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Chemical Compound Review

KST-1A8515     (3S,8S,9S,10R,13R,14S,17R)- 17-[(2S,5S)-5...

Synonyms: AR-1A5002, AC1L1N7J, (3|A,20s,24s)-stigmast-5-en-3-ol
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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


Biological context of Angelicin


Anatomical context of Angelicin


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].


  1. Repair of psoralen-induced cross-links and monoadducts in normal and repair-deficient human fibroblasts. Gruenert, D.C., Cleaver, J.E. Cancer Res. (1985) [Pubmed]
  2. Oxidative DNA damage photo-induced by 3-carbethoxypsoralen and other furocoumarins. Mechanisms of photo-oxidation and recognition by repair enzymes. Sage, E., Le Doan, T., Boyer, V., Helland, D.E., Kittler, L., Helene, C., Moustacchi, E. J. Mol. Biol. (1989) [Pubmed]
  3. 4'-Methylangelicins: new potential agents for the photochemotherapy of psoriasis. Dall'Acqua, F., Vedaldi, D., Bordin, F., Baccichetti, F., Carlassare, F., Tamaro, M., Rodighiero, P., Pastorini, G., Guiotto, A., Recchia, G., Cristofolini, M. J. Med. Chem. (1983) [Pubmed]
  4. Enhanced sensitivity of Escherichia coli umuC to photodynamic inactivation by angelicin (isopsoralen). Miller, S.S., Eisenstadt, E. J. Bacteriol. (1985) [Pubmed]
  5. Photodynamic inactivation and mutagenesis by angelicin (isopsoralen) or thiopyronin (methylene red) in wild-type and repair-deficient strains of bacteriophage T4. Drake, J.W. J. Bacteriol. (1985) [Pubmed]
  6. N-ras mutation in ultraviolet radiation-induced murine skin cancers. Pierceall, W.E., Kripke, M.L., Ananthaswamy, H.N. Cancer Res. (1992) [Pubmed]
  7. DNA repair in human cells containing photoadducts of 8-methoxypsoralen or angelicin. Kaye, J., Smith, C.A., Hanawalt, P.C. Cancer Res. (1980) [Pubmed]
  8. Molecular cloning and functional characterization of psoralen synthase, the first committed monooxygenase of furanocoumarin biosynthesis. Larbat, R., Kellner, S., Specker, S., Hehn, A., Gontier, E., Hans, J., Bourgaud, F., Matern, U. J. Biol. Chem. (2007) [Pubmed]
  9. Preferential repair incision of cross-links versus monoadducts in psoralen-damaged plasmid DNA by human cell-free extracts. Calsou, P., Sage, E., Moustacchi, E., Salles, B. Biochemistry (1996) [Pubmed]
  10. Repair of psoralen adducts in human DNA: differences among xeroderma pigmentosum complementation groups. Cleaver, J.E., Gruenert, D.C. J. Invest. Dermatol. (1984) [Pubmed]
  11. Lack of micronucleus induction by 'Sobatum' in bone marrow erythrocytes of Swiss mice. Mohanan, P.V., Rathinam, K., Devi, K.S. Mutat. Res. (1996) [Pubmed]
  12. Phototoxicity from furocoumarins (psoralens) of Heracleum laciniatum in a patient with vitiligo. Action spectrum studies on bergapten, pimpinellin, angelicin and sphondin. Kavli, G., Midelfart, K., Raa, J., Volden, G. Contact Derm. (1983) [Pubmed]
  13. A multicentric, placebo-controlled, double-blind clinical trial of beta-sitosterol (phytosterol) for the treatment of benign prostatic hyperplasia. German BPH-Phyto Study group. Klippel, K.F., Hiltl, D.M., Schipp, B. British journal of urology. (1997) [Pubmed]
