Bioactive Diarylheptanoids from Alpinia coriandriodora

doi:10.1007/s13659-020-00264-y

应用天然产物 ›› 2021, Vol. 11 ›› Issue (1): 63-72.DOI: 10.1007/s13659-020-00264-y

Bioactive Diarylheptanoids from Alpinia coriandriodora

Xiao-Li Cheng^1,3, Han-Xiang Li^1,2, Juan Chen^1,2, Ping Wu^1,2,3, Jing-Hua Xue^1,2, Zhong-Yu Zhou^1,2,3, Nia-He Xia^1,2,3, Xiao-Yi Wei^1,2,3

1 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Tianhe District, Xingke Road 723, Guangzhou 510650, People's Republic of China;
2 Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China;
3 School of Life Sciences, University of Chinese Academy of Sciences, Yuquanlu 19 A, Beijing 100049, People's Republic of China

收稿日期:2020-08-14 修回日期:2020-08-30 出版日期:2021-02-24 发布日期:2021-03-11
通讯作者: Xiao-Yi Wei
基金资助:
We are grateful to Mr. Yunfei Yuan, South China Botanical Garden, Chinese Academy of Sciences (CAS), for NMR spectroscopic measurements and Ms. Aijun Sun, South China Sea Institute of Oceanology, CAS, for HRESIMS measurements. We also gratefully acknowledge support from the Guangzhou Branch of the Supercomputing Center of CAS. This work was financially supported by NSFC Grants (Nos. 81172942 and 81872773).

Bioactive Diarylheptanoids from Alpinia coriandriodora

Xiao-Li Cheng^1,3, Han-Xiang Li^1,2, Juan Chen^1,2, Ping Wu^1,2,3, Jing-Hua Xue^1,2, Zhong-Yu Zhou^1,2,3, Nia-He Xia^1,2,3, Xiao-Yi Wei^1,2,3

1 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Tianhe District, Xingke Road 723, Guangzhou 510650, People's Republic of China;
2 Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China;
3 School of Life Sciences, University of Chinese Academy of Sciences, Yuquanlu 19 A, Beijing 100049, People's Republic of China

Received:2020-08-14 Revised:2020-08-30 Online:2021-02-24 Published:2021-03-11
Contact: Xiao-Yi Wei
Supported by:
We are grateful to Mr. Yunfei Yuan, South China Botanical Garden, Chinese Academy of Sciences (CAS), for NMR spectroscopic measurements and Ms. Aijun Sun, South China Sea Institute of Oceanology, CAS, for HRESIMS measurements. We also gratefully acknowledge support from the Guangzhou Branch of the Supercomputing Center of CAS. This work was financially supported by NSFC Grants (Nos. 81172942 and 81872773).

摘要/Abstract

摘要： Eight new diarylheptanoids, coriandralpinins A-H (1-8), were isolated from the rhizomes of Alpinia coriandriodora, an edible plant of the ginger family. Their structures, including the absolute configurations, were established by extensive spectroscopic analysis and ECD calculations. Compounds 1-8 have a 1,5-O-bridged diarylheptanoid structure featuring polyoxygenated aryl units. When evaluated for intracellular antioxidant activity using t-BHP stressed RAW264.7 macrophages, all these compounds scavenged reactive oxygen species (ROS) in a concentration-dependent manner. Compounds 3 and 5 also showed inhibitory activity against NO release in LPS-induced RAW 264.7 cells. Six known flavonols, 7,4'-diO-methylkaempferol, 7-O-methylquercetin, 7,4'-di-O-methylquercetin, 7,3',4'-tri-O-methylquercetin, kaempferol 3-O-β-D-(6-O-α-L-rhamnopyranosyl)glucopyranoside, and 3-O-β-D-glucopyranuronosylquercetin were also isolated and characterized from the rhizomes.

关键词: Alpinia coriandriodora, Diarylheptanoid, Antioxidant, Anti-inflammatory

Abstract: Eight new diarylheptanoids, coriandralpinins A-H (1-8), were isolated from the rhizomes of Alpinia coriandriodora, an edible plant of the ginger family. Their structures, including the absolute configurations, were established by extensive spectroscopic analysis and ECD calculations. Compounds 1-8 have a 1,5-O-bridged diarylheptanoid structure featuring polyoxygenated aryl units. When evaluated for intracellular antioxidant activity using t-BHP stressed RAW264.7 macrophages, all these compounds scavenged reactive oxygen species (ROS) in a concentration-dependent manner. Compounds 3 and 5 also showed inhibitory activity against NO release in LPS-induced RAW 264.7 cells. Six known flavonols, 7,4'-diO-methylkaempferol, 7-O-methylquercetin, 7,4'-di-O-methylquercetin, 7,3',4'-tri-O-methylquercetin, kaempferol 3-O-β-D-(6-O-α-L-rhamnopyranosyl)glucopyranoside, and 3-O-β-D-glucopyranuronosylquercetin were also isolated and characterized from the rhizomes.

