Skip to main content
Log in

NF-κB inhibitory, antimicrobial and antiproliferative potentials of compounds from Hawaiian fungus Aspergillus polyporicola FS910

  • Original Article
  • Published:
3 Biotech Aims and scope Submit manuscript

Abstract

Bioassay-guided experimental design and chromatographic analysis led to the isolation and identification of ten compounds (1–10) including two unusual sulfur-containing curvularin macrolides (1 and 2) from a Hawaiian fungal strain Aspergillus polyporicola FS910. Compounds 1 and 2 are rare curvularin macrolides each with a five-membered cyclic sulfur-containing moiety. The structures of the compounds were identified by HRESIMS, NMR spectroscopy, X-ray crystallography, ECD and DFT energy calculation, as well as comparing with previous literatures. Compounds 4, 6 and 8 were active against TNF-α-induced NF-κB inhibitory activity with IC50 values of 26.45, 5.41 and 15.8 µM, respectively. Compounds 3 and 5–8 exhibited anti-proliferative activity against HT1080, T46D, and A2780S cell lines, with IC50 values ranging from 2.48 to 29.17 μM. Additionally, Compound 3 showed promising antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA), Bacillus subtilis, Escherichia coli and Candida albicans. Moreover, when tested in combination with antibiotic adjuvant disulfiram [4 µg/mL], compounds 4, 5 and 10 also displayed significant antibacterial activity against S. aureus.

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

Access this article

Subscribe and save

Springer+
from $39.99 /Month
  • Starting from 10 chapters or articles per month
  • Access and download chapters and articles from more than 300k books and 2,500 journals
  • Cancel anytime
View plans

Buy Now

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

Availability of data

Accession Number: GenBank (Accession Number CCDC 2026987 and CCDC 2026988).

References

  • Alvin A, Miller KI, Neilan BA (2014) Exploring the potential of endophytes from medicinal plants as sources of antimycobacterial compounds. Microbiol Res 169:483–495

    Article  CAS  Google Scholar 

  • Aparicio-Cuevas MA, Rivero-Cruz I, Sánchez-Castellanos M, Menéndez D, Raja HA, Joseph-Nathan P, González MD, Figueroa M (2017) Dioxomorpholines and derivatives from a marine-facultative Aspergillus species. J Nat Prod 80:2311–2318

    Article  CAS  Google Scholar 

  • Arai K, Rawlings BJ, Yoshizawa Y, Vederas JC (1989) Biosyntheses of antibiotic A26771B by Penicillium turbatum and dehydrocurvularin by Alternaria cinerariae: comparison of stereochemistry of polyketide and fatty acid enoyl thiol ester reductases. J Am Chem Soc 111:3391–3399

    Article  CAS  Google Scholar 

  • Bruker AXS (2016) APEX3, Madison, Wisconsin

  • Chen M, Wang KL, Liu M, She ZG, Wang CY (2015) Bioactive steroid derivatives and butyrolactone derivatives from a gorgonian-derived Aspergillus sp. fungus. Chem Biodiverse 12:1398–1406

    Article  CAS  Google Scholar 

  • Dai J, Krohn K, Flörke U, Pescitelli G, Kerti G, Papp T, Kövér KE, Bényei AS, Draeger S, Schulz B, Kurtán T (2010) Curvularin type metabolites from the fungus Curvularia sp. isolated from a marine alga. Eur J Org Chem 36:6928–6937

    Article  Google Scholar 

  • de Castro MV, Ióca LP, Williams DE, Costa BZ, Mizuno CM, Santos MF, de Jesus K, Ferreira EL, Seleghim MH, Sette LD, Pereira Filho ER, Ferreira AG, Gonçalves NS, Santos RA, Patrick BO, Andersen RJ, Berlinck RGS (2016) Condensation of macrocyclic polyketides produced by Penicillium sp. DRF2 with mercaptopyruvate represents a new fungal detoxification pathway. J Nat Prod 79:1668–1678

    Article  Google Scholar 

  • Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) OLEX2: a complete structure solution, refinement and analysis program. J Appl Cryst 42:339–341

