应用天然产物 ›› 2022, Vol. 12 ›› Issue (3): 16-16.DOI: 10.1007/s13659-022-00340-5
Xin Zhang1,2, Yun-Bao Ma1, Xiao-Feng He1, Tian-Ze Li1, Chang-An Geng1, Li-Hua Su1, Shuang Tang1, Zhen Gao1,2, Ji-Jun Chen1,2
收稿日期:
2022-03-04
出版日期:
2022-06-24
发布日期:
2022-06-24
通讯作者:
Ji-Jun Chen,E-mail:chenjj@mail.kib.ac.cn
基金资助:
Xin Zhang1,2, Yun-Bao Ma1, Xiao-Feng He1, Tian-Ze Li1, Chang-An Geng1, Li-Hua Su1, Shuang Tang1, Zhen Gao1,2, Ji-Jun Chen1,2
Received:
2022-03-04
Online:
2022-06-24
Published:
2022-06-24
Contact:
Ji-Jun Chen,E-mail:chenjj@mail.kib.ac.cn
Supported by:
摘要: Ten new germacrane-type sesquiterpenoids, artemyrianosins A–J (1–10), were isolated from the aerial parts of Artemisia myriantha. Their structures were elucidated by spectral analyses including UV, IR, HRESIMS, 1D and 2D NMR, ECD and the absolute configurations of compounds 1 and 7–9 were characterized using X-ray crystallography. All isolates were tested their cytotoxicity against three human hepatoma cell lines (HepG2, Huh7, and SK-Hep-1), and compounds 1–3, 7, and 10 showed cytotoxicity with IC50 values ranging from 43.7 to 89.3 μM. Among them, the most active compound 3 exhibited activity against three human hepatoma cell lines with IC50 values of 43.7 μM (HepG2), 47.9 μM (Huh7), and 44.9 μM (SK-Hep-1).
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]. 应用天然产物, 2022, 12(3): 16-16.
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.
1.Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A.Global cancer statistics 2018:GLOBOCAN estimates of incidence and mor-tality worldwide for 36 cancers in 185 countries.CA Cancer J Clin.2018;68:394-424. 2.Fattovich G, Strofolini T, Zagni I, Donato F.Hepatocellular carcinoma in cirrhosis:incidence and risk factors.Gastroenterology.2004;127:35-50. 3.Fitzmaurice C, Akinyemiju TF, Al Lami FH, Alam T, Alizadeh-Navaei R, Allen C, Alsharif U, Alvis-Guzman N, Amini E, Anderson BO, Aremu O, Artaman A, Asgedom SW, Assadi R, Atey TM, Avila-Burgos L, Awasthi A, Ba Saleem HO, Barac A, Bennett JR, Bensenor IM, Bhakta N, Brenner H, Cahuana-Hurtado L, Castaneda-Orjuela CA, Catala-Lopez F, Choi JYJ, Christopher DJ, Chung SC, Curado MP, Dandona L, Dandona R, et al.Global, regional, and national cancer incidence, mortality, years ofife lost, years lived with disability, and disability-adjusted life-years for 29 cancer groups, 1990 to 2016:a systematic analysis for the global burden of disease study.JAMA Oncol.2018;4:1553-68. 4.Sung H, Ferlay J, Siegel RL, Laversanne M, Soerjomataram I, Jemal A, Bray F.Global cancer statistics 2020:GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries.CA Cancer J Clin.2021;71:209-49. 5.Llovet JM, Kelley RK, Villanueva A, Singal AG, Pikarsky E, Roayaie S, Len-cioni R, Koike K, ZucmanRossi J, Finn RS.Hepatocellular carcinoma.Nat Rev Dis Primers.2021;7:6. 6.Anwanwan D, Singh SK, Singh S, Saikam V, Singh R.Challenges in liver cancer and possible treatment approaches.Biochim Biophys Acta Rev Cancer.2020;1873:188314. 