Natural Products and Bioprospecting    2020, Vol. 10 Issue (2) : 89-100     DOI: 10.1007/s13659-020-00239-z
ORIGINAL ARTICLES |
Irlactane and Tremulane Sesquiterpenes from the Cultures of the Medicinal Fungus Irpex lacteus HFG1102
He-Ping Chen1, Xu Ji2, Zheng-Hui Li1, Tao Feng1, Ji-Kai Liu1
1 School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, People's Republic of China;
2 School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
Download: PDF(5228 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  A new irlactane-type, namely irlactin K (1), and 22 tremulane-type sesquiterpenes including fourteen previously undescribed ones, namely irpexolactins A-N (2-15), and a known irlactane-type sesquiterpenoid, were isolated from the fermentation broth of the medicinal fungus Irpex lacteus HFG1102. The structures of all the isolates were characterized by extensive spectroscopic methods, including 1D and 2D NMR and MS spectroscopic analysis. The absolute configurations of irlactin K and the known compound conocenol B (20) were established by single-crystal X-ray diffraction analysis. The vasorelaxant effects of irlactin K (1), irpexolactins A (2), C (4), K (12), and irlactam (22) were evaluated.
Keywords Irpex lacteus      Meruliaceae      Irlactane      Tremulane      Sesquiterpene     
Fund:This work was financially supported by National Natural Science Foundation of China (Nos.81903512, 21961142008). We thank Analytical & Measuring Center, School of Pharmaceutical Sciences, South-Central University for Nationalities for MS and NMR spectra tests.
Corresponding Authors: Ji-Kai Liu     E-mail: jkliu@mail.kib.ac.cn,liujikai@mail.scuec.edu.cn
Issue Date: 06 May 2020
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
He-Ping Chen
Xu Ji
Zheng-Hui Li
Tao Feng
Ji-Kai Liu
Trendmd:   
Cite this article:   
He-Ping Chen,Xu Ji,Zheng-Hui Li, et al. Irlactane and Tremulane Sesquiterpenes from the Cultures of the Medicinal Fungus Irpex lacteus HFG1102[J]. Natural Products and Bioprospecting, 2020, 10(2): 89-100.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-020-00239-z     OR     http://npb.kib.ac.cn/EN/Y2020/V10/I2/89
1. H.P. Chen, J.K. Liu, Prog. Chem. Org. Nat. Prod. 106, 1-201(2017)
2. X.M. Dong, X.H. Song, K.B. Liu, C.H. Dong, Mycosystema 36, 28-34(2017)
3. W.A. Ayer, E.R. Cruz, J. Org. Chem. 58, 7529-7534(1993)
4. J.H. Ding, T. Feng, B.K. Cui, K. Wei, Z.H. Li, J.K. Liu, Tetrahedron Lett. 54, 2651-2654(2013)
5. J.H. Ding, Z.H. Li, T. Feng, J.K. Liu, Fitoterapia 125, 245-248(2018)
6. J.H. Ding, Z.H. Li, T. Feng, J.K. Liu, Nat. Prod. Res. 33, 316-320(2019)
7. L.L. Chen, F.D. Kong, P. Wang, J.Z. Yuan, Z.K. Guo, H. Wang, H.F. Dai, W.L. Mei, Chin. Chem. Lett. 28, 222-225(2017)
8. H.P. Chen, M.Y. Jiang, Z.Z. Zhao, T. Feng, Z.H. Li, J.K. Liu, Nat. Prod. Bioprospect. 8, 37-45(2018)
9. X.Y. Yang, T. Feng, X. Yin, Z.H. Li, L. Zhang, J.K. Liu, Chin. J. Chem. 30, 1231-1235(2012)
10. Z.Y. Zhou, J.G. Tang, F. Wang, Z.J. Dong, J.K. Liu, J. Nat. Prod. 71, 1423-1426(2008)
11. D.Z. Liu, F. Wang, J.K. Liu, J. Nat. Prod. 70, 1503-1506(2007)
12. Y.M. Ying, W.G. Shan, L.W. Zhang, Z.J. Zhan, Phytochemistry 95, 360-367(2013)
13. L.Y. Liu, Z.H. Li, J. Si, Z.J. Dong, J.K. Liu, J. Asian Nat. Prod. Res. 15, 300-304(2013)
14. X.L. Wu, S. Lin, C.G. Zhu, Z.G. Yue, Y. Yu, F. Zhao, B. Liu, J.G. Dai, J.G. Shi, J. Nat. Prod. 73, 1294-1300(2010)
15. R.H. Yin, Z.Z. Zhao, H.P. Chen, X. Yin, X. Ji, Z.J. Dong, Z.H. Li, T. Feng, J.K. Liu, Phytochem. Lett. 10, 300-303(2014)
16. G.J. Chang, T.P. Lin, Y.S. Ko, M.S. Lin, Life Sci. 86, 869-879(2010)
17. X. Ji, C.C. Trandafir, A.M. Wang, K. Kurahashi, J. Stroke Cerebrovasc. 22, 1258-1262(2013)
[1] Yang Tang, Zhen-Zhu Zhao, Zheng-Hui Li, Tao Feng, He-Ping Chen, Ji-Kai Liu. Irpexoates A-D, Four Triterpenoids with Malonyl Modifications from the Fruiting Bodies of the Medicinal Fungus Irpex lacteus[J]. Natural Products and Bioprospecting, 2018, 8(3): 171-176.
