Cipacinerasins A-K, structurally diverse limonoids from Cipadessa baccifera.

De-Yu Zhang, Hua-Yong Lou, Chao Chen, Han-Fei Liu, Ni Zhang, Chao-Yi Deng, Jin-Yu Li, Wei-Dong Pan

Phytochemistry 2022 Aug

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Eleven undescribed limonoids, cipacinerasins A-K, involving of four diverse carbon skeletal types, along with fifteen known analogues, were isolated from the branches and leaves of Cipadessa baccifera. Within them, cipacinerasins A and B feature a rearranged tetrahydropyranyl ring B formed between C-8 and C-30, are unusual miscellaneous-type limonoids. Cipacinerasins E and F are rare trijugin-type limonoids, of which the D-ring δ-lactone is cleaved. Their structures were elucidated on the basis of extensive spectroscopic data (HRESIMS, NMR, UV and IR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. All compounds were evaluated in vitro cytotoxicity against five human tumor cell lines (K562, HeLa, PC3, LN-Cap and Hell), and cipacinerasin E showed moderate antitumor activity with IC50 values ranging from 8.0 to 24.8 μM. Copyright © 2022 Elsevier Ltd. All rights reserved.

Citation

De-Yu Zhang, Hua-Yong Lou, Chao Chen, Han-Fei Liu, Ni Zhang, Chao-Yi Deng, Jin-Yu Li, Wei-Dong Pan. Cipacinerasins A-K, structurally diverse limonoids from Cipadessa baccifera. Phytochemistry. 2022 Aug;200:113186