Abstract
Eleven new polycyclic polyprenylated acylphloroglucinols (PPAPs, 1–11) and three new monocyclic polyprenylated acylphloroglucinols (MPAPs, 12–14), together with ten known analogues were isolated from the fruits of Garcinia multiflora. These PPAPs belong to three types including the bicyclic polyprenylated acylphloroglucinols (BPAPs), the caged PPAPs, and the complicated PPAPs. Their structures and absolute configurations were determined through HRESIMS, NMR spectroscopy data, electronic circular dichroism (ECD) calculations, and gauge-independent atomic orbital (GIAO) NMR calculations with DP4+ analyses. Moreover, compounds 2 and 7 exhibited moderate cytotoxicity against three human cancer lines (MCF-7, T98, and HepG2) with IC50 values ranging from 9.81 ± 1.56 to 17.00 ± 2.75 μM.
Highlights
The plants of Guttiferae and Hypericaceae family mainly including the genus Garcinia and Hypericum are well-known for producing structurally diverse and biologically polycyclic polyprenylated acylphloroglucinols (PPAPs)
In case of exo-bicyclic polyprenylated acylphloroglucinols (BPAPs), the chemical shifts of C-7 and Me-38 displayed upfield signals at 41–44 and 16–17 ppm resulting from a γ-gauche effect between Me-38 and the CH232
The phytochemical investigation of the fruits of G. multiflora resulted in the isolation and structure elucidation of 24 structurally diverse polyprenylated acylphloroglucinols (PAPs) including 11 new PPAPs (1–11) and 3 new MPAPs (12–14)
Summary
The plants of Guttiferae and Hypericaceae family mainly including the genus Garcinia and Hypericum are well-known for producing structurally diverse and biologically polycyclic polyprenylated acylphloroglucinols (PPAPs). Previous phytochemical studies indicated that more than 500 PPAPs have been isolated the plants of Guttiferae family with diverse structural scaffolds including the bicyclic polyprenylated acylphloroglucinols (BPAPs), the caged PPAPs, and the complicated PPAPs. BPAPs comprise approximate 60% of PPAPs which share a bicyclo [3.3.1]nonane-2,4,9-trione core (Yang et al, 2018). Depending on the relative position of the acyl group connected to the phloroglucinol core, BPAPs are categorized into type A or B. BPAPs have attracted noticeable attention from both natural product and medicinal chemists due to their fascinating chemical structures and intriguing biological activities (Phang et al, 2020)
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