Skip to main content
SpringerLink
Log in

Marinamide, a novel alkaloid and its methyl ester produced by the application of mixed fermentation technique to two mangrove endophytic fungi from the South China Sea

  • Articles
  • Published:
Chinese Science Bulletin

Abstract

A novel 1-isoquinolone analog designated as marinamide (A) and its methyl ester (B), were produced by the application of mixed fermentation technique to two mangrove endophytic fungi (strains Nos. 1924 and 3893) from the South China Sea. Their structures were elucidated by comprehensive spectra methods (mainly by 2D NMR) as 4-(2-pyrrolyl)-1-isoquinolone-3-carboxylic acid (A) and methyl 4-(2-pyrrolyl)-1-isoquinolone-3-carboxylate (B), respectively. Compounds A and B were not obtained when either strain was cultured individually under the same conditions. The results showed that the application of mixed fermentation technique maybe represents a potentially important approach to discover novel metabolites.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Blunt J W, Copp B R, Munro M H G, et al. Marine natural products. Nat Prod Rep, 2005, 22: 15–61

    Article  Google Scholar 

  2. Wei H, Itoh T, Kinoshita M, et al. Shimalactone A, a novel polyketide, from marine derived fungus Emericella variecolor GF10. Tetrahedron, 2005, 61(33): 8054–8058

    Article  Google Scholar 

  3. Wei H, Itoh T, Kinoshita M, et al. Cytotoxic sesterterpenes, 6-epi-ophiobolin G and 6-epi-ophiobolin N, from marine derived fungus Emericella variecolor GF10. Tetrahedron, 2004, 60(28): 6015–6019

    Article  Google Scholar 

  4. Klemke C, Kehraus S, Wright A D, et al. New secondary metabolites from the marine endophytic fungus Apiospora montagnei. J Nat Prod, 2004, 67(6): 1058–1063

    Article  Google Scholar 

  5. Tsukamote S, Miura S, Yamashita Y, et al. Aspermytin A: A new neurotrophic polyketide isolated from a marine-derived fungus of the genus Aspergillus. Bioorg & Med Chem Lett, 2004, 14(2): 417–420

    Article  Google Scholar 

  6. Koch I, Maskey R P, Biabani M A F, et al. 1-hydroxy-1-norresistomycin and resistoflavinmethyl ether: New antibiotics from marine-derived streptomycetes. J Antibiot, 2005, 58(8): 530–534

    Article  Google Scholar 

  7. Li F C, Maskey R P, Qin S, et al. Chinkomycins A and B: Isolation, structure elucidation, and biological activity of novel antibiotics from a marine Streptomyces sp. Isolate M045. J Nat Prod, 2005, 68(3): 349–353

    Article  Google Scholar 

  8. Maskey R P, Helmke E, Kayser O, et al. Anti-cancer and antibacterial trioxacarcins with high anti-malaria activity from a marine streptomycete and their absolute stereochemistry. J Antibiot, 2004, 57(12): 771–779

    Google Scholar 

  9. Stritzke K, Schulz S, Laatsch H, et al. Novel caprolactones from a marine streptomycete. J Nat Prod, 2004, 67(3): 395–401

    Article  Google Scholar 

  10. Maskey R P, Sevvana M, Uson I, et al. Gutingimycin: A highly complex metabolite from a marine streptomycete. Angew Chem Int Ed, 2004, 43(10): 1281–1283

    Article  Google Scholar 

  11. Liu H W, Fujiwara T, Nishikawa T, et al. Lissoclibadins 1–3, three new polysulfur alkoloids, from the ascidian Lissoclinum cf. badium. Tetrahedron, 2005, 61(36): 8611–8615

    Article  Google Scholar 

  12. Silipo A, Leone S, Molinaro A, et al. Complete structural elucidation of a novel lipooligosaccharide from the outer menbrane of the marine bacterium Shewanella pacifica. Eur J Org Chem, 2005, (11): 2281–2291

  13. Matsuo Y, Imagawa H, Nishizawa M, et al. Isolation of an algal morphogenesis inducer from a marine bacterium. Science, 2005, 307(5715): 1598–1598

    Article  Google Scholar 

  14. Hickford S J H, Kupper F C, Zhang G P, et al. Petrobactin sulfonate, a new siderophore produced by the marine bacterium marinobacter hydrocarbonoclasticus. J Nat Prod, 2004, 67(11): 1897–1899

    Article  Google Scholar 

  15. Wu X Y, Liu X H, Jiang G C, et al. Xyloketal G, a novel metabolite from the mangrove fungus Xylaria sp. 2508. Chem Nat Comp, 2005, 41(1): 27–29

    Article  Google Scholar 

  16. Yin W Q, Zou J M, She Z G, et al. Two cyclic peptides produced by the endophytic fungus #2221 from Castaniopsis fissa on the South China Sea coast. Chin Chem Lett, 2005, 16(2): 219–222

    Google Scholar 

  17. Li H J, Lin Y C, Yao J H, et al. Two new metabolites from the mangrove endophytic fungus no. 2524. J Asian Nat Prod Res, 2004, 6(3): 185–191

