Lignans from the Heartwood of Nothotsuga longibracteata

doi:10.6023/cjoc202003021

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2120-2126.DOI: 10.6023/cjoc202003021 Previous Articles Next Articles

长苞铁杉中木脂素类化学成分研究

刘贵园^a, 郭大乐^b, 邓赟^b, 令狐浪^a, 张茂生^a, 何芋歧^a, 肖世基^a

a 遵义医科大学药学院贵州遵义 563006;
b 成都中医药大学药学院成都 611137

收稿日期:2020-03-08 修回日期:2020-04-23 发布日期:2020-05-08
通讯作者: 肖世基 E-mail:sjxiao@zmu.edu.cn
基金资助:
国家自然科学基金（No.31560102）资助项目

Lignans from the Heartwood of Nothotsuga longibracteata

Liu Guiyuan^a, Guo Dale^b, Deng Yun^b, Linghu Lang^a, Zhang Maosheng^a, He Yuqi^a, Xiao Shiji^a

a School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563006;
b School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137

Received:2020-03-08 Revised:2020-04-23 Published:2020-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31560102).

1. 202120S.pdf(918KB)

Abstract

3-(4'-Hydroxy-3'-methoxybenzyl)-2(5H)-furanone (1), a rare benzyl furanone derivate, and two new lignans (2 and 3) were isolated from the heartwood of Nothotsuga longibracteata, together with nineteen known lignans compounds. The structures and absolute configurations of the undescribed compounds were elucidated on the basis of HR-ESI-MS, 1D NMR, 2D NMR, and CD spectroscopies. The cytotoxic effects of the isolated new lignan compounds on three human tumour cell lines (A172, SHSY5Y, and Hela) were evaluated by methyl thiazolyl tetrazolium (MTT) assay. Their showed no cytotoxic activities at the concentration of 50 μmol/L. Gastrointestinal motility test of zebrafish showed that compound 3 has the function of promoting gastrointestinal motility of zebrafish to excrete Nile red at doses 8 and 24 μmol/L by means of acting on the cholinergic nervous system.

Key words: pinaceae, Nothotsuga longibracteata, benzyl furanone, lignans

Cite this article

Liu Guiyuan, Guo Dale, Deng Yun, Linghu Lang, Zhang Maosheng, He Yuqi, Xiao Shiji. Lignans from the Heartwood of Nothotsuga longibracteata[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2120-2126.

