Tanzawaic acids I–L: Four new polyketides from Penicillium sp. IBWF104-06

Louis P. Sandjo, Eckhard Thines, Till Opatz and Anja Schüffler
Beilstein J. Org. Chem. 2014, 10, 251–258. https://doi.org/10.3762/bjoc.10.20

Supporting Information

Supporting Information File 1: NMR spectra and crystallographic data.
Format: PDF Size: 1.5 MB Download

Cite the Following Article

Tanzawaic acids I–L: Four new polyketides from Penicillium sp. IBWF104-06
Louis P. Sandjo, Eckhard Thines, Till Opatz and Anja Schüffler
Beilstein J. Org. Chem. 2014, 10, 251–258. https://doi.org/10.3762/bjoc.10.20

How to Cite

Sandjo, L. P.; Thines, E.; Opatz, T.; Schüffler, A. Beilstein J. Org. Chem. 2014, 10, 251–258. doi:10.3762/bjoc.10.20

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Chen, C.; Xiao, L.; Luo, X.; Cai, J.; Huang, L.; Tao, H.; Zhou, X.; Tan, Y.; Liu, Y. Identifying Marine-Derived Tanzawaic Acid Derivatives as Novel Inhibitors against Osteoclastogenesis and Osteoporosis via Downregulation of NF-κB and NFATc1 Activation. Journal of medicinal chemistry 2024, 67, 2602–2618. doi:10.1021/acs.jmedchem.3c01748
  • Tanaka, K.; Suzuki, S.; Lee, D.; Arima, S.; Ohte, S.; Ohshiro, T.; Uchida, R.; Tomoda, H.; Nagamitsu, T. Total synthesis of tanzawaic acid A. Tetrahedron 2023, 143, 133556. doi:10.1016/j.tet.2023.133556
  • Murata, T.; Tsutsui, H.; Yoshida, T.; Kubota, H.; Hiraishi, S.; Natsukawa, H.; Suzuki, Y.; Hiraga, D.; Mori, T.; Maekawa, Y.; Tateyama, S.; Toyoyama, K.; Ito, K.; Suzuki, K.; Yonekura, K.; Shibata, N.; Sato, T.; Tasaki, Y.; Inohana, T.; Takano, A.; Egashira, N.; Honda, M.; Umezaki, Y.; Shiina, I. First Total Synthesis of Tanzawaic Acid B. ACS omega 2023, 8, 27703–27709. doi:10.1021/acsomega.3c03634
  • Song, Y.; Tan, Y.; She, J.; Chen, C.; Wang, J.; Hu, Y.; Pang, X.; Wang, J.; Liu, Y. Tanzawaic Acid Derivatives from the Marine-Derived Penicillium steckii as Inhibitors of RANKL-Induced Osteoclastogenesis. Journal of natural products 2023, 86, 1171–1178. doi:10.1021/acs.jnatprod.2c00865
  • Islam, T.; Ansary, M. W. R.; Rahman, M. M. Magnaporthe oryzae and Its Pathotypes: A Potential Plant Pandemic Threat to Global Food Security. Plant Relationships; Springer International Publishing, 2022; pp 425–462. doi:10.1007/978-3-031-16503-0_18
  • Bernal, A.; Jacob, S.; Andresen, K.; Yemelin, A.; Hartmann, H.; Antelo, L.; Thines, E. Identification of the polyketide synthase gene responsible for the synthesis of tanzawaic acids in Penicillium steckii IBWF104-06. Fungal genetics and biology : FG & B 2022, 164, 103750. doi:10.1016/j.fgb.2022.103750
  • Zhang, D.; Li, S.; Fan, M.; Zhao, C. The Novel Compounds with Biological Activity Derived from Soil Fungi in the Past Decade. Drug design, development and therapy 2022, 16, 3493–3555. doi:10.2147/dddt.s377921
  • Chakraborty, M.; Islam, T. Antifungal Secondary Metabolites Against Blast Fungus Magnaporthe oryzae. Fungal Biology; Springer International Publishing, 2022; pp 23–51. doi:10.1007/978-3-031-04805-0_2
  • Hu, X.-Y.; Li, X.-M.; Wang, B.-G.; Meng, L.-H. Tanzawaic Acid Derivatives: Fungal Polyketides from the Deep-Sea Coral-Derived Endozoic Penicillium steckii AS-324. Journal of natural products 2022, 85, 1398–1406. doi:10.1021/acs.jnatprod.2c00211
