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

Junjie Tong; Yang Zhang; Yang Xu; Yangyang Han; Chuan Li; Wenying Zhuang; Yongsheng Che

doi:10.1039/d3ra00665d

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

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

Authors

Junjie Tong^{1

2}, Yang Zhang³, Yang Xu², Yangyang Han², Chuan Li², Wenying Zhuang⁴, Yongsheng Che^{1

2}

Affiliations

¹ Tianjin University of Traditional Chinese Medicine Tianjin 300193 People's Republic of China.
² NHC Key Laboratory of Biotechnology of Antibiotics, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College Beijing 100050 People's Republic of China [email protected] [email protected].
³ State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology Beijing 100850 People's Republic of China.
⁴ State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences Beijing 100101 People's Republic of China.

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.