Jump to main content
Jump to site search


Garciyunnanimines A–C, novel cytotoxic polycyclic polyprenylated acylphloroglucinol imines from Garcinia yunnanensis

Author affiliations

Abstract

Three novel polycyclic polyprenylated acylphloroglucinol imines (PPAP imines), garciyunnanimines A–C (1–3), which contain unprecedented imine functionality at C-10, together with their presumed biogenetic precursors, guttiferone K (6), garcinol (7) and oblongifolin C (8), were isolated from Garcinia yunnanensis. The imines’ synthesis pathways and structures were elucidated by conversion of the known PPAPs 6–8 to the corresponding imines 1–3 in good yields in the presence of ammonia in dioxane and acetic acid. Using the established method, two new PPAP imine derivatives, garciyunnanimines D and E (4 and 5), were easily synthesized using the corresponding PPAPs, oblongifolins A and B (9 and 10). Structures of the new compounds were assigned by spectroscopic analysis and verified by biomimetic conversion and calculations of the ECD (electron circular dichroism) spectra. In addition, the cytotoxicities of these compounds were evaluated using a CCK-8 assay against three human cancer cell lines, A549, HepG2, and RPMI-8226.

Graphical abstract: Garciyunnanimines A–C, novel cytotoxic polycyclic polyprenylated acylphloroglucinol imines from Garcinia yunnanensis

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Jun 2017, accepted on 27 Jul 2017 and first published on 28 Jul 2017


Article type: Research Article
DOI: 10.1039/C7QO00485K
Citation: Org. Chem. Front., 2017, Advance Article
  •   Request permissions

    Garciyunnanimines A–C, novel cytotoxic polycyclic polyprenylated acylphloroglucinol imines from Garcinia yunnanensis

    D. Zheng, H. Zhang, C. Zheng, Y. Lao, D. Xu, L. Xiao and H. Xu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00485K

Search articles by author

Spotlight

Advertisements