Issue 3, 2019

Ciliatasecones A–C, three rearranged limonoids from Toona ciliata var. yunnanensis

Abstract

Ciliatasecones A–C (1–3), three rearranged limonoids with a novel ring-seco model and an unprecedented cycle system, were isolated from the root bark of Toona ciliata var. yunnanensis. Ciliatasecones A–B (1–2) share a novel cyclopenta[b]furan ring C/D system through C-9/11-seco and C-11/14 ether linkage. Ciliatasecone C (3) was found to possess a rare rearranged six-membered lactone ring B between C-7 and C-9. Plausible biogenetic pathway speculation indicated that C-9/11 cleavage and oxygen bridge formation played the key roles in the framework rearrangement of 1–3.

Graphical abstract: Ciliatasecones A–C, three rearranged limonoids from Toona ciliata var. yunnanensis

Supplementary files

Article information

Article type
Paper
Submitted
04 Nov 2018
Accepted
10 Dec 2018
First published
11 Dec 2018

Org. Biomol. Chem., 2019,17, 555-560

Ciliatasecones A–C, three rearranged limonoids from Toona ciliata var. yunnanensis

P. Zhang, Z. Cui, Y. Li, L. Heng, S. Wei, X. Wang, M. Yang, J. Luo and L. Kong, Org. Biomol. Chem., 2019, 17, 555 DOI: 10.1039/C8OB02736F

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