Planta Med 2019; 85(09/10): 701-707
DOI: 10.1055/a-0855-4051
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Four New Cytotoxic Arborinane-Type Triterpenes from the Endolichenic Fungus Myrothecium inundatum

Buddha Bahadur Basnet*
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing, China
2   International College, University of Chinese Academy of Sciences, Beijing, China
,
Li Liu*
4   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, China
,
Baosong Chen*
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing, China
3   Savaid Medical School, University of Chinese Academy of Sciences, Beijing, China
,
Yerlan Melsuly Suleimen
5   Institute of Applied Chemistry, Chemistry Department of L. N. Gumilyov Eurasian National University, Astana, Republic of Kazakhstan
,
Haiyang Yu
6   Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, China
,
Shouyu Guo
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing, China
,
Li Bao
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing, China
3   Savaid Medical School, University of Chinese Academy of Sciences, Beijing, China
,
Jinwei Ren
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing, China
3   Savaid Medical School, University of Chinese Academy of Sciences, Beijing, China
,
Hongwei Liu
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing, China
3   Savaid Medical School, University of Chinese Academy of Sciences, Beijing, China
› Author Affiliations
Further Information

Publication History

received 14 November 2018
revised 21 January 2019

accepted 07 February 2019

Publication Date:
19 February 2019 (online)

Abstract

Two new arborinane-type triterpenes, myrotheols A (1) and B (2), two new arborinane-type glycosides, myrothesides C (3) and D (4), together with four known diterpenes (5 – 8) were isolated from the ethyl acetate extract of the endolichenic fungus Myrothecium inundatum. The structures of new compounds 1 – 4 were elucidated by NMR and MS analyses. The absolute configuration of 1 was assigned by a single-crystal X-ray diffraction experiment. Compounds 3 and 4 represent the first two natural 4-O-methyl-α-D-mannosides. Compounds 1 – 8 exhibited cytotoxicity against K562 and RKO human cancer cell lines.

* These authors contributed equally to this work.


