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. 2023 Feb 20;13(9):6124-6129.
doi: 10.1039/d3ra00665d. eCollection 2023 Feb 14.

Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3'-isochromane] skeleton from Penicillium citrinum

Junjie Tong  1   2 , Yang Zhang  3 , Yang Xu  2 , Yangyang Han  2 , Chuan Li  2 , Wenying Zhuang  4 , Yongsheng Che  1   2
Affiliations

Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3'-isochromane] skeleton from Penicillium citrinum

Junjie Tong et al. RSC Adv. .

Abstract

Spirocitrinols A (1) and B (2), two new citrinin-derived metabolites possessing a spiro[chromane-2,3'-isochromane] skeleton, were isolated from cultures of Penicillium citrinum. Their structures were elucidated primarily by NMR experiments. The absolute configurations of 1 and 2 were assigned by electronic circular dichroism calculations. Compound 2 is the first naturally occurring trimeric citrinin derivative with a spiro[chromane-2,3'-isochromane] core. Compound 1 showed modest cytotoxicity against A549 human tumor cells.

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Conflict of interest statement

The authors declare no conflict interest.

Figures

Fig. 1
Fig. 1. Two types of skeletons in naturally occurring bisbenzannulated 6,6-spiroketals.
Fig. 2
Fig. 2. Structures of compounds 1 and 2.
Fig. 3
Fig. 3. Key 1H–1H COSY and HMBC correlations of 1 and 2.
Fig. 4
Fig. 4. Key NOESY correlations of 1 and 2 and NOE correlation of 2.
Fig. 5
Fig. 5. Experimental ECD spectrum of 1 in MeOH and the calculated ECD spectra of 1a and 1b.
Fig. 6
Fig. 6. Experimental ECD spectrum of 2 in MeOH and the calculated ECD spectra of 2a and 2b.
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References

    1. Brown J. P. Cartwright N. J. Robertson A. Whalley W. B. Nature. 1948;162:72–73. - PubMed
    2. Kovac S. Nemec P. Balan J. Nature. 1961;190:1104–1105.
    3. Hill R. K. Gardella L. A. J. Org. Chem. 1964;29:766–767.
    1. Wakana D. Hosoe T. Itabashi T. Okada K. Takaki G. M. D. C. Yaguchi T. Fukushima K. Kawai K. I. J. Nat. Med. 2006;60:279–284. - PubMed
    2. Lu Z. Y. Lin Z. J. Wang W. L. Du L. Zhu T. J. Fang Y. C. Gu Q. Q. Zhu W. M. J. Nat. Prod. 2008;71:543–546. - PubMed
    3. Du L. Li D. H. Zhang G. J. Zhu T. J. Ai J. Gu Q. Q. Tetrahedron. 2010;66:9286–9290.
    4. Guo W. Q. Li D. Pen J. X. Zhu T. J. Gu Q. Q. Li D. H. J. Nat. Prod. 2015;78:306–310. - PubMed
    5. Chen L. Zhao Y. Y. Lan R. F. Du L. Wang B. S. Zhou T. Li Y. P. Zhang Q. Q. Ying M. G. Zheng Q. H. Liu Q. Y. Tetrahedron. 2017;73:5900–5911.
    6. Wang L. Li C. L. Yu G. H. Sun Z. C. Zhang G. J. Gu Q. Q. Zhu T. J. Che Q. Guan H. S. Li D. H. Tetrahedron Lett. 2019;60:151182.
    7. Wang W. Y. Liao Y. Y. Zhang B. B. Gao M. L. Ke W. Q. Li F. Shao Z. Z. Mar. Drugs. 2019;17:46. - PMC - PubMed
    8. Sabdaningsih A. Liu Y. Mettal U. Heep J. Riyanti Wang L. Cristianawati O. Nuryadi H. Sibero M. T. Marner M. Radjasa O. K. Sabdono A. Trianto A. Schäberle T. F. Mar. Drugs. 2020;18:227. - PMC - PubMed
    9. Li H. T. Duan R. T. Liu T. Yang R. N. Wang J. P. Liu S. X. Yang Y. B. Zhou H. Ding Z. T. Fitoterapia. 2020;146:104711. - PubMed
    10. Cheng M. M. Li P. L. Jiang Y. Tang X. L. Zhang W. J. Wang Q. Li G. Q. J. Nat. Prod. 2021;84:1345–1352. - PubMed
    11. Fan H. Shi Z. M. Lei Y. H. Si-Tu M. X. Zhou F. G. Feng C. Wei X. Shao X. H. Chen Y. Zhang C. X. Mar. Drugs. 2022;20:443. - PMC - PubMed
    1. Du L. Liu H. C. Fu W. Li D. H. Pan Q. M. Zhu T. J. Geng M. Y. Gu Q. Q. J. Med. Chem. 2011;54:5796–5810. - PubMed
    2. Wei J. H. Chen X. X. Ge Y. C. Yin Q. Z. Wu X. D. Tang J. S. Zhang Z. J. Wu B. J. Org. Chem. 2022;87:13270–13279. - PubMed
    1. Gao J. M. Yang S. X. Qin J. C. Chem. Rev. 2013;113:4755–4811. - PubMed
    1. Sperry J. Wilson Z. E. Rathwell D. C. K. Brimble M. A. Nat. Prod. Rep. 2010;27:1117–1137. - PubMed
    2. Atkinson D. J. Brimble M. A. Nat. Prod. Rep. 2015;32:811–840. - PubMed
    3. Hiesinger K. Dar’in D. Proschak E. Krasavin M. J. Med. Chem. 2021;64:150–183. - PubMed