Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells

doi:10.1007/s13659-020-00255-z

Natural Products and Bioprospecting ›› 2020, Vol. 10 ›› Issue (4): 251-260.DOI: 10.1007/s13659-020-00255-z

• ORIGINAL ARTICLES • Previous Articles Next Articles

Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells

Shuang Tang^1,2, Yun-Bao Ma¹, Chang-An Geng¹, Cheng Shen^1,2, Tian-Ze Li¹, Xue-Mei Zhang¹, Li-Hua Su^1,2, Zhen Gao^1,2, Jing Hu¹, Ji-Jun Chen^1,2

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Yunnan Key Laboratory of Natural Medicinal Chemistry, 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

Received:2020-04-27 Revised:2020-06-17 Online:2020-08-19 Published:2020-08-24
Contact: Ji-Jun Chen
Supported by:
This work was financially supported by the Yunnan Wanren Project (YNWR-KJLJ-2019-002), the Program of Yunling Scholarship, the Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province, and the Youth Innovation Promotion Association, CAS (2013252).

Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells

Shuang Tang^1,2, Yun-Bao Ma¹, Chang-An Geng¹, Cheng Shen^1,2, Tian-Ze Li¹, Xue-Mei Zhang¹, Li-Hua Su^1,2, Zhen Gao^1,2, Jing Hu¹, Ji-Jun Chen^1,2

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Yunnan Key Laboratory of Natural Medicinal Chemistry, 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

通讯作者: Ji-Jun Chen
基金资助:
This work was financially supported by the Yunnan Wanren Project (YNWR-KJLJ-2019-002), the Program of Yunling Scholarship, the Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province, and the Youth Innovation Promotion Association, CAS (2013252).

Abstract

Abstract: Four new sesquiterpenoids, artemyrianins A-D (1-4), and three new norlignans, artemyrianins E-G (5-7), together with five known compounds (8-12), were isolated from the aerial parts of Artemisia myriantha (Asteraceae). The new compounds were established by spectroscopic data analyses (HRMS, IR, 1D and 2D NMR), and their absolute configurations were confirmed by the single-crystal X-ray diffraction or ECD calculations. The isolates showed cytotoxicity against HepG2 cells with IC₅₀ values ranging from 33.3 to 145.2 μM.

Key words: Artemisia myriantha, Artemyrianins A-G, Sesquiterpenoids, Norlignans, Cytotoxicity, HepG2 cells

摘要： Four new sesquiterpenoids, artemyrianins A-D (1-4), and three new norlignans, artemyrianins E-G (5-7), together with five known compounds (8-12), were isolated from the aerial parts of Artemisia myriantha (Asteraceae). The new compounds were established by spectroscopic data analyses (HRMS, IR, 1D and 2D NMR), and their absolute configurations were confirmed by the single-crystal X-ray diffraction or ECD calculations. The isolates showed cytotoxicity against HepG2 cells with IC₅₀ values ranging from 33.3 to 145.2 μM.

关键词: Artemisia myriantha, Artemyrianins A-G, Sesquiterpenoids, Norlignans, Cytotoxicity, HepG2 cells

Shuang Tang, Yun-Bao Ma, Chang-An Geng, Cheng Shen, Tian-Ze Li, Xue-Mei Zhang, Li-Hua Su, Zhen Gao, Jing Hu, Ji-Jun Chen. Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells[J]. Natural Products and Bioprospecting, 2020, 10(4): 251-260.