    Article  CAS  Google Scholar 

  • Fei-Zhang DJ, Li C, Cao S (2016) Hawaii natural compounds are promising to reduce ovarian cancer deaths. Cancer Biol Ther 17:709–712

    Article  CAS  Google Scholar 

  • Huang P, Li C, Sarotti AM, Turkson J, Cao S (2017) Sphaerialactonam, a γ-lactam–isochromanone from the Hawaiian endophytic fungus Paraphaeosphaeria sp. FT462. Tetrahedron Lett 58:1330–1333

    Article  CAS  Google Scholar 

  • Kondratyuk TP, Park EJ, Yu R, VanBreemen RB, Asolkar RN, Murphy BT, Fenical W, Pezzuto J (2012) Novel marine phenazines as potential cancer chemopreventive and anti-inflammatory agents. Mar Drugs 10:451–464

    Article  CAS  Google Scholar 

  • Lai S, Shizuri Y, Yamamura S, Kawai K, Terada Y, Furukawa H (1989) Novel curvularin-type metabolites of a hybrid strain ME 0005 derived from Penicillium citreo-viride B. IFO 6200 and 4692. Tetrahedron Lett 30:2241–2244

    Article  CAS  Google Scholar 

  • Li CS, Ding Y, Yang BJ, Miklossy G, Yin HQ, Walker LA, Turkson J, Cao S (2015a) A new metabolite with a unique 4-pyranone−γ-lactam–1,4-thiazine moiety from a Hawaiian-plant associated fungus. Org Lett 17:3556–3559

    Article  CAS  Google Scholar 

  • Li C, Yang B, Fenstemacher R, Turkson J, Cao S (2015b) Lycopodiellactone, an unusual δ-lactone-isochromanone from a Hawaiian plant-associated fungus Paraphaeosphaeria neglecta FT462. Tetrahedron Lett 56:1724–1727

    Article  CAS  Google Scholar 

  • Li CS, Ding Y, Yang BJ, Hoffman N, Yin HQ, Mahmud T, Turkson J, Cao S (2016a) Eremophilane sesquiterpenes from Hawaiian endophytic fungus Chaetoconis sp. FT087. Phytochemistry 126:41–46

    Article  CAS  Google Scholar 

  • Li CS, Ren G, Yang BJ, Miklossy G, Turkson J, Fei P, Ding Y, Walker LA, Cao S (2016b) Meroterpenoids with antiproliferative activity from a Hawaiian-plant associated fungus Peyronellaea coffeae-arabicae FT238. Org Lett 18:2335–2338

    Article  CAS  Google Scholar 

  • Li C, Sarotti AM, Yang B, Turkson J, Cao S (2017) A New N-methoxypyridone from the co-cultivation of Hawaiian endophytic fungi Camporesia sambuci FT1061 and Epicoccum sorghinum FT1062. Molecules 22:1166

    Article  Google Scholar 

  • Li C, Hu Z, Liu Q, Wu X, Cao S (2018a) Two new tricycloalternarenes from Hawaiian endophytic fungus Didymella sp. FT433. Tetrahedron Lett 59:3381–3383

    Article  CAS  Google Scholar 

  • Li C, Sarotti AM, Yoshida W, Cao S (2018b) Two new polyketides from Hawaiian endophytic fungus Pestalotiopsis sp. FT172. Tetrahedron Lett 59:42–45

    Article  CAS  Google Scholar 

  • Li C, Sarotti AM, Wu X, Yang B, Turkson J, Chen Y, Liu Q, Cao S (2019) An unusual benzoisoquinoline-9-one derivative and other related compounds with antiproliferative activity from Hawaiian endophytic Fungus Peyronellaea sp. FT431. Molecules 24:196

    Article  Google Scholar 

  • Liang Q, Sun Y, Yu B, She X, Pan X (2007) First total syntheses and spectral data corrections of 11-α-methoxycurvularin and 11-β-methoxycurvularin. J Org Chem 72:9846–9849

    Article  CAS  Google Scholar 

  • Lin ZJ, Zhang GJ, Zhu TJ, Liu R, Wei HJ, Gu QQ (2009) Bioactive cytochalasins from Aspergillus flavipes, an endophytic fungus associated with the mangrove plant Acanthus ilicifolius. Helv Chim Acta 92:1538–1544

    Article  CAS  Google Scholar 

  • Martinez-Klimova E, Rodríguez-Peña K, Sánchez S (2017) Endophytes as sources of antibiotics. Biochem Pharmacol 134:1–17

    Article  CAS  Google Scholar 

  • Newman DJ, Cragg GM (2020) Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod 83:770–803

    Article  CAS  Google Scholar 

  • Sheldrick GM (2015) SHELXT—integrated space-group and crystal-structure determination. Acta Cryst A71:3–8

    Google Scholar 

  • Spek AL (2009) Structure validation in chemical crystallography. Acta Crystallogr Sect D 65:148–155

    Article  CAS  Google Scholar 

  • Thom C, Church MB (1926) The Aspergilli. Williams & Wilkins Comp, Baltimore, pp 1–272

    Google Scholar 

  • Vadlapudi V, Borah N, Yellusani KR, Gade S, Reddy P, Rajamanikyam M, Vempati LNS, Gubbala SP, Chopra P, Upadhyayula SM, Amanchy R (2017) Aspergillus secondary metabolite database, a resource to understand the secondary metabolome of Aspergillus genus. Sci Rep 7:7325

    Article  Google Scholar 

  • Wang F, Hu Z, Li C, Wu X, Cao S (2019) Circumdatin M, a new benzodiazepine alkaloid with a unique pyrimidone-4-pyrone moiety from a Hawaiian marine fungus Aspergillus sp. Tetrahedron Lett 60:1724–1726

    Article  CAS  Google Scholar 

  • Wang C, Wu X, Bai H, Zaman KA, Hou S, Saito J, Wongwiwatthananukit S, Kim HS, Cao S (2020a) Antibacterial and NF-κB inhibitory lumazine peptides, aspochalasin, γ-butyrolactone derivatives, and cyclic peptides from a Hawaiian Aspergillus flavipes. J Nat Prod 83:2233–2240

    Article  CAS  Google Scholar 

  • Wang F, Sarotti AM, Jiang G, Huguet-Tapia JC, Zheng SL, Wu X, Li C, Ding Y, Cao S (2020b) Waikikiamides A-C: Complex diketopiperazine dimer and diketopiperazine–polyketide hybrids from a Hawaiian marine fungal strain Aspergillus sp. FM242. Org Lett 22:4408–4412

    Article  CAS  Google Scholar 

  • Zaman KA, Hu Z, Wu X, Cao S (2020a) Tryptoquivalines W and X, two new compounds from a Hawaiian fungal strain and their biological activities. Tetrahedron Lett 61:151730

    Article  Google Scholar 

  • Zaman KA, Hu Z, Wu X, Hou S, Saito J, Kondratyuk TP, Pezzuto JM, Cao S (2020b) NF-κB inhibitory and antibacterial helvolic and fumagillin derivatives from Aspergillus terreus. J Nat Prod 83:730–737

    Article  Google Scholar 

Download references

Acknowledgements

This work was financially supported by start-up funding from Daniel K. Inouye College of Pharmacy (DKICP), Seed Grants from University of Hawaii at Hilo (UH Hilo), and the Victoria S. and Bradley L. Geist Foundation (15ADVC-74420, 17CON-86295, and 20CON-102163) (to SC). Funding for this work was also supported by Hawaii IDeA Network for Biomedical Research Excellence III and IV (INBRE-III and INBRE-IV) project: NIGMS Grant 5P20GM103466. We would also like to express our gratitude to Mr. Justin Reinicke for his help with HRMS, NMR, optical rotation and ECD data collection.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Shugeng Cao.

Ethics declarations

Conflict of interest

No conflict of interest was reported by the authors.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 5963 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, C., Zaman, K.H.A.u., Sarotti, A.M. et al. NF-κB inhibitory, antimicrobial and antiproliferative potentials of compounds from Hawaiian fungus Aspergillus polyporicola FS910. 3 Biotech 11, 391 (2021). https://doi.org/10.1007/s13205-021-02877-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s13205-021-02877-7

Keywords