    Article  Google Scholar 

  18. Li H J, Lin Y C, Vrijmoed L L P, et al. A new cytotoxic sterol produced by an endophytic fungus from Castaniopsis fissa at the South China Sea coast. Chin Chem Lett, 2004, 15(4): 419–422

    Google Scholar 

  19. Zhu F, Lin Y C, Zhou S N. Anthroquinone derivatives isolated from marine fungus #2526 from the South China Sea. Chin J Org Chem, 2004, 24(9): 1114–1117

    Google Scholar 

  20. Chen G Y, Lin Y C, Wen L, et al. Two new metabolites of a marine endophytic fungus (No. 1893) from an estuarine mangrove on the South China Sea coast. Tetrahedron, 2003, 59(26): 4907–4909

    Article  Google Scholar 

  21. Lin Y C, Li H J, Jiang G C, et al. A novel γ-lactone, eutypoid-A and other metabolites from marine fungus Eutypa sp. (#424) from the South China Sea. India J Chem Sec B, 2002, 41B: 1542–1544

    Google Scholar 

  22. Lin Y C, Wang J, Wu X Y, et al. A novel compound enniatin G from the mangrove fungus Halosarpheia sp. (strain 732) from the South China Sea. Aust J Chem, 2002, 55: 225–227

    Article  Google Scholar 

  23. Lin Y C, Wang J, Zhou S N, et al. New isocoumarins from the mangrove endophytic fungus #2533. Chem J Internet, 2001, 3(7): 30–33

    Google Scholar 

  24. Lin Y C, Wu X Y, Feng S, et al. A novel N-cinnamoylcyclopeptide containing an allenic ether from the fungus Xylaria sp. (strain #2508) from the South China Sea. Tetrahedron Lett, 2001, 42: 449–451

    Article  Google Scholar 

  25. Lin Y C, Wu X Y, Feng S, et al. Five unique compounds: Xyloketals from mangrove fungus Xylaria sp. From the South China Sea coast. J Org Chem, 2001, 66: 6252–6256

    Article  Google Scholar 

  26. Zhu F, Liu X H, Wen L, et al. Metabolites of marine fungus #1924 from the South China Sea. Acta Scientia Natur Univ Sunyatseni, 2005, 44(4): 66–69

    Google Scholar 

  27. Zhu F, Lin Y C. Two sphingolipids isolated from a mangrove endophytic fungus. Chin J Org Chem, 2005, 25(S2): 584

    Google Scholar 

  28. Maeda H, Suzuki M, Sugano H, et al. Synthesis and central nervous system actions of thyrotropin-releasing hormone analogs containing a 1-oxo-1,2,3,4-tetrahydroisoquinoline moiety. Chem Pharm Bull, 1988, 36(1): 190–201

    Google Scholar 

  29. Ukita T, Nakamura Y, Kubo A, et al. Novel, potent, and selective phosphodiesterase 5 inhibitors: Synthsesis and biological activities of a series of 4-aryl-1-isoquinolinone derivatives. J Med Chem, 2001, 44: 2204–2218

    Article  Google Scholar 

  30. Wiesel I, Rehm H J, Bisping B. Improvement of tempe fermentations by application of mixed cultures consisting of Rhizopus sp. and bacterial strains. Appl Microbiol Biotechnol, 1997, 47: 218–225

    Article  Google Scholar 

  31. Gutierrez-Corres M, Tengerdy R P. Xylanase production by fungal mixed culture solid substrate fermentation on sugar canebagasse. Biotechnol Lett, 1998, 20: 45–47

    Article  Google Scholar 

  32. Strongman D B, Miller J D, Calhoun L, et al. The biochemical basis for interference competition among some lignicolous marine fungi. Bot Mar, 1987, 30(1): 21–26

    Article  Google Scholar 

  33. Burgess J G, Jordan E M, Bregu M, et al. Microbial antagonism: A neglected avenue of natural products research. J Biotechnol, 1999, 70: 27–32

    Article  Google Scholar 

  34. Sonnenbichler J, Dietrich J, Peipp H. Secondary fungal metabolites and their biological activities, 5. Investigations concerning the induction of the biosynthesis toxic secondary metabolites in basidiomycetes. Biol Chem Hoppe-Seyler, 1994, 375(1): 71–79

    Google Scholar 

  35. Cueto M, Jensen P R, Kauffman C, et al. Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge. J Nat Prod, 2001, 64: 1444–1446

    Article  Google Scholar 

  36. Oh D C, Jensen P R, Kauffman C A, et al. Libertellenones A-D: Induction of cytotoxic diterpenoid biosynthesis by marine microbial competition. Bioorg & Med Chem, 2005, 13(17): 5267–5273

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Foshan University, Foshan, 528000, China

    Zhu Feng

  2. School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou, 510275, China

    Lin Yongcheng

Authors
  1. Zhu Feng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lin Yongcheng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhu Feng.

About this article

Cite this article

Zhu, F., Lin, Y. Marinamide, a novel alkaloid and its methyl ester produced by the application of mixed fermentation technique to two mangrove endophytic fungi from the South China Sea. CHINESE SCI BULL 51, 1426–1430 (2006). https://doi.org/10.1007/s11434-006-1426-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11434-006-1426-4

Keywords

Search

Navigation