Disease relevance of Angelicin

• SV40-transformed normal, xeroderma pigmentosum (XP) and Fanconi's anemia (FA) fibroblasts have distinct repair capacities for monoadducts and DNA interstrand cross-links produced by exposure to near-UV (320-400 nm) light in the presence of 8-methoxypsoralen or angelicin [1].
• DNA photosensitization by several furocoumarins (including 3-carbethoxypsoralen (3-CPs), 8-methoxypsoralen (8-MOP), 5-methoxypsoralen (5-MOP) and angelicin was investigated by using DNA sequencing methodology [2].
• Three derivatives of angelicin (1) [4'-methyl-, 4,4'-dimethyl-, and 4',5-dimethylangelicin (2a-c)] have been prepared with the aim of obtaining new agents for the photochemotherapy of psoriasis [3].
• Enhanced sensitivity of Escherichia coli umuC to photodynamic inactivation by angelicin (isopsoralen) [4].
• Photodynamic inactivation and mutagenesis by angelicin (isopsoralen) or thiopyronin (methylene red) in wild-type and repair-deficient strains of bacteriophage T4 [5].

High impact information on Angelicin

• Interestingly, none of the 8-methoxypsoralen + UVA- or angelicin + UVA-induced tumors we analyzed contained mutations in any of the ras genes [6].
• DNA repair in human cells containing photoadducts of 8-methoxypsoralen or angelicin [7].
• The studies suggested that several point mutations are necessary to pave the road toward angelicin synthase evolution [8].
• The incision reaction was performed with HeLa cell-free extracts on angelicin or 8-methoxypsoralen (8-MOP)-modified plasmid DNA substrates carrying known amounts of mono- and biadducts, within various relative ratios [9].
• Xeroderma pigmentosum group A cells excised about 20% of the angelicin adducts, group D cells excised 55-60%, and group E, 80% [10].

Chemical compound and disease context of Angelicin

• The first group (as control) received only dimethyl sulfoxide, the second, third and fourth groups received different doses of the Sobatum (100, 200, 400 mg/kg body weight), and the fifth group (as positive control) received cyclophosphamide (100 mg/kg body weight) by i.p. injection [11].
• Phototoxicity from furocoumarins (psoralens) of Heracleum laciniatum in a patient with vitiligo. Action spectrum studies on bergapten, pimpinellin, angelicin and sphondin [12].
• OBJECTIVE: To report the results of a double-blind, placebo-controlled trial to evaluate Azuprostat, a beta-sitosterol, in patients with symptoms of outlet obstruction caused by benign prostatic hyperplasia (BPH) [13].

Biological context of Angelicin

• The extent of the side chain hydroxylation of cholesterol, campesterol (24 alpha-methylcholesterol), and beta-sitosterol (24 alpha-ethylcholesterol) in rat liver mitochondria has been compared [14].
• As observed previously with 8-methoxypsoralen, photodynamic mutagenesis with angelicin is abolished by defects in the uvsW-uvsX-uvsY system [5].
• Synthesis of 2,3-dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from epoxy aldehydes. One-step syntheses of brosimacutin G, vaginidiol, vaginol, smyrindiol, xanthoarnol, and Avicenol A. Biomimetic syntheses of angelicin and psoralen [15].
• 8-Methoxypsoralen and angelicin led to a significant induction of CYP1A1 mRNA in hepatocytes, while all furocoumarins except bergamottin increased xenobiotic-responsive element-driven reporter gene expression in transfected H4IIE rat hepatoma cells when light was excluded [16].
• It does, however, produce almost twice as many sister-chromatid exchanges per lethal event than angelicin [17].

Anatomical context of Angelicin

• SV40 induction from a mammalian cell line by ultraviolet radiation and the photosensitizers 8-methoxypsoralen and angelicin [18].
• Here, an effort was made to evaluate the induction of micronucleus by the Sobatum in the bone marrow of swiss mice [11].
• Lack of micronucleus induction by 'Sobatum' in bone marrow erythrocytes of Swiss mice [11].
• Accumulation of gamma-globin mRNA in human erythroid cells treated with angelicin [19].
• The average leukocyte count and haemoglobin level of the Sobatum-treated group was considerably improved at the end of the experimental period [20].

Associations of Angelicin with other chemical compounds

• Group D cells seem exceptionally able to repair angelicin adducts in comparison to their repair of pyrimidine dimers, suggesting that these cells lack a gene product that is required to a greater extent for the repair of pyrimidine dimers than for the repair of angelicin adducts [10].
• The results showed that angelicin, pimpinellin, sphondin, byakangelicol, oxypeucedanin, oxypeucedanin hydrate, xanthotoxin, and cnidilin are potential NO production inhibitors, and their IC50 values for inhibition of nitrite production were 19.5, 15.6, 9.8, 16.9, 16.8, 15.8, 16.6, and 17.7 microg/mL, respectively [21].
• The molecular conformation is close to that of angelicin, the additional methyl groups being sandwiched with respect to the molecular plane, in order to minimize their steric hindrance [22].
• The antiinflammatory effect of solasodine (50 mg/kg p.o.), of a purified component named sobatum (50 mg/kg p.o.) and of methanol extract of Solanum trilobatum (100 mg/kg p.o.) was evaluated [23].

Gene context of Angelicin

• However, the psoralen analog angelicin (monoadduct damage) induced a significant S-phase delay in the rad14 Delta mutant [24].
• To broaden our knowledge about the mutagenic specificity of SOS-dependent mutagens, we determined the mutational specificity of 233 suppressible lacI mutations induced by angelicin [25].
• Angelicin- plus near-UV-induced mutations were umuC dependent in Escherichia coli K-12 [25].
• Baculovirus-mediated expression of the CYP6B4v1 protein in lepidopteran cell lines demonstrates that this P450 isozyme metabolizes isopimpinellin, imperatorin, and bergapten at high rates, xanthotoxin and psoralen at intermediate rates and angelicin, sphondin, and trioxsalen only at very low rates [26].
• In strains of Escherichia coli deficient in excision repair (uvrA or uvrB), plasmid pKM101 muc+ but not pGW219 mucB::Tn5 enhanced resistance to angelicin monoadducts but reduced resistance to 8-methoxy-psoralen interstrand DNA crosslinks [27].

Analytical, diagnostic and therapeutic context of Angelicin

• Complete cellular recovery could be observed when the cell cultures were treated with angelicin-plus-UVA (320-400 nm) or 8-MOP-plus-395 nm [28].
• The partition coefficient (P) of 82 furocoumarins and analogs (psoralens, angelicins, allopsoralens, 8-azapsoralens, angular furoquinolin-2-ones, sulfur and selenium isosters of psoralen and angelicin) has been determined by reversed-phase HPLC [29].
• Regarding histopathological evaluation, there was no development of gross abnormalities or pathological lesions observed in any of the tissues in sobatum-treated and control groups [30].
• In the acute toxicity test, there was a single exposure of sobatum in mice in order to evaluate toxicity symptoms [30].
• The phagodepression activity of five furanocoumarins (FC), bergapten, xanthotoxin, psoralen, imperatorin, and angelicin, has been studied against larvae of Egyptian cotton leafworm Spodoptera littoralis (Boisduval) (Lepidoptera: Noctuidae) using a leaf-disk choice bioassay [31].

References