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A Review on Bioactive Compounds from Marine-Derived Chaetomium Species

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초록

Filamentous marine fungi have proven to be a plentiful source of new natural products. Chaetomium, a widely distributed fungal genus in the marine environment, has gained much interest within the scientific community. In the last 20 years, many potential secondary metabolites have been detected from marine-derived Chaetomium. In this review, we attempt to provide a comprehensive summary of the natural products produced by marine-derived Chaetomium species. A total of 122 secondary metabolites that were described from 2001 to 2021 are covered. The structural diversity of the compounds, along with details of the sources and relevant biological properties are also provided, while the relationships between structures and their bioactivities are discussed. It is our expectation that this review will be of benefit to drug development and innovation.

Abstract

Filamentous marine fungi have proven to be a plentiful source of new natural products. Chaetomium, a widely distributed fungal genus in the marine environment, has gained much interest within the scientific community. In the last 20 years, many potential secondary metabolites have been detected from marine-derived Chaetomium. In this review, we attempt to provide a comprehensive summary of the natural products produced by marine-derived Chaetomium species. A total of 122 secondary metabolites that were described from 2001 to 2021 are covered. The structural diversity of the compounds, along with details of the sources and relevant biological properties are also provided, while the relationships between structures and their bioactivities are discussed. It is our expectation that this review will be of benefit to drug development and innovation.

참고문헌 (75)

