Four intricately caged polycyclic polyprenylated acylphloroglucinols from Garcinia multiflora fruits

Abstract

Garmultinones A–C (1–3), three polycyclic polyprenylated acylphloroglucinols (PPAPs) with a unique caged tricyclo[3.3.1.1.4,8]decane skeleton, and one PPAP garmultinone D (4) with the tricyclo[4.3.1.03,7]decane skeleton bearing the 2,2-dimethyl-3-isopropenylcyclopentyl ring were isolated from the fruits of Garcinia multiflora.

Polyprenylated Acylphloroglucinols With Different Carbon Skeletons From the Fruits of Garcinia multiflora

“…By comparison of NMR data of 3 with those of hyperattenin C and otogirinin D ( Ishida et al, 2010 ) indicated that the chemical shifts of C-18, 19, 20, and 21 of 3 were consistent with those of hyperattenin C, suggesting the β -orientation of H-18. Many PPAPs with the isogeranyl group have been isolated from G. multiflora ( Wang et al, 2018 ; Chen et al, 2019b ; Teng et al, 2019 ). Owing to the characteristics of structural flexibility of the isogeranyl group, it is difficult to solve the absolute configuration of C-23 of the isogeranyl group by conventional structural elucidation methods.…”

“…The assignment was further corroborated by the HMBC correlations from H 2 -22 to C-5 and C-9 (Figure 2). The relative configuration of 3 was determined by ROESY spectrum (Supplementary FIGURE 2 | Key HMBC for compounds 1, 3, 5, 8, 10-12, and 14, and 1 H-1 H COSY correlations for 1, 3, 8, 10, 12, and 14. multiflora (Wang et al, 2018;Chen et al, 2019b;Teng et al, 2019). Owing to the characteristics of structural flexibility of the isogeranyl group, it is difficult to solve the absolute configuration of C-23 of the isogeranyl group by conventional structural elucidation methods.…”

“…In our previous study, four new complicated PPAPs with new carbon skeletons tricyclo [3.3.1.1. 4,8 ]decane, 14 new-caged PPAPs, and two new cyclohexanone—monocyclic polycyclic polyprenylated acylphloroglucinols (MPAPs) from the fruits of G. multiflora were reported ( Chen et al, 2019a ; Chen et al, 2019b ; Teng et al, 2019 ; Teng et al, 2020 ). As part of ongoing research, phytochemical investigations of an extract of the fruits of G. multiflora afforded 11 new PPAPs and three new MPAPs ( Figure 1 ).…”

Acylphloroglucinol Derivatives with a Tricyclo-[4.4.1.11,4] Dodecane Skeleton from Garcinia bracteata Fruits

“…To date, more than 20 complicated PPAPs have been isolate from Garcinia plants, which share a basic tricyclo­[4.3.1.0 3,7 ]­decane-2,9-dione moiety and exhibit diverse carbon skeleton, including tetracyclo­[5.4.1.1 1,5 .0 9,13 ]­tridecane, the coupling of 2,11-dioxatricyclo­[4.4.1.0 3,9 ]-undecane and tricyclo­[4.3.1.0 3,7 ]­decane and tricyclo­[3.3.1.1. 4,8 ]­decane isolated from Garcinia multiflora. − Garcibractinones A ( 1 ) and B ( 2 ), featuring an unprecedented tricyclo-[4.4.1.1 1,4 ] dodecane bridged system, were isolated from the fruits of G. bracteata.…”

“…The NO production and cell viability were determined by the Griess reaction and CCK-8 method, respectively, which have been described in our previous paper. 18 ■ ASSOCIATED CONTENT * sı Supporting Information…”