Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:56:44 UTC |
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Updated at | 2021-11-26 17:46:34 UTC |
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NP-MRD ID | NP0044201 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Calceolarioside A |
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Description | Calceolarioside A belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Calceolarioside A is found in Aeschynanthus bracteatus , Ajuga nipponensis, Avicennia marina, Buddleja officinalis, Byblis liniflora, Calceolaria dentata, Calceolaria hypericina, Cassinopsis madagascariensis, Digitalis purpurea, Digitalis thapsi , Echinacea pallida, Ellisiophyllum pinnatum (Wall.ex.Benth.), Forsythia suspensa, Fraxinus insularis, Globularia alypum, Globularia orientalis, Isoplexis sceptrum, Lantana strigocamara, Meehania urticifolia, Nyctanthes arbor-tristis, Phlomoides hamosa, Plantago lanceolata, Plantago major and Primulina sinensis. It was first documented in 2017 (PMID: 30549826). Based on a literature review a significant number of articles have been published on Calceolarioside A (PMID: 32247053) (PMID: 34498959) (PMID: 30676780) (PMID: 27533742). |
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Structure | OC[C@H]1O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 InChI=1S/C23H26O11/c24-11-18-22(34-19(29)6-3-12-1-4-14(25)16(27)9-12)20(30)21(31)23(33-18)32-8-7-13-2-5-15(26)17(28)10-13/h1-6,9-10,18,20-28,30-31H,7-8,11H2/b6-3+/t18-,20-,21-,22-,23-/m1/s1 |
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Synonyms | Value | Source |
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Calceolarioside | MeSH |
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Chemical Formula | C23H26O11 |
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Average Mass | 478.4500 Da |
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Monoisotopic Mass | 478.14751 Da |
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IUPAC Name | (2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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Traditional Name | (2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 |
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InChI Identifier | InChI=1S/C23H26O11/c24-11-18-22(34-19(29)6-3-12-1-4-14(25)16(27)9-12)20(30)21(31)23(33-18)32-8-7-13-2-5-15(26)17(28)10-13/h1-6,9-10,18,20-28,30-31H,7-8,11H2/b6-3+/t18-,20-,21-,22-,23-/m1/s1 |
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InChI Key | UHIGZYLCYRQESL-VJWFJHQPSA-N |
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Experimental Spectra |
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| Not Available | 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 coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Coumaric acids and derivatives |
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Alternative Parents | |
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Substituents | - Coumaric acid or derivatives
- Hexose monosaccharide
- Cinnamic acid ester
- Glycosyl compound
- O-glycosyl compound
- Tyrosol derivative
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Phenol
- Fatty acyl
- Benzenoid
- Monocyclic benzene moiety
- Oxane
- Monosaccharide
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Acetal
- Monocarboxylic acid or derivatives
- Primary alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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 | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Morikawa T, Inoue N, Nakanishi Y, Manse Y, Matsuura H, Okino K, Hamasaki S, Yoshikawa M, Muraoka O, Ninomiya K: Collagen synthesis-promoting and collagenase inhibitory activities of constituents isolated from the rhizomes of Picrorhiza kurroa Royle ex Benth. Fitoterapia. 2020 Jun;143:104584. doi: 10.1016/j.fitote.2020.104584. Epub 2020 Apr 1. [PubMed:32247053 ]
- Winiewski V, Mesquita Fonseca M, Salvador MJ, Lemos de Sa E, Alves Stefanello ME: Three new naphthoquinones from the tubers of Sinningia mauroana. Nat Prod Res. 2021 Sep 9:1-6. doi: 10.1080/14786419.2021.1969564. [PubMed:34498959 ]
- Wei Q, Zhang R, Wang Q, Yan XJ, Yu QW, Yan FX, Li C, Pei YH: Iridoid, phenylethanoid and flavonoid glycosides from Forsythia suspensa. Nat Prod Res. 2020 May;34(9):1320-1325. doi: 10.1080/14786419.2018.1560288. Epub 2019 Jan 24. [PubMed:30676780 ]
- Kirmizibekmez H, Kusz N, Karaca N, Demirci F, Hohmann' J: Secondary Metabolites from the Leaves of Digitalis viridiflora. Nat Prod Commun. 2017 Jan;12(1):59-61. [PubMed:30549826 ]
- Chen Y, Xue G, Liu F, Gong X: Immunosuppressive effect of extracts from leaves of Fraxinus Mandshurica Rupr. Bioengineered. 2017 May 4;8(3):212-216. doi: 10.1080/21655979.2016.1221023. Epub 2016 Aug 17. [PubMed:27533742 ]
- Søren Damtoft and Søren Rosendal Jensen (1994). Three phenylethanoid glucosides of unusual structure from Chirita sinensis (gesneriaceae). Phytochemistry, Volume 37, Issue 2, 1994, Pages 441-443. DOI: Volume 37, Issue 2, 1994, Pages 441-443. Phytochemistry.
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