Abstract
One new pentenoic acid derivative, named 1,1′-dioxine-2,2′-dipropionic acid (1) and a new natural product, named 2-methylacetate-3,5,6-trimethylpyrazine (2), along with six known compounds (3–8), were obtained from the Cladosporium sp. JS1-2, an endophytic fungus isolated from the mangrove Ceriops tagal collected in South China Sea. Their structures were elucidated by detailed analysis of comprehensive spectroscopic data, and the structure of 1 was further determined by X-ray diffraction analyses. 13C NMR chemical shifts of structure 2 was further determined by GIAO based 13C NMR chemical shifts calculations. Compounds 1–4 and 6 showed growth inhibition activities against newly hatched larvae of Helicoverpa armigera Hubner with the IC50 values ranging from 100 to 150 μg ml−1. Compounds 1, 2, 4, 6 and 7 showed moderate antibacterial activities against Staphylococcus aureus with the MIC values of 25.0, 12.5, 6.25, 1.25, and 6.25 μg ml−1, respectively.
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Carroll AR, et al. Marine natural products. Nat Prod Rep. 2019;36:122–73.
Rateb ME, et al. Secondary metabolites of fungi from marine habitats. Nat Prod Rep 2011;28:290–344.
Chen Y, et al. Citrofulvicin, an antiosteoporotic polyketide from Penicillium velutinum. Org Lett. 2018;20:3741–4.
Liu S, et al. An anti-inflammatory PPAR-γ agonist from the jellyfish-derived fungus Penicillium chrysogenum J08NF-4. J Nat Prod. 2018;81:356–63.
Meng LH, et al. Antimicrobial alkaloids produced by the mangrove endophyte Penicillium brocae MA-231 using the OSMAC approach. Rsc Adv. 2017;7:55026–33.
Li HL, et al. Simpterpenoid A, a meroterpenoid with a highly functionalized cyclohexadiene moiety featuring gem-propane-1,2-dione and methylformate groups, from the mangrove-derived Penicillium simplicissimum Ma-332. Org Lett 2018;20:1465–8.
Zheng CJ, et al. Penicilindoles A-C, cytotoxic indole diterpenes from the mangrove-derived fungus Eupenicillium sp. HJ002. J Nat Prod. 2018;84:1045–9.
He KY, et al. New chlorinated xanthone and anthraquinone produced by a mangrove-derived fungus Penicillium citrinum HL-5126. J Antibiot. 2017;70:823–7.
Zhou XM, et al. Bioactive anthraquinone derivatives from the mangrove-derived fungus Stemphylium sp. 33231. J Nat Prod. 2014;77:2021–8.
Huang GL, et al. Dihydroisocoumarins from the mangrove-derived fungus Penicillium citrinum. Mar Drugs. 2016;14:1771–8.
Mei RQ, et al. Two new isocoumarins isolated from a mangrove-derived fungus Penicillium citrinum HL-5126. Chinese J Org Chem. 2019; https://doi.org/10.6023/cjoc201812008.
Pierens GK. 1H and 13C NMR scaling factors for the calculation of chemical shifts in commonly used solvents using density functional theory. J Comput Chem. 2014;35:1388–94.
Klein B, et al. Pyrazines. II. the rearrangement of pyrazine-N-oxides. J Org Chem. 1961;26:126–31.
Liu YY, et al. Vermistatin derivatives with α-Glucosidase inhibitory activity from the mangrove endophytic fungus Penicillium sp. HN29-3B1. Planta Med. 2014;80:912–7.
Ngan NTT, et al. Anti-inflammatory effects of secondary metabolites isolated from the marine-derived fungal strain Penicillium sp. SF-5629[J]. Arch Pharmacal Res. 2017;40:328–37.
Liu F, et al. The bioactive metabolites of the mangrove endophytic fungus Talaromyces sp. ZH-154 isolated from Kandelia candel (L.) Druce. Planta Med. 2010;76:185–9.
Zhang ZZ, et al. Clindanones A and B and cladosporols F and G, polyketides from the deep-sea derived fungus Cladosporium cladosporioides HDN14-342†. RSC Adv. 2016;6:76498–504.
Li HL, et al. Characterization of cladosporols from the marine algal-derived endophytic fungus Cladosporium cladosporioides EN-399 and configurational revision of the previously reported cladosporol derivatives. J Org Chem. 2017;82:9946–54.
Xu H, Fang WS, Chen XG, He WY, Cheng KD. Cytochalasin D from Hypocrella Bambusae. J Asian Nat Prod Res. 2001;3:151–5.
Pierce CG, et al. A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing. Nat Protoc. 2008;3:1494–500.
Guo ZK, et al. Metabolites with insecticidal activity from Aspergillus fumigatus JRJ111048 isolated from mangrove plant Acrostichum specioum endemic to Hainan Island. Mar Drugs. 2017;15:381–7.
Acknowledgements
This work was supported by the National Natural Science Foundation of China (Nos. 21662012, 41866005), Program for Innovative Research Team in University (No. IRT-16R19), Innovation project of university students (No. cxcyxj2018009) and Innovation project of Postgraduate (No. Hyb2018-26).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher’s note: Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
Rights and permissions
About this article
Cite this article
Bai, M., Zheng, CJ., Tang, DQ. et al. Two new secondary metabolites from a mangrove-derived fungus Cladosporium sp. JS1-2. J Antibiot 72, 779–782 (2019). https://doi.org/10.1038/s41429-019-0206-8
Received:
Revised:
Accepted:
Published:
Version of record:
Issue date:
DOI: https://doi.org/10.1038/s41429-019-0206-8
This article is cited by
-
Mangrove-associated endomycota: diversity and functional significance as a source of novel drug leads
Archives of Microbiology (2023)
-
Penicixanthene E, a new xanthene isolated from a mangrove-derived fungus Penicillium sp.
The Journal of Antibiotics (2022)
-
Two new benzophenones isolated from a mangrove-derived fungus Penicillium sp.
The Journal of Antibiotics (2021)
-
Antimicrobial compounds from marine fungi
Phytochemistry Reviews (2021)
-
A New Sesquiterpene Derivative from the Mangrove Endophytic Fungus Trichoderma harzianum (Strain No. R1)
Chemistry of Natural Compounds (2021)