  1. Von Arx JA, "The ascomycete genus Chaetomium", Beih. Nova. Hedw, 84, pp.1~162 (1986)
  2. Zhang Q, "Chemical and bioactive diversities of the genus Chaetomium secondary metabolites", Mini Rev. Med. Chem, 12, pp.127~148 (2012)
  3. Nighat F, "Chaetomium endophytes : a repository of pharmacologically active metabolites", Acta Physiol. Plant, 38, pp.136~ (2016)
  4. Xu GB, "Review on the secondary metabolites and its biological activities from Chaetomium fungi", Nat. Prod. Res. Dev, 30, pp.515~525 (2018)
  5. Liang HL, "Secondary metabolites from Chaetomiun globosum and their bioactivities", Nat. Prod. Res. Dev, 30, pp.702~707 (2018)
  6. Shin HJ, "Natural products from marine fungi", Mar. Drugs, 18, pp.230~ (2020)
  7. Pang KL, "‘Marine fungi’and ‘marine-derived fungi’in natural product chemistry research : toward a new consensual definition", Fungal Biol. Rev, 30, pp.163~175 (2016)
  8. Overy DP, "The neglected marine fungi, sensu stricto, and their isolation for natural products’ discovery", Mar. Drugs, 17, pp.42~ (2019)
  9. Schumann J, "Molecular basis of cytochalasan biosynthesis in fungi : gene cluster analysis and evidence for the involvement of a PKS-NRPS hybrid synthase by RNA silencing", J. Am. Chem. Soc, 129, pp.9564~9565 (2007)
  10. Haidle AM, "An enantioselective, modular, and general route to the cytochalasins : Synthesis of L-696, 474 and cytochalasin B", Proc. Natl. Acad. Sci. USA, 101, pp.12048~12053 (2004)
  11. Scherlach K, "The chemistry and biology of cytochalasans", Nat. Prod. Rep, 27, pp.869~886 (2010)
  12. Skellam E, "The biosynthesis of cytochalasans", Nat. Prod. Rep, 34, pp.1252~1263 (2017)
  13. Cui CM, "Cytoglobosins A-G, cytochalasans from a marine-derived endophytic fungus, Chaetomium globosum QEN-14", J. Nat. Prod, 73, pp.729~733 (2010)
  14. Ge HM, "Precursor-directed fungal generation of novel halogenated chaetoglobosins with more preferable immunosuppressive action", Chem. Commun, 47, pp.2321~2323 (2011)
  15. Zhang Z, "Cytoglobosins H and I, new antiproliferative cytochalasans from deepdea-derived fungus Chaetomium globosum", Mar. Drugs, 14, pp.233~ (2016)
  16. Guo ZL, "Chemical constituents of the gorgonian-derived fungus Chaetomium globosum", Chem. Nat. Comp, 53, pp.199~202 (2017)
  17. Qi J, "Chaetoglobosins and azaphilones from Chaetomium globosum associated with Apostichopus japonicus", Appl. Microbiol. Biotechnol, 104, pp.1545~1553 (2020)
  18. Luo XW, "HPLC-DAD-guided isolation of diversified chaetoglobosins from the coral-associated fungus Chaetomium globosum C2F17", Molecules, 25, pp.1237~ (2020)
  19. Hirose T, "Maruyama", Chem. Pharm. Bull., 38, pp.971~974 (1990)
  20. Minato H, "Chem", Pharm. Bull, 21, pp.2268~2277 (1973)
  21. Scherlach K, "The chemistry and biology of cytochalasans", Nat. Prod. Rep, 27, pp.869~886 (2010)
  22. Flashner M, "Structural features of cytochalasins responsible for Gram-positive bacterial inhibitions", J. Antibiot, 35, pp.1345~1350 (1982)
  23. Jiang CS, "Epipolythiodioxopiperazines from fungi : chemistry and bioactivities", Mini Rev. Med. Chem, 11, pp.728~745 (2011)
  24. Zhu M, "Irregularly bridged epipolythiodioxopiperazines and related analogues : sources, structures, and biological activities", J. Nat. Prod, 83, pp.2045~2053 (2020)
  25. Gomes NGM, "Double the chemistry, double the fun : structural diversity and biological activity of marine-derived diketopiperazine dimers", Mar. Drugs, 17, pp.551~ (2019)
  26. Yun K, "Cristazine, a new cytotoxic dioxopiperazine alkaloid from the mudflat-sediment-derived fungus Chaetomium cristatum", Chem. Pharm. Bull, 64, pp.59~62 (2016)
  27. Jo MJ, "Cristazine, a novel dioxopiperazine alkaloid, induces apoptosis via the death receptor pathway in A431 cells", Drug Dev. Res, 80, pp.504~512 (2019)
  28. Mcinnes AG, "The structure of chetomin", J. Am. Chem. Soc, 98, pp.6741~6741 (1976)
  29. Staab A, "Effects of HIF-1 inhibition by chetomin on hypoxiarelated transcription and radiosensitivity in HT1080 human fibrosarcoma cells", BMC Cancer, 7, pp.213~ (2007)
  30. Viziteu E, "Chetomin, targeting HIF-1α", p300 complex, exhibits antitumour activity in multiple myeloma, 2016, pp.114, 519~523
  31. Min S, "Chetomin, a Hsp90", HIF1α pathway inhibitor, effectively targets lung cancer stem cells and non-stem cells, 2020, pp.21, 698~708
  32. Dewangan J, "Chetomin induces apoptosis in human triple-negative breast cancer cells by promoting calcium overload and mitochondrial dysfunction", Biochem. Biophys. Res. Commun, 495, pp.1915~1921 (2018)
  33. Kyoung-Su Kim, "Anti-Inflammatory Effect of Neoechinulin A from the Marine Fungus Eurotium sp. SF-5989 through the Suppression of NF-кB and p38 MAPK Pathways in Lipopolysaccharide-Stimulated RAW264.7 Macrophages", Molecules, 18(11), pp.13245~13259 (2013), MDPI AG[DOI]
  34. Alhadrami HA, "Neoechinulin A as a promising SARS-CoV-2 Mpro inhibitor : in vitro and in silico study showing the ability of simulations in discerning active from inactive enzyme inhibitors", Mar. Drugs, 20, pp.163~ (2022)
  35. Maruyama K, "Protective properties of Neoechinulin A against SIN-1-induced neuronal cell death", J. Biochem, 136, pp.81~87 (2004)
  36. Sasaki-Hamada S, "Neoechinulin A induced memory improvements and antidepressant-like effects in mice", Prog. Neuropsychopharmacol. Biol. Psychiatry, 71, pp.155~161 (2016)
  37. Kimoto K, "Structure-activity relationships of neoechinulin A analogues with cytoprotection against peroxynitrite-induced PC12 cell death", J. Antibiot, 60, pp.614~621 (2007)
  38. Singh TP, "Recent progress in biological activities of indole and indole alkaloids", Mini-Rev. Med. Chem, 18, pp.9~25 (2018)
  39. Li SM, "Prenylated indole derivatives from fungi : Structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis", Nat. Prod. Rep, 27, pp.57~78 (2010)
  40. Kochanowska-Karamyan AJ, "Marine indole alkaloids : potential new drug leads for the control of depression and anxiety", Chem. Rev, 110, pp.4489~4497 (2010)
  41. Netz N, "Marine indole alkaloids", Mar. Drugs, 13, pp.4814~4914 (2015)
  42. Yan W, "Pictet–Spengler reaction-based biosynthetic machinery in fungi", Proc. Natl. Acad. Sci. USA, 111, pp.18138~18143 (2014)
  43. Yan W, "Generation of indoles with agrochemical significance through biotransformation by Chaetomium globosum", J. Nat. Prod, 82, pp.2132~2137 (2019)
  44. Osmanova N, "Azaphilones : a class of fungal metabolites with diverse biological activities", Phytochem. Rev, 9, pp.315~342 (2010)
  45. Xiaowei Luo, "Isochromophilones A–F, Cytotoxic Chloroazaphilones from the Marine Mangrove Endophytic Fungus Diaporthe sp. SCSIO 41011", Journal of Natural Products, 81(4), pp.934~941 (2018), American Chemical Society (ACS)[DOI]
  46. Gao JM, "Azaphilones : chemistry and biology", Chem. Rev, 113, pp.4755~4811 (2013)
  47. Yamada T, "Absolute stereostructures of cytotoxic metabolites, chaetomugilins A–C, produced by a Chaetomium species separated from a marine fish", Tetrahedron Lett, 49, pp.4192~4195 (2008)
  48. Yasuhide M, "Chaetomugilins, new selectively cytotoxic metabolites, produced by a marine fish-derived Chaetomium species", J. Antibiot, 61, pp.615~622 (2008)
  49. Yamada T, "Absolute stereostructures of chaetomugilins G and H produced by a marine-fish-derived Chaetomium species", J. Antibiot, 62, pp.353~357 (2009)
  50. Yasuhide Muroga, "Chaetomugilins I–O, new potent cytotoxic metabolites from a marine-fish-derived Chaetomium species. Stereochemistry and biological activities", Tetrahedron, 65(36), pp.7580~7586 (2009), Elsevier BV[DOI]
  51. Yamada T, "New azaphilones, seco-chaetomugilins A and D, produced by a marine-fish-derived Chaetomium globosum", Mar. Drugs, 7, pp.249~257 (2009)
  52. Muroga Y, "11-and 4′-Epimers of chaetomugilin A, novel cytostatic metabolites from marine fish-derived fungus Chaetomium globosum", Helv. Chim. Acta, 93, pp.542~549 (2010)
  53. Yamada T, "New class azaphilone produced by a marine fish-derived Chaetomium globosum. The stereochemistry and biological activities", Bioorg. Med. Chem, 19, pp.4106~4113 (2011)
  54. Yamada T, "Three new azaphilones produced by a marine fish-derived Chaetomium globosum", J. Antibiot, 65, pp.413~417 (2012)
  55. Hu X, "Chaetomugilin J enhances apoptosis in human ovarian cancer A2780 cells induced by cisplatin through inhibiting pink1", parkin mediated mitophagy, 2020, pp.13, 9967~9976
  56. Wang W, "Chlorinated azaphilonepigments with antimicrobial and cytotoxic activities isolated from the deep sea derived fungus Chaetomium sp", NA-S01-R1. Mar. Drugs 1, 6, pp.61~ (2018)
  57. Sun C, "New glutamine-containing azaphilone alkaloids from deep-sea-derived fungus Chaetomium globosum HDN151398", Mar. Drugs, 17, pp.53~ (2019)
  58. Wang W, "Cytotoxic nitrogenated azaphilones from the deep-sea-derived fungus Chaetomium globosum MP4-S01-7", J. Nat. Prod, 83, pp.1157~1166 (2020)
  59. Piyasena KGNP, "Two phytotoxic azaphilone derivatives from Chaetomium globosum, a fungal endophyte isolated from Amaranthus viridis leaves", Mycology, 6, pp.158~160 (2015)
  60. Wang D, "Potential allelopathic azaphilones produced by the endophytic Chaetomium globosum TY1 inhabited in Ginkgo biloba using the one strain-many compounds method", Nat. Prod. Res, 31, pp.724~728 (2017)
  61. Youn UJ, "Determination of the absolute configuration of chaetoviridins and other bioactive azaphilones from the endophytic fungus Chaetomium globosum", Bioorg. Med. Chem. Lett, 25, pp.4719~4723 (2015)
  62. Phonkerd N, "Bio-spiro-azaphilones and azaphilones from the fungi Chaetomium cochliodes VTh01 and C. cochliodes Cth05", Tetrahedron, 64, pp.9636~9645 (2008)
  63. Awad NE, "Bioassays guided isolation of compounds from Chaetomium globosum", J. Mycol. Med, 24, pp.35~42 (2014)
  64. Loureiro DRP, "Structures, activities and drug-likeness of anti-infective xanthone derivatives isolated from the marine environment : a review", Molecules, 24, pp.243~ (2019)
  65. Santos CMM, "A comprehensive review on xanthone derivatives as α-glucosidase inhibitors", Eur. J. Med. Chem, 157, pp.1460~1479 (2018)
  66. Wezeman T, "Xanthone dimers : a compound family which is both common and privileged", Nat. Prod. Rep, 32, pp.6~28 (2015)
  67. Resende DISP, "Lichen xanthones as models for new antifungal agents", Molecules, 23, pp.2617~ (2018)
  68. Pinto MMM, "Xanthones from marine-derived microorganisms : isolation, structure elucidation and biological activities", Encycl. Anal. Chem, 27, pp.1~21 (2014)
  69. Bedi P, "Synthesis and biological properties of pharmaceutically important xanthones and benzoxanthone analogs : A brief review", Asian J. Pharm. Clin. Res, 11, pp.12~20 (2018)
  70. Lösgen S, "Structure and biosynthesis of chaetocyclinones, new polyketides produced by an endosymbiotic fungus", Eur. J. Org. Chem, 13, pp.2191~2196 (2007)
  71. Pontius A, "Antiprotozoal activities of heterocyclic-substituted xanthones from the marine-derived fungus Chaetomium sp", J. Nat. Prod, 71, pp.1579~1584 (2008)
  72. Wang S, "Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphoniaurceolata", J. Nat. Prod, 69, pp.1622~1625 (2006)
  73. Abdel-LateffA, "Chaetominedione, a new tyrosine kinase inhibitor isolated from the algicolous marine fungus Chaetomium sp", Tetrahedron Lett, 49, pp.6398~6400 (2008)
  74. Jin M, "Properties and applications of extremozymes from deep-sea extremophilic microorganisms : amini review", Mar. Drugs, 17, pp.656~ (2019)
  75. Tortorella E, "Antibiotics from deep-sea microorganisms : current discoveries and perspectives", Mar. Drugs, 16, pp.355~ (2018)

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