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Alterchromanone A, one new chromanone derivative from the mangrove endophytic fungus Alternaria longipes

The Journal of Antibiotics volume 74, pages 152–155 (2021)Cite this article

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Abstract

One new chromanone derivative, alterchromanone A (1), and four known curvularin-type macrolides (2–5) were isolated from the crude extract of the mangrove-derived endophytic fungus Alternaria longipes. Their structures were elucidated by MS and NMR spectroscopic analyses and by a comparison with data from the literature. The absolute configuration of 1 was assigned by combination of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity with an IC50 value of 56.3 μg ml−1. According to the structural features of these compounds, the plausible biosynthetic pathways of 1–5 were also proposed.

The strain was cultured on rice for 30 days and then was extracted repeatedly with EtOAc (4 × 4.0 l), and the organic solvent was evaporated to dryness under vacuum to afford the crude extract (11 g), which was fractionated by silica gel vacuum liquid chromatography using petroleum ether–EtOAc gradient elution. The fractions (933 mg) eluted with 45–55% EtOAc were combined and separated by ODS CC using MeOH–H2O gradient elution. Subfraction (55 mg) eluted with 55% MeOH was separated by RP HPLC (Agilent Zorbax SB-C18 column; 5 μm; 9.4 × 250 mm; 40–45% MeOH in H2O for 30 min, 2.0 ml min−1) to afford 2 (5.8 mg, tR 22.75 min). Subfraction (28.5 mg) eluted with 60% MeOH was separated by RP HPLC (45–55% MeOH in H2O for 30 min, 2.0 ml min−1) to afford 5 (2.5 mg, tR 25.15 min). The fractions (907 mg) eluted with 60–75% EtOAc were combined and separated by ODS CC using MeOH–H2O gradient elution. Subfraction (90.4 mg) eluted with 45% MeOH was separated by RP HPLC (35% ACN in H2O for 35 min, 2.0 ml min−1) to afford 3 (1.6 mg, tR 18.57 min). Subfraction (80.4 mg) eluted with 50% MeOH was separated by RP HPLC (30% ACN in H2O for 30 min, 2.0 ml min−1) to afford 4 (1.6 mg, tR 20.81 min). Subfraction (32.0 mg) eluted with 55% MeOH was separated by RP HPLC (65–70% MeOH in H2O for 35 min, 2.0 ml min−1) to afford 1 (2.7 mg, tR 22.91 min).

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Fig. 1
Fig. 2
Scheme 1

References

  1. Beekman AM, Barrow RA. Fungal metabolites as pharmaceuticals. Aust J Chem. 2014;67:827–43.

    Article  CAS  Google Scholar 

  2. Wu ZH, et al. Antioxidant xanthones and anthraquinones isolated from a marine-derived fungus Aspergillus versicolor. Chin J Nat Med. 2018;16:219–24.

    PubMed  Google Scholar 

  3. Liu MT, et al. Bipolarins A–H, eight new ophiobolin-type sesterterpenes with antimicrobial activity from fungus Bipolaris sp. TJ403-B1. Chin J Nat Med. 2019;17:935–44.

    PubMed  Google Scholar 

  4. Guo LF, Liu GR, Liu L. Caryophyllene-type sesquiterpenoids and α-furanones from the plant endophytic fungus Pestalotiopsis theae. Chin J Nat Med. 2020;18:261–7.

    PubMed  Google Scholar 

  5. Zhang YX, et al. Eutypellacytosporins A–D, meroterpenoids from the arctic fungus Eutypella sp. D-1. J Nat Prod. 2019;82:3089–95.

    Article  CAS  Google Scholar 

  6. Yu GH, et al. Neosartoryadins A and B, fumiquinazoline alkaloids from a mangrove-derived fungus Neosartorya udagawae HDN13-313. Org Lett. 2016;18:244–7.

    Article  CAS  Google Scholar 

  7. Xu J. Bioactive natural products derived from mangrove-associated microbes. RSC Adv. 2015;5:841–92.

    Article  CAS  Google Scholar 

  8. Carroll AR, et al. Marine natural products. Nat Prod Rep. 2019;36:122–73.

    Article  CAS  Google Scholar 

  9. Proksch P, et al. Bioactive natural products from marine sponges and fungal endophytes. Phytochem Rev. 2010;9:475–89.

    Article  CAS  Google Scholar 

  10. Pang XY, et al. Perylenequione derivatives with anticancer activities isolated from the marine sponge-derived fungus, Alternaria sp. SCSIO41014. Mar Drugs. 2018;16:280–92.

    Article  Google Scholar 

  11. Wang JH, et al. Three new resveratrol derivatives from the mangrove endophytic fungus Alternaria sp. Mar Drugs. 2014;12:2840–50.

    Article  CAS  Google Scholar 

  12. Wang JH, et al. Identification and bioactivity of compounds from the mangrove endophytic fungus Alternaria sp. Mar Drugs. 2015;13:4492–504.

    Article  CAS  Google Scholar 

  13. Guo LF, Niu SB, Chen SL, Liu L. Diaporone A, a new antibacterial secondary metabolite from the plant endophytic fungus Diaporthe sp. J Antibiot. 2020;73:116–9.

    Article  CAS  Google Scholar 

  14. Guo LF, et al. Pestalotiones A–D: four new secondary metabolites from the plant endophytic fungus Pestalotiopsis theae. Molecules. 2020;25:470–9.

    Article  CAS  Google Scholar 

  15. Xie LW, et al. Isolation and difference in anti-Staphylococcus aureus bioactivity of curvularin derivates from fungus Eupenicillium sp. Appl Biochem Biotechnol. 2009;159:284–93.

    Article  CAS  Google Scholar 

  16. Lai S, et al. New curvularin-type metabolites from the hybrid strain ME0005 derived from penicillium citreo-viride B. IFO 4692 and 6200. Bull Chem Soc Jpn. 1991;64:1048–50.

    Article  CAS  Google Scholar 

  17. Kusano M, et al. βγ-dehydrocurvularin and related compounds as nematicides of pratylenchus penetrans from the fungus Aspergillus sp. Biosci Biotechnol Biochem. 2003;67:1413–6.

    Article  CAS  Google Scholar 

  18. Zhao DL, et al. Chromone derivatives from a sponge-derived strain of the fungus Corynespora cassiicola. J Nat Prod. 2015;78:286–93.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Key R&D Program of China (2018YFC0311002) and the National Natural Science Foundation of China (21772228 and 21977113).

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Authors and Affiliations

  1. State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, 100101, Beijing, China

    Gaoran Liu & Ling Liu

  2. University of Chinese Academy of Sciences, 100039, Beijing, China

    Gaoran Liu

  3. School of Biological Medicine, Beijing City University, 100083, Beijing, China

    Shubin Niu

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Correspondence to Ling Liu.

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Liu, G., Niu, S. & Liu, L. Alterchromanone A, one new chromanone derivative from the mangrove endophytic fungus Alternaria longipes. J Antibiot 74, 152–155 (2021). https://doi.org/10.1038/s41429-020-00364-4

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