Polycyclic Polyprenylated Acylphloroglucinols and Chromone O‐Glucosides from Hypericum henryi subsp. uraloides

Abstract

Two new C(30)-epimeric polycyclic polyprenylated acylphloroglucinols (PPAPs), named uralodins B and C (1 and 2, resp.), were isolated from the aerial parts of Hypericum henryi subsp. uraloides together with two new chromone glucosides, urachromones A and B (3 and 4, resp.), as well as 16 known compounds. Their structures were established by extensive NMR techniques and MS analysis. The epimers 1 and 2 always behaved like a single compound when examined by TLC, and were separated by HPLC. Their configuration was distinguished by comparative analysis of the NMR data with known analogues together with the ROESY experiment. All the isolated PPAPs were evaluated for their cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines. Compound 1 showed modest cytotoxic activities against SGC7901 and HL-60 cell lines, and 2 showed modest cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines.

Evaluation of DNA Damage in HepG2 Cells and Mutagenicity of Garcinielliptone FC, A Bioactive Benzophenone

“…Distributed in 30 genera, the plants of the Clusiaceae family include economically relevant trees, shrubs, lianas and herbs used in the production of edible fruit, hardwood and chemical derivatives with interesting pharmacological and industrial properties . More specifically, the plants of the Platonia genus are rich in natural products with relevant biological activities , such as antimicrobial , leishmanicidal , antidepressant , cytotoxic , anti‐HIV , anti‐inflammatory , anticonvulsant and antitumour effects.…”

Dorstenpictanone: a new bicyclic polyprenylated compound from Dorstenia picta

“…Besides 15 signals for three prenyl groups, 13 C NMR spectrum showed signals for three methylene and four quaternary carbons including signals for two nonconjugated carbonyl groups at d 208.2 and 207.9 and two methine signals. In addition, the key HMBC correlations (Figure 2) of H-4 with C-3, C-5, C-6, and C-2, H-5 with C-1, C-4, C-6, and C-20, H-8 with C-9, C-7, and C-6, and H-7 with C-1, C-6, and C-9 verified the core bicyclo[3.3.1]nonane-1,9-dione system [11,12]. HREIMS required the compound to be bicyclic, considering the subtraction of five double bond equivalents for two carbonyl groups and three prenyl double bonds.…”

“…The above ROESY peaks indicated that 1 had the same relative configuration at C-2, C-3, and C-6 as furohyperforin and uralodin B [12]. Hence, the structure of 1 was elucidated and named as dorstenpictanone (1).…”

Hypercohones D–G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens

“…Fraction B was subjected to a series of chromatographic methods, and led to the isolation of four new acylphloroglucinol derivatives, hypercohones D–G ( 1 – 4 ), together with four known ones, uralodin A ( 5 ), [17] uralodin B ( 6 ), [18] oxepahyperforin ( 7 ) [19], and tomoeone E ( 8 ) [20]. …”