Download PDF
Planta Med
DOI: 10.1055/a-2592-1627
Original Papers

Stachybotrins G and H, Two New Phenylspirodrimane Derivatives from the Fungus Stachybotrys chartarum

Yi Wang‡
1   School of Life Sciences, Chongqing Normal University, Chongqing, Peopleʼs Republic of China
,
Kang Chen  ‡
2   Biotechnology Research Institute, Chinese Academy of Agricultural Sciences, Beijing, Peopleʼs Republic of China
,
Qiao Xing
1   School of Life Sciences, Chongqing Normal University, Chongqing, Peopleʼs Republic of China
,
Tao Zhang
1   School of Life Sciences, Chongqing Normal University, Chongqing, Peopleʼs Republic of China
,
Yuquan Xu
2   Biotechnology Research Institute, Chinese Academy of Agricultural Sciences, Beijing, Peopleʼs Republic of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (32070053 and 22277137 to Y. X.) and the Agricultural Science and Technology Innovation Program of the Chinese Academy of Agricultural Sciences (CAAS-ASTIP to Y. X.).
› Further Information
Also available at
    Permissions and Reprints

Abstract

Two new phenylspirodrimane derivatives, designated as stachybotrins G and H (1 and 2), which feature an N-isobutyl side chain, along with four known analogues (3−6), were isolated from the fungus Stachybotrys chartarum. All the structures were determined through comprehensive spectroscopic analyses, primarily based on HRESIMS and NMR data. The antibacterial activity of all isolated compounds was evaluated. Compound 5 demonstrated antibacterial activity against the Gram-positive bacterium Staphylococcus aureus ATCC 6538, with a minimum inhibitory concentration (MIC) value of 6.25 µg/mL.

Keywords

Stachybotrys chartarum - Stachybotryaceae - phenylspirodrimane derivatives - N-isobutyl group - antibacterial activity

Supporting Information

    HRESIMS, 1D, and 2D NMR spectra for compounds 1 and 2 and 1D NMR spectra of compounds 3−6 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 16 February 2025

