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New citrinin derivatives isolated from Penicillium citrinum

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Abstract

Three new coupling compounds derived from citrinin (9) and 2,3,4-trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran (8) – penicitrinone A (1), penicitrinol A (2) and penicitrinone B (3) – and a new citrinin derivative – decarboxydihydrocitrinin (4) – were isolated along with 3-methoxy-1-methyl-4(1H)-quinolone (5), quinolactacin A2 (6), dihydrocitrinone (7), 2,3,4-trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran (8), citrinin (9), quinocitrinin A or B (10), and decarboxydihydrocitrinone (11) from the extract of Penicillium citrinum IFM 53298. The relative structures of compounds 1–4 were confirmed on the basis of spectroscopic investigations and chemical correlations. Citrinin (9) and quinolactacin A2 (6) both showed antifungal activity.

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Acknowledgements

We are grateful to Dr. H. Kasai and Miss N. Kobayashi of Hoshi University for the NMR and MS spectral measurements. This study was supported in part by the Hoshi University Science/Technology Frontier Research Base from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and by a Cooperative Research Program of the Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University (2004–2022).

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo, 142-8501, Japan

    Daigo Wakana, Tomoo Hosoe, Takeshi Itabashi & Ken-ichi Kawai

  2. Nucleo de Pesquisas em Ciencias Ambientais, Universidade Catolica de Pernambuco, Rua Nunes Machado, 42 Boa Vista, Bl.J., CEP 50050-200 , Recife, PE, Brasil

    Kaoru Okada & Galba Maria de Campos Takaki

  3. Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8673, Japan

    Takashi Yaguchi & Kazutaka Fukushima

Authors
  1. Daigo Wakana
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  2. Tomoo Hosoe
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  3. Takeshi Itabashi
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  4. Kaoru Okada
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  5. Galba Maria de Campos Takaki
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  6. Takashi Yaguchi
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  7. Kazutaka Fukushima
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  8. Ken-ichi Kawai
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Correspondence to Ken-ichi Kawai.

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Wakana, D., Hosoe, T., Itabashi, T. et al. New citrinin derivatives isolated from Penicillium citrinum . J Nat Med 60, 279–284 (2006). https://doi.org/10.1007/s11418-006-0001-2

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  • DOI: https://doi.org/10.1007/s11418-006-0001-2

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