Four new diterpenoids from Isodon eriocalyx var. laxiflora

doi:10.1007/s13659-013-0057-0

Natural Products and Bioprospecting ›› 2013, Vol. 3 ›› Issue (4): 145-149.DOI: 10.1007/s13659-013-0057-0

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Four new diterpenoids from Isodon eriocalyx var. laxiflora

Wei-Guang WANG^a,b, Xue DU^a, Xiao-Nian LI^a, Bing-Chao YAN^a,b, Min ZHOU^a,b, Hai-Yan WU^a,b, Rui ZHAN^a,b, Ke DONG^a, Jian-Xin PU^a, Han-Dong SUN^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received:2013-07-18 Revised:2013-08-02 Online:2018-02-11 Published:2013-08-24
Supported by:
The authors are grateful to Prof. Xi-Wen Li of the Kunming Institute of Botany, Chinese Academy of Sciences, for the identification of the plant. This project was supported financially by the National Natural Science Foundation of China (No. 81172939), the West Light Foundation of the Chinese Academy of Sciences (J.X. Pu), the Major State Basic Research Development Program of China (No. 2009CB522300), the reservation talent project of Yunnan Province (2011CI043 to J.X. Pu), the Science and Technology Program of Yunnan Province (Nos. 2008IF010), and the Major Direction Projection Foundation of CAS Intellectual Innovation Project (No. KSCX2-EW-J-24 to J.X. Pu).

Four new diterpenoids from Isodon eriocalyx var. laxiflora

Wei-Guang WANG^a,b, Xue DU^a, Xiao-Nian LI^a, Bing-Chao YAN^a,b, Min ZHOU^a,b, Hai-Yan WU^a,b, Rui ZHAN^a,b, Ke DONG^a, Jian-Xin PU^a, Han-Dong SUN^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

通讯作者: Jian-Xin PU,E-mail:pujianxin@mail.kib.ac.cn;Han-Dong SUN,E-mail:hdsun@mail.kib.ac.cn
基金资助:
The authors are grateful to Prof. Xi-Wen Li of the Kunming Institute of Botany, Chinese Academy of Sciences, for the identification of the plant. This project was supported financially by the National Natural Science Foundation of China (No. 81172939), the West Light Foundation of the Chinese Academy of Sciences (J.X. Pu), the Major State Basic Research Development Program of China (No. 2009CB522300), the reservation talent project of Yunnan Province (2011CI043 to J.X. Pu), the Science and Technology Program of Yunnan Province (Nos. 2008IF010), and the Major Direction Projection Foundation of CAS Intellectual Innovation Project (No. KSCX2-EW-J-24 to J.X. Pu).

Abstract

Abstract: Four new diterpenoids, laxiflorins S-V (1-4), bearing four different types, and one known compound, laxiflorin O (5), were isolated from Isodon eriocalyx var. laxiflora. Compound 1 was the first example of ent-kauranoids bearing a unique C₂₄ carbon framework and compound 4 was the first example of 3,4-seco-ent-abietane diterpenoids from the Isodon genus. Their structures were determined by spectroscopic methods (UV, IR, MS, NMR).

Key words: Isodon eriocalyx var. laxiflora, laxiflorins, diterpenoid, ent-kaurane, ent-abietane

摘要： Four new diterpenoids, laxiflorins S-V (1-4), bearing four different types, and one known compound, laxiflorin O (5), were isolated from Isodon eriocalyx var. laxiflora. Compound 1 was the first example of ent-kauranoids bearing a unique C₂₄ carbon framework and compound 4 was the first example of 3,4-seco-ent-abietane diterpenoids from the Isodon genus. Their structures were determined by spectroscopic methods (UV, IR, MS, NMR).

关键词: Isodon eriocalyx var. laxiflora, laxiflorins, diterpenoid, ent-kaurane, ent-abietane

Wei-Guang WANG, Xue DU, Xiao-Nian LI, Bing-Chao YAN, Min ZHOU, Hai-Yan WU, Rui ZHAN, Ke DONG, Jian-Xin PU, Han-Dong SUN. Four new diterpenoids from Isodon eriocalyx var. laxiflora[J]. Natural Products and Bioprospecting, 2013, 3(4): 145-149.

References

[1] Li, J. W.; Vederas, J. C. Science 2009, 325, 161-165.
[2] Dandapani, S.; Marcaurelle, L. A. Nat. Chem. Biol. 2010, 6, 861-863.
[3] Medina-Franco, J. Drug Des. 2012, 1, e105.
[4] Sun, H. D.; Huang, S. X.; Han, Q. B. Nat. Prod. Rep. 2006, 23, 673-698.
[5] Zhan, R.; Du, X.; Su, J.; Li, X. N.; Wang, W. G.; Liang, C. Q.; Yang, J. H.; Li, Y.; Pu, J. X.; Sun, H. D. Nat. Prod. Bioprospect. 2011, 1, 116-120.
[6] Niu, X. M.; Li, S. H.; Li, M. L.; Zhao, Q. S.; Mei, S. X.; Na, Z.; Wang, S. J.; Lin, Z. W.; Sun, H. D. Planta Med. 2002, 68(6), 528-533.
[7] Wang, W. G.; Wu, H. Y.; Du, X.; Yan, J. M.; Li, Y.; Pu, J. X.; Sun, H. D. Chin. J. Chem. 2012, 30, 1226-1230.
[8] Niu, X. M.; Li, S. H.; Mei, S. X.; Na, Z.; Zhao, Q. S.; Lin, Z. W.; Sun, H. D. J. Nat. Prod. 2002, 65, 1892-1896.
[9] Sun, H. D.; Lin, Z. W.; Niu, F. D.; Shen, P. Q.; Pan, L. T.; Lin, L. Z.; Cordell, G. A. Phytochemistry 1995, 38, 1451-1455.
[10] Niu, X.; Li, S.; Zhao, Q.; Lin, Z.; Sun, H.; Lu, Y.; Wang, C.; Zheng, Q. Tetrahedron Lett. 2002, 43, 661-664.
[11] Niu, X.; Li, S.; Zhao, Q.; Mei, S.; Lin, Z.; Sun, H.; Lu, Y.; Wang, C.; Zheng, Q. Helv. Chim. Acta 2003, 86, 299-306.
[12] Wang, W. G.; Li, X. N.; Du, X.; Dong, K.; Zhao, W.; Wu, H. Y.; Kong, L. M.; Li, Y.; Pu, J. X.; Sun, H. D., Tetrahedron Lett. 2012, 53, 2777-2781.
[13] Wang, W. G.; Li, X. N.; Du, X.; Wu, H. Y.; Liu, X.; Su, J.; Li, Y.; Pu, J. X.; Sun, H. D. J. Nat. Prod. 2012, 75, 1102-1107.
[14] Wang, W. G.; Du, X.; Li, X. N.; Wu, H. Y.; Liu, X.; Shang, S. Z.; Zhan, R.; Liang, C. Q.; Kong, L. M.; Li, Y.; Pu, J. X.; Sun, H. D. Org. Lett. 2012, 14, 302-305.
[15] Niu, X. M.; Li, S. H.; Li, M. L.; Zhao, Q. S.; Mei, S. X.; Na, Z.; Wang, S. J.; Lin, Z. W.; Sun, H. D. Planta Med. 2002, 68, 528-533.
[16] Shen, P.; Sun, H.; Lin, Z. Yunnan Zhiwu Yanjiu 1986, 8, 163-166.
[17] Fujita, E.; Fujita, T.; Shibuya, M. Chem. Commun. 1967, 148-149.
[18] Flack, H.; Bernardinelli, G. Acta Crystallogr., Sect. A 1999, 55, 908-915.
[19] Flack, H. D. Acta Crystallogr., Sect. A 1983, 39, 876-881.

Four new diterpenoids from Isodon eriocalyx var. laxiflora

Four new diterpenoids from Isodon eriocalyx var. laxiflora

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