Supporting Information

 
  • References

  • 1 Xu R, Fazio GC, Matsuda SP. On the origins of triterpenoid skeletal diversity. Phytochemistry 2004; 65: 261-291
  • 2 Hill RA, Connolly JD. Triterpenoids. Nat Prod Rep 2015; 32: 273-327
  • 3 Son JK, Jung JH, Lee CS, Moon DC, Choi SW, Min BS, Woo MH. DNA topoisomerases I and II inhibition and cytotoxicity of constituents from the roots of Rubia cordifolia . Bull Korean Chem Soc 2006; 27: 1231-1234
  • 4 Ragasa CY, Puno MRA, Sengson JMAP, Shen CC, Rideout JA, Raga DD. Bioactive triterpenes from Diospyros blancoi . Nat Prod Res 2009; 23: 1252-1258
  • 5 Jeong EJ, Bae JY, Rho JR, Kim YC, Ahn MJ, Sung SH. Anti-inflammatory triterpenes from Euonymus alatus leaves and twigs on lipopolysaccharide-activated RAW264.7 macrophage Cells. Bull Korean Chem Soc 2014; 35: 2945-2949
  • 6 Hauke V, Graff R, Wehrung P, Trendel JM, Albrecht P, Riva A, Hopfgartner G, Gülaçar FO, Buchs A, Eakin PA. Novel triterpene-derived hydrocarbons of the arborane/fernane series in sediments: Part II. Geochim Cosmochim Acta 1992; 56: 3595-3602
  • 7 Fan JT, Kuang B, Zeng GZ, Zhao SM, Ji CJ, Zhang YM, Tan NH. Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis . J Nat Prod 2011; 74: 2069-2080
  • 8 Liou MJ, Wu TS. Triterpenoids from Rubia yunnanensis . J Nat Prod 2002; 65: 1283-1287
  • 9 Morikawa T, Tao J, Ando S, Matsuda H, Yoshikawa M. Absolute stereo-structures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis . J Nat Prod 2003; 66: 638-645
  • 10 Quan KT, Park HS, Oh J, Park HB, Ferreira D, Myung CS, Na M. Arborinane triterpenoids from Rubia philippinensis inhibit proliferation and migration of vascular smooth muscle cells induced by the platelet-derived growth factor. J Nat Prod 2016; 79: 2559-2569
  • 11 González AG, Barrera JB, Rodriguez P, Elsa M. Chemical constituents of the lichen Cladina macaronesica . Z Naturforsch C Biosci 1991; 46: 12-18
  • 12 Calcott MJ, Ackerley DF, Knight A, Keyzers RA, Owen JG. Secondary metabolism in the lichen symbiosis. Chem Soc Rev 2018; 47: 1730-1760
  • 13 Spribille T, Tuovinen V, Resl P, Vanderpool D, Wolinski H, Aime MC, Schneider K, Stabentheiner E, Toome-Heller M, Thor G, Mayrhofer H, Johannesson H, McCutcheon JP. Basidiomycete yeasts in the cortex of ascomycete macrolichens. Science 2016; 353: 488-492
  • 14 Wu W, Dai H, Bao L, Ren B, Lu J, Luo Y, Guo L, Zhang L, Liu H. Isolation and structural elucidation of proline-containing cyclopentapeptides from an endolichenic Xylaria sp. J Nat Prod 2011; 74: 1303-1308
  • 15 Li G, Wang HY, Zhu RX, Sun LM, Wang LN, Li M, Li YY, Liu YQ, Zhao ZT, Lou HX. Phaeosphaerins A–F, cytotoxic perylenequinones from an endolichenic fungus, Phaeosphaeria sp. J Nat Prod 2012; 75: 142-147
  • 16 Paudel B, Bhattarai K, Bhattarai HD. Antimicrobial and antioxidant activities of two polyketides from lichen-endophytic fungus Preussia sp. Z Naturforsch C 2018; 73: 161-163
  • 17 Kim JW, Ko W, Kim E, Kim GS, Hwang GJ, Son S, Jeong MH, Hur JS, Oh H, Ko SK, Jang JH, Ahn JS. Anti-inflammatory phomalichenones from an endolichenic fungus Phoma sp. J Antibiot 2018; 71: 753-756
  • 18 Zhao Q, Chen GD, Feng XL, Yu Y, He RR, Li XX, Huang Y, Zhou WX, Guo LD, Zheng YZ, Yao XS, Gao H. Nodulisporiviridins A–H, bioactive viridins from Nodulisporium sp. J Nat Prod 2015; 78: 1221-1230
  • 19 Banerjee D, Strobel GA, Booth E, Geary B, Sears J, Spakowicz D, Busse S. An endophytic Myrothecium inundatum producing volatile organic compounds. Mycosphere 2010; 1: 229-240
  • 20 Fu Y, Wu P, Xue J, Wei X. Cytotoxic and antibacterial quinone sesquiterpenes from a Myrothecium fungus. J Nat Prod 2014; 77: 1791-1799
  • 21 Hsu YH, Hirota A, Shima S, Nakagawa M, Nozaki H, Tada T, Nakayama M. Structure of myrocin C, a new diterpene antibiotic produced by a strain of Myrothecium sp. Agric Biol Chem 1987; 51: 3455-3457
  • 22 Evidente A, Sparapano L, Fierro O, Bruno G, Giordano F, Motta A. Sphaeropsidins B and C, phytotoxic pimarane diterpenes from Sphaeropsis sapinea f. sp. cupressi and Diplodia mutila . Phytochemistry 1997; 45: 705-713
  • 23 Jossang A, Mbeminack B, Pinon J, Bodo B. Hymatoxins K and L, novel phytotoxins from Hypoxylon mammatum, fungal pathogen of Aspens. Nat Prod Lett 1995; 6: 37-42
  • 24 Shiono Y, Motoki S, Koseki T, Murayama T, Tojima M, Kimura K. Isopimarane diterpene glycosides, apoptosis inducers, obtained from fruiting bodies of the ascomycete Xylaria polymorpha . Phytochemistry 2009; 70: 935-939