially by Yunnan Key Laboratory Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan (APR202301), Yunnan Revitalization Talent Support Program “Innovation Team” Project (202305AS350014), and Foundation of DR. PLANT.

Enantiomeric diarylheptanoids from Ottelia acuminata var. acuminata and their α-glucosidase inhibitory activity

Jia-Ru Zhou^1,2, Xin-Yue Hu^1,2, Hong-Xing Liu¹, Yu Zhou^1,2, Fei-Fei Xiong^1,2, Jian-Jun Zhao¹, Xing-Ren Li¹, Gang Xu¹

1. State Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China;
2. University of Chinese Academy of Sciences, Beijing, 100049, China

通讯作者: Xing-Ren Li, E-mail:lixingren@mail.kib.ac.cn;Gang Xu, E-mail:xugang008@mail.kib.ac.cn
基金资助:
This study was supported financially by Yunnan Key Laboratory Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan (APR202301), Yunnan Revitalization Talent Support Program “Innovation Team” Project (202305AS350014), and Foundation of DR. PLANT.

Abstract

Abstract: Otteacumienes G–K (1–5), five pairs of enantiomeric diarylheptanoids, along with one undescribed diarylheptanoid glycoside and one new lignan, were isolated from Ottelia acuminata var. acuminata. Compounds 1–5 were identified as five pairs of enantiomers and their structural configurations were determined through a combination of spectroscopic analysis, X-ray crystallography, and ECD calculation. Notably, compound 6 was the first diarylheptanoid glycoside isolated from this aquatic species, and its absolute configuration was unequivocally established through semi-synthesis. Biological evaluation demonstrated that compound 1 exhibited α-glucosidase inhibitory activity, with an inhibition ratio of 38.97% (acarbose as the positive control, inhibition ratio = 13.52%).

Key words: Ottelia acuminata, Diarylheptanoids, Enantiomers, α-Glucosidase inhibitory activity

摘要： Otteacumienes G–K (1–5), five pairs of enantiomeric diarylheptanoids, along with one undescribed diarylheptanoid glycoside and one new lignan, were isolated from Ottelia acuminata var. acuminata. Compounds 1–5 were identified as five pairs of enantiomers and their structural configurations were determined through a combination of spectroscopic analysis, X-ray crystallography, and ECD calculation. Notably, compound 6 was the first diarylheptanoid glycoside isolated from this aquatic species, and its absolute configuration was unequivocally established through semi-synthesis. Biological evaluation demonstrated that compound 1 exhibited α-glucosidase inhibitory activity, with an inhibition ratio of 38.97% (acarbose as the positive control, inhibition ratio = 13.52%).

关键词: Ottelia acuminata, Diarylheptanoids, Enantiomers, α-Glucosidase inhibitory activity

Jia-Ru Zhou, Xin-Yue Hu, Hong-Xing Liu, Yu Zhou, Fei-Fei Xiong, Jian-Jun Zhao, Xing-Ren Li, Gang Xu. Enantiomeric diarylheptanoids from Ottelia acuminata var. acuminata and their α-glucosidase inhibitory activity[J]. Natural Products and Bioprospecting, 2025, 15(4): 33-33.

References

[1] American Diabetes Association Professional Practice Committee; 2. Diagnosis and classification of diabetes: standards of care in diabetes—2025. Diabetes Care. 2025; 48 (Supplement_1): S27-S49.
[2] Lu X, Xie QX, Pan XH, Zhang RN, Zhang XY, Peng G, Zhang YW, Shen SM, Tong NW. Type 2 diabetes mellitus in adults: pathogenesis, prevention and therapy. Sig Transduct Target Ther. 2024;9(1):262.
[3] Gong LX, Feng DN, Wang TX, Ren YQ, Liu YL, Wang J. Inhibitors of α-amylase and α-glucosidase: potential linkage for whole cereal foods on prevention of hyperglycemia. Food Sci Nutr. 2020;8(12):6320-37.
[4] Hossain U, Das AK, Ghosh S, Sil PC. An overview on the role of bioactive α-glucosidase inhibitors in ameliorating diabetic complications. Food Chem Tox. 2020;145: 111738.
[5] Lian WX, Lin YQ. Research progress of α-glucosidase inhibitors and their clinical applications. Practical J Med Pharm. 2014;31(6):556-9.
[6] Jiang ZT, Li H, Dao ZL, Long CL. Ethnobotanical study on the traditional food plant Ottelia acuminata in Yunnan. J Inn Mong Norm Univ. 2010;39(2):163-8.
[7] Xia CL, Qian JY. Dali cangshan phytopharmacognosy. Yunnan Science and Technology Press. 2016; 393.
[8] Liu HX, Ma JZ, Ye YS, Zhao JJ, Wan SJ, Hu XY, Xu G. α-Glucosidase inhibitive diarylheptanoids from Ottelia acuminata var. acuminata, a traditional vegetable of Bai Nationality in Yunnan. Nat Prod Bioprospect. 2022;12(1):22.
[9] He XF, Chen JJ, Li TZ, Hu J, Huang XY, Zhang XM, Guo YQ, Geng CA. Diarylheptanoid-flavanone hybrids as multiple-target antidiabetic agents from Alpinia katsumadai. Chin J Chem. 2021;39:3051-63.
[10] Xu LJ, Huang T, Huang CY, Wu CZ, Jia A, Hu X. Chiral separation, absolute configuration, and bioactivity of two pairs of flavonoid enantiomers from Morus nigra. Phytochemistry. 2019;163:33-7.
[11] Costantino V, Fattorusso E, Mangoni A, Perinu C, Teta R, Panza E, Ianaro A. Tedarenes A and B: structural and stereochemical analysis of two new strained cyclic diarylheptanoids from the Marine Sponge Tedania ignis. J Org Chem. 2012;77(15):6377-83.
[12] Morikawa T, Tao J, Toguchida I, Matsuda H, Yoshikawa M. Structures of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense. J Nat Prod. 2003;66:86-91.
[13] Makule E, Schmidt T, Heilmann J, Kraus B. Diarylheptanoid glycosides of Morella salicifolia Bark. Molecules. 2017;22(12):2266.
[14] Wadzinski TJ, Steinauer A, Hie L, Pelletier G, Schepartz A, Miller SJ. Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent. Nature Chem. 2018;10:644-52.
[15] Moritani Y, Fukushima C, Miyagishima T, Ohmizu H, Iwasaki T. Simple synthesis of trans-α,β-dibenzyl-γ-butyrolactone lignans by diastereoselective reduction of α-benzylidene-β-benzyl-γ-butyrolactones using NaBH₄-NiCl₂. Bull Chem Soc Jpn. 1996;69(8):2281-6.
[16] Ikeda R, Nagao T, Okabe H, Nakano Y, Matsunaga H, Katano M, Mori M. Antiproliferative constituents in umbelliferae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm. Chem Pharm Bull (Tokyo). 1998;46(5):871-4.

Enantiomeric diarylheptanoids from Ottelia acuminata var. acuminata and their α-glucosidase inhibitory activity

Enantiomeric diarylheptanoids from Ottelia acuminata var. acuminata and their α-glucosidase inhibitory activity

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[1]	Hong-Xing Liu, Jun-Zeng Ma, Yan-Song Ye, Jian-Jun Zhao, Shi-Jie Wan, Xin-Yue Hu, Gang Xu. α-Glucosidase inhibitive diarylheptanoids from Ottelia acuminata var. acuminata, a traditional vegetable of Bai Nationality in Yunnan [J]. Natural Products and Bioprospecting, 2022, 12(4): 22-22.
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