Polyprenylated Phloroglucinols and Xanthones

Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

“…Two monocyclic acylphloroglucinol derivatives, 3-geranyl-1-(2-methylpropanoyl) phloroglucinol and 3-geranyl-1-(2-methylbutanoyl)phloroglucinol have been isolated from H. linarioides Bosse [20], but until Supplementary material is available under https://doi.org/10.1055/a-1617-7573 ABSTR AC T 1 H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), while 5 further compounds showed an adamantane skeleton (15)(16)(17)(18)(19). Except for hookerione C (15), all isolated metabolites are hitherto unknown.…”

“…Based on diverse substitution patterns of the acylphloroglucinol core with prenyl and geranyl moieties followed by cyclizations and oxidations, this class of metabolites showed high structural diversity and is a valuable source of pharmacologically active compounds [4][5][6][7][8][9][10]. The formation of monocyclic [8], bicyclic [11], tricyclic [12], and complex caged representatives with an adamantane [13] or homoadamantane [14] core has been described. In addition, the biosynthesis of heterocyclic [15,16] and spiro [17] acylphloroglucinols has been reported.…”

Drug-like Properties and ADME of Xanthone Derivatives: The Antechamber of Clinical Trials

“…1) and reached phase III clinical trials towards antitumor activity 3 . Due to a great number of studies in isolation, synthesis and biological/pharmacological properties of xanthone derivatives, several reviews 1,[4][5][6][7][8][9][10][11][12][13][14][15][16] have gathered important information to guide the design of these compounds as potential drug candidates. Nevertheless, little focus was given to drug pharmacokinetics (PK), toxicity studies, and structure-properties relationships of xanthone derivatives.…”

Diverse Polycyclic Polyprenylated Acylphloroglucinol Congeners with Anti-Nonalcoholic Steatohepatitis Activity from Hypericum forrestii

“…Prior investigations of the chemical constituents of Hypericum species have revealed polycyclic polyprenylated acylphloroglucinols (PPAPs) with fascinating chemical structures . The type of acyl groups, the various kinds of prenyl-derived substituent, and the different modes of secondary cyclization collectively create the structural diversity of biologically active PPAPs. , In a systematic phytochemical investigation for diverse PPAPs from H. forrestii , a folk medicinal plant used for treating hepatitis, scalds, burns, and snakebite diseases in southwest China, 40 PPAPs with diverse carbon skeletons were isolated, including the ten new compounds, hyperforcinols A–J ( 1 – 10 ), and 30 known biogenetic congeners ( 11 – 40 ). The structures of hyperforcinols A–J ( 1 – 10 ) were determined by HRESIMS and NMR spectroscopic data analysis, and the absolute configurations were established using electronic circular dichroism (ECD) exciton chirality method and X-ray diffraction analysis combining with examining experimental and calculated ECD data.…”