Hypascyrins A–E, Prenylated Acylphloroglucinols from Hypericum ascyron

Abstract

Six new prenylated acylphloroglucinols with menthane moieties, hypascyrins A−E (1−5) and ent-hyphenrone J (6), together with four known analogues, were isolated from Hypericum ascyron roots. Detailed spectroscopic data analyses resulted in the assignment of their structures. The absolute configuration of 1 was deduced by experimental and calculated ECD data, while those of 2−6 were assigned by ECD data analyses as well as chemical conversions. Hypascyrins A (1), C (3), and E (5) and ent-hyphenrone J (6) exhibited antimicrobial activity against MRSA (MIC 50 values of 4.0, 8.0, 2.0, and 4.0 μM, respectively) and Bacillus subtilis (MIC values of 4.0, 4.0, 2.0, and 4.0 μM, respectively).

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.…”

Characteristic metabolites of Hypericum plants: their chemical structures and biological activities

“…The whole plants of H. ascyron collected in Tokushima prefecture, Japan were separated into the aerial parts and roots. Their chemical constituents were separately investigated by chromatographic techniques to isolate some PAPs (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Their structures were established based on spectroscopic analyses.…”

“…Investigation of H. ascyron roots gave six new PAPs with menthane moieties, hypascyrins A–E ( 9 – 13 ) and ent -hyphenrone J ( 14 ) (Fig. 1 ) [ 14 ]. The absolute configuration of 9 was deduced by comparison of experimental and time-dependent density functional theory (TDDFT) calculated electronic circular dichroism (ECD) spectra, while those of 10 – 14 were assigned by ECD analyses as well as chemical conversions.…”

(±)-Walskiiglucinol A, a pair of rearranged acylphloroglucinol derivative enantiomers from Hypericum przewalskii

“…3,4 The structural diversity of acylphloroglucinol derivatives leads to a wide range of biological and pharmacological effects, 3 including anticancer, 5 anti-inflammatory, 6,7 antidepressive, 8 and antimicrobial activities. 9,10…”

“…3,4 The structural diversity of acylphloroglucinol derivatives leads to a wide range of biological and pharmacological effects, 3 including anticancer, 5 anti-inflammatory, 6,7 antidepressive, 8 and antimicrobial activities. 9,10 Hypericum przewalskii (Hypericaceae), a perennial herb, mainly distributed in Shaanxi, Gansu and Hubei provinces of China, is extensively used as a folk medicine to treat traumatic injuries, irregular menstruation and rheumatic pain. [11][12][13] Previous phytochemical investigations on H. przewalskii revealed that special acylphloroglucinol derivatives were found in this plant.…”