Meroterpenes with Toll-Like Receptor 3 Regulating Activity from the Endophytic Fungus Guignardia mangiferae

Wen Bo Han; Huan Dou; Wei Hua Yuan; Wei Gong; Ya Yi Hou; Seik Weng Ng; Ren Xiang Tan

doi:10.1055/s-0034-1383392

Planta Medica, Inhaltsverzeichnis

Planta Med 2015; 81(02): 145-151
DOI: 10.1055/s-0034-1383392

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Meroterpenes with Toll-Like Receptor 3 Regulating Activity from the Endophytic Fungus Guignardia mangiferae

Wen Bo Han^*

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

²State Key Laboratory of Element Organic Chemistry, Nankai University, Tianjin, P. R. China

,

Huan Dou^*

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

,

Wei Hua Yuan

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

,

Wei Gong

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

,

Ya Yi Hou

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

,

Seik Weng Ng

³Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia and Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia

,

Ren Xiang Tan

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

› Institutsangaben

Abstract

The endophytic fungus Guignardia mangiferae isolated from Ilex cornuta leaves was shown to produce a family of meroterpenes with toll-like receptor 3 regulating activity (1–9), of which 1–3 possessed new structures. The absolute stereochemistry of 1–3 was assigned through a combination of nuclear magnetic resonance experiments, chemical derivation, CD spectra, and single-crystal X-ray diffraction analyses (CuK _α ). The precursor labeled cultivation suggests that these meroterpenes are most likely assembled through terpenoid-shikimate pathways. Moreover, meroterpenes 1–3, 5–7, and 9 selectively upregulate, but 4 and 8 downregulate the toll-like receptor 3 expression in mouse dendritic cells at 10.0 µM.

Key words

Guignardia mangiferae - Dothideaceae - configuration determination - TLR3 regulation - meroterpenes

