Synthesis of L-Ascorbic Acid Lactone Derivatives

doi:10.1007/s13659-014-0022-6

Natural Products and Bioprospecting ›› 2014, Vol. 4 ›› Issue (3): 181-188.DOI: 10.1007/s13659-014-0022-6

• Original article • Previous Articles Next Articles

Synthesis of L-Ascorbic Acid Lactone Derivatives

Li-Dong Shao^1,3, Ya-Nan Wu^1,3, Jun Xu^1,3, Juan He¹, Yu Zhao¹, Li-Yan Peng¹, Yan Li¹, Yu-Rong Yang¹, Cheng-Feng Xia¹, Qin-Shi Zhao²

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. Graduate School of the Chinese Academy of Sciences, University of Chinese Academy of Sciences, Beijing 100049, China

Received:2014-04-13 Revised:2014-04-28 Online:2018-02-11 Published:2014-06-24
Supported by:
This work was financially supported by the National Natural Science Foundation of China(No. U0932602) and the National Basic Research Program of China(973 Program No. 2011CB915503). All authors do not have any financial/commercial conflicts of interest.

Synthesis of L-Ascorbic Acid Lactone Derivatives

Li-Dong Shao^1,3, Ya-Nan Wu^1,3, Jun Xu^1,3, Juan He¹, Yu Zhao¹, Li-Yan Peng¹, Yan Li¹, Yu-Rong Yang¹, Cheng-Feng Xia¹, Qin-Shi Zhao²

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. Graduate School of the Chinese Academy of Sciences, University of Chinese Academy of Sciences, Beijing 100049, China

通讯作者: Cheng-Feng Xia,e-mail:xiachengfeng@mail.kib.ac.cn;Qin-Shi Zhao,e-mail:qinshizhao@mail.kib.ac.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China(No. U0932602) and the National Basic Research Program of China(973 Program No. 2011CB915503). All authors do not have any financial/commercial conflicts of interest.

Abstract

Abstract: A small focused library which comprised of L-AA lactone derivatives was built with a facile method. This reported method was optimized by modifying the acidity of the solvent. As a result, 12 L-AA lactones were synthesized. Among these lactones, lactones 8-12 were new compounds. The cytotoxicity of these synthetic compounds were investigated.

Key words: L-Ascorbic acid lactone, Cytotoxicity, Focused library

摘要： A small focused library which comprised of L-AA lactone derivatives was built with a facile method. This reported method was optimized by modifying the acidity of the solvent. As a result, 12 L-AA lactones were synthesized. Among these lactones, lactones 8-12 were new compounds. The cytotoxicity of these synthetic compounds were investigated.

关键词: L-Ascorbic acid lactone, Cytotoxicity, Focused library

Li-Dong Shao, Ya-Nan Wu, Jun Xu, Juan He, Yu Zhao, Li-Yan Peng, Yan Li, Yu-Rong Yang, Cheng-Feng Xia, Qin-Shi Zhao. Synthesis of L-Ascorbic Acid Lactone Derivatives[J]. Natural Products and Bioprospecting, 2014, 4(3): 181-188.

Li-Dong Shao, Ya-Nan Wu, Jun Xu, Juan He, Yu Zhao, Li-Yan Peng, Yan Li, Yu-Rong Yang, Cheng-Feng Xia, Qin-Shi Zhao. Synthesis of L-Ascorbic Acid Lactone Derivatives[J]. 应用天然产物, 2014, 4(3): 181-188.

References

1. M.W. Davey, M.V. Montagu, D. Inze, M. Sanmartin, A. Kanellis, N. Smirnoff, I.J. Benzie, J.J. Strain, D. Favell, J. Fletcher, J. Sci. Food Agric. 80, 825-860 (2000)
2. T. Gazivoda, M. Plevnik, J. Plavec, S. Kraljević, M. Kralj, K. Pavelić, J. Balzarini, E.D. Clercq, M. Mintas, S. Raić-Malić, Bioorg. Med. Chem. 13, 131-139 (2005)
3. T. Gazivoda, S. Raić-Malić, M. Marjanović, M. Kralj, K. Pavelić, J. Balzarini, E.D. Clercq, M. Mintas, Bioorg. Med. Chem. 15, 749-758 (2007)
4. T. Gazivoda, M. Sokcević, M. Kralj, L. Suman, K. Pavelić, E. De Clercq, G. Andrei, R. Snoeck, J. Balzarini, M. Mintas, S. Raić-Malić, J. Med. Chem. 50, 4105-4112 (2007)
5. S. Raić-Malić, A. Hergold-Brundić, A. Nagl, M. Grdiša, K. Pavelić, E. De Clercq, M. Mintas, J. Med. Chem. 42, 2673-2678 (1999)
6. M.W. Roomi, D. House, M. Eckert-Maksić, Z.B. Maksić, C.S. Tsao, Cancer Lett. 122, 93-99 (1998)
7. K. Morisaki, S. Ozaki, Chem. Pharm. Bull. 44, 1647-1655 (1996)
8. I. Yamamoto, A. Tai, Y. Fujinami, K. Sasaki, S. Okazaki, J. Med. Chem. 45, 462-468 (2001)
9. A. Tai, S. Goto, Y. Ishiguro, K. Suzuki, T. Nitoda, I. Yamamoto, Bioorg. Med. Chem. Lett. 14, 623-627 (2004)
10. S. Manfredini, B. Pavan, S. Vertuani, M. Scaglianti, D. Compagnone, C. Biondi, A. Scatturin, S. Tanganelli, L. Ferraro, P. Prasad, A. Dalpiaz, J. Med. Chem. 45, 559-562 (2001)
11. S. Palma, R.H. Manzo, D. Allemandi, L. Frationi, P.L. Nostro, J. Pharm. Sci. 91, 1810-1816 (2002)
12. M.H. Sung, C. Park, S.C. Kim, G.S. Park, H. Uyama, H.R. Poo, J.J. Song. WO2006001567A1, (2006)
13. D.J. Ko, J.W. Choi, B.S. Seo, M.J. Lim. KR2012017299A, (2012)
14. N.G. Kesinger, J.F. Stevens, Phytochemistry 70, 1930-1939 (2009)
15. Z. Zhang, X. Liu, X. Zhang, J. Liu, Y. Hao, X. Yang, Y. Wang, Arch. Pharm. Res. 34, 801-810 (2011)
16. A. Tai, Bitamin 87, 70-80 (2013)
17. J.C. Yvin, A.M. Chevolot-Magueur, L. Chevolot, J.Y. Lallemand, P. Potier, J. Guilhem, J. Am. Chem. Soc. 104, 4497-4498 (1982)
18. T. Iwagawa, T. Hase, Phytochemistry 23, 2299-2301 (1984)
19. J. He, X.Q. Chen, M.M. Li, Y. Zhao, G. Xu, X. Cheng, L.Y. Peng, M.J. Xie, Y.T. Zheng, Y.P. Wang, Org. Lett. 11, 1397-1400 (2009)
20. L.B. Dong, J. Yang, J. He, H.R. Luo, X.D. Wu, X. Deng, L.Y. Peng, X. Cheng, Q.S. Zhao, Chem. Comm. 48, 9038-9040 (2012)
21. J.T. Cheng, F. Liu, X.N. Li, X.D. Wu, L.B. Dong, L.Y. Peng, S.X. Huang, J. He, Q.S. Zhao, Org. Lett. 15, 2438-2441 (2013)
22. F. Liu, X.D. Wu, J. He, X. Deng, L.Y. Peng, H.R. Luo, Q.S. Zhao, Tetrahedron Lett. 54, 4555-4557 (2013)
23. X.Y. Zhang, L.B. Dong, F. Liu, X.D. Wu, J. He, L.Y. Peng, H.R. Luo, Q.S. Zhao, Nat. Prod. Bioprospec. 3, 52-55 (2013)
24. X.L. Li, X. Cheng, L.M. Yang, R.R. Wang, Y.T. Zheng, W.L. Xiao, Y. Zhao, G. Xu, Y. Lu, Y. Chang, Q.T. Zheng, Q.S. Zhao, H.D. Sun, Org. Lett. 8, 1937-1940 (2006)
25. Z. Wang, K. Zhao, J. Fu, J. Zhang, W. Yin, Y. Tang, Org. Biomol. Chem. 11, 2093-2097 (2013)
26. A.J. Poss, R.K. Belter, J. Org. Chem. 53, 1535-1540 (1988)
27. A.M. Korolev, É.I. Lazhko, M.N. Preobrazhenskaya, Y. Bal'zarini, É. Klerk, Pharm. Chem. J. 25, 805-808 (1991)

[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]	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.
[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]. Natural Products and Bioprospecting, 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]. Natural Products and Bioprospecting, 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]. Natural Products and Bioprospecting, 2022, 12(6): 38-38.
[9]	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.
[10]	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.
[11]	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]. Natural Products and Bioprospecting, 2021, 11(6): 651-658.
[12]	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]. Natural Products and Bioprospecting, 2021, 11(5): 489-544.
[13]	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]. Natural Products and Bioprospecting, 2021, 11(2): 235-241.
[14]	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]. Natural Products and Bioprospecting, 2021, 11(1): 73-79.
[15]	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]. Natural Products and Bioprospecting, 2020, 10(5): 307-316.

Synthesis of L-Ascorbic Acid Lactone Derivatives

Synthesis of L-Ascorbic Acid Lactone Derivatives

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments