The Natural Occurrence and Uses of the Toxic Coumarins

Perone, Vernon B.

doi:10.1016/b978-0-12-046508-8.50009-x

Cited by 8 publications

(8 citation statements)

References 76 publications

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“…Psoralens are naturally occurring linear furocoumarins synthesized in plants that have been used in the treatment of skin diseases for thousands of years. 8 The most widely used psoralen, 8-methoxypsoralen, has been used more recently for the treatment of vitiligo, psoriasis, and cutaneous T cell lymphoma. 9 Psoralens are actively used for the treatment of these diseases because of their ability to interact with DNA.…”

Section: Introductionmentioning

confidence: 99%

Rapid characterization of cross-links, mono-adducts, and non-covalent binding of psoralens to deoxyoligonucleotides by LC-UV/ESI-MS and IRMPD mass spectrometry

Smith

Brodbelt

2010

Analyst

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SummaryUpon UV photoactivation, psoralen analogs form covalent mono-adducts and cross-links with DNA at thymine residues. Electrospray ionization mass spectrometric analysis allowed rapid and efficient determination of the reaction percentages of each psoralen analog with DNA duplexes containing different binding sites after exposure to UV irradiation. The distribution of cross-linked products and mono-adducts was monitored by both LC-UV and IRMPD-MS methods with the highest ratio of cross-linked products to mono-adducts obtained for 8-methoxypsoralen (8-MOP), psoralen (P), and 5-methoxypsoralen (5-MOP). Reactions at 5'-TA sites were favored over 5'-AT sites, and duplexes containing two and three binding sites showed extensive binding by the psoralens. 4'-aminomethyl-4,5',8-trimethylpsoralen (AMP) bound non-selectively via non-covalent interactions and was the only psoralen analog to show significant binding in the absence of UV irradiation. 8-MOP binding displayed the greatest sequence selectivity among the psoralen analogs. The sites of interstrand cross-linking were determined by fragmentation of the duplex/psoralen complexes by infrared multiphoton dissociation (IRMPD), which produced cross-linked product ions containing an intact single strand, the psoralen analog, and either a w n or a n -B portion of the complementary strand. IRMPD of DNA/AMP complexes after UV irradiation also produced high abundances of the intact single strands with the AMP ligand attached, products indicative of a significant population of mono-adducts.

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Section: Introductionmentioning

confidence: 99%

Rapid characterization of cross-links, mono-adducts, and non-covalent binding of psoralens to deoxyoligonucleotides by LC-UV/ESI-MS and IRMPD mass spectrometry

Smith

Brodbelt

2010

Analyst

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“…Psoralens are used in a number of diverse ways. Clinically, psoralens are used for the treatment of psoraisis (41), vitiligo (42), and other skin disorders (43). Extensive studies on the metabolism of these compounds have been made (44).…”

Section: Introductionmentioning

confidence: 99%

Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry

Cimino

Gamper

Isaacs

et al. 1985

Annu. Rev. Biochem.

750

361

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“…24 Urea is the major nitrogen containing metabolic product of protein metabolism; uric acid is the major product of purine bases, adenine and guanine; creatinine is endogenously produced and released into body fluids and its clearance is measured as an indicator of glomerular filtration rate. 25,26 Treatment with rutin and quercetin brought these parameters to near normal level which could be due to decreased disturbances of protein and nucleic acid metabolism as evidenced by improved glycaemic control as well as renal functions. After treatment with rutin and quercetin, we found that combination of rutin and quercetin lowered fasting blood glucose and HbA1c of diabetic rats.…”

Section: Discussionmentioning

confidence: 99%

Effect of compounds isolated from Filicium decipiens and Ventilago madraspatana against diabetic nephropathy in streptozotocin induced diabetic rats

Sasikala¹,

Sudhakar²

2015

IJPER

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Context: Diabetes mellitus is a group of syndromes characterized by hyperglycemia, altered metabolism of lipids, carbohydrates and proteins and an increased risk of complications from vascular diseases. Filicum decipiens Wight & Arn., (Sapindaceae) and Ventilago madraspatana Gaertn., (Rhamnaceae) are traditionally used for diabetic and other different folk medical uses. Objective: The present study compares the antihperglycemic activity exerted by methanolic extracts of Filicum decipiens (400 mg/kg), Ventilago madraspatana (400 mg/kg), rutin (100 mg/kg), quercetin (50 mg/kg) and combined treatment of rutin with quercetin (100 mg/kg+ (50 mg/kg) on diabetic rats. Material and methods: Methanolic extracts of Filicum decipiens and Ventilago madraspatana leaves were prepared and isolated by soxhlet and solubilization method. Rats were made diabetic by a single dose of streptozotocin (45 mg/kg i.p.). The animals with fasting blood glucose level more than 250 mg/dL were given methanolic leaves extract of Filicum decipiens (400 mg/kg), Ventilago madraspatana (400 mg/kg), quercetin (50 mg/kg), rutin (100 mg/kg) and rutin with quercetin (100 mg/kg + 50 mg/kg) were administered for 45 days and screened for antidiabetic activity. Results and discussion: After 45 days we observed that supplementation with combined dose of rutin and quercetin significantly (p<0.05) decreased glycosylated hemoglobin (HbA 1 C) (6.01 mg/g ) and increased the levels of plasma insulin 11.98 μU/mL, hemoglobin 12.12 g/dL, urea 42.16 mg/dL, creatinine 1.41 mg/dL, plasma sodium141.00 mEq/L and urinary potassium 5.11 mEq/L and decrease the activities of enzymatic antioxidant upon STZ treatment and also significantly (p<0.05) reversed the altered levels and activities of above mentioned diabetic, renal and antioxidant markers in experimental rats as compared to their individual supplementation. Conclusion: Summed effect of quercetin with rutin seems to have a promising value for the development of a potent phytomedicine for diabetic nephropathy.

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The Natural Occurrence and Uses of the Toxic Coumarins

Cited by 8 publications

References 76 publications

Rapid characterization of cross-links, mono-adducts, and non-covalent binding of psoralens to deoxyoligonucleotides by LC-UV/ESI-MS and IRMPD mass spectrometry

Rapid characterization of cross-links, mono-adducts, and non-covalent binding of psoralens to deoxyoligonucleotides by LC-UV/ESI-MS and IRMPD mass spectrometry

Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry

Effect of compounds isolated from Filicium decipiens and Ventilago madraspatana against diabetic nephropathy in streptozotocin induced diabetic rats

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