Xanthotoxin
Methoxsalen is a member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis. It has a role as a dermatologic drug, an antineoplastic agent, a photosensitizing agent, a cross-linking reagent and a plant metabolite AChE IC50= 0.76 +/- 0.03 Ben Salem et al. || acetylcholinesterase inhibitory activity IC50=0.76+/-0.03 microM
General
Type : Natural, Toxin, Chromen
Chemical_Nomenclature : 9-methoxyfuro[3,2-g]chromen-7-one
Canonical SMILES : COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2
InChI : InChI=1S\/C12H8O4\/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12\/h2-6H,1H3
InChIKey : QXKHYNVANLEOEG-UHFFFAOYSA-N
Other name(s) : methoxsalen || 8-Methoxypsoralen || Meladinine || Oxsoralen || Oxypsoralen || 8-MOP || Zanthotoxin || SCHEMBL19168 || SCHEMBL29376525
MW : 216.19
Formula : C12H8O4
CAS_number : 298-81-7
PubChem : 4114
UniChem : QXKHYNVANLEOEG-UHFFFAOYSA-N
Target
Families : Xanthotoxin ligand of proteins in family
Carb_B_Arthropoda
ACHE
Protein :
spolt-SlituCOE052
human-ACHE
References (36)
| Title : Expansion of a Lepidopteran Carboxylesterase Gene Cluster Drives Xanthotoxin Detoxification in Spodoptera litura - Huang_2025_J.Agric.Food.Chem_73_13351 |
| Author(s) : Huang X , Li J , Xiao T , Xu X , Jiang Y , Yang Z , Sun Z , Lu K |
| Ref : Journal of Agricultural and Food Chemistry , 73 :13351 , 2025 |
| Abstract : |
| PubMedSearch : Huang_2025_J.Agric.Food.Chem_73_13351 |
| PubMedID: 40388639 |
| Gene_locus related to this paper: spolt-SlituCOE052 |
| Title : Bifunctional Carboxylesterase COE52 Mediates Xanthotoxin Detoxification through Hormonal Regulation and Structural Adaptation in Spodoptera litura - Li_2025_J.Agric.Food.Chem__2 |
| Author(s) : Li J , Huang X , Zhao X , Deng M , Xu X , Xiao T , Yao Q , Yang Z , Lu K |
| Ref : Journal of Agricultural and Food Chemistry , : , 2025 |
| Abstract : |
| PubMedSearch : Li_2025_J.Agric.Food.Chem__2 |
| PubMedID: 41188003 |
| Gene_locus related to this paper: spolt-SlituCOE052 |
| Title : Expansion of a Lepidopteran Carboxylesterase Gene Cluster Drives Xanthotoxin Detoxification in Spodoptera litura - Huang_2025_J.Agric.Food.Chem_73_13351 |
| Author(s) : Huang X , Li J , Xiao T , Xu X , Jiang Y , Yang Z , Sun Z , Lu K |
| Ref : Journal of Agricultural and Food Chemistry , 73 :13351 , 2025 |
| Abstract : |
| PubMedSearch : Huang_2025_J.Agric.Food.Chem_73_13351 |
| PubMedID: 40388639 |
| Gene_locus related to this paper: spolt-SlituCOE052 |
| Title : Bifunctional Carboxylesterase COE52 Mediates Xanthotoxin Detoxification through Hormonal Regulation and Structural Adaptation in Spodoptera litura - Li_2025_J.Agric.Food.Chem__2 |
| Author(s) : Li J , Huang X , Zhao X , Deng M , Xu X , Xiao T , Yao Q , Yang Z , Lu K |
| Ref : Journal of Agricultural and Food Chemistry , : , 2025 |
| Abstract : |
| PubMedSearch : Li_2025_J.Agric.Food.Chem__2 |
| PubMedID: 41188003 |
| Gene_locus related to this paper: spolt-SlituCOE052 |
