Trioxygenated naturally occurring xanthones

Peres, Valdir; Nagem, Tânus Jorge

doi:10.1016/s0031-9422(96)00421-9

Cited by 123 publications

(74 citation statements)

References 199 publications

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“…2). 13) In addition, treatment of the coumarins 1-4 with CH 3 I and K 2 CO 3 in acetone produced ten methylated derivatives (1a-1d, 2a-2b, 3a-3b, 4a-4c) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Coumarins from the Bark of Mammea siamensis

Ngo

Nguyen

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D-and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC 50 in the range of 1.6-5.7 mM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.

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“…2). 13) In addition, treatment of the coumarins 1-4 with CH 3 I and K 2 CO 3 in acetone produced ten methylated derivatives (1a-1d, 2a-2b, 3a-3b, 4a-4c) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Coumarins from the Bark of Mammea siamensis

Ngo

Nguyen

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The study leadered by Healy et al (2004) resulted on the isolation of xanthones, compounds isolated from endophytic fungi identified as Xylaria sp. The fungus isolated from Glochidion ferdinandi plant, and the metabolites extracted showed important pharmacological activities (Peres & Nagem, 1996;Peres et al, 2000) as for example, anti-inflammatory (Lin et al, 1996), antimicrobial (Malet-Cascon et al, 2003), antioxidants (Minami et al, 1994), antifungical (Rocha et al, 1994) e anticancer properties (Ho et al, 2002). Krohn et al (2004), developed an similar research, describing the syntesis of xyloketal D, a natural product that belongs to a group of secondary metabolites isolated from Xylaria sp.…”

Section: Xylariaceae Metabolites Biological Activitymentioning

confidence: 99%

Xylariaceae Endophytic Fungi Metabolites Against Salmonella

Ribeiro¹,

Fonseca²,

Reis³

et al. 2012

Salmonella - A Diversified Superbug

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“…Xanthones are aromatic oxygencontaining compounds synthesized by fungi, lichens, lower vascular plants, and higher plants (Berti and Bottari, 1968;Culberson, 1969;Chexal et al, 1975;Devon and Scott, 1975;and Peres et al, 2000). Highly substituted xanthones (with hydroxy-, methoxy-and alkylgroups) occur in many different terrestrial plants (Tomasek and Crawford, 1986;and Peres and Nagem, 1997) especially those that prefer tropical or subtropical climates. Many shrubs and herbs, which occur widely in temperate regions of the world, contain xanthones (Wu et al, 1998).…”

Section: Introductionmentioning

confidence: 99%

Occurrence and Geochemical Significance of Carbazoles and Xanthones in Crude Oil from the Western Desert, Egypt

Bakr¹

2009

ear

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Abstract. This paper describes an approach that involves the evaluation of the occurrence and distributions of nitrogen-and oxygen-containing aromatic compounds in Egyptian crude oils and source rocks. Carbazoles and xanthones represent nitrogen-and oxygen-containing aromatic compounds, respectively.Alkylcarbazoles and benzocarbazoles were quantitatively studied in crude oils taken from the Abu Gharadig and Shushan basins in north Western Desert of Egypt in order to investigate their occurrence, concentrations and distributions. The abundances of carbazole, methylcarbazoles and dimethylcarbazoles in the marine Abu Gharadig oils are much higher than that of the terrestrial Shushan oils. The results presented here indicate that thermal maturation can be ruled out as a major factor in controlling the changes in the carbazole ratios in the crude oils. Most likely, source characteristics of the studied samples play a significant role in controlling the distribution of carbazole compounds in reservoired oils. The alkylcarbazoles 1MC/1MC+1EC, 3MC/4MC and 18DMC/18DMC+1EC when correlated with specific biomarker signatures provide background information discriminating between two main types of depositional setting: 1) Terrestrial dominated source deposited in oxidizing conditions for the Shushan oils and, 2) marine shale dominated sourced oils deposited in suboxic environments for the Abu Gharadig samples. Similarly, benzocarbazole distributions were found to be independent of maturity, but influenced by organic facies and depositional environments. Therefore, in this study, alkylcarbazole and benzocarbazoles compounds are well suited for the differentiation of Abu Gharadig and Shushan crude oils with respect to origin and variations of facies and depositional environment. M.M.Y. Bakr 128Using various kinds of Egyptian crude oils derived from marine carbonates, marine clastics and terrestrial sources, the current study indicates that xanthones and its alkylated homologues are abundant only in source extracts and crude oils that have terrestrial organic matter input. This is the second description of xanthones in crude oils, and the first in Egyptian petroleum systems. Overall, based on the data of this study, xanthones signatures show great promise as terrestrial source markers in a given petroleum system.

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Trioxygenated naturally occurring xanthones

Cited by 123 publications

References 199 publications

Cytotoxic Coumarins from the Bark of Mammea siamensis

Cytotoxic Coumarins from the Bark of Mammea siamensis

Xylariaceae Endophytic Fungi Metabolites Against Salmonella

Occurrence and Geochemical Significance of Carbazoles and Xanthones in Crude Oil from the Western Desert, Egypt

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