7.Llovet JM, Ricci S, Mazzaferro V, Hilgard P, Gane E, Blanc JF, de Oliveira AC, Santoro A, Raoul JL, Forner A, Schwartz M, Porta C, Zeuzem S, Bolondi L, Greten TF, Galle PR, Seitz JF, Borbath I, Haussinger D, Giannaris T, Shan M, Moscovici M, Voliotis D, Bruix J.Sorafenib in advanced hepatocellular carcinoma.N Engl J Med.2008;359:378-90. 8.Dai Q, Zhang C, Yuan Z, Sun Q, Jiang Y.Current discovery strategies for hepatocellular carcinoma therapeutics.Expert Opin Drug Discov.2020;15:243-58. 9.Su L-H, Ma Y-B, Geng C-A, Li T-Z, Huang X-Y, Hu J, Zhang X, Tang S, Shen C, Gao Z, Zhang X-M, Chen J-J.Artematrovirenins A-P, guaiane-type ses-quiterpenoids with cytotoxicities against two hepatoma cell lines from Artemisia atrovirens.Bioorg Chem.2021;114:105072. 10.Tu Y-Y.The discovery of artemisinin (qinghaosu) and gifts from Chinese medicine.Nat Med.2011;17:1217-20. 11.Wang S, Li J, Sun J, Zeng K-W, Cui J-R, Jiang Y, Tu P-F.NO inhibitory guaianolide-derived terpenoids from Artemisia argyi.Fitoterapia.2013;85:169-75. 12.Geng C-A, Huang X-Y, Chen X-L, Ma Y-B, Rong G-Q, Zhao Y, Zhang X-M, Chen J-J.Three new anti-HBV active constituents from the traditional Chinese herb of Yin-Chen (Artemisia scoparia).J Ethnopharmacol.2015;176:109-17. 13.Bora KS, Sharma A.The genus Artemisia:a comprehensive review.Pharm Biol.2011;49:101-9. 14.Wang J, Xu C, Wong Y-K, Li Y-J, Liao F-L, Jiang T-L, Tu Y-Y.Artemisinin, the magic drug discovered from traditional Chinese medicine.Engineering.2019;5:32-9. 15.Yao W, Wang F, Wang H.Immunomodulation of artemisinin and its derivatives.Sci Bull.2016;61:1399-406. 16.Lone SH, Bhat KA, Khuroo MA.Arglabin:from isolation to antitumor evaluation.Chem Biol Interact.2015;240:180-98. 17.Lee SH, Lee MY, Kang HM, Han DC, Son KH, Yang DC, Sung ND, Lee CW, Kim HM, Kwon BM.Anti-tumor activity of the farnesyl-protein transferase inhibitors arteminolides, isolated from Artemisa.Bioorg Med Chem.2003;11:4545-9. 18.Su L-H, Zhang X-T, Ma Y-B, Geng C-A, Huang X-Y, Hu J, Li T-Z, Tang S, Shen C, Gao Z, Zhang X-M, Chen J-J.New guaiane-type sesquiterpenoid dimers from Artemisia atrovirens and their antihepatoma activity.Acta Pharm Sin B.2021;11:1648-66. 19.Su L-H, Li T-Z, Ma Y-B, Geng C-A, Huang X-Y, Zhang X, Gao Z, Chen J-J.Artematrovirenolides A-D and Artematrolides S-Z, Sesquiterpenoid dimers with cytotoxicity against three hepatoma cell lines from Artemisia atrovirens.Chin J Chem.2022;40:104-14. 20.Su L-H, Li T-Z, Geng C-A, Ma Y-B, Huang X-Y, Wang J-P, Zhang X-M, Chen J-J.Trimeric and dimeric sesquiterpenoids from Artemisia atrovirens and their cytotoxicities.Org Chem Front.2021;8:1249-56. 21.Su L-H, Geng C-A, Li T-Z, Ma Y-B, Huang X-Y, Zhang X-M, Chen J-J.Artatro-virenols A and B:Two cagelike sesquiterpenoids from Artemisia atrovirens.J Org Chem.2020;85:13466-71. 22.Zhang X-T, Hu J, Su L-H, Geng C-A, Chen J-J.Artematrolide A inhibited cervical cancer cell proliferation via ROS/ERK/mTOR pathway and meta-bolic shift.Phytomedicine.2021;91:153707. 