| Title : Expansion of a Lepidopteran Carboxylesterase Gene Cluster Drives Xanthotoxin Detoxification in Spodoptera litura - Huang_2025_J.Agric.Food.Chem_73_13351 |
| Author(s) : Huang X , Li J , Xiao T , Xu X , Jiang Y , Yang Z , Sun Z , Lu K |
| Ref : Journal of Agricultural and Food Chemistry , 73 :13351 , 2025 |
| Abstract : |
| PubMedSearch : Huang_2025_J.Agric.Food.Chem_73_13351 |
| PubMedID: 40388639 |
| Gene_locus related to this paper: spolt-SlituCOE052 |
| Title : Bifunctional Carboxylesterase COE52 Mediates Xanthotoxin Detoxification through Hormonal Regulation and Structural Adaptation in Spodoptera litura - Li_2025_J.Agric.Food.Chem__2 |
| Author(s) : Li J , Huang X , Zhao X , Deng M , Xu X , Xiao T , Yao Q , Yang Z , Lu K |
| Ref : Journal of Agricultural and Food Chemistry , : , 2025 |
| Abstract : |
| PubMedSearch : Li_2025_J.Agric.Food.Chem__2 |
| PubMedID: 41188003 |
| Gene_locus related to this paper: spolt-SlituCOE052 |
| Title : Nematicidal Coumarins from Cnidium monnieri Fruits and Angelica dahurica Roots and Their Physiological Effect on Pine Wood Nematode (Bursaphelenchus xylophilus) - Feng_2023_Molecules_28_ |
| Author(s) : Feng J , Qin C , Liu X , Li R , Wang C , Li C , Du G , Guo Q |
| Ref : Molecules , 28 : , 2023 |
| Abstract : |
| PubMedSearch : Feng_2023_Molecules_28_ |
| PubMedID: 37241850 |
| Title : Effects of Methyl Jasmonate Fumigation on the Growth and Detoxification Ability of Spodoptera litura to Xanthotoxin - Chen_2023_Insects_14_ |
| Author(s) : Chen L , Song J , Wang J , Ye M , Deng Q , Wu X , Ren B |
| Ref : Insects , 14 : , 2023 |
| Abstract : |
| PubMedSearch : Chen_2023_Insects_14_ |
| PubMedID: 36835714 |
| Title : Nematicidal Coumarins from Cnidium monnieri Fruits and Angelica dahurica Roots and Their Physiological Effect on Pine Wood Nematode (Bursaphelenchus xylophilus) - Feng_2023_Molecules_28_ |
| Author(s) : Feng J , Qin C , Liu X , Li R , Wang C , Li C , Du G , Guo Q |
| Ref : Molecules , 28 : , 2023 |
| Abstract : |
| PubMedSearch : Feng_2023_Molecules_28_ |
| PubMedID: 37241850 |
| Title : Effects of Methyl Jasmonate Fumigation on the Growth and Detoxification Ability of Spodoptera litura to Xanthotoxin - Chen_2023_Insects_14_ |
| Author(s) : Chen L , Song J , Wang J , Ye M , Deng Q , Wu X , Ren B |
| Ref : Insects , 14 : , 2023 |
| Abstract : |
| PubMedSearch : Chen_2023_Insects_14_ |
| PubMedID: 36835714 |
| Title : Nematicidal Coumarins from Cnidium monnieri Fruits and Angelica dahurica Roots and Their Physiological Effect on Pine Wood Nematode (Bursaphelenchus xylophilus) - Feng_2023_Molecules_28_ |
| Author(s) : Feng J , Qin C , Liu X , Li R , Wang C , Li C , Du G , Guo Q |
| Ref : Molecules , 28 : , 2023 |
| Abstract : |
| PubMedSearch : Feng_2023_Molecules_28_ |
| PubMedID: 37241850 |
| Title : Effects of Methyl Jasmonate Fumigation on the Growth and Detoxification Ability of Spodoptera litura to Xanthotoxin - Chen_2023_Insects_14_ |
| Author(s) : Chen L , Song J , Wang J , Ye M , Deng Q , Wu X , Ren B |
| Ref : Insects , 14 : , 2023 |
| Abstract : |
| PubMedSearch : Chen_2023_Insects_14_ |