Accepted after revision: 16 April 2025

Accepted Manuscript online:
22 April 2025

Article published online:
14 May 2025

© 2025. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

  • References

  • 1 Wang A, Xu Y, Gao Y, Huang Q, Luo X, An H, Dong J. Chemical and bioactive diversities of the genera Stachybotrys and Memnoniella secondary metabolites. Phytochem Rev 2015; 14: 623-655
    PubMedSearch in Google Scholar
  • 2 Ibrahim SRM, Choudhry H, Asseri AH, Elfaky MA, Mohamed SGA, Mohamed GA. Stachybotrys chartarum–a hidden treasure: Secondary metabolites, bioactivities, and biotechnological relevance. J Fungi 2022; 8: 504
    PubMedSearch in Google Scholar
  • 3 Jiang M, Wu Z, Liu L, Chen S. The chemistry and biology of fungal meroterpenoids (2009–2019). Org Biomol Chem 2021; 19: 1644-1704
    PubMedSearch in Google Scholar
  • 4 Kaise H, Shinohara M, Miyazaki W, Izawa T, Nakano Y, Sugawara M, Sugiura K, Sasaki K. Structure of K-76, a complement inhibitor produced by Stachybotrys complementi nov. Sp. K-76. J Chem Soc, Chem Commun 1979; 16: 726-727
    PubMedSearch in Google Scholar
  • 5 Ma X, Li L, Zhu T, Ba M, Li G, Gu Q, Guo Y, Li D. Phenylspirodrimanes with anti-HIV activity from the sponge-derived fungus Stachybotrys chartarum MXH-X73. J Nat Prod 2013; 76: 2298-2306
    PubMedSearch in Google Scholar
  • 6 Zhao J, Feng J, Tan Z, Liu J, Zhao J, Chen R, Xie K, Zhang D, Li Y, Yu L, Chen X, Dai J. Stachybotrysins A–G, phenylspirodrimane derivatives from the fungus Stachybotrys chartarum . J Nat Prod 2017; 80: 1819-1826
    PubMedSearch in Google Scholar
  • 7 Wu B, Oesker V, Wiese J, Malien S, Schmaljohann R, Imhoff JF. Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347. Mar Drugs 2014; 12: 1924-1938
    CrossrefPubMedSearch in Google Scholar
  • 8 Liu D, Li Y, Guo X, Ji W, Lin W. Chartarlactams Q−T, dimeric phenylspirodrimanes with antibacterial and antiviral activities. Chem Biodivers 2020; 17: e2000170
    PubMedSearch in Google Scholar
  • 9 Zhao J, Feng J, Tan Z, Liu J, Zhang M, Chen R, Xie K, Chen D, Li Y, Chen X, Dai J. Bistachybotrysins A–C, three phenylspirodrimane dimers with cytotoxicity from Stachybotrys chartarum . Bioorg Med Chem Lett 2018; 28: 355-359
    PubMedSearch in Google Scholar
  • 10 Zhang H, Yang MH, Zhuo FF, Gao N, Cheng XB, Wang XB, Pei YH, Kong LY. Seven new cytotoxic phenylspirodrimane derivatives from the endophytic fungus Stachybotrys chartarum . RSC Adv 2019; 9: 3520-3531
    PubMedSearch in Google Scholar
  • 11 Wang S, Li S, Chen Y, Wang Y, Liu Z, Zhang W, Deng H. A new phenylspirodrimane derivative from the deep-sea-derived fungus Stachybotrys chartarum FS705. Nat Prod Res 2024; 39: 1-7
    PubMedSearch in Google Scholar
  • 12 Jarvis BB. Stachybotrys chartarum: a fungus for our time. Phytochemistry 2003; 64: 53-60
    PubMedSearch in Google Scholar
  • 13 Li Y, Wu C, Liu D, Proksch P, Guo P, Lin W. Chartarlactams A–P, phenylspirodrimanes from the sponge-associated fungus Stachybotrys chartarum with antihyperlipidemic activities. J Nat Prod 2014; 77: 138-147
    PubMedSearch in Google Scholar
  • 14 Li Y, Liu D, Cheng Z, Proksch P, Lin W. Cytotoxic trichothecene-type sesquiterpenes from the sponge-derived fungus Stachybotrys chartarum with tyrosine kinase inhibition. RSC Adv 2017; 7: 7259-7267
    PubMedSearch in Google Scholar
  • 15 Li YF, Zhang PP, Yan SJ, Xu JY, Niaz SI, Chand R, Eddie Ma CH, Lin YC, Li J, Liu L. Atranones with enhancement neurite outgrowth capacities from the crinoid-derived fungus stachybotrys chartarum 952. Tetrahedron 2017; 73: 7260-7266
    PubMedSearch in Google Scholar
  • 16 Yoganathan K, Yang LK, Rossant C, Huang Y, Ng S, Butler MS, Buss AD. Cochlioquinones and epi-cochlioquinones: Antagonists of the human chemokine receptor CCR5 from Bipolaris brizae and Stachybotrys chartarum. J Antibiot 2004; 57: 59-63
