Record Information |
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Version | 2.0 |
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Created at | 2021-06-20 19:14:28 UTC |
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Updated at | 2021-08-20 00:00:32 UTC |
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NP-MRD ID | NP0035932 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | euxanthone |
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Provided By | JEOL Database |
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Description | Euxanthone, also known as purrenone, belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Euxanthone has been detected, but not quantified in, fruits and mammee apples (Mammea americana). This could make euxanthone a potential biomarker for the consumption of these foods. Euxanthone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. euxanthone is found in Bonnetia paniculata, Bonnettia spp., Calophyllum teysmannii, Cratoxylum arborescens, Cratoxylum cochinchinense, Cratoxylum formosum, Garcinia afzelii ENGL. , Garcinia bracteata, Garcinia subelliptica, Goniothalamus griffithii, Harungana madagascariensis, Hypericum androsaemum, Hypericum canariense, Hypericum erectum, Hypericum ericoides, Hypericum inodorum, Hypericum perforatum, Hypericum sampsonii, Mammea africana, Kayea assamica, Mesua ferrea, Pentadesma butyracea, Ploiarium alternifolium, Polygala tenuifolia, Senna obtusifolia, Syphonia globifera, Vismia latifolia and Weddellina squamulosa. euxanthone was first documented in 2000 (PMID: 10665986). Based on a literature review a small amount of articles have been published on Euxanthone (PMID: 11488451) (PMID: 12451499) (PMID: 16678494) (PMID: 17825492). |
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Structure | [H]OC1=C([H])C2=C(OC3=C(C2=O)C(O[H])=C([H])C([H])=C3[H])C([H])=C1[H] InChI=1S/C13H8O4/c14-7-4-5-10-8(6-7)13(16)12-9(15)2-1-3-11(12)17-10/h1-6,14-15H |
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Synonyms | Value | Source |
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1,7-Dihydroxyxanthone | ChEBI | Eyxanthone | ChEBI | Purrenone | ChEBI | 1,7-Dihydroxy-9H-xanthen-9-one | HMDB | 1,7-Dihydroxy-9H-xanthen-9-one, 9ci | HMDB |
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Chemical Formula | C13H8O4 |
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Average Mass | 228.2002 Da |
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Monoisotopic Mass | 228.04226 Da |
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IUPAC Name | 1,7-dihydroxy-9H-xanthen-9-one |
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Traditional Name | euxanthone |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C([H])C2=C(OC3=C(C2=O)C(O[H])=C([H])C([H])=C3[H])C([H])=C1[H] |
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InChI Identifier | InChI=1S/C13H8O4/c14-7-4-5-10-8(6-7)13(16)12-9(15)2-1-3-11(12)17-10/h1-6,14-15H |
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InChI Key | KDXFPEKLLFWHMN-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | Xanthones |
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Alternative Parents | |
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Substituents | - Xanthone
- Chromone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Vinylogous acid
- Oxacycle
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 6.88 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Mak NK, Li WK, Zhang M, Wong RN, Tai LS, Yung KK, Leung HW: Effects of euxanthone on neuronal differentiation. Life Sci. 2000;66(4):347-54. doi: 10.1016/s0024-3205(99)00596-2. [PubMed:10665986 ]
- Mak NK, Lung HL, Wong RN, Leung HW, Tsang HY, Leung KN: Expression of protein kinase C isoforms in euxanthone-induced differentiation of neuroblastoma cells. Planta Med. 2001 Jul;67(5):400-5. doi: 10.1055/s-2001-15809. [PubMed:11488451 ]
- Saraiva L, Fresco P, Pinto E, Kijjoa A, Gonzalez MJ, Goncalves J: Differential activation of protein kinase C isoforms by euxanthone, revealed by an in vivo yeast phenotypic assay. Planta Med. 2002 Nov;68(11):1039-41. doi: 10.1055/s-2002-35655. [PubMed:12451499 ]
- Fang LH, Mu YM, Lin LL, Xiao PG, Du GH: Vasorelaxant effect of euxanthone in the rat thoracic aorta. Vascul Pharmacol. 2006 Aug;45(2):96-101. doi: 10.1016/j.vph.2006.03.011. Epub 2006 May 5. [PubMed:16678494 ]
- Naidu M, Kuan CY, Lo WL, Raza M, Tolkovsky A, Mak NK, Wong RN, Keynes R: Analysis of the action of euxanthone, a plant-derived compound that stimulates neurite outgrowth. Neuroscience. 2007 Sep 21;148(4):915-24. doi: 10.1016/j.neuroscience.2007.07.037. Epub 2007 Aug 1. [PubMed:17825492 ]
- Ren, Y., et al. (2011). Ren, Y., et al, J. Nat. Prod. 74, 1117 (2011). J. Nat. Prod..
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