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

Abstract

Four new polycyclic polyprenylated acylphloroglucinol type metabolites, hypercohones D–G (1–4), along with four known analogues (5–8), were isolated from the aerial parts of Hypericum cohaerens. The structures of these isolates were elucidated by extensive spectroscopic methods. The inhibitory activities of these isolates against five human cancer cell lines in vitro were also tested.Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-014-0007-5) contains supplementary material, which is available to authorized users.

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

“…Twenty-nine other known compounds, ascyronone E ( 11 ), 3-hydroxyhyperforin-3,9-hemiketal ( 12 ), hyphenrone G ( 13 ), oxepahyperforin ( 14 ), hypercohone F ( 15 ), hypercohins G and H ( 16 and 17 ), furohyperforin ( 18 ), uraloidin A ( 19 ), uralione E ( 20 ), furoadhyperforin ( 21 ), hypercohin I ( 22 ), uralodins B and C ( 23 and 24 ), attenuatumione E ( 25 ), hypercalin C ( 26 ), the 2-(2-methyl)­butyrylated homologue of hypercalin C ( 27 ), hyphenrone K ( 28 ), hypascyrin C ( 29 ), hyperuralone E ( 31 ), hyphenrone A ( 32 ), hypersampsone E ( 33 ), hypersampsone D ( 34 ), sampsonione J ( 35 ), plukenetione C ( 36 ), hyphenrone L ( 37 ), hypatulin B ( 38 ), hypatulin A ( 39 ), and hypercohin K ( 40 ), were also isolated. Their structures were identified from their NMR and MS data, as well as by comparing these with reported values.…”

Research Progress of Polycyclic Polyprenylated Acylphloroglucinols

“…Some PPAPs were isolated simultaneously by different groups working independently, who then gave the PPAP different names. The structures of adhyperfirin and garcinielliptone K were initially misassigned; , later revision showed them to be identical to the already known hyperibine J ( 2 ) and propolone C ( 24 ). , Furthermore, the structures of hyperibine J ( 2 ) and hyperpolyphyllirin, , hypersampson R ( 88 ) and hyperattenin B, , hypercohone F ( 107 ) and uralione H, , guttiferone J ( 137 ) and garciyunnanin A, , oblongifolin C ( 141 ) and (+)-guttiferone G, , cowanone ( 160 ) and chamuangone, , sampsonione P ( 196 ) and hyperscabrone L, , hyperattenin E ( 199 ) and hyperibrin D, , pyramidatone A ( 365 ) and chipericumin E, , and hypelodin B ( 394 ) and hyphenrone L 1 were reported repeatedly and given two different names. In the tables, we arrange these names according to the order of publication.…”

Polyprenylated Phloroglucinols from Hypericum maculatum

“…The 13 C NMR spectrum of 1c (Table 1) exhibited signals for 32 carbons, including eleven quarternary (including three carbonyl, four olefinic, and one oxygenated sp 2 carbon), five methines, five methylenes, and eleven methyls (including one oxygenated). These data indicated the characteristic signals of an acylphloroglucinol core with two nonconjugated carbonyl groups [δ C 208.1 (C-9), δ C 206.6 (C-10)], a 1,3-keto-enol system [δ C 169.9 (C-2), δ C 123.2 (C-3), δ C 196.7 (C-4)], and two quaternary carbons at δ C 78.3 (C-1), and δ C 60.3 (C-5) [4]. -4) and δ C 208.1 (C-9), to a methylene at δ C 42.2 (C-6), as well as to a quaternary carbon at δ C 60.3 (C-5) pointing out that Me-19 is a substituent of C-5.The three-proton singlet of the artificial methoxy group at δ H 4.03 gave a cross peak with the carbon signal of C-2.…”