Phomosines H-J, novel highly substituted biaryl ethers, isolated from the endophytic fungus Phomopsis sp. from Ligustrum vulgare

Natural Product Communications

Volumn 6, Issue 12, 2011, Pages 1907-1912

  Krohn, Karsten ^a   Farooq, Umar ^a,e   Hussain, Hidayat ^a   Ahmed, Ishtiaq ^a   Rheinheimer, Joachim ^b   Draeger, Siegfried ^c   Schulz, Barbara ^c   Van Ree, Teunis ^d  

^a UNIVERSITY OF PADERBORN   (Germany)

^b BASF SE   (Germany)

^c TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^d UNIVERSITY OF VENDA   (South Africa)

^e Tobe Camp University Road Abbottabad   (Pakistan)

Author keywords

Endophytic fungi; Fungal metabolites; Phomopsis sp; Phomosines

Indexed keywords

3 [2 (BENZYLOXYMETHYL) 3 HYDROXY 5 METHYLPHENOXY] 4 HYDROXY 2,5 DIMETHYLBENZOIC ACID; ANTIINFECTIVE AGENT; FUNGAL EXTRACT; METHYL 3 [2 (BENZYLOXYMETHYL) 3 HYDROXY 5 METHYLPHENOXY] 4 HYDROXY 2,5 DIMETHYLBENZOATE; METHYL 4 HYDROXY 3 [3 HYDROXY 5 METHYL 2 (3 OXOBUT 1 ENYL)PHENOXY] 2,5 DIMETHYLBENZOATE; PHOMOPSIS EXTRACT; PHOMOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENDOPHYTE; FUNGUS; LIGUSTRUM VULGARE; MASS SPECTROMETRY; NONHUMAN; PHOMOPSIS; PLANT; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 83455235185     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1100601229     Document Type: Article

References (27)

1. Meng L, Sun P, Li L, Draeger S, Schulz B, Krohn K, Yia Y, Zhang W. (2011) Endophytic fungus Penicillium chrysogenum, a new source of hypocrellins. Biochemical Systematics and Ecology, 39, 163-165.
2. (a) Schulz B, Boyle C, Draeger S, Römmert A, Krohn K. (2002) Endophytic fungi: a source of novel biologically active secondary metabolites. Mycological Research, 106, 996-1004;
3. (b) Tan RX Zou WZ. (2001) Endophytes: a rich source of functional metabolites. Natural Products Reports, 18, 448-459. (Pubitemid 32773844)
4. Cole RJ. (1981) Handbook of Toxic Fungal Metabolites. Cox RH. (Ed.), Academic Press, New York, London.
5. Wheeler MM, Wheeler DMS, Peterson GW. (1975) Anthraquinone pigments from the phytopathogen Phomopsis juniperovora Hahn. Phytochemistry, 14, 288-289.
6. Izawa Y, Shimizu T, Koyama K, Natori S. (1989) Six new 10-pheynl-[11]cytochalasans, cytochalasins N - S from Phomopsis sp. Tetrahedron, 45, 2323-2335. (Pubitemid 19108228)
7. Tomioka T, Izawa Y, Koyama K, Natori S. (1987) Three 10-phenyl [11]cytochalasana, cytochalasins N, O, and P from Phomopsis sp. Chemical & Pharmaceutical Bulletin, 35, 902-905. (Pubitemid 17039983)
8. Horn WS, Simmonds MSJ, Schwartz RE, Blaney WM (1995) Phomopsichalasin, a novel antimicrobial agent from an endophytic Phomopsis sp. Tetrahedron, 51, 3969-3978.
9. Tomoda H, Namatame I, Si S, Kawaguchi K, Masuma R, Namikoshi M, Omura S. (1999) Phenochalasins, inhibitors of lipid droplet formation in mouse macrophages produced by Phomopsis sp. FT-0211. Journal of Antibiotics, 52, 851-856. (Pubitemid 29532954)
10. Tsantrizos YS, Ogilvie KK, Watson AK. (1992) Phytotoxic metabolites of Phomopsis convolvulus, a host-specific pathogen of field bindweed. Canadian Journal of Chemistry, 70, 2276-2284.
11. Isaka M, Jaturapat A, Rukseree K, Danwisetkanjana K, Tantichareon M, Thebtaranonth Y. (2001) Phomoxanthones A and B, novel xanthone dimers from the endophytic fungus Phomopsis species. Journal of Natural Products, 64, 1015-1018. (Pubitemid 32800329)
12. Elsässer B, Krohn K, Flörke U, Root N, Aust H-J, Draeger S, Schulz B, Antus S, Kurtán T. (2005) X-Ray structure determination, absolute configuration and biological activity of phomoxanthone A. European Journal of Organic Chemistry, 4563-4570.
13. Rukachaisirikul V, Sommart U, Phongpaichit S, Sakayaroj J, Kirtikara K. (2008) Metabolites from the endophytic fungus Phomopsis sp. PSU-D15. Phytochemistry, 69, 783-787.
14. Claydon N, Grove JF, Pople M. (1985) Elm bark beetle boring and feeding deterrents from Phomopsis oblonga. Phytochemistry, 24, 937-943.
15. Dai J, Krohn K, Gehle D, Kock I, Flörke U, Aust H-J, Draeger S, Schulz B, Rheinheimer J. (2005) New oblongolides isolated from the endophytic fungus Phomopsis sp. from Melilotus dentata from the shores of the Baltic Sea. European Journal of Organic Chemistry, 4009-4016. (Pubitemid 41323540)
16. Hussain H, Akhtar N, Draeger S, Schulz B, Pescitelli G, Salvadori P, Antus S, Kurtán T, Krohn K. (2009) New bioactive 2,3- epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. from Laurus azorica. European Journal of Organic Chemistry, 749-756.
17. Edgar JA, Frahn JL, Cockrum PA, Culvenor CCJ. (1986) Lupinosis. the chemistry and biochemistry of phompsins. Bioactive Molecules, 169-184.
18. Nouguier R, Bertrand MP, Picon P, Perfetti P. (1994) Diastereoselective synthesis of a methylated derivative of phomozin, a phytotoxin isolated from Phomopsis helianthi, a phytopathogenic fungus of sunflowers. Tetrahedron Letters, 35, 8171-8172.
19. Huang Z, Cai X, Shao C, She Z, Xia X, Chen Y, Yang J, Zhou, S Lin Y. (2008) Chemistry and weak antimicrobial activities of phomopsins produced by mangrove endophytic fungus Phomopsis sp. ZSU-H76. Phytochemistry, 69, 1604-1608.
20. Du X, Lu C, Li Y, Zheng Z, Su W, Shen Y (2008) Three new antimicrobial metabolites of Phomopsis sp. Journal of Antibiotics, 61, 250-253.
21. Davis RA, Andjic V, Kotiw M, Shivas RG. (2005) Phomoxins B and C: Polyketides from an endophytic fungus of the genus Eupenicillium. Phytochemistry, 66, 2771-2775. (Pubitemid 41727665)
22. Krohn K, Michel A, Roemer E, Flörke U, Aust H-J, Draeger S, Schulz B, Wray V. (1995) Biologically active metabolites from fungi, 6. Phomosines A-C. Three new biaryl ethers from Phomopsis sp. Natural Product Letters, 9, 309-314.
23. Dai J, Krohn K, Flörke U, Gehle D, Aust H-J, Draeger S, Schulz B, Rheinheimer K. (2005) Novel highly substituted biaryl ethers, phomosines D-G, isolated from the endophytic fungus Phomopsis sp. from Adenocarpus foliolosus. European Journal of Organic Chemistry, 5100-5105. (Pubitemid 41736466)
24. Kanai K, Sakamoto I, Ogawa S, Suami T. (1987) Synthesis of 1,4-diaminocyclitol antibiotics. III. Synthesis of 4-hydroxypurpurosamine B derivatives. Bulletin of the Chemical Society of Japan, 60, 1529-1531. (Pubitemid 17087408)
25. Horita K, Yoshioka T, Tanaka T, Oikawa Y, Yonemitsu O. (1986) On the selectivity of deprotection of benzyl, mpm (4-methoxybenzyl) and dmpm (3,4-dimethoxybenzyl) protecting groups for hydroxy functions. Tetrahedron, 42, 3021-3028.
26. Schulz B, Sucker J, Aust H-J, Krohn K, Ludewig K, Jones PG, Doering D. (1995) Biologically active secondary metabolites of endopyhtic Pezicula species. Mycological Research, 99, 1007-1015.
27. Höller U, Wright AD, Matthée GF, König GM, Draeger S, Aust H-J, Schulz B. (2000) Fungi from marine sponges: Diversity, biological activity and secondary metabolites. Mycological Research, 104, 1354-1365. (Pubitemid 32102798)