Phloroglucinols with Antioxidant Activity and Xanthonolignoids from the Heartwood of <i>Hypericum geminiflorum</i>

Wu, Chien-Chang; Yen, Ming‐Hong; Yang, Shyh‐Chyun; Lin, Chun‐Nan

doi:10.1021/np8001145

Cited by 29 publications

(35 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For a review of polycyclic polyprenylated acylphloroglucinols, see: Ciochina & Grossman (2006). For background to Clusiaceae metabolites, see: Garnsey et al (2011); Zhang et al (2010); Christian et al (2008); Wu et al (2008). For relativeconfiguration structure determinatons, see: Santos et al (1998); Xiao et al (2007); Martins et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

Redetermination and absolute configuration of (+)-7-epiclusianone

Christian¹,

Fronczek²,

Ky³

et al. 2012

Acta Cryst E

View full text Add to dashboard Cite

The absolute configuration of 3-benzoyl-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-enyl)bicyclo[3.3.1]non-3-ene-2,9-dione, C33H42O4, isolated from Hypericum hypericoides, has been determined. The previous study [Xiao et al. (2007 ▶). J. Nat. Prod. 70, 1779–1782] gave only the established relative configuration. The three stereogenic centers are now established as 1R, 5R and 7S on the basis of the refinement of the Flack absolute structure parameter against Cu Kα data and correspond to a specific rotation of [α]D 20 = +66°. The enol–hydroxy group forms an intramolecular O—H⋯O hydrogen bond to close an S(6) ring.

show abstract

Section: Related Literaturementioning

confidence: 99%

Redetermination and absolute configuration of (+)-7-epiclusianone

Christian¹,

Fronczek²,

Ky³

et al. 2012

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…This kind of spirocyclic acylphloroglucinols, possessing an 6/6/5 carbon skeleton, were very seldom in the natural products, and only isolated twice from Hypericum plants up to now. 5,29) Biogenetically, these metabolites were derived from monocyclic polyprenylated acylphloroglucinols type precursor and often isolated as stereoisomers, such as tomoeones A-H and hyperielliptone HB. 5,29) In the present study, hyperbeanols A-D should be derived from the hypercalin B (5) by an intramolecular cyclization reaction between C-4 and C-14.…”

mentioning

confidence: 99%

“…5,29) Biogenetically, these metabolites were derived from monocyclic polyprenylated acylphloroglucinols type precursor and often isolated as stereoisomers, such as tomoeones A-H and hyperielliptone HB. 5,29) In the present study, hyperbeanols A-D should be derived from the hypercalin B (5) by an intramolecular cyclization reaction between C-4 and C-14. Since acylphloroglucinols were always isolated as gum, it is difficult to get the single crystal.…”

mentioning

confidence: 99%

Spirocyclic Acylphloroglucinol Derivatives from <i>Hypericum beanii</i>

Chen

et al. 2011

Chem. Pharm. Bull.

View full text Add to dashboard Cite

Polyprenylated acylphloroglucinols, featured a highly oxygenated bicyclo[3.3.1]-nonane-2,4,9-trione or bicyclo[3.2.1]-octane-2,4,8-trione core decorated with C 5 H 9 or C 10 H 17 (prenyl, geranyl, etc.) side chains, were only isolated from the Guttiferae plants so far.1) This type of metabolites were reported to possess a wide variety of biological activities such as antimicrobial, antidepressant, antioxidant, cytotoxic, and anti-human immunodeficiency virus (HIV) effects. 2-7)As an important member of the family Guttiferae, the genus Hypericum have been proved to be a prolific source of this special type metabolites. [8][9][10][11] H. beanii N. Robson is a shrub of this genus and widely distributed in Guizhou and Yunnan Provinces, P. R. China. 12) Two anti-staphylococcal acylphloroglucinols have been isolated from this plant previously.13) Our phytochemical investigation on the methanol extract of this plant led to the isolation of four new acylphloroglucinols, hyperbeanols A-D (1-4), together with the known hypercalin B (5), 14) (1S,4S,5S,10R)-4,10-guaianediol (6), 15) (ϩ)-alismoxide (7), 16) guaia-6,10(14)-dien-4-ol (8), 17 calycinoxanthone D (9), 18) ugaxanthone (10), 19) 2,5-dihydroxyxanthone (11), 20) 1,3-dihydroxy-6-methoxyxanthone (12), 21) 3,6,7-trihydroxy-1-methoxyxanthone (13), 22) 1,2,5-trihydroxyxanthone (14),28) The cytotoxicity of 1-5 against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 were examined. Reported herein are the isolation, structure elucidation, and cytotoxic evaluation of compounds 1-5. The MeOH extract (611 g) of the aerial parts of H. beanii (5.3 kg) was successively partitioned with petroleum ether and ethyl acetate. The petroleum ether soluble fraction (252 g) was subjected to silica gel column chromatography, Sephadex LH-20, and preparative HPLC to afford compounds 1-8. The ethyl acetate portion (167 g) was also purified by column chromatography, semipreparative, and preparative HPLC to obtain compounds 9-20.Compound 1 (d 197.3, 113.6, 193.7), one monobenzoyl group (d 197.0, 136.9, 127.8ϫ2, 128.0ϫ2, 132.2) Four new acylphloroglucinols with an unusual 6/6/5 spirocyclic skeleton, hyperbeanols A-D (1-4), were isolated from the methanol extract of Hypericum beanii along with 16 known compounds. Their structures were established on the basis of spectroscopic and X-ray diffraction analysis. Hyperbeanols A-C were three stereoisomers different only at the relative configuration of C-4 and C-13, which were distinguished by the nuclear Overhauser effect spectroscopy (NOESY) spectroscopic data in combination with the single X-ray analysis of hyperbeanol A (1). The cytotoxic activity of hyperbeanols A-D against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 was also evaluated.

show abstract

“…192.4 184.6 197.5 196.4 197.2 196.6 196.8 196.1 196.7 195.0 197.8 196 The molecular formula of hyperascyrone G (7), C 31 H 46 O 6 , was deduced from HRESIMS (m/z 515.3315 [M+H] + , calcd for C 31 H 47 O 6 , 515.3373). Comparison of the 1 H and 13 C NMR spectroscopic data of 7 with those of hyperielliptone HA (Wu et al, 2008) established structural similarities, except for substitution patterns at C-2 and C-27. The methyl group at C-2 and the secbutyl group at C-27 in hyperielliptone HA were replaced by an isoprenyl group and an isobutyl group in 7, respectively.…”

Section: Resultsmentioning

confidence: 82%

“…Besides H. ascyron Linn., PSAPs occurs only in a limited number of plants belonging to the families Hypericaceae and Simaroubaceae, including H. geminiflorum Hemsl. (Wu et al, 2008), H. beanii N. Robson (Chen et al, 2011), H. chinense L. (Abe et al, 2011), H. pyramidatum Ait. (Force et al, 2014), and Harrisonia perforata (Blanco) Merr.…”

Section: Compoundmentioning

confidence: 99%