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[1] Qiu, Y. J.; Yi, G. M.; Ning, Z. L.; Huang, H. W. J. Plant Resour. Environ. 2011, 20, 53.
[2] Zhang, H. Y.; Zhang, Z. Y. The Chinese Traditional Medicine Resource Records, Science Press, Beijing, 1994 (in Chinese). (张惠源, 张志英, 中国中药资源志要, 科学出版社, 北京, 1994.)
[3] Xiao, S. J.; Shi, D. B.; Yuan, Z. L.; Chen, Y. Z.; Zhang, M. S.; Ding, L. S.; Zhou, Y. Chin. J. Org. Chem. 2016, 36, 1686(in Chinese). (肖世基, 史大斌, 袁泽利, 陈永正, 张茂生, 丁立生, 周燕, 有机化学, 2016, 36, 1686.)
[4] Liu, G. Y.; Nie, Q. F.; Weng, Q. H.; Zhang, M. S.; Ding, L. S.; Zhou, Y.; Chen, F.; Xiao, S. J. Biochem. Syst. Ecol. 2018, 77, 4.
[5] Xiao, S. J.; Chen, F.; Ding, L. S.; Zhou, Y. Chin. J. Nat. Med. 2015, 13, 65.
[6] Xiao, S. J.; Zhang, M. S.; Guo, D. L.; Chen, F.; Zhou, Y.; Ding, L. S. Chin. Chem. Lett. 2017, 28, 1049.
[7] Zhang, M. S.; Deng, Y.; Fu, S. B.; Guo, D. L.; Xiao, S. J. Molecules 2018, 23, 1539.
[8] Xiao, S. J.; Guo, D. L.; Xia, B.; Allen, S.; Gu, Y. C.; Chen, F.; Ding, L. S.; Zhou, Y. Planta Med. 2016, 82, 723.
[9] Schmidt, B.; Wolf, F.; Ehlert, C. J. Org. Chem. 2016, 81, 11235.
[10] Sugahara, T.; Yamauchi, S.; Kondo, A.; Ohno, F.; Tominaga, S.; Nakashima, Y.; Kishida, T.; Akiyama, K.; Maruyama, M. Biosci. Biotechnol. Biochem. 2007, 71, 2962.
[11] Chang, C. C.; Lien, Y. C.; Liu, K. C. S. C.; Lee, S. S. Phyto- chemistry 2003, 63, 825.
[12] Yamamoto, S.; Otto, A.; Simoneit, B. R. J. Mass Spectrom. 2004, 39, 1337.
[13] Li, N.; Wu, J. L.; Hasegawa, T.; Sakai, J.; Bai, L. M.; Wang, L. Y.; Kakuta, S.; Furuya, Y.; Ogura, H.; Kataoka, T.; Tomida, A.; Tsuruo, T.; Ando, M. J. Nat. Prod. 2007, 70, 544.
[14] Wang, L. N.; Qin, L. L.; He, J. L.; Li, X. H.; Cao, Z. X.; Gu, Y. C.; Deng, F.; Deng, Y. J. Asian Nat. Prod. Res. 2019, 21, 999.
[15] Prabhu, B. R.; Mulchandani, N. B. Phytochemistry 1985, 24, 329.
[16] Tiwari, A. K.; Srinivas, P. V.; Kumar, S. P.; Rao, J. M. J. Agric. Food Chem. 2001, 49, 4642.
[17] Kawamura, F.; Miyachi, M.; Kawai, S.; Ohashi, H. J. Wood Sci. 1998, 44, 47.
[18] Eklund, P. C.; Sundell, F. J.; Smeds, A. I.; Sjoholm, R. E. Org. Biomol. Chem. 2004, 2, 2229.
[19] Fischer, J.; Reynolds, A. J.; Sharp, L. A.; Sherburn, M. S. Org. Lett. 2004, 6, 1345.
[20] Fang, J.; Wei, K.; Cheng, Y.; Cheng, M.; Wang, Y. Phytochemistry 1985, 24, 1363.
[21] Cambie, R. C.; Clark, G. R.; Craw, P. A.; Jones, T. C.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1985, 38, 1631.
[22] Zhao, Y. X.; Luo, X. D.; Zhou, J. Acta Bot. Yunnanica 2004, 26, 229(in Chinese). (赵友兴, 李承森, 罗晓东, 刘玉清, 周俊, 云南植物研究, 2004, 26, 229.)
[23] Kawamura, F.; Kawai, S.; Ohashi, H. Phytochemistry 1997, 44, 1351.
[24] Zao, Y. X.; Li, C. S.; Luo, X. D.; Liu, Y. Q.; Zhou, J. Acta Bot. Yunnanica 2005, 27, 217(in Chinese). (赵友兴, 李承森, 罗晓东, 刘玉清, 周俊, 云南植物研究, 2005, 27, 217.)
[25] Kawamura, F.; Kawai, S.; Ohashi, H. Phytochemistry 2000, 54, 439.
[26] Yamauchi, S.; Sugahara, T.; Nakashima, Y.; Okada, A.; Akiyama, K.; Kishida, T.; Maruyama, M.; Masuda, T. Biosci. Biotechnol. Biochem. 2006, 70, 1934.
[27] Jutiviboonsuk, A.; Zhang, H.; Tan, G. T.; Ma, C.; Van Hung, N.; Manh Cuong, N.; Bunyapraphatsara, N.; Soejarto, D. D.; Fong, H. H. Phytochemistry 2005, 66, 2745.
[28] Estévez-Braun, A.; Estévez-Reyes, R.; González-Pérez, J. A.; González, A. G. J. Nat. Prod. 1995, 58, 887.
[29] Bi, Y. F.; Zhen, X. K.; Liu, H. M.; Feng, W. S.; Ji, C. R.; Zhang, Y. Z. Acta Pharm. Sin. 2001, 33, 832(in Chinese). (毕跃峰, 郑晓珂, 刘宏民, 冯卫生, 冀春茹, 张勇忠, 药学学报, 2001, 33, 832.)
[30] Yang, M.; Wang, C. M.; Zhang, Q.; Han, Y. F.; Jia, Z. J. Pharmazie 2004, 59, 972.
[31] Lu, C. Y.; Li, H. X.; Li, S.; Qiu, L.; Yu, S.; Cao, Z. X.; Guo, D. L.; Deng, Y. Nat. Prod. Commun. 2017, 12, 1463.
[32] He, X.; Yang, J.; Qiu, L.; Feng, D.; Ju, F.; Tan, L.; Li, Y. Z.; Gu, Y. C.; Zhang, Z.; Guo, D. L.; Deng, Y. Molecules 2019, 24, 299.
[33] Li, S.; Chen, J. F.; Qin, L. L.; Li, X. H.; Cao, Z. X.; Gu, Y. C.; Guo, D. L.; Deng, Y. J. Asian Nat. Prod. Res. 2020, 22, 138.
[34] Li, X. H.; Hu, H. W.; Tan, L.; Wu, W. L.; Cao, Z. X.; Gu, Y. C.; Deng, Y.; Guo, D. L. Nat. Prod. Commun. 2018, 13, 1419.

长苞铁杉中木脂素类化学成分研究

Lignans from the Heartwood of Nothotsuga longibracteata

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[2]	Liu Yanze, Chang Junbiao, Xie Jingxi. Progress of Aryl-aryl Oxidative Coupling Reagents in the Synthetic Chemistry of Dibenzocyclooctadiene Lignans [J]. Chin. J. Org. Chem., 2012, 32(11): 2040-2053.
[3]	Pan Xinfu;Chen Xiaochuan. Study on the total synthesis of lignan compounds [J]. Chin. J. Org. Chem., 2001, 21(11): 1060-1064.
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