Key words: Alpinia coriandriodora, Diarylheptanoid, Antioxidant, Anti-inflammatory

Xiao-Li Cheng, Han-Xiang Li, Juan Chen, Ping Wu, Jing-Hua Xue, Zhong-Yu Zhou, Nia-He Xia, Xiao-Yi Wei. Bioactive Diarylheptanoids from Alpinia coriandriodora[J]. 应用天然产物, 2021, 11(1): 63-72.

Xiao-Li Cheng, Han-Xiang Li, Juan Chen, Ping Wu, Jing-Hua Xue, Zhong-Yu Zhou, Nia-He Xia, Xiao-Yi Wei. Bioactive Diarylheptanoids from Alpinia coriandriodora[J]. Natural Products and Bioprospecting, 2021, 11(1): 63-72.

参考文献

1. A.M. Pisoschi, A. Pop, Eur. J. Med. Chem. 97, 55-74 (2015)
2. B.C. Dickinson, C.J. Chang, Nat. Chem. Biol. 7, 504-511 (2011)
3. A.S. Marchev, P.A. Dimitrova, A.J. Burns, R.V. Kostov, A.T. Dinkova-Kostova, M.I. Georgiev, Ann. N. Y. Acad. Sci. 1401, 114-135 (2017)
4. N. Braidy, M. Izadi, A. Sureda, N. Jonaidi-Jafari, A. Banki, S.F. Nabavi, S.M. Nabavi, J. Cell. Physiol. 233, 2705-2714 (2018)
5. S. Prasad, S.C. Gupta, A.K. Tyagi, Cancer Lett. 387, 95-105 (2017)
6. V. Rani, G. Deep, R.K. Singh, K. Palle, U.C. Yadav, Life Sci. 148, 183-193 (2016)
7. C. Calixto-Campos, T.T. Carvalho, M.S. Hohmann, F.A. PinhoRibeiro, V. Fattori, M.F. Manchope, A.C. Zarpelon, M.M. Baracat, S.R. Georgetti, R. Casagrande, J. Nat. Prod. 78, 1799-1808 (2015)
8. X. Hou, Q. Tong, W. Wang, C. Shi, W. Xiong, J. Chen, X. Liu, J. Fang, J. Nat. Prod. 78, 1689-1696 (2015)
9. L. Zhou, G.-D. Yao, X.-Y. Song, J. Wang, B. Lin, X.-B. Wang, X.-X. Huang, S.-J. Song, J. Agric. Food Chem. 66, 331-338 (2017)
10. Y.H. Seo, J.H. Jeon, M. Jeong, S.M. Ryu, W.K. Jeon, D.S. Jang, S.H. Shim, D. Lee, J.H. Choi, J. Lee, J. Nat. Prod. 81, 1598-1603 (2018)
11. K. Gao, D. Ma, Y. Cheng, X. Tian, Y. Lu, X. Du, H. Tang, J. Chen, J. Agric. Food Chem. 63, 1067-1075 (2015)
12. X.X. Huang, M. Bai, L. Zhou, L.L. Lou, Q.-B. Liu, Y. Zhang, L.Z. Li, S.J. Song, J. Agric. Food Chem. 63, 7252-7260 (2015)
13. A. Kumorkiewicz, E. Szneler, S. Wybraniec, J. Agric. Food Chem. 66, 12815-12826 (2018)
14. Y. Tang, Z.Z. Zhao, J.N. Yao, T. Feng, Z.H. Li, H.-P. Chen, J.K. Liu, J. Nat. Prod. 81, 2163-2168 (2018)
15. Q.Y. Bian, S.Y. Wang, L.J. Xu, C.O. Chan, D.K. Mok, S.B. Chen, J. Asian Nat. Prod. Res. 15, 1094-1099 (2013)
16. T.N. Ly, M. Shimoyamada, K. Kato, R. Yamauchi, J. Agric. Food Chem. 51, 4924-4929 (2003)
17. Y.J. Kuo, P.C. Hsiao, L.J. Zhang, M.D. Wu, Y.H. Liang, H.O. Ho, Y.H. Kuo, J. Nat. Prod. 72, 1097-1101 (2009)
18. R. Singh, P. Sharma, Toxicol. Int. 18, 124-129 (2011)
19. D. Liu, Y.W. Liu, F.Q. Guan, J.Y. Liang, Fitoterapia 96, 76-80 (2014)
20. N. An, Z.M. Zou, Z. Tian, X.Z. Luo, S.L. Yang, L.Z. Xu, Fitoterapia 79, 27-31 (2008)
21. H. Kikuzaki, N. Nakatani, Phytochemistry 43, 273-277 (1996)
22. M.A.M. Nawwar, A.M.A. Souleman, J. Buddrus, M. Linscheid, Phytochemistry 23, 2347-2349 (1984)
23. X.W. Yang, Y.M. Jiang, J.S. Li, Z.C. Lou, Zhong Cao Yao 27, 707-712 (1996)
24. J.Y. Si, D.H. Chen, Q. Chang, L.G. Shen, Z.Y. Zhu, Acta Botanica Sinica 36, 239-243 (1994)
25. H. Dong, Y.L. Gou, S.G. Cao, S.X. Chen, K.Y. Sim, S.H. Goh, R.M. Kini, Phytochemistry 50, 899-902 (1999)
26. J.T. Han, M.H. Bang, O.K. Chun, D.O. Kim, C.Y. Lee, N.L. Baek, Arch. Pharm. Res. 27, 390-395 (2004)
27. G. Goetz, A. Fkyerat, N. Métais, M. Kunz, R. Tabacchi, R. Pezet, V. Pont, Phytochemistry 52, 759-767 (1999)
28. D.J. Sun, L.J. Zhu, Y.Q. Zhao, Y.Q. Zhen, L. Zhang, C.C. Lin, L.X. Chen, Fitoterapia 142, 104490 (2020)
29. F. Cheng, Y. Chen, Z. Zhan, Y. Liu, P. Hu, H. Ren, H. Tang, M. Peng, Inflammation 41, 1-16 (2018)
30. Q.F. Tao, Y. Xu, R.Y.Y. Lam, B. Schneider, H. Dou, P.S. Leung, S.Y. Shi, C.X. Zhou, L.X. Yang, R.P. Zhang, Y.C. Xiao, X. Wu, J. Stöckigt, S. Zeng, C.H.K. Cheng, Y. Zhao, J. Nat. Prod. 71, 12-17 (2008)
31. J.F. Shi, P. Wu, Z.H. Jiang, X.Y. Wei, Eur. J. Med. Chem. 71, 219-228 (2014)
32. P. Wu, J. Xue, L. Yao, L. Xu, H. Li, X. Wei, Org. Lett. 17, 4922-4925 (2015)
33. Gaussian 09, revision D.01, Gaussian, Inc., Wallingford, CT 2010
34. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 7, 3297-3305 (2005)
35. Y. Zhao, D.G. Truhlar, Theor. Chem. Acc. 120, 215-241 (2008)
36. J.P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 77, 3865-3868 (1996)
37. C. Adamo, V. Barone, J. Chem. Phys. 110, 6158-6170 (1999)
38. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 97, 2571-2577 (1992)
39. T. Bruhn, A. Schaumlöffel, Y. Hemberger, G. Bringmann, Chirality 25, 243-249 (2013)
40. R. Ditchfield, J. Chem. Phys. 56, 5688-5691 (1972)
41. R. Ditchfield, Mol. Phys. 27, 789-807 (1974)
42. K. Wolinski, J.F. Hinton, P. Pulay, J. Am. Chem. Soc. 112, 8251-8260 (1990)
43. M.W. Lodewyk, C. Soldi, P.B. Jones, M.M. Olmstead, J. Rita, J.T. Shaw, D.J. Tantillo, J. Am. Chem. Soc. 134, 18550-18553 (2012)
44. S.G. Smith, J.M. Goodman, J. Am. Chem. Soc. 132, 12946-12959 (2010)
45. N.S. Grimblat, M.M. Zanardi, A.M. Sarotti, J. Org. Chem. 80, 12526-12534 (2015)

[1]	Qiang Yin, Jianying Han, Guixiang Yang, Zhijun Song, Keke Zou, Kangjie Lv, Zexu Lin, Lei Ma, Miaomiao Liu, Yunjiang Feng, Ronald J. Quinn, Tom Hsiang, Lixin Zhang, Xueting Liu, Guoliang Zhu, Jingyu Zhang. New sesquiterpenoids with anti-inflammatory effects from phytopathogenic fungus Bipolaris sorokiniana 11134[J]. 应用天然产物, 2025, 15(3): 29-29.
[2]	Hongyan Wen, Sheng Li, Yu Zhang. Phthalide mono- and dimers from the rhizomes of Angelica sinensis and their anti-inflammatory activities[J]. 应用天然产物, 2025, 15(3): 26-26.
[3]	Mukul Shyam, Evan Prince Sabina. Harnessing the power of Arctium lappa root: a review of its pharmacological properties and therapeutic applications[J]. 应用天然产物, 2024, 14(6): 49-49.
[4]	Yuru Shi, Xiaoqian Zhang, Shengji Pei, Yuhua Wang. Ethnopharmacological study on Adenosma buchneroides Bonati inhibiting inflammation via the regulation of TLR4/MyD88/NF-κB signaling pathway[J]. 应用天然产物, 2024, 14(5): 36-36.
[5]	Shi-Yan Feng, Na Jiang, Jia-Ying Yang, Lin-Yao Yang, Jiang-Chao Du, Xuan-Qin Chen, Dan Liu, Rong-Tao Li, Jin-Dong Zhong. Antiviral and anti-inflammatory activities of chemical constituents from twigs of Mosla chinensis Maxim[J]. 应用天然产物, 2024, 14(3): 26-26.
[6]	Srijan Banerjee, Gustavo Cabrera-Barjas, Jaime Tapia, João Paulo Fabi, Cedric Delattre, Aparna Banerjee. Characterization of Chilean hot spring-origin Staphylococcus sp. BSP3 produced exopolysaccharide as biological additive[J]. 应用天然产物, 2024, 14(2): 3-3.
[7]	Li Wu, Ning Yang, Meng Guo, Didi Zhang, Reza A. Ghiladi, Hasan Bayram, Jun Wang. The role of sound stimulation in production of plant secondary metabolites[J]. 应用天然产物, 2023, 13(6): 40-40.
[8]	Orawan Jongsomjainuk, Jutatip Boonsombat, Sanit Thongnest, Hunsa Prawat, Paratchata Batsomboon, Sitthivut Charoensutthivarakul, Saroj Ruchisansakun, Kittipong Chainok, Jitnapa Sirirak, Chulabhorn Mahidol, Somsak Ruchirawat. Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis[J]. 应用天然产物, 2023, 13(6): 55-55.
[9]	Teresa S. Catalá, Linn G. Speidel, Arlette Wenzel-Storjohann, Thorsten Dittmar, Deniz Tasdemir. Bioactivity profile of dissolved organic matter and its relation to molecular composition[J]. 应用天然产物, 2023, 13(5): 32-32.
[10]	Yang Yu, Yang Wang, Gui-Chun Wang, Cheng-Yong Tan, Yi Wang, Jin-Song Liu, Guo-Kai Wang. Andropanilides A-C, the novel labdane-type diterpenoids from Andrographis paniculata and their anti-inflammation activity[J]. 应用天然产物, 2023, 13(5): 31-31.
[11]	Cintia Cristina Santi Martignago, Beatriz Soares-Silva, Julia Risso Parisi, Lais Caroline Souza e Silva, Renata Neves Granito, Alessandra Mussi Ribeiro, Ana Cláudia Muniz Renno, Lorena Ramos Freitas de Sousa, Anna Caroline Campos Aguiar. Terpenes extracted from marine sponges with antioxidant activity: a systematic review[J]. 应用天然产物, 2023, 13(4): 23-23.
[12]	Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin. New halimane and clerodane diterpenoids from Croton cnidophyllus[J]. 应用天然产物, 2023, 13(3): 21-21.
[13]	Cheng-Yong Tan, Bao-Bao Shi, Mei-Fen Bao, Xiang-Hai Cai. Anti-inflammatory maistemonine-class alkaloids of Stemona japonica[J]. 应用天然产物, 2023, 13(2): 8-8.
[14]	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]. 应用天然产物, 2022, 12(4): 22-22.
[15]	Sitian Zhang, Shuyuan Mo, Fengli Li, Yaxin Zhang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05[J]. 应用天然产物, 2022, 12(4): 27-27.

Bioactive Diarylheptanoids from Alpinia coriandriodora

Bioactive Diarylheptanoids from Alpinia coriandriodora

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价