  14. Side chain hydroxylation of cholesterol, campesterol and beta-sitosterol in rat liver mitochondria. Aringer, L., Eneroth, P., Nordström, L. J. Lipid Res. (1976) [Pubmed]
  15. 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. Zou, Y., Lobera, M., Snider, B.B. J. Org. Chem. (2005) [Pubmed]
  16. Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. Baumgart, A., Schmidt, M., Schmitz, H.J., Schrenk, D. Biochem. Pharmacol. (2005) [Pubmed]
  17. Photobiological studies with dictamnine, a furoquinoline alkaloid. Ashwood-Smith, M.J., Towers, G.H., Abramowski, Z., Poulton, G.A., Liu, M. Mutat. Res. (1982) [Pubmed]
  18. SV40 induction from a mammalian cell line by ultraviolet radiation and the photosensitizers 8-methoxypsoralen and angelicin. Moore, S.P., Blount, H., Coohill, T.P. Photochem. Photobiol. (1983) [Pubmed]
  19. Accumulation of gamma-globin mRNA in human erythroid cells treated with angelicin. Lampronti, I., Bianchi, N., Borgatti, M., Fibach, E., Prus, E., Gambari, R. Eur. J. Haematol. (2003) [Pubmed]
  20. Effect of Sobatum on radiation-induced toxicity in mice. Mohanan, P.V., Devi, K.S. Cancer Lett. (1998) [Pubmed]
  21. Inducible nitric oxide synthase inhibitors of Chinese herbs. Part 2: naturally occurring furanocoumarins. Wang, C.C., Lai, J.E., Chen, L.G., Yen, K.Y., Yang, L.L. Bioorg. Med. Chem. (2000) [Pubmed]
  22. Molecular conformation of N,N-dimethyl-4-amino-3-chloroangelicin C13H10O3NCl. Benetollo, F., Bombieri, G., Mosti, L., Vedaldi, D., Dall'Acqua, n.u.l.l. Il Farmaco; edizione scientifica. (1984) [Pubmed]
  23. Antiinflammatory activity of Solanum trilobatum. Emmanuel, S., Ignacimuthu, S., Perumalsamy, R., Amalraj, T. Fitoterapia (2006) [Pubmed]
  24. S. cerevisiae has three pathways for DNA interstrand crosslink repair. Grossmann, K.F., Ward, A.M., Matkovic, M.E., Folias, A.E., Moses, R.E. Mutat. Res. (2001) [Pubmed]
  25. Suppressible base substitution mutations induced by angelicin (isopsoralen) in the Escherichia coli lacI gene: implications for the mechanism of SOS mutagenesis. Miller, S.S., Eisenstadt, E. J. Bacteriol. (1987) [Pubmed]
  26. Isolation and characterization of CYP6B4, a furanocoumarin-inducible cytochrome P450 from a polyphagous caterpillar (Lepidoptera:papilionidae). Hung, C.F., Berenbaum, M.R., Schuler, M.A. Insect Biochem. Mol. Biol. (1997) [Pubmed]
  27. Paradoxical behaviour of pKM101; inhibition of uvr-independent crosslink repair in Escherichia coli by muc gene products. Cupido, M., Bridges, B.A. Mutat. Res. (1985) [Pubmed]
  28. Photoinactivation and recovery in skin fibroblasts after formation of mono- and bifunctional adducts by furocoumarins-plus-UVA. Pohl, J., Christophers, E. J. Invest. Dermatol. (1980) [Pubmed]
  29. Reversed-phase high-performance liquid chromatography (RP-HPLC) determination of lipophilicity of furocoumarins: relationship with DNA interaction. Caffieri, S. Journal of pharmaceutical sciences. (2001) [Pubmed]
  30. Toxicological evaluation of sobatum. Mohanan, P.V., Devi, K.S. Cancer Lett. (1998) [Pubmed]
  31. Evaluation of synergism in the feeding deterrence of some furanocoumarins on Spodoptera littoralis. Calcagno, M.P., Coll, J., Lloria, J., Faini, F., Alonso-Amelot, M.E. J. Chem. Ecol. (2002) [Pubmed]
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