| PubMedID: 36835714 |
| Title : Mechanisms of the Procognitive Effects of Xanthotoxin and Umbelliferone on LPS-Induced Amnesia in Mice - Kurach_2021_Int.J.Mol.Sci_22_ |
| Author(s) : Kurach L , Kulczycka-Mamona S , Kowalczyk J , Skalicka-Wozniak K , Boguszewska-Czubara A , El Sayed N , Osmani M , Iwaniak K , Budzynska B |
| Ref : Int J Mol Sci , 22 : , 2021 |
| Abstract : |
| PubMedSearch : Kurach_2021_Int.J.Mol.Sci_22_ |
| PubMedID: 33579030 |
| Title : Mechanisms of the Procognitive Effects of Xanthotoxin and Umbelliferone on LPS-Induced Amnesia in Mice - Kurach_2021_Int.J.Mol.Sci_22_ |
| Author(s) : Kurach L , Kulczycka-Mamona S , Kowalczyk J , Skalicka-Wozniak K , Boguszewska-Czubara A , El Sayed N , Osmani M , Iwaniak K , Budzynska B |
| Ref : Int J Mol Sci , 22 : , 2021 |
| Abstract : |
| PubMedSearch : Kurach_2021_Int.J.Mol.Sci_22_ |
| PubMedID: 33579030 |
| Title : Mechanisms of the Procognitive Effects of Xanthotoxin and Umbelliferone on LPS-Induced Amnesia in Mice - Kurach_2021_Int.J.Mol.Sci_22_ |
| Author(s) : Kurach L , Kulczycka-Mamona S , Kowalczyk J , Skalicka-Wozniak K , Boguszewska-Czubara A , El Sayed N , Osmani M , Iwaniak K , Budzynska B |
| Ref : Int J Mol Sci , 22 : , 2021 |
| Abstract : |
| PubMedSearch : Kurach_2021_Int.J.Mol.Sci_22_ |
| PubMedID: 33579030 |
| Title : Scopolamine-Induced Memory Impairment Is Alleviated by Xanthotoxin: Role of Acetylcholinesterase and Oxidative Stress Processes - Skalicka-Wozniak_2018_ACS.Chem.Neurosci_9_1184 |
| Author(s) : Skalicka-Wozniak K , Budzynska B , Biala G , Boguszewska-Czubara A |
| Ref : ACS Chem Neurosci , 9 :1184 , 2018 |
| Abstract : |
| PubMedSearch : Skalicka-Wozniak_2018_ACS.Chem.Neurosci_9_1184 |
| PubMedID: 29378112 |
| Title : Scopolamine-Induced Memory Impairment Is Alleviated by Xanthotoxin: Role of Acetylcholinesterase and Oxidative Stress Processes - Skalicka-Wozniak_2018_ACS.Chem.Neurosci_9_1184 |
| Author(s) : Skalicka-Wozniak K , Budzynska B , Biala G , Boguszewska-Czubara A |
| Ref : ACS Chem Neurosci , 9 :1184 , 2018 |
| Abstract : |
| PubMedSearch : Skalicka-Wozniak_2018_ACS.Chem.Neurosci_9_1184 |
| PubMedID: 29378112 |
| Title : Scopolamine-Induced Memory Impairment Is Alleviated by Xanthotoxin: Role of Acetylcholinesterase and Oxidative Stress Processes - Skalicka-Wozniak_2018_ACS.Chem.Neurosci_9_1184 |
| Author(s) : Skalicka-Wozniak K , Budzynska B , Biala G , Boguszewska-Czubara A |
| Ref : ACS Chem Neurosci , 9 :1184 , 2018 |
| Abstract : |
| PubMedSearch : Skalicka-Wozniak_2018_ACS.Chem.Neurosci_9_1184 |
| PubMedID: 29378112 |
| Title : Synthesis of imperatorin analogs and their evaluation as acetylcholinesterase and butyrylcholinesterase inhibitors - Granica_2013_Arch.Pharm.(Weinheim)_346_775 |
| Author(s) : Granica S , Kiss AK , Jaronczyk M , Maurin JK , Mazurek AP , Czarnocki Z |
| Ref : Arch Pharm (Weinheim) , 346 :775 , 2013 |
| Abstract : |
| PubMedSearch : Granica_2013_Arch.Pharm.(Weinheim)_346_775 |
| PubMedID: 24123207 |