References

1. F. Bray, J. Ferlay, I. Soerjomataram, R.L. Siegel, L.A. Torre, A. Jemal, CA Cancer J. Clin. 68, 394-424 (2018)
2. Q.Z. Dai, C.L. Zhang, Z.G. Yuan, Q.S. Sun, Y.Y. Jiang, Expert Opin. Drug Discov. 15, 243-258 (2020)
3. A. Ghantous, H. Gali-Muhtasib, H. Vuorela, N.A. Saliba, N. Darwiche, Drug Discov. Today 15, 668-678 (2010)
4. S.H. Lone, K.A. Bhat, M.A. Khuroo, Chem. Biol. Interact. 240, 180-198 (2015)
5. H.F. Wong, G.D. Brown, J. Nat. Prod. 65, 481-486 (2002)
6. H.F. Wong, G.D. Brown, Phytochemistry 59, 529-536 (2002)
7. Q.J. Li, W.P. Chen, J.H. Fan, Q. Zhao, X.H. Li, Q. Yang, C.Y. Liu, Chin. J. Mod. Appl. Pharm. 31, 706-710 (2014)
8. K. Zan, X.Q. Chen, M.B. Zhao, P.F. Tu, China J. Chin. Mater. Med. 41, 2833-2837 (2016)
9. K. Zan, X.Q. Chen, P.F. Tu, China J. Chin. Mater. Med. 43, 2295-2299 (2018)
10. G.C. Shah, C.S. Mathela, J. Essent. Oil Res. 18, 633-634 (2006)
11. G.D. Bagchi, F. Haider, N. Kumar, S.C. Singh, A.A. Naqvi, J. Essent. Oil Res. 21, 43-45 (2009)
12. X.Y. Dai, X. Li, X.R. Dong, B.L. Zhou, M. Xie, J. Anhui, Agric. Sci. 40, 11562-11564, 11597 (2012)
13. Y. Uchio, Tetrahedron 34, 2893-2899 (1978)
14. L.Y. Nie, J.J. Qin, Y. Huang, L. Yan, Y.B. Liu, Y.X. Pan, H.Z. Jin, W.D. Zhang, J. Nat. Prod. 73, 1117-1120 (2010)
15. L. Cardona, R.A. Aleman, B. Garcia, J.R. Pedro, Phytochemistry 31, 3630-3632 (1992)
16. C. Song, Y.Q. Li, Y.M. Yan, M. Hu, Q.Z. Zhang, Chem. Nat. Compd. 50, 414-416 (2014)
17. Q.M. Xu, Q. Li, Y.L. Liu, Y.L. Feng, S.L. Yang, X.R. Li, Chem. Nat. Compd. 46, 366-369 (2010)
18. G. Zhang, S. Shimokawa, M. Mochizuki, T. Kumamoto, W. Nakanishi, T. Watanabe, T. Ishikawa, K. Matsumoto, K. Tashima, S. Horie, Y. Higuchi, O.P. Dominguez, J. Nat. Prod. 71, 1167-1172 (2008)
19. B. Raffaelli, K. Wähälä, T. Hase, Org. Biomol. Chem. 4, 331-341 (2006)
20. P. Panichayupakaranant, H. Noguchi, W. De-Eknamkul, U. Sankawa, Phytochemistry 40, 1141-1143 (1995)
21. J.H. Kwak, W.Y. Jang, O.P. Zee, K.R. Lee, Planta Med. 63, 474-476 (1997)
22. M. Talbi, B. Saadali, D. Boriky, L. Bennani, M. Elkouali, T. Ainane, J. Asian Nat. Prod. Res. 18, 724-729 (2016)
23. Y. Li, X.Y. Cheng, C.L. Chen, H.J. Wu, H. Zhao, W. Liu, Z. Xiang, Q. Wang, Pathol. Res. Pract. 216, 152701 (2020)

