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Planta Med 2017; 83(07): 654-660
DOI: 10.1055/s-0042-119650
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Novel Isochroman Dimers from Stachybotrys sp. PH30583: Fermentation, Isolation, Structural Elucidation and Biological Activities

Wei Li   *
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
2   School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, China
,
Ya-Bin Yang   *
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Xue-Qiong Yang
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Hui-Ding Xie
2   School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, China
,
Zhi-Hui Shao
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Hao Zhou
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Cui-Ping Miao
3   Yunnan Institute of Microbiology, Yunnan University, Kunming, China
,
Li-Xing Zhao
3   Yunnan Institute of Microbiology, Yunnan University, Kunming, China
,
Zhong-Tao Ding
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
› Author Affiliations
Further Information

Publication History

received 08 April 2016
revised 10 July 2016

accepted 18 October 2016

Publication Date:
02 November 2016 (online)

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Abstract

The rare anishidiol and five new isochromans, including three novel dimers with unprecedented skeletons, were isolated from Stachybotrys sp. PH30583. Their structures were determined by spectral analyses. The bioactivities of these compounds were also investigated. The dimers (6–10) inhibited acetylcholinesterase at 50 µM, but the monomers did not. To investigate the biogenesis of the novel dimers, a time-course investigation of metabolite production was undertaken.

Key words

Stachybotrys sp. - Hypocreales - isochroman - bioactivity - dimer - anti-acetylcholinesterase

* W. Li and Y. B. Yang contributed equally to this paper.


Supporting Information

1D, 2D NMR, MS, and CD spectra of the new compounds 2–10 (Figs. 6 S–31 S), HPLC investigation on the metabolic production of these compounds from PH30583 (Fig. 1 S), chiral HPLC analyses of the compounds (Fig. 2 S), lowest-energy conformers of stachydein and stachiol with different configurations (Fig. 3 S), and Tables 1 S with the biological activity test of these compounds are available as Support Information.

 

  • References

  • 1 Johanning E, Biagini R, Hull D, Morey P, Jarvis B, Landsbergis P. Health and immunology study following exposure to toxigenic fungi (Stachybotrys chartarum) in a water-damaged office environment. Int Arch Occup Environ Health 1996; 68: 207-218
    PubMedGoogle Scholar
  • 2 Wang Y, Hyde KD, McKenzie EHC, Jiang YL, Li DW, Zhao DG. Overview of Stachybotrys (Memnoniella) and current species status. Fungal Divers 2015; 71: 17-83
    CrossrefPubMedGoogle Scholar
  • 3 Hinkley SF, Jiang J, Mazzola EP, Jarvis BB. Atranones: novel diterpenoids from the toxigenic mold Stachybotrys atra . Tetrahedron Lett 1999; 40: 2725-2728
    CrossrefPubMedGoogle Scholar
  • 4 Gao JM. New biologically active metabolites from Chinese higher fungi. Curr Org Chem 2006; 10: 849-871
    CrossrefPubMedGoogle Scholar
  • 5 Jarvis BB. Stachybotrys chartarum: a fungus for our time. Phytochemistry 2003; 64: 53-60
    CrossrefPubMedGoogle Scholar
  • 6 Jarvis BB, Lee YW, Comezoglu SN, Yatawara CS. Trichothecenes produced by Stachybotrys atra from Eastern Europe. App Environ Microbiol 1986; 51: 915-918
    PubMedGoogle Scholar
  • 7 Sakai K, Watanabe K, Masuda K, Tsuji M, Hasumi K, Endo A. Isolation, characterization and biological activities of novel triprenyl phenols as pancreatic cholesterol esterase inhibitors produced by Stachybotrys sp. F-1839. J Antibiot 1995; 48: 447-456
    CrossrefPubMedGoogle Scholar
  • 8 Ayer WA, Miao S. Secondary metabolites of aspen fungus Stachybotrys cylindrospora . Can J Chem 1993; 71: 487-493
    CrossrefPubMedGoogle Scholar
  • 9 Wang AR, Xu YB, Gao YX, Huang Q, Luo X, An HM, Dong JY. Chemical and bioactive diversities of the genera Stachybotrys and Memnoniella secondary metabolites. Phytochem Rev 2015; 14: 623-655
    CrossrefPubMedGoogle Scholar
  • 10 Fujioka T, Yao K, Hamano K, Hosoya T, Kagasaki T, Furukawa Y, Haruyama H, Sato S, Koga T, Tsujita Y. Epi-cochlioquinone A, a novel acyl-CoA: cholesterol acyltransferase inhibitor produced by Stachybotrys bisbyi . J Antibiot 1996; 49: 409-413
    CrossrefPubMedGoogle Scholar
  • 11 Sawadjoon S, Kittakoop P, Isaka M, Kirtikara K, Madla S, Thebtaranonth Y. Antiviral and antiplasmodial spirodihydrobenzofuran terpenes from the fungus Stachybotrys nephrospora . Planta Med 2004; 70: 1085-1087
    Article in Thieme ConnectPubMedGoogle Scholar
  • 12 Qi QY, Bao L, Ren JW, Han JJ, Zhang ZY, Li Y, Yao YJ, Cao R, Liu HW. Sterhirsutins A and B, two new heterodimeric sesquiterpenes with a new skeleton from the culture of Stereum hirsutum collected in Tibet plateau. Org Lett 2014; 16: 5092-5095
    CrossrefPubMedGoogle Scholar
  • 13 Hosoe T, Mori N, Kamano K, Itabashi T, Yaguchi T, Kawai K. A new antifungal yellow pigment from Aspergillus nishimurae . J Antibiot 2011; 64: 211-212
    CrossrefPubMedGoogle Scholar
  • 14 Giorgio E, Minichino C, Viglione RG, Zanasi R, Rosini C. Assignment of the molecular absolute configuration through the ab initio Hartree-Fock calculation of the optical rotation: can the circular dichroism data help in reducing basis set requirements?. J Org Chem 2003; 68: 5186-5192
    CrossrefPubMedGoogle Scholar
  • 15 Emke A, Macmanus SM, Powell JW, Whalley WB, Wilkins AL. The chemistry of fungi. Part 82. Isochromans related to the sclerotiorin pigments. J Chem Res 1987; 3: 77
    PubMedGoogle Scholar
  • 16 Luo J, Liu XY, Li EW, Guo LD, Che YS. Arundinols A–C and arundinones A and B from the plant endophytic fungus Microsphaeropsis arundinis . J Nat Prod 2013; 76: 107-112
    CrossrefPubMedGoogle Scholar
  • 17 Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Mohan CG, Vuorela P. Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorgan Med Chem 2012; 20: 6669-6679
    CrossrefPubMedGoogle Scholar
  • 18 Ellman GL, Courtney KD, Andres VJ, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharma 1961; 7: 88-95
    CrossrefPubMedGoogle Scholar