| Title : Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells - Wang_2013_Evid.Based.Complement.Alternat.Med_2013_937370 |
| Author(s) : Wang Y , Pan WL , Liang WC , Law WK , Tsz-Ming Ip D , Ng TB , Miu-Yee Waye M , Wan DC |
| Ref : Evid Based Complement Alternat Med , 2013 :937370 , 2013 |
| Abstract : |
| PubMedSearch : Wang_2013_Evid.Based.Complement.Alternat.Med_2013_937370 |
| PubMedID: 24302971 |
| Title : New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire - Ben Salem_2013_Bioorg.Med.Chem.Lett_23_4248 |
| Author(s) : Ben Salem S , Jabrane A , Harzallah-Skhiri F , Ben Jannet H |
| Ref : Bioorganic & Medicinal Chemistry Lett , 23 :4248 , 2013 |
| Abstract : |
| PubMedSearch : Ben Salem_2013_Bioorg.Med.Chem.Lett_23_4248 |
| PubMedID: 23746477 |
| Title : Synthesis of imperatorin analogs and their evaluation as acetylcholinesterase and butyrylcholinesterase inhibitors - Granica_2013_Arch.Pharm.(Weinheim)_346_775 |
| Author(s) : Granica S , Kiss AK , Jaronczyk M , Maurin JK , Mazurek AP , Czarnocki Z |
| Ref : Arch Pharm (Weinheim) , 346 :775 , 2013 |
| Abstract : |
| PubMedSearch : Granica_2013_Arch.Pharm.(Weinheim)_346_775 |
| PubMedID: 24123207 |
| Title : Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells - Wang_2013_Evid.Based.Complement.Alternat.Med_2013_937370 |
| Author(s) : Wang Y , Pan WL , Liang WC , Law WK , Tsz-Ming Ip D , Ng TB , Miu-Yee Waye M , Wan DC |
| Ref : Evid Based Complement Alternat Med , 2013 :937370 , 2013 |
| Abstract : |
| PubMedSearch : Wang_2013_Evid.Based.Complement.Alternat.Med_2013_937370 |
| PubMedID: 24302971 |
| Title : New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire - Ben Salem_2013_Bioorg.Med.Chem.Lett_23_4248 |
| Author(s) : Ben Salem S , Jabrane A , Harzallah-Skhiri F , Ben Jannet H |
| Ref : Bioorganic & Medicinal Chemistry Lett , 23 :4248 , 2013 |
| Abstract : |
| PubMedSearch : Ben Salem_2013_Bioorg.Med.Chem.Lett_23_4248 |
| PubMedID: 23746477 |
| Title : Synthesis of imperatorin analogs and their evaluation as acetylcholinesterase and butyrylcholinesterase inhibitors - Granica_2013_Arch.Pharm.(Weinheim)_346_775 |
| Author(s) : Granica S , Kiss AK , Jaronczyk M , Maurin JK , Mazurek AP , Czarnocki Z |
| Ref : Arch Pharm (Weinheim) , 346 :775 , 2013 |
| Abstract : |
| PubMedSearch : Granica_2013_Arch.Pharm.(Weinheim)_346_775 |
| PubMedID: 24123207 |
| Title : Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells - Wang_2013_Evid.Based.Complement.Alternat.Med_2013_937370 |
| Author(s) : Wang Y , Pan WL , Liang WC , Law WK , Tsz-Ming Ip D , Ng TB , Miu-Yee Waye M , Wan DC |
| Ref : Evid Based Complement Alternat Med , 2013 :937370 , 2013 |
| Abstract : |
| PubMedSearch : Wang_2013_Evid.Based.Complement.Alternat.Med_2013_937370 |
| PubMedID: 24302971 |
| Title : New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire - Ben Salem_2013_Bioorg.Med.Chem.Lett_23_4248 |
| Author(s) : Ben Salem S , Jabrane A , Harzallah-Skhiri F , Ben Jannet H |
| Ref : Bioorganic & Medicinal Chemistry Lett , 23 :4248 , 2013 |
| Abstract : |