[1]	Pengkun Li, Qin Li, Aimin Fu, Yang Xiao, Chunmei Chen, Hucheng Zhu, Changxing Qi, Wei Wei, Yuan Zhou, Yonghui Zhang. Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways [J]. Natural Products and Bioprospecting, 2025, 15(2): 17-17.
[2]	Dong-Yang Wang, Ming-Xing Li, Yan-Chao Xu, Peng Fu, Wei-Ming Zhu, Li-Ping Wang. Dibohemamines I-O from Streptomyces sp. GZWMJZ-662, an endophytic actinomycete from the medicinal and edible plant Houttuynia cordata Thunb. [J]. Natural Products and Bioprospecting, 2025, 15(1): 9-9.
[3]	Yue-Mei Chen, Nan-Kai Cao, Si-Si Zhu, Meng Ding, Hai-Zhen Liang, Ming-Bo Zhao, Ke-Wu Zeng, Peng-Fei Tu, Yong Jiang. Euchrestifolines A-O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia [J]. Natural Products and Bioprospecting, 2025, 15(1): 5-5.
[4]	Alica Fischle, Mika Lutsch, Florian Hübner, Linda Sch?ker-Hübner, Lina Schürmann, Finn K. Hansen, Svetlana A. Kalinina. Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family [J]. Natural Products and Bioprospecting, 2024, 14(6): 51-51.
[5]	Lu Cao, Jun-Feng Tan, Zeng-Guang Zhang, Jun-Wei Yang, Yu Mu, Zhi-Long Zhao, Yi Jiang, Xue-Shi Huang, Li Han. Discovery of structurally diverse sesquiterpenoids from Streptomyces fulvorobeus isolated from Elephas maximus feces and their antifungal activities [J]. Natural Products and Bioprospecting, 2024, 14(6): 61-61.
[6]	Qi-Xiu Hai, Kun Hu, Su-Ping Chen, Yang-Yang Fu, Xiao-Nian Li, Han-Dong Sun, Hong-Ping He, Pema-Tenzin Puno. Silvaticusins A-D: ent-kaurane diterpenoids and a cyclobutane-containing ent-kaurane dimer from Isodon silvaticus [J]. Natural Products and Bioprospecting, 2024, 14(5): 45-45.
[7]	Jin-Ning Chu, Premanand Krishnan, Kuan-Hon Lim. A comprehensive review on the chemical constituents, sesquiterpenoid biosynthesis and biological activities of Sarcandra glabra [J]. Natural Products and Bioprospecting, 2023, 13(6): 53-53.
[8]	Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti [J]. Natural Products and Bioprospecting, 2023, 13(3): 17-17.
[9]	Li Hou, Cui-Xuan Mei, Chun-Mao Yuan, Gui-Hua Tang, Duo-Zhi Chen, Qing Zhao, Hong-Ping He, Ming-Ming Cao, Xiao-Jiang Hao. Five new limonoids isolated from Walsura robusta [J]. Natural Products and Bioprospecting, 2023, 13(2): 7-7.
[10]	Ya-Li Hu, Xing-Ren Li, Gang Xu. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C₆ unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron [J]. Natural Products and Bioprospecting, 2022, 12(6): 38-38.
[11]	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]. Natural Products and Bioprospecting, 2022, 12(4): 27-27.
[12]	Xin Zhang, Yun-Bao Ma, Xiao-Feng He, Tian-Ze Li, Chang-An Geng, Li-Hua Su, Shuang Tang, Zhen Gao, Ji-Jun Chen. Artemyrianosins A–J, cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha [J]. Natural Products and Bioprospecting, 2022, 12(3): 16-16.
[13]	Shui-Mei Zhang, Kun Hu, Xiao-Nian Li, Han-Dong Sun, Pema-Tenzin Puno. Lignans and sesquiterpenoids from the stems of Schisandra bicolor var. tuberculata [J]. Natural Products and Bioprospecting, 2022, 12(3): 19-19.
[14]	Natividad Herrera Cano, Sebastian A. Andujar, Cristina Theoduloz, Daniel A. Wunderlin, Ana N. Santiago, Guillermo Schmeda-Hirschmann, Ricardo D. Enriz, Gabriela E. Feresin. Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations [J]. Natural Products and Bioprospecting, 2022, 12(2): 9-9.
[15]	Lu Zhang, Ping Yi, Hui Yan, Xiao-Nian Li, Meng-Yuan Xia, Jun Yang, Ji-Feng Luo, Yue-Qiu He, Yue-Hu Wang. Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China [J]. Natural Products and Bioprospecting, 2022, 12(1): 1-14.

Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells

Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments