Sesquiterpenoids from the Rhizomes of Homalomena occulta

doi:10.1007/s13659-016-0104-8

应用天然产物 ›› 2016, Vol. 6 ›› Issue (4): 211-216.DOI: 10.1007/s13659-016-0104-8

• Original article • 上一篇下一篇

Sesquiterpenoids from the Rhizomes of Homalomena occulta

Jun-Li Yang¹, Ya-Min Zhao¹, Yan-Ping Shi^1,2

1. Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China;
2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China

收稿日期:2016-05-22 修回日期:2016-06-23 出版日期:2016-08-24 发布日期:2018-02-08
通讯作者: Yan-Ping Shi,e-mail:shiyp@licp.cas.cn
基金资助:
The work was financially supported by the National Nature Science Foundation of China (Nos.21375136 and 21575150),and the scientific research project of Central Asia Drug Discovery and Development Centre of Chinese Academy of Sciences (No.CAM201404) and the CAS Pioneer Hundred Talents Program

Sesquiterpenoids from the Rhizomes of Homalomena occulta

Jun-Li Yang¹, Ya-Min Zhao¹, Yan-Ping Shi^1,2

1. Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China;
2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China

Received:2016-05-22 Revised:2016-06-23 Online:2016-08-24 Published:2018-02-08
Supported by:
The work was financially supported by the National Nature Science Foundation of China (Nos.21375136 and 21575150),and the scientific research project of Central Asia Drug Discovery and Development Centre of Chinese Academy of Sciences (No.CAM201404) and the CAS Pioneer Hundred Talents Program

摘要/Abstract

摘要： Naturally occurring oplopanane sesquiterpenoids are rarely reported. A phytochemical investigation on the rhizomes of Homalomena occulta (Lours) has resulted in the discovery of six oplopanane sesquiterpenoids (1-6), including four new (1-4) and one 3,5-seco-oplopanane (6), together with three previously reported sesquiterpenoids (7-9). In addition three new oplopananes (2a-4a) were also obtained by chemical transformation. All structures of these sesquiterpenoids were established based on the comprehensive spectroscopic analyses, including NMR, MS, and IR, and comparing with the literatures.

关键词: Homalomena occulta, Sesquiterpenoids, Oplopananes

Abstract: Naturally occurring oplopanane sesquiterpenoids are rarely reported. A phytochemical investigation on the rhizomes of Homalomena occulta (Lours) has resulted in the discovery of six oplopanane sesquiterpenoids (1-6), including four new (1-4) and one 3,5-seco-oplopanane (6), together with three previously reported sesquiterpenoids (7-9). In addition three new oplopananes (2a-4a) were also obtained by chemical transformation. All structures of these sesquiterpenoids were established based on the comprehensive spectroscopic analyses, including NMR, MS, and IR, and comparing with the literatures.

Key words: Homalomena occulta, Sesquiterpenoids, Oplopananes

Jun-Li Yang, Ya-Min Zhao, Yan-Ping Shi. Sesquiterpenoids from the Rhizomes of Homalomena occulta[J]. 应用天然产物, 2016, 6(4): 211-216.

Jun-Li Yang, Ya-Min Zhao, Yan-Ping Shi. Sesquiterpenoids from the Rhizomes of Homalomena occulta[J]. Natural Products and Bioprospecting, 2016, 6(4): 211-216.

参考文献

1. Chinese Pharmacopoeia Commission, Chinese Pharmacopoeia (Part I, 2015 Edition), p33, China Medical Science Press (2015)
2. M. Elbandy, H. Lerche, H. Wagner, M.A. Lacaille-Dubois, Biochem. Syst. Ecol. 32, 1209-1213 (2004)
3. Y.M. Hu, C. Liu, K.W. Cheng, H.H.Y. Sung, L.D. Williams, Z.L. Yang, W.C. Ye, Phytochemistry 69, 2367-2373 (2008)
4. Y.M. Hu, Z.L. Yang, H. Wang, W.C. Ye, Nat. Prod. Res. 23, 1279-1283 (2009)
5. X.Y. Tian, Y. Zhao, S.S. Yu, W.S. Fang, Chem. Biodivers. 7, 984-992 (2010)
6. Y.F. Wang, X.Y. Wang, G.F. Lai, C.H. Lu, S.D. Luo, Chem. Biodivers. 4, 925-931 (2007)
7. X.H. Li, W.J. Zhang, H.Y. Qi, Y.P. Shi, Can. J. Chem. 87, 1218-1221 (2009)
8. R. Wang, W.H. Chen, Y.P. Shi, J. Nat. Prod. 73, 17-21 (2010)
9. R. Wang, L.L. Liu, Y.P. Shi, Helv. Chim. Acta 93, 2081-2085 (2010)
10. J.L. Yang, L.L. Liu, Y.P. Shi, Tetrahedron Lett. 50, 6315-6317 (2009)
11. G.Y. Zhu, G.P. Peng, Nat. Prod. Res. Dev. 14, 85-88 (2002)
12. Y.H. Kuo, C.F. Chyu, Tetrahedron Lett. 44, 7221-7223 (2003)
13. T.V. Sung, L. Kutschabsky, A. Porzel, W. Steglich, G. Adam, Phytochemistry 31, 1659-1661 (1992)
14. W. Herz, K. Watanabe, Phytochemistry 22, 1457-1459 (1983)
15. H. Heymann, Y. Tezuka, T. Kikichi, S. Supriyatna, Chem. Pharm. Bull. 42, 138-146 (1994)
16. G.P. Peng, F.C. Lou, Nat. Prod. Res. Dev. 13, 9-11 (2001)
17. G.Y. Zhu, G.P. Peng, Nat. Prod. Res. Dev. 14, 85-88 (2002)
18. Z.F. Li, Z.H. Wu, G. Chen, Q.H. Zhang, Y.H. Pei, J. Asian Nat. Prod. Res. 11, 715-718 (2009)
19. K.C. Wong, A. Hamid, I.M.S. Eldeen, M.Z. Asmawi, S. Baharuddin, H.S. Abdillahi, J. van Staden, Nat. Prod. Res. 26, 850-858 (2012)
20. L.S. Gan, Z.J. Zhan, S.P. Yang, J.M. Yue, J. Asian Nat. Prod. Res. 8, 589-594 (2006)
21. S. Yang, H, Chen. J. Yue Chin. J. Chem. 30, 1243-1248 (2012)
22. H.B. Xu, Y.B. Ma, X.Y. Huang, C.A. Geng, H. Wang, Y. Zhao, T.H. Yang, X.L. Chen, C.Y. Yang, X.M. Zhang, J.J. Chen, J. Ethnopharmacol. 171, 131-140 (2015)
23. G.J. Zhang, Y.H. Li, J.D. Jiang, S.S. Yu, X.J. Wang, P.Y. Zhuang, Y. Zhang, J. Qu, S.G. Ma, Y. Li, Y.B. Liu, D.Q. Yu, Tetrahedron 70, 4494-4499 (2014)
24. L. Zhang, J.H. Zhang, S.M. Yang, C.H. Tan, H.F. Luo, D.Y. Zhu, J. Asian Nat. Prod. Res. 12, 215-219 (2010)
25. Y. Narukawa, C. Komatsu, R. Yamauchi, S. Shibayama, M. Hachisuka, F. Kiuchi, J. Nat. Med. p 1-7, (2016)
26. W. Wang, Z. Ali, X.C. Li, T.A. Smillie, D.A. Guo, I.A. Khan, Fitoterapia 80, 404-407 (2009)
27. N. Liu, X. Yu, H. Zhao, Y. Zhao, Zhongcaoyao 40, 29-32 (2009)

[1]	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]. 应用天然产物, 2024, 14(6): 61-61.
[2]	Jin-Ning Chu, Premanand Krishnan, Kuan-Hon Lim. A comprehensive review on the chemical constituents, sesquiterpenoid biosynthesis and biological activities of Sarcandra glabra[J]. 应用天然产物, 2023, 13(6): 53-53.
[3]	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]. 应用天然产物, 2022, 12(4): 27-27.
[4]	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]. 应用天然产物, 2022, 12(3): 19-19.
[5]	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.
[6]	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]. 应用天然产物, 2022, 12(1): 1-14.
[7]	Shu-Ya Wei, Dong-Bao Hu, Meng-Yuan Xia, Ji-Feng Luo, Hui Yan, Jing-Hua Yang, Yun-Song Wang, Yue-Hu Wang. Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis[J]. 应用天然产物, 2021, 11(5): 545-555.
[8]	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]. 应用天然产物, 2020, 10(4): 251-260.
[9]	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.
[10]	Jun-Li Yang, Lei-Lei Liu, Yan-Ping Shi. Two New Eudesmane Sesquiterpenoids from the Flowers of Chrysanthemum indicum[J]. 应用天然产物, 2019, 9(2): 145-148.
[11]	Michel Feussi Tala, Jianchun Qin, Joseph T. Ndongo, Hartmut Laatsch. New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus[J]. 应用天然产物, 2017, 7(3): 269-273.
[12]	Ce Kuang, Shu-Xi Jing, Yan Liu, Shi-Hong Luo, Sheng-Hong Li. Drimane Sesquiterpenoids and Isochromone Derivative from the Endophytic Fungus Pestalotiopsis sp. M-23[J]. 应用天然产物, 2016, 6(3): 155-160.
[13]	Xiao-Yan YANG, Tao FENG, Jian-Hai DING, Zheng-Hui LI, Yan LI, Qiong-Ying FAN, Ji-Kai LIU. Two new drimane sesquiterpenoids from cultures of the basidiomycete Trichaptum biforme[J]. 应用天然产物, 2013, 3(4): 154-157.
[14]	Xiao-Yan YANG, Tao FENG, Jian-Hai DING, Xia YIN, Hua GUO, Zheng-Hui LI, Ji-Kai LIU. Five new 5, 6-seco-tremulane sesquiterpenoids from the basidiomycete Conocybe siliginea[J]. 应用天然产物, 2013, 3(2): 48-51.
[15]	Liang-Yan LIU, Zheng-Hui LI, Ze-Jun DONG, Xing-Yao LI, Jia SU, Yan LI, Ji-Kai LIU. Two novel fomannosane-type sesquiterpenoids from the culture of the basidiomycete Agrocybe salicacola[J]. 应用天然产物, 2012, 2(3): 130-132.

Sesquiterpenoids from the Rhizomes of Homalomena occulta

Sesquiterpenoids from the Rhizomes of Homalomena occulta

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价