Volltext

Referenzen

References
1 Murray PJ, Smale ST. Restraint of inflammatory signaling by interdependent strata of negative regulatory pathways. Nat Immunol 2012; 13: 916-924
2 Sharma S, Zhu L, Davoodi M, Harris-White M, Lee JM, St John M, Salgia R, Dubinett S. TLR3 agonists and proinflammatory antitumor activities. Exp Opin Ther Tar 2013; 17: 481-483
3 Siednienko J, Maratha A, Yang S, Mitkiewicz M, Miggin SM, Moynagh PN. Nuclear factor κB subunits RelB and cRel negatively regulate Toll-like receptor 3-mediated β-interferon production via induction of transcriptional repressor protein YY1. J Biol Chem 2011; 286: 44750-44763
4 Hajishengallis G, Lambris JD. Microbial manipulation of receptor crosstalk in innate immunity. Nat Rev Immunol 2011; 11: 187-200
5 Lee SW, Han SW, Bartley LE, Ronald PC. Unique characteristics of Xanthomonas oryzae pv. oryzae AvrXa21 and implications for plant innate immunity. Proc Natl Acad Sci 2006; 103: 18395-18400
6 Aliprantis AO, Yang RB, Mark MR, Suggett S, Devaux B, Radolf JD, Klimpel GR, Godowski P, Zych-linsky A. Cell activation and apoptosis by bacterial lipoproteins through toll-like receptor-2. Science 1999; 285: 736-739
7 Singh BP, Chauhan RS, Singhal LK. Toll-like receptors and their role in innate immunity. Curr Sci 2003; 85: 1156-1164
8 Kumar H, Kawai T, Akira S. Toll-like receptors and innate immunity. Biochem Biophys Res Commun 2009; 388: 621-625
9 Appleton DR, Chuen CS, Berridge MV, Webb VL, Copp BR. Rossinones A and B, biologically active meroterpenoids from the Antarctic ascidian, Aplidium species. J Org Chem 2009; 74: 9195-9198
10 Simon-Levert A, Menniti C, Soulère L, Genevière AM, Barthomeuf C, Banaigs B, Witczak A. Marine natural meroterpenes: synthesis and antiproliferative activity. Mar Drugs 2010; 8: 347-358
11 Fang W, Ji S, Jiang N, Wang W, Zhao GY, Zhang S, Ge HM, Xu Q, Zhang AH, Zhang YL, Song YC, Zhang J, Tan RX. Naphthol radical couplings determine structural features and enantiomeric excess of dalesconols in Daldinia eschscholzii . Nat Commun 2012; 3: 1039
12 Zhang YL, Zhang J, Jiang N, Lu YH, Wang L, Xu SH, Wang W, Zhang GF, Xu Q, Ge HM, Ma J, Song YC, Tan RX. Immunosuppressive polyketides from mantis-associated Daldinia eschscholzii . J Am Chem Soc 2011; 133: 5931-5940
13 Zhang YL, Ge HM, Zhao W, Dong H, Xu Q, Li SH, Li J, Zhang J, Song YC, Tan RX. Unprecedented immunosuppressive polyketides from Daldinia eschscholzii, a mantis-associated fungus. Angew Chem Int Ed 2008; 47: 5823-5826
14 Yuan WH, Liu M, Jiang N, Guo ZK, Ma J, Zhang J, Song YC, Tan RX. Guignardones A–C: three meroterpenes from Guignardia mangiferae . Eur J Org Chem 2010; 6348-6353
15 Mei WL, Zheng B, Zhao YX, Zhong HM, Chen XL, Zeng YB, Dong WH, Huang JL, Proksch P, Dai HF. Meroterpenes from endophytic fungus A1 of mangrove plant Scyphiphora hydrophyllacea . Mar Drugs 2012; 10: 1993-2001
16 Sommart U, Rukachaisirikul V, Trisuwan K, Tadpetch K, Phongpaichit S, Preedanon S, Sakayaroj J. Tricycloalternarene derivatives from the endophytic fungus Guignardia bidwellii PSU-G11. Phytochem Lett 2012; 5: 139-143
17 Harada N, Iwabuchi J, Yokota Y, Uda H, Nakanishi K. Chiroptical method for determining the absolute configuration of allylic alcohols. J Am Chem Soc 1981; 103: 5590-5591
18 Bagdžiūnas G, Butkus E, Stončius S. Synthesis of diastereomeric bicycle [3.3.1] nonane dibenzoyl esters and study of their chiroptical properties. Chirality 2012; 24: 810-816
19 Fan CQ, Wang XN, Yin S, Zhang CR, Wang FD, Yue JM. Tabularisins A–D, phragmalin ortho esters with new skeleton isolated from the seeds of Chukrasia tabularis . Tetrahedron 2007; 63: 6741-6747
20 Draths KM, Frost JW. Conversion of D-glucose into catechol: the not-so-common pathway of aromatic biosynthesis. J Am Chem Soc 1991; 113: 9361-9363
21 Seshime Y, Juvvadi PR, Kitamoto K, Ebizuka Y, Nonaka T, Fujii I. Aspergillus oryzae type III polyketide synthase CsyA is involved in the biosynthesis of 3,5-dihydroxybenzoic acid. Bioorg Med Chem Lett 2010; 20: 4785-4788
22 Kim D, Filtz MR, Proteau PJ. The methylerythritol phosphate pathway contributes to carotenoid but not phytol biosynthesis in Euglena gracilis . J Nat Prod 2004; 67: 1067-1069
23 Matsuzawa M, Katsuyama Y, Funa N, Horinouchi S. Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa . Phytochemistry 2010; 71: 1059-1067
24 Nakajima M, Nishino Y, Tamura M, Mase K, Masai E, Otsuka Y, Nakamura M, Sato K, Fukuda M, Shigehara K, Ohara S, Katayama Y, Kajita S. Microbial conversion of glucose to a novel chemical building block, 2-pyrone-4,6-dicarboxylic acid. Metab Eng 2009; 11: 213-220
25 Banthorpe DV, Charlwood BV, Francis MJO. Biosynthesis of monoterpenes. Chem Rev 1972; 72: 115-155
26 Yoon SI, Hong M, Wilson IA. An unusual dimeric structure and assembly for TLR4 regulator RP105-MD-1. Nat Struct Mol Biol 2011; 18: 1028-1035
27 Seyberth T, Voss S, Brock R, Wiesmüller KH, Jung G. Lipolanthionine peptides act as inhibitors of TLR2-mediated IL-8 secretion. Synthesis and structure-activity relationships. J Med Chem 2006; 49: 1754-1765
28 Khan S, Weterings JJ, Britten CM, de Jong AR, Graafland D, Melief CJ, van der Burg SH, van der Marel G, Overkleeft HS, Filippov DV, Ossendorp F. Chirality of TLR-2 ligand Pam3CysSK4 in fully synthetic peptide conjugates critically influences the induction of specific CD8⁺ T-cells. Mol Immunol 2009; 46: 1084-1091

Zusatzmaterial

Supporting Information