Stachybotrys chartarum: A fungus for our time

Phytochemistry

Volumn 64, Issue 1, 2003, Pages 53-60

  Jarvis, Bruce B ^a  

^a Bldg 142   (United States)

Author keywords

Atranones; Dolabellanes; Drimanes; Memnoniella echinata; Stachybotrys chartarum; Trichothecenes; Triprenyl phenols

Indexed keywords

ATRANONE; DITERPENOID; NATURAL PRODUCT; PHENOL DERIVATIVE; TRICHOTHECENE DERIVATIVE; UNCLASSIFIED DRUG;

DECARBOXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS; FUNGUS CULTURE; HYDROLYSIS; MEMNONIELLA ECHINATA; METABOLITE; MICHAEL ADDITION; NONHUMAN; PRENYLATION; REVIEW; STACHYBOTRYS CHARTARUM; STRUCTURE ANALYSIS;

FUNGI; STACHYBOTRYS CHARTARUM; STACHYBOTRYS ECHINATA;

EID: 0041821540     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(03)00275-9     Document Type: Review

References (51)

1. Andersen, B., Nielsen, K.F., Jarvis, B.B., 2002. Characterization of Stachybotrys from water-damaged buildings based on morphology, growth and metabolite production. Mycologia 94, 392-403.
2. Andersen, B., Nielsen, K.F., Thrane, U., Cruse, M., Taylor, J., Jarvis, B.B., 2003. Stachybotrys chlorohalonata, a new species from water-damaged buildings. Mycologia, in press.
3. Assouline-Dayan, Y., Leong, A., Shoenfeld, Y., Gershwin, M.E., 2002. Studies of sick building syndrome. IV. Mycotoxicosis. J. Asthma 39, 191-201.
4. Ayer, W.A., Miao, S., 1992. Secondary metabolites of the aspen fungus Stachybotrys cylindrospora. Can. J. Chem. 71, 487-493.
5. Burge, H.A., 2001. Fungi: toxic killers or unavoidable nuisances? Ann. Aller. Asthma Immun. 87 (Suppl. 3), 52-56.
6. Croft, W.A., Jarvis, B.B., Yatawara, C.S., 1986. Airborne outbreak of trichothecene toxicosis. Atmospheric Environ. 20, 549-552.
7. Cruse, M., Telerant, R., Gallagher, T., Lee, T., Taylor, J.W., 2002. Cryptic species in Stachybotrys chartarum. Mycologia 94, 814-822.
8. Dearborn, D.G., Yike, I., Sorenson, W.G., Miller, M.J., Etzel, R.A., 1999. Overview of investigations into pulmonary hemorrhage among infants in Cleveland, Ohio. Environmental Health Perspectives 107 (Suppl. 3), 495-499.
9. Drobotko, V.G., 1945. Stachybotryotoxicosis: a new disease of horses and humans. American Review Soviet Medicine 2, 238-242.
10. El-Kady, I.A., Moubasher, M.H., 1982. Some cultural conditions that control production of roridin E and satratoxiun H. Cryptog., Mycol. 3, 151-162.
11. El Maghraby, O.M.O., Bean, G.A., Jarvis, B.B., Aboul-Nasr, M.B., 1991. Macrocyclic trichothecenes produced by Stachybotrys isolates from Egypt and Eastern Europe. Mycopathologia 113, 109-115.
12. Eppley, R.M., Bailey, W.J., 1973. 12,13-Epoxy-delta 9-trichothecenes as the probable mycotoxins responsible for stachybotryotoxicosis. Science 181, 758-760.
13. Ferrari, P., Stefananelli, S., Islam, K., 1995. Reassignment of the structure of myo-inositol monophosphatase inhibitor L-671,776. J. Chem. Research (S) 110-111.
14. Forgacs, J., 1972. Stachybotryotoxicosis. In: Kadis, S., Ceigler, A., Ajl, S.J. (Eds.), Microbial Toxins, Vol. VIII. Academic Press, New York, pp. 95-128.
15. Frisvad, J.C., Filtenborg, O., 1989. Terverticillate penicillia: chemotaxonomy and mycotoxin production. Mycologia 81, 837-861.
16. Haugland, R.A., Vesper, S.J., Harmon, S., 2001. Phylogenetic relationships of Memnoniella and Stachybotrys species inferred from ribosomal DNA sequences and evaluation of morphological features for Memnoniella species identification. Mycologia 93, 54-65.
