Polyprenylated Acylphloroglucinols With Different Carbon Skeletons From the Fruits of .

Eleven new polycyclic polyprenylated acylphloroglucinols (PPAPs, -) and three new monocyclic polyprenylated acylphloroglucinols (MPAPs, -), together with ten known analogues were isolated from the fruits of . 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.

Structural Elucidation of Garcipaucinones A and B From Using Quantum Chemical Calculations.

Two tocotrienol derivatives, garcipaucinones A () and B (), and a biosynthetically related known analogue () were isolated from the fruit of . Their structures including absolute configurations were unequivocally determined by spectroscopic methods complemented with electronic circular dichroism (ECD) calculations and gauge-independent atomic orbital (GIAO) NMR calculations. Compounds and are the first naturally occurring tocotrienol derivatives with a 3,10-dioxatricyclo-[7.

Prenylated xanthones and benzophenones from the fruits of Garcinia bracteata and their potential antiproliferative and anti-inflammatory activities.

Ten previously undescribed compounds, including five prenylated xanthones (1-5), two caged xanthones (16-17) and three rearranged benzophenones (27-29), together with nineteen known compounds were isolated from the fruits of Garcinia bracteata. Their structures were established on the basis of spectroscopic analysis, electronic circular dichroism calculations, and X-ray crystallographic data. Compound 17 was a caged xanthone bearing a rare 8, 8a-epoxy moiety.

Anti-inflammatory and antiproliferative prenylated sulphur-containing amides from the leaves of Glycosmis pentaphylla.

Glycosmis pentaphylla (Retz.) DC (Rutaceae) has been traditionally considered as anti-cancer and anti-inflammatory medicine. However, active compounds of sulphur-containing amides remain largely unknown.

Two novel cyclohexanone-monocyclic polycyclic polyprenylated acylphloroglucinols from fruits.

Two novel cyclohexanone-monocyclic polyprenylated acylphloroglucinol (C-MPAP) derivatives, named norgarmultinones A () and B (), were isolated from the fruits of . Their structures were clarified by NMR, HRESIMS and calculated electronic circular dichroism (ECD) spectra. Compound is the first example of naturally occurring C-MPAPs containing tetrahydropyran moiety by the cyclization of an enolic hydroxyl with an isogeranyl side chain.

Acylphloroglucinol Derivatives with a Tricyclo-[4.4.1.1] Dodecane Skeleton from Fruits.

Two novel polycyclic polyprenylated acylphloroglucinols (PPAPs), garcibractinones A () and B (), as well as three known analogues doitunggarcinones A-B (-) and garcibracteatone () were isolated from fruits. Their structures were elucidated by comprehensive spectroscopic methods and single crystal X-ray diffraction. Compounds and possess an unprecedented caged tricyclo-[4.

Homoadamantane polycyclic polyprenylated acylphloroglucinols from the fruits of Garcinia multiflora.

Five new homoadamantane polycyclic polyprenylated acylphloroglucinols (PPAPs, 1-5) were isolated from the fruits of Garcinia multiflora. Their structures and absolute configurations were determined by extensive spectroscopic analyses including NMR, HRESIMS and electronic circular dichroism (ECD). Compounds 1-3 possessed an unique core structure consisting of tetracyclo[7.

Adamantyl and homoadamantyl derivatives from fruits.

Nine undescribed caged polycyclic polyprenylated acylphloroglucinols (PPAPs), including adamantane type PPAPs (1-2), and homoadamantane type PPAPs (3-9), were isolated from the fruits of , along with three known analogues. A new epimeric pair of isohypersampsonone B (5) and epi-isohypersampsonone B (6), featuring an unusual hexahydrofuro[2,3-b]furan-diepoxy ring system fused in a homoadamantane skeleton, was not separated due to the rapid equilibration between the two isomeric forms. All new caged PPAPs (1-9), sharing a common isogeranyl group, were determined on the basis of comprehensive NMR and MS spectroscopic data.