Xanthone Constituents of Hypericum androsaemum

Nielsen, Hanne Mørck; Arends, Peter

doi:10.1021/np50003a012

Cited by 39 publications

(22 citation statements)

References 5 publications

(9 reference statements)

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“…Data from 1 Hand/or 13 C-NMR confirmed the oxygenation pattern and allowed the localization of the prenyl, pyran and methoxyl groups. Compounds 1, 3, 5 and 6 were isolated previously from H. androsaemum roots [18], while compounds 7 (g-mangostin), 10 (garcinone B), and 11 (paxanthone) were isolated from H. patulum cell cultures [19,20]. The data obtained by us were in good agreement with those reported in the literature.…”

Section: Identified Xanthonessupporting

confidence: 89%

“…The high l value of protons in position C-11 (l 4.12) indicates that the prenyl group is located at C8, in the neighborhood of the carbonyl group [18,20]. Besides, the whole set of values obtained for the prenyl group is in good agreement with those obtained for compound 5.…”

Section: Identified Xanthonessupporting

confidence: 76%

“…1). Compounds 1 and 2 showed the UV spectral characteristics of the 1,3,5,6 oxygenated xanthones, with band IV reduced to shoulder [17], while all the other identified xanthones had an UV similar to mangiferin, typical of the 1,3,6,7 oxygenation pattern with a very well-defined band IV [18][19][20]. Data from 1 Hand/or 13 C-NMR confirmed the oxygenation pattern and allowed the localization of the prenyl, pyran and methoxyl groups.…”

Section: Identified Xanthonesmentioning

confidence: 99%

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Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

et al. 2000

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Calli and suspended cells of Hypericum androsaemum accumulated high levels of 1,3,5,6 and 1,3,6,7 oxygenated xanthones. The major compounds include simple oxygenated xanthones or derivatives with prenyl, pyran or methoxyl groups, four of them being new natural compounds. A hypothetical biosynthetic scheme is proposed based on the isolated compounds and statistical analysis. Xanthone accumulation was influenced greatly by medium factors, namely hormone supplementation. Calli grown with 4.5 mM a-naphtaleneacetic acid (NAA) +2.3 mM kinetin (KIN) had the highest specific xanthone production (1.3% biomass dry weight (DW)), whereas suspended cells grown in similar medium accumulated a lower amount (0.87% DW). Calli displayed a negative linear relationship between total xanthone accumulation and NAA concentration, in the range of 4.5 -22.5 mM. However, in this range the xanthone 1,3,6,7/1,3,5,6 ratio and the biomass production showed a positive linear relationship with NAA concentration. Substitution of 4.5 mM of NAA by the same molar amount of 2,4-dichlorophenoxyacetic acid (2,4-D), in the presence of 2.3 mM of KIN, caused a decrease in xanthone accumulation in calli. The use of N 6 -benzyladenine (BA) instead of KIN reduced xanthone production, independently of the auxin used. This effect was attenuated when both hormones were present.

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Section: Identified Xanthonessupporting

confidence: 89%

Section: Identified Xanthonessupporting

confidence: 76%

Section: Identified Xanthonesmentioning

confidence: 99%

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Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

et al. 2000

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“…was maculatoxanthone from the roots of H. maculatum Crantz (Arends 1969). The occurrence of hydroxy-and methoxy-substituted xanthones in roots of H. androsaemum L. is mentioned in the study of Nielsen and Arends (1979). Thereafter, four new xanthones were isolated from the roots of H. roeperanum Schimp.…”

Section: Introductionmentioning

confidence: 99%

Xanthones from roots, hairy roots and cell suspension cultures of selected Hypericum species and their antifungal activity against Candida albicans

et al. 2015

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Highest xanthone contents were found in Hypericum pulchrum and H. annulatum untransformed roots. The best anti- Candida activity was obtained for hairy roots extracts of H. tetrapterum clone 2 ATCC 15834. Extracts of root cultures, hairy roots and cell suspensions of selected Hypericum spp. were screened for the presence of xanthones and tested for their antifungal activity against Candida albicans strain ATCC 10231. At least one of the following xanthones, 5-methoxy-2-deprenylrheediaxanthone; 1,3,6,7-tetrahydroxyxanthone; 1,3,5,6-tetrahydroxyxanthone; paxanthone; kielcorin or mangiferin was identified in methanolic extracts of the untransformed root cultures. The highest total xanthone content, with five xanthones, was found in untransformed H. pulchrum and H. annulatum root cultures. Hairy roots and the controls of H. tetrapterum contained 1,7-dihydroxyxanthone, while hairy root cultures and the corresponding controls of H. tomentosum contained toxyloxanthone B, 1,3,6,7- and 1,3,5,6-tetrahydroxyxanthone. Two xanthones, cadensin G and paxanthone, were identified in cell suspension cultures of H. perforatum. Their content increased about two-fold following elicitation with salicylic acid. The anti-Candida activity of the obtained extracts ranged from MIC 64 to >256 µg ml(-1). Among the extracts of Hypericum untransformed roots, the best antifungal activity was obtained for extracts of H. annulatum grown under CD conditions. Extracts of hairy roots clones A4 and 7 ATCC15834 of H. tomentosum and clone 2 ATCC15834 of H. tetrapterum displayed inhibition of 90% of Candida growth with 256 μg ml(-1). Extracts from chitosan-elicitated cells did not show antifungal activity.

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“…1 Published papers on H. maculatum refer to flavonols, flavones, xanthones, coumarines and phenolic acids. 2,3 In this paper, we present the results of the investigation of the composition and antimicrobial activity of H. maculatum essential oil.…”

Section: Introductionmentioning

confidence: 99%

Composition and antimicrobial activity of the essential oil of Hypericum maculatum Crantz

Gudžić¹,

Djokovic

Vajs

et al. 2002

Flavour & Fragrance J

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For the first time the composition of the essential oil of Hypericum maculatum Crantz has been determined by GC and GC-MS. The oil consisted of a large number of components in low percentages. Only five components exceeded a 5% level:ˇ-farnesene (10.0%), n-undecane (8.2%),ˇ-caryophyllene (7.6%), υ-cadinene (7.2%) and -muurolene (5.2%). The oil showed strong antimicrobiological activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis, Klebsiella pneumoniae, Bacillus subtilis, Sarcina lutea, Aspergillus niger and Candida albicans, documented in vitro by MIC and MMC values.

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Xanthone Constituents of Hypericum androsaemum

Cited by 39 publications

References 5 publications

Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

Xanthones from roots, hairy roots and cell suspension cultures of selected Hypericum species and their antifungal activity against Candida albicans

Composition and antimicrobial activity of the essential oil of Hypericum maculatum Crantz

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