17. Hinkley, S.F., Jarvis, B.B., 2000. Method for Stachybotrys toxins. In: Trucksess, M.W., Pohland, A.E. (Eds.), Methods in Molecular Biology: The Mycotoxin Protocols, Vol. 157. Humana Press, pp. 173-194.
18. Hinkley, S.F., Fettinger, J.C., Dudley, K., Jarvis, B.B., 1999a. Memnobotrins and memnoconols: novel metabolites from Memnoniella echinata. J. Antibiotics 52, 988-997.
19. Hinkley, S.F., Jiang, J., Mazzola, E.P., Jarvis, B.B., 1999b. Atranones: novel diterpenoids from the toxigenic mold Stachybotrys atra. Tetrahedron Letters 40, 2725-2728.
20. Hinkley, S.F., Mazzola, E.P., Fettinger, J.C., Lam, Y.-F., Jarvis, B.B., 2000. Atranones A-G: a unique series of metabolites from the toxigenic mold Stachybotrys chartarum. Phytochemistry 55, 663-673.
21. Hinkley, S. F., Moore, J. A., Squillari, J., Tak, H., Oleszewski, R., Mazzola, E. P., Jarvis, B. B., 2003. New atranones from the fungus Stachybotrys chartarum. Magn. Reson. Chem., 47, 337-343.
22. Jarvis, B.B., Stahly, G.P., Pavanasasivam, G., Midiwo, J.O., DeSilva, T., Holmlund, C.E., Mazzola, E.P., Geoghegan Jr., R.F., 1982. Isolation and characterization of the trichoverroids and new roridins and verrucarins. J. Org. Chem. 47, 1117-1124.
23. Jarvis, B.B., Yatawara, C.S., 1986. Roritoxins, new macrocyclic trichothecenes from Myrothecium roridum. J. Org. Chem. 51, 2906-2910.
24. Jarvis, B.B., Lee, Y.-W., Yatawara, S.N., Cömezoglu, C.S., 1986a. Trichothecenes produced by Stachybotrys atra from Eastern Europe. Appl. Environ. Microbiol. 51, 915-918.
25. Jarvis, B.B., Cömezoglu, F.T., Lee, Y.-W., Flippen-Anderson, J.L., Gilardi, R.D., George, C.F., 1986b. Novel macrocyclic trichothecenes from Myrothecium roridum. Bull. Soc. Chim. Belg. 95, 681-697.
26. Jarvis, B.B., 1991. Macrocyclic trichothecenes. In: Sharma, R.P., Salunkhe, D.K. (Eds.), Mycotoxins and Phytoalexins in Human and Animal Health. CRC Press, Boca Raton, FL, pp. 361-421.
27. Jarvis, B.B., 1992. Macrocyclic trichothecenes from Brazilian Baccharis species: from microanalysis to large scale isolation. Phytochemical Analysis 3, 241-249.
28. Jarvis, B.B., Salemme, J., Morais, A., 1995. Stachybotrys toxins. 1. Natural Toxins 3, 10-16.
29. Jarvis, B.B., Sorenson, W.G., Hintikka, E.-L., Nikulin, M., Zhou, Y., Jiang, J., Wang, S., Hinkley, S., Etzel, R.A., Dearborn, D., 1998. Study of toxin production by isolates of Stachybotrys chartarum and Memnoniella echinata isolated during a study of pulmonary hemosiderosis in infants. Appl. Environ. Microbiol. 64, 3620-3625.
30. Jarvis, B.B., Zhou, Y., Jiang, J., Wang, S., Sorenson, W.G., Hintikka, E.-L., Nikulin, M., Parikka, P., Etzel, R.A., Dearborn, D.G., 1996. Toxigenic molds in water-damaged buildings: dechlorogriseofulvins from Memnoniella echinata. J. Nat. Prod. 59, 553-554.
31. Jenny, L., Borschberg, H.-J., 1995. Synthesis of the dolabellane diterpene hydrocarbon (±)-δ-araneosene. Helv. Chim. Acta 78, 715-731.
32. Jong, S.C., Davis, E.E., 1976. Contribution to the knowledge of Stachybotrys and Memnoniella in culture. Mycotaxon 3, 409-485.
33. Kaise, H., Shinohara, M., Miyazaki, W., Izawa, T., Nakano, Y., Sugawara, M., Sugiura, K., 1979. Structure of K-76, a complement inhibitor produced by Stachybotrys complementi nov. sp. K-76. J. Chem. Soc. Chem. Commun. 726-727.
34. Kaneto, R., Dobashi, K., Kojima, I., Sakai, K., Shibamoto, N., Yoshioka, T., Nishida, H., Okamoto, R., Akagawa, H., Mizuno, S., 1994. Mer-NF5003B, E and F, novel sesquiterpenoids as avian myeloblastosis virus protease inhibitors produced by Stachybotrys sp. J. Antibiotics 47, 727-730.