| PubMedSearch : Ben Salem_2013_Bioorg.Med.Chem.Lett_23_4248 |
| PubMedID: 23746477 |
| Title : Inhibition of acetylcholinesterase by extracts and constituents from Angelica archangelica and Geranium sylvaticum - Sigurdsson_2007_Z.Naturforsch.C_62_689 |
| Author(s) : Sigurdsson S , Gudbjarnason S |
| Ref : Z Naturforsch C , 62 :689 , 2007 |
| Abstract : |
| PubMedSearch : Sigurdsson_2007_Z.Naturforsch.C_62_689 |
| PubMedID: 18069242 |
| Title : Inhibition of acetylcholinesterase by extracts and constituents from Angelica archangelica and Geranium sylvaticum - Sigurdsson_2007_Z.Naturforsch.C_62_689 |
| Author(s) : Sigurdsson S , Gudbjarnason S |
| Ref : Z Naturforsch C , 62 :689 , 2007 |
| Abstract : |
| PubMedSearch : Sigurdsson_2007_Z.Naturforsch.C_62_689 |
| PubMedID: 18069242 |
| Title : Inhibition of acetylcholinesterase by extracts and constituents from Angelica archangelica and Geranium sylvaticum - Sigurdsson_2007_Z.Naturforsch.C_62_689 |
| Author(s) : Sigurdsson S , Gudbjarnason S |
| Ref : Z Naturforsch C , 62 :689 , 2007 |
| Abstract : |
| PubMedSearch : Sigurdsson_2007_Z.Naturforsch.C_62_689 |
| PubMedID: 18069242 |
| Title : Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster - Miyazawa_2004_J.Agric.Food.Chem_52_4401 |
| Author(s) : Miyazawa M , Tsukamoto T , Anzai J , Ishikawa Y |
| Ref : Journal of Agricultural and Food Chemistry , 52 :4401 , 2004 |
| Abstract : |
| PubMedSearch : Miyazawa_2004_J.Agric.Food.Chem_52_4401 |
| PubMedID: 15237943 |
| Title : Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster - Miyazawa_2004_J.Agric.Food.Chem_52_4401 |
| Author(s) : Miyazawa M , Tsukamoto T , Anzai J , Ishikawa Y |
| Ref : Journal of Agricultural and Food Chemistry , 52 :4401 , 2004 |
| Abstract : |
| PubMedSearch : Miyazawa_2004_J.Agric.Food.Chem_52_4401 |
| PubMedID: 15237943 |
| Title : Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster - Miyazawa_2004_J.Agric.Food.Chem_52_4401 |
| Author(s) : Miyazawa M , Tsukamoto T , Anzai J , Ishikawa Y |
| Ref : Journal of Agricultural and Food Chemistry , 52 :4401 , 2004 |
| Abstract : |
| PubMedSearch : Miyazawa_2004_J.Agric.Food.Chem_52_4401 |
| PubMedID: 15237943 |
| Title : Natural pesticides and bioactive components in foods - Beier_1990_Rev.Environ.Contam.Toxicol_113_47 |
| Author(s) : Beier RC |
| Ref : Rev Environ Contam Toxicol , 113 :47 , 1990 |
| Abstract : |
| PubMedSearch : Beier_1990_Rev.Environ.Contam.Toxicol_113_47 |
| PubMedID: 2404325 |
| Title : Natural pesticides and bioactive components in foods - Beier_1990_Rev.Environ.Contam.Toxicol_113_47 |
| Author(s) : Beier RC |
| Ref : Rev Environ Contam Toxicol , 113 :47 , 1990 |
| Abstract : |
| PubMedSearch : Beier_1990_Rev.Environ.Contam.Toxicol_113_47 |
| PubMedID: 2404325 |
| Title : Natural pesticides and bioactive components in foods - Beier_1990_Rev.Environ.Contam.Toxicol_113_47 |
| Author(s) : Beier RC |
| Ref : Rev Environ Contam Toxicol , 113 :47 , 1990 |
| Abstract : |
| PubMedSearch : Beier_1990_Rev.Environ.Contam.Toxicol_113_47 |
| PubMedID: 2404325 |