Xanthones in Hypericum: Synthesis and Biological Activities

Demirkiran, Özlem

doi:10.1007/7081_2007_079

Cited by 22 publications

(14 citation statements)

References 97 publications

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“…In contrast, subterraneous parts of Hypericum received less attention, even though they are known to contain phenolic acids, flavonols, flavan‐3‐ols, and xanthones . As interesting natural plant constituents, xanthones hold a distinct position in the phytochemistry and pharmacology of Hypericum . Specifically, several structural types, e.g .…”

Section: Introductionmentioning

confidence: 99%

Lipid and Phenolic Constituents from Seeds of Hypericum perforatum L. and Hypericum tetrapterum Fr. and their Antioxidant Activity

Heinrich¹,

Lorenz²,

Daniels³

et al. 2017

Chemistry & Biodiversity

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Seeds of Hypericum perforatum and H. tetrapterum were extracted with dichloromethane and methanol and investigated by chromatographic and mass spectrometric methods. Both species yielded a fatty oil fraction amounting to 30.5% and 18.0% of the seed weight, respectively. Linoleic acid (C18:2n-6) was shown to be the predominant fatty acid constituent. Moreover, xanthone derivatives, i.e. tetrahydroxyxanthones (THX), xanthone-glycosides and xanthone-sulfonates, were assigned in methanolic extracts. For structure elucidation, one representative xanthone, namely 1,3,6,7-THX, was synthesized and analyzed via HPLC-DAD/MS and GC/MS. Total THX contents were quantitated applying a validated HPLC-DAD method, resulting in 1.25 g/kg (H. perforatum) and 0.27 g/kg (H. tetrapterum), respectively. Moreover, the free radical scavenging capacity of the methanol extracts was tested using the DPPH antioxidant assay. Both, H. perforatum (IC = 8.7 mg/l) and 1,3,6,7-THX (IC = 3.0 mg/l), exhibited good DPPH free radical scavenging activity compared to Trolox (IC = 6.6 mg/l).

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Section: Introductionmentioning

confidence: 99%

Lipid and Phenolic Constituents from Seeds of Hypericum perforatum L. and Hypericum tetrapterum Fr. and their Antioxidant Activity

Heinrich¹,

Lorenz²,

Daniels³

et al. 2017

Chemistry & Biodiversity

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“…Thus, for instance, xanthone derivatives with anti-cancer [3,4], cytotoxic [5,6], topoisomerase II inhibitory [5], monoamine oxidase inhibitory [6], antioxidant [6], and antimicrobial activity [7] have been described in the recent literature. In view of this fact synthetic derivatives of xanthones are attractive compounds for medicinal chemists.…”

Section: Introductionmentioning

confidence: 99%

Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data

et al. 2010

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The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations (1H, 13C, 15N) of the ring systems and their precursors are presented.

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“…Xanthones are usually classified in 5 major groups: Simple oxygenated xanthones, xanthone glycosides, prenylated and related xanthones, xanthonolignoids and miscellaneous. Their in vitro and in vivo antitumor potential has recently been object of a considerable numbert of studies [22].…”

Section: Xanthonesmentioning

confidence: 99%

The Role of Phenolic Compounds in the Fight against Cancer – A Review

Carocho¹,

Ferreira

2013

ACAMC

238

144

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Abstract:Cancer is a worldwide scourge; it's the leading cause of death in developed countries and is increasing in developing countries. Mankind has been trying with effort to find better and cheaper treatments with fewer side effects, to reduce the incidence of the disease and its consequent mortality. For many years, phenolic compounds have been intensely studied for their antitumor, proapoptotic and antiangiogenic effects. In recent years, the usage of these compounds has increased considerably.This manuscript intends to structurally characterize the different phenolic compounds (flavonoids, hydroxycinnamates, hydroxybenzoates, coumarins, xanthones, chalcones, stilbenes, lignins and lignans) and their metabolic pathways as well as review the most important results regarding these compounds and their derivatives in cancer treatment and prevention both in tumor cell lines in vitro, in murine models in vivo and finally some results regarding human trials.

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Xanthones in Hypericum: Synthesis and Biological Activities

Cited by 22 publications

References 97 publications

Lipid and Phenolic Constituents from Seeds of Hypericum perforatum L. and Hypericum tetrapterum Fr. and their Antioxidant Activity

Lipid and Phenolic Constituents from Seeds of Hypericum perforatum L. and Hypericum tetrapterum Fr. and their Antioxidant Activity

Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data

The Role of Phenolic Compounds in the Fight against Cancer – A Review

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