[2] He-Ping Chen, Zhen-Zhu Zhao, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Seco-tremulane Sesquiterpenoids from the Cultures of the Medicinal Fungus Irpex lacteus HFG1102[J]. Natural Products and Bioprospecting, 2018, 8(2): 113-119.
[3] Kennedy D. Nyongbela, Fidele Ntie-Kang, Thomas R. Hoye, Simon M. N. Efange. Antiparasitic Sesquiterpenes from the Cameroonian Spice Scleria striatinux and Preliminary In Vitro and In Silico DMPK Assessment[J]. Natural Products and Bioprospecting, 2017, 7(3): 235-247.
[4] Hui Zhou, Yan-Long Yang, Jun Zeng, Ling Zhang, Zhi-Hui Ding, Ying Zeng. Identification and Characterization of a d-Cadinol Synthase Potentially Involved in the Formation of Boreovibrins in Boreostereum vibrans of Basidiomycota[J]. Natural Products and Bioprospecting, 2016, 6(3): 167-171.
[5] Can-Bin Ouyang, Xiao-Man Liu, Qi Liu, Jie Bai, Hou-Yong Li, Yuan Li, Qiu-Xia Wang, Dong-Dong Yan, Lian-Gang Mao, Aocheng Cao, Mei-Xia Guo. Toxicity Assessment of Cadinene Sesquiterpenes from Eupatorium adenophorum in Mice[J]. Natural Products and Bioprospecting, 2015, 5(1): 29-36.
[6] Rong-Hua Yin, Zhen-Zhu Zhao, Xu Ji, Ze-Jun Dong, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Steroids and Sesquiterpenes From Cultures of the Fungus Phellinus igniarius[J]. Natural Products and Bioprospecting, 2015, 5(1): 17-22.
[7] Zi-Ming Chen, Qiong-Ying Fan, Xia Yin, Xiao-Yan Yang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Three New Humulane Sesquiterpenes from Cultures of the Fungus Antrodiella albocinnamomea[J]. Natural Products and Bioprospecting, 2014, 4(4): 207-211.
[8] 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]. Natural Products and Bioprospecting, 2013, 3(2): 48-51.
[9] Xia YIN, Tao FENG, Ji-Kai LIU. Structures and cytotoxicities of three new sesquiterpenes from cultures of Armillaria sp.[J]. Natural Products and Bioprospecting, 2012, 2(6): 245-248.
[10] Li-Yan PENG, Juan HE, Gang XU, Xing-De WU, Liao-Bin DONG, Xiu GAO, Xiao CHENG, Jia SU, Yan LI, Qin-Shi ZHAO. Euglobal-IIIa, a novel acylphloroglucinol-sesquiterpene derivative from Eucalyptus robusta: absolute structure and cytotoxicity[J]. Natural Products and Bioprospecting, 2011, 1(2): 101-103.
[11] Xia YIN, Tao FENG, Zheng-Hui LI, Jia SU, Yan LI, Ning-Hua TAN, Ji-Kai LIU. Chemical investigation on the cultures of the fungus Xylaria carpophila[J]. Natural Products and Bioprospecting, 2011, 1(2): 75-80.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed