Daphcalycines A–D, four highly rearranged Daphniphyllum alkaloids with cardioprotective activity fromDaphniphyllum calycinum.

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Title:Daphcalycines A–D, four highly rearranged Daphniphyllum alkaloids with cardioprotective activity fromDaphniphyllum calycinum.

Author(s):Ji-Hui Zhang, Hui-Lin Ou, Ting Lu, Si-Yu Yang, Ding Luo, Peng Wu, Yao-Lan Li, Neng-Hua Chen*, Guo-Cai Wang*,Yu-Bo Zhang*.

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Chinese Chemical Letters, 2026,37(3): 111314.

DOI:https://doi.org/10.1016/j.cclet.2025.111314

Abstract:Four novel Daphniphyllum alkaloids with highly rearranged skeletons involving a 6/5/7/7/5 pentacyclic scaffold (1), a 6/5/7/5/6/5/6 heptacyclic scaffold (2 and 4), and a 6/5/7/5/6/5 hexacyclic scaffold (3), were isolated from Daphniphyllum calycinum. Particularly, compound 1 contains a unique 13-oxa-17-aza-pentacyclo[7.6.4.112,15.04,8.09,15] eicosane core. Their structures were elucidated by comprehensive spectroscopic analyses, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Putative biosynthetic pathways for compounds 1–4 were discussed with caldaphnidine C (5) as their biosynthetic precursor. Compound 2 markedly enhanced the survival of H9c2 cardiomyocytes under oxygen glucose deprivation and reoxygenation conditions. Mechanistic study revealed that 2 exerted its cardioprotective effects by activating the nuclear factor erythroid 2-related factor 2/heme oxygenase-1 (Nrf2/HO-1) antioxidant pathway, thereby enhancing cellular antioxidant capacity and alleviating oxidative stress induced by hypoxia.

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