  • Wang, J.; Li, T.; Wang, P.; Ding, W.; Xu, J. Tanzawaic Acids from a Deep-Sea Derived Penicillium Species. Journal of natural products 2022, 85, 1218–1228. doi:10.1021/acs.jnatprod.1c01020
  • Dramae, A.; Intaraudom, C.; Bunbamrung, N.; Boonyuen, N.; Auncharoen, P.; Pittayakhajonwut, P. Antimicrobial tanzawaic acid derivatives from the endophytic Penicillium citrinum BCC71086. Tetrahedron 2022, 106-107, 132645. doi:10.1016/j.tet.2022.132645
  • Bernal, A.; Jacob, S.; Andresen, K.; Yemelin, A.; Hartmann, H.; Antelo, L.; Thines, E. Identification of the Polyketide Synthase Gene Responsible for the Synthesis of Tanzawaic Acids in Penicillium Steckii Ibwf104-06. SSRN Electronic Journal 2022. doi:10.2139/ssrn.4112817
  • Chakraborty, M.; Mahmud, N. U.; Ullah, C.; Rahman, M.; Islam, T. Biological and biorational management of blast diseases in cereals caused by Magnaporthe oryzae. Critical reviews in biotechnology 2021, 41, 994–1022. doi:10.1080/07388551.2021.1898325
  • Abdelwahab, M. F.; Fouad, M. A.; Kamel, M.; Özkaya, F. C.; Kalscheuer, R.; Müller, W. E.; Lin, W.; Liu, Z.; Ebrahim, W.; Daletos, G.; Proksch, P. Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp. Fitoterapia 2018, 128, 258–264. doi:10.1016/j.fitote.2018.05.019
  • Tominaga, T.; Uchida, R.; Koyama, N.; Tomoda, H. Anti-Rhizopus activity of tanzawaic acids produced by the hot spring-derived fungus Penicillium sp. BF-0005. The Journal of antibiotics 2018, 71, 626–632. doi:10.1038/s41429-018-0049-8
  • Surup, F.; Pommerehne, K.; Schroers, H.-J.; Stadler, M. Elsinopirins A–D, Decalin Polyketides from the Ascomycete Elsinoё pyri. Biomolecules 2018, 8, 8. doi:10.3390/biom8010008
  • Getino, M.; Fernandez-Lopez, R.; Palencia-Gándara, C.; Campos-Gómez, J.; Sánchez-López, J. M.; Martínez, M.; Fernández, A.; de la Cruz, F. Tanzawaic Acids, a Chemically Novel Set of Bacterial Conjugation Inhibitors. PloS one 2016, 11, e0148098. doi:10.1371/journal.pone.0148098
  • Shin, H. J.; Pil, G. B.; Heo, S.-J.; Lee, H.-S.; Lee, J. S.; Lee, Y.-J.; Lee, J.; Won, H. S. Anti-Inflammatory Activity of Tanzawaic Acid Derivatives from a Marine-Derived Fungus Penicillium steckii 108YD142. Marine drugs 2016, 14, 14. doi:10.3390/md14010014
  • Cardoso-Martínez, F.; De la Rosa, J. M.; Díaz-Marrero, A. R.; Darias, J.; Cerella, C.; Diederich, M.; Cueto, M. Tanzawaic acids isolated from a marine-derived fungus of the genus Penicillium with cytotoxic activities. Organic & biomolecular chemistry 2015, 13, 7248–7256. doi:10.1039/c5ob00773a
  • Quang, T. H.; Ngan, N. T. T.; Ko, W.; Kim, D.-C.; Yoon, C.-S.; Sohn, J. H.; Yim, J. H.; Kim, Y.-C.; Oh, H. Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities. Bioorganic & medicinal chemistry letters 2014, 24, 5787–5791. doi:10.1016/j.bmcl.2014.10.035

Patents

  • SIEPE ISABELLA; JABS THORSTEN; SCHUEFFLER ANJA; SANDJO LOUIS PERGAUD; ANKE HEIDRUN; THINES ECKHARD; OPATZ TILL. Antifungal penicillium strains, fungicidal extrolites thereof, and their use. US 10240216 B2, March 26, 2019.
  • SIEPE ISABELLA; JABS THORSTEN; SCHÜFFLER ANJA; THINES ECKHARD; ANKE HEIDRUN; OPATZ TILL. ANTIFUNGAL PENICILLIUM STRAINS, FUNGICIDAL EXTROLITES THEREOF, AND THEIR USE. WO 2015067800 A1, May 14, 2015.
Other Beilstein-Institut Open Science Activities