23.Li T-Z, Yang X-T, Wang J-P, Geng C-A, Ma Y-B, Su L-H, Zhang X-M, Chen J-J.Biomimetic synthesis of lavandiolides H, I, and K and Artematrolide F via diels-alder reaction.Org Lett.2021;23:8380-4. 24.Zan K, Chen X-Q, Zhao M-B, Jiang Y, Tu P-F.Cytotoxic sesquiterpene lactones from Artemisia myriantha.Phytochem Lett.2020;37:33-6. 25.Tang S, Zhang X-T, Ma Y-B, Huang X-Y, Geng C-A, Li T-Z, Zhang X-M, Shen C, Su L-H, Gao Z, Chen J-J.Artemyrianolides A-S, Cytotoxic Sesquiterpe-noids from Artemisia myriantha.J Nat Prod.2020;83:2618-30. 26.Zan K, Chen X-Q, Zhao M-B, Tu P-F.Sesquiterpenoids from aerial parts of Artemisia myriantha.China J Chin Mater Med.2016;41:2833-7. 27.Zan K, Chen X-Q, Tu P-F.Guaianolides from aerial parts of Artemisia myriantha.China J Chin Mater Med.2018;43:2295-9. |
[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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 2024, 14(6): 51-51. |
[5] | 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]. 应用天然产物, 2024, 14(5): 45-45. |
[6] | 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]. 应用天然产物, 2023, 13(3): 17-17. |
[7] | 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]. 应用天然产物, 2023, 13(2): 7-7. |
[8] | 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]. 应用天然产物, 2022, 12(6): 38-38. |
[9] | 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]. 应用天然产物, 2022, 12(2): 9-9. |
[10] | Ruo-Song Zhang, Yang-Yang Liu, Pei-Feng Zhu, Qiong Jin, Zhi Dai, Xiao-Dong Luo. Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity[J]. 应用天然产物, 2021, 11(6): 651-658. |
[11] | Patrick O. Sakyi, Richard K. Amewu, Robert N. O. A. Devine, Emahi Ismaila, Whelton A. Miller, Samuel K. Kwofie. The Search for Putative Hits in Combating Leishmaniasis: The Contributions of Natural Products Over the Last Decade[J]. 应用天然产物, 2021, 11(5): 489-544. |
[12] | Chen Shi, Yue-Ling Peng, Juan He, Zheng-Hui Li, Ji-Kai Liu, Tao Feng. Structures, Chemical Conversions, and Cytotoxicity of Tricholopardins C and D, Two Tricholoma Triterpenoids from the Wild Mushroom Tricholoma pardinum[J]. 应用天然产物, 2021, 11(2): 235-241. |
[13] | Yi Chen, Song-Wei Li, Fang-Zhou Yin, Min Yang, Xia-Juan Huan, Ze-Hong Miao, Xiao-Ming Wang, Yue-Wei Guo. Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus[J]. 应用天然产物, 2021, 11(1): 73-79. |
[14] | Mohammad Sanad Abu-Darwish, Célia Cabral, Zulfigar Ali, Mei Wang, Shabana I. Khan, Melissa R. Jacob, Surendra K. Jain, Babu L. Tekwani, Fazila Zulfiqar, Ikhlas A. Khan, Hatem Taifour, Lígia Salgueiro, Thomas Efferth. Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities[J]. 应用天然产物, 2020, 10(5): 307-316. |
[15] | Cheng Shen, Xiao-Yan Huang, Chang-An Geng, Tian-Ze Li, Shuang Tang, Li-Hua Su, Zhen Gao, Xue-Mei Zhang, Jing Hu, Ji-Jun Chen. Artemlavanins A and B from Artemisia lavandulaefolia and Their Cytotoxicity Against Hepatic Stellate Cell Line LX2[J]. 应用天然产物, 2020, 10(4): 243-250. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||