    PubMedSearch in Google Scholar
  • 17 Yang B, Long J, Pang X, Lin X, Liao S, Wang J, Zhou X, Li Y, Liu Y. Structurally diverse polyketides and phenylspirodrimanes from the soft coral-associated fungus Stachybotrys chartarum SCSIO41201. J Antibiot 2021; 74: 190-198
    PubMedSearch in Google Scholar
  • 18 Jarvis BB, Salemme J, Morais A. Stachybotrys toxins. 1. Nat Toxins 1995; 3: 10-16
    PubMedSearch in Google Scholar
  • 19 Ibrahim SRM, Choudhry H, Asseri AH, Elfaky MA, Mohamed SGA, Mohamed GA. Stachybotrys chartarum–a hidden treasure: Secondary metabolites, bioactivities, and biotechnological relevance. J Fungi 2022; 8: 504
    PubMedSearch in Google Scholar
  • 20 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
    PubMedSearch in Google Scholar
  • 21 Liu J, Jia X, Zhao J, Feng J, Chen M, Chen R, Xie K, Chen D, Li Y, Zhang D, Peng Y, Si S, Dai J. Bistachybotrysins L–V, bioactive phenylspirodrimane dimers from the fungus Stachybotrys chartarum . Org Chem Front 2020; 7: 531-542
    PubMedSearch in Google Scholar
  • 22 Vázquez MJ, Vega A, Rivera-Sagredo A, Jiménez-Alfaro MD, Díez E, Hueso-Rodríguez JA. Novel sesquiterpenoids as tyrosine kinase inhibitors produced by Stachybotrys chortarum . Tetrahedron 2004; 60: 2379-2385
    PubMedSearch in Google Scholar
  • 23 El Maddah F, Eguereva E, Kehraus S, König GM. Biosynthetic studies of novel polyketides from the marine sponge-derived fungus Stachylidium sp. 293K04. Org Biomol Chem 2019; 17: 2747-2752
    PubMedSearch in Google Scholar
  • 24 Sanchez JF, Entwistle R, Corcoran D, Oakley BR, Wang CCC. Identification and molecular genetic analysis of the cichorine gene cluster in Aspergillus nidulans . Medchemcomm 2012; 3: 997-1002
    PubMedSearch in Google Scholar
  • 25 Guo Y, Contesini FJ, Wang X, Ghidinelli S, Tornby DS, Andersen TE, Mortensen UH, Larsen TO. Biosynthesis of calipyridone A represents a fungal 2-pyridone formation without ring expansion in Aspergillus californicus . Org Lett 2022; 24: 804-808
    PubMedSearch in Google Scholar
  • 26 Shi QW, Kiyota H. New natural taxane diterpenoids from Taxus species since 1999. Chem Biodivers 2005; 2: 1597-1623
    PubMedSearch in Google Scholar
  • 27 Hampel D, Mau CJD, Croteau RB. Taxol biosynthesis: Identification and characterization of two acetyl CoA: Taxoid-O-acetyl transferases that divert pathway flux away from taxol production. Arch Biochem Biophys 2009; 487: 91-97
    PubMedSearch in Google Scholar
  • 28 Chau M, Walker K, Long R, Croteau R. Regioselectivity of taxoid-O-acetyltransferases: Heterologous expression and characterization of a new taxadien-5α-ol-O-acetyltransferase. Arch Biochem Biophys 2004; 430: 237-246
    PubMedSearch in Google Scholar
  • 29 Jiang B, Gao L, Wang H, Sun Y, Zhang X, Ke H, Liu S, Ma P, Liao Q, Wang Y, Wang H, Liu Y, Du R, Rogge T, Li W, Shang Y, Houk KN, Xiong X, Xie D, Huang S, Lei X, Yan J. Characterization and heterologous reconstitution of Taxus biosynthetic enzymes leading to baccatin III. Science 2024; 383: 622-629
    PubMedSearch in Google Scholar
  • 30 De La Peña R, Hodgson H, Liu JCT, Stephenson MJ, Martin AC, Owen C, Harkess A, Leebens-Mack J, Jimenez LE, Osbourn A, Sattely ES. Complex scaffold remodeling in plant triterpene biosynthesis. Science 2023; 379: 361-368
    PubMedSearch in Google Scholar
  • 31 Zhang P, Li Y, Jia C, Lang J, Niaz SI, Li J, Yuan J, Yu J, Chen S, Liu L. Antiviral and anti-inflammatory meroterpenoids: Stachybonoids A–F from the crinoid-derived fungus Stachybotrys chartarum 952. RSC Adv 2017; 7: 49910-49916
    PubMedSearch in Google Scholar
  • 32 Xiao D, Zhang M, Wu P, Li T, Li W, Zhang L, Yue Q, Chen X, Wei X, Xu Y, Wang C. Halovirs I–K, antibacterial and cytotoxic lipopeptaibols from the plant pathogenic fungus Paramyrothecium roridum NRRL 2183. J Antibiot 2022; 75: 247-257
    PubMedSearch in Google Scholar