35. Kazutoshi, S., Eisaku, T., Miyauchi, M., Nakanishi, T., Tamashita, M., Shigematsu, N., Tada, T., Izumi, S., Okuhara, M., 1993. FR901459, a novel immunosuppressant isolated from Stachybotrys chartarum No. 19392. J. Antibiotics 46, 1788-1798.
36. Kordula, T., Banbula, A., Macomson, J., Travis, J., 2002. Isolation and properties of stachyrase A, a chymotrypsin-like serine proteinase from Stachybotrys chartarum. Infect. Immun. 70, 419-421.
37. Koster, B., Scott, J., Wong B., Malloch, D., Straus, N., 2003. A geographically diverse set of isolates indicates two phylogenetic lineages within Stachybotrys chartarum. Can. J. Botany, in press.
38. Loukaci, A., Kayser, O., Bindseil, K.U., Siems, K., Frevert, J., Abreu, P.M., 2000. New trichothecenes isolated from Holarrhena floribunda. J. Nat. Prod. 63, 52-56.
39. Minagawa, K., Kouzuki, S., Tani, H., Ishii, K., Tanimoto, T., Terui, Y., Kamigauchi, T., 2002. Novel stachyflin derivatives from Stachybotrys sp. RF-7260. J. Antibiotics 55, 239-248.
40. Page, E.H., Trout, D.B., 2001. The role of Stachybotrys mycotoxins in building-related illness. AIHAJ. 62, 644-648.
41. Peltola, J., Niessen, L., Nielsen, K.F., Jarvis, B.B., Andersen, B., Salkinoja-Salonen, M., Möller, E.M., 2002. Toxigenic diversity of two different RAPD groups of Stachybotrys chartarum isolates analyzed by potential for trichothecene production and for boar sperm cell motility inhibition. Can. J. Microbiol. 48, 1017-1029.
42. Proctor, R.H., 2000. Fusarium toxins: trichothecenes and fumonisins. In: Cary, J.W., Linz, J.E., Bhatnagar, D. (Eds.), Microbial Foodborne Diseases: Mechanisms of Pathogenisis and Toxin Synthesis. Technomic, Lancaster, PA, pp. 363-381.
43. Rodríguez, A.D., González, E., Ramírez, C., 1998. The structural chemistry, reactivity, and total synthesis of dolabellane diterpenes. Tetrahedron 54, 11683-11729.
44. Roggo, B.E., Petersen, F., Sills, M., Roesel, J.L., Moerker, T., Peter, H.H., 1995. Novel spirodihydrobenzofuranlactams as antagonists of endothelin and as inhibitors of HIV-1 protease produced by Stachybotrys sp. I. Fermentation, isolation and biological activity. J. Antibiotics 49, 13-19.
45. Saikawa, Y., Okamoto, H., Inui, T., Makabe, M., Okuno, T., Suda, T., Hashimoto, K., Nakata, M., 2001. Toxic principles of a poisonous mushroom Podostroma cornu-damae. Tetrahedron 57, 8277-8281.
46. Sakai, K., Watanabe, K., Masuda, K., Tsuji, M., Hasumi, K., Endo, A., 1995. Isolation, characterization and biological activities of novel triprenyl phenols as pancreatic cholesterol esterase inhibitors produced by Stachybotrys sp. F-1839. J. Antibiotics 48, 447-456.
47. Stefanelli, S., Sponga, F., Ferrari, P., Sottani, C., Corti, E., Brunati, C., Islam, K., 1996. Inhibitors of myoinositol monophosphatase, ATLC 20928 factors A and C isolation, physico-chemical characterization and biological properties. J. Antibiotics 49, 611-616.
48. Trapp, S.C., Jarvis, B.B., Hohn, T.M., 1998. Characterization of the macrocyclic trichothecene pathway gene cluster in Myrothecium roridum. Mol. Gen. Genet. 257, 421-432.
49. Ueno, Y. (Ed.), 1983. Trichothecenes: Chemical, Biological, and Toxicological Aspects. Elsevier, Amsterdam.
50. Vértesy, L., Kogler, H., Markus, A., Schiell, M., Vogel, M., Wink, J., 2001. Memmnopeptide A, a novel terpene peptide from Memnoniella with an activating effect on SERCA2. J. Antibiotics 54, 771-782.
51. Vesper, S.J., Magnuson, M.L., Dearborn, D.G., Yike, I., Haugland, R.A., 2001. Initial characterization of the hemolysin stachylysin from Stachybotrys chartarum. Infect. Immun. 69, 912-916.