Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 17:44:16 UTC |
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Updated at | 2021-06-29 23:50:46 UTC |
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NP-MRD ID | NP0025672 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Rosiridin |
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Provided By | JEOL Database |
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Description | Rosiridin is found in Phodiola sachalinensis, Rhodiola crenulata, Rhodiola linearifolia, Rhodiola rosea and Rhodiola sachalinensis . It was first documented in 2003 (PMID: 12938105). Based on a literature review a significant number of articles have been published on Rosiridin (PMID: 33638206) (PMID: 32781473) (PMID: 30098734) (PMID: 22811209) (PMID: 21615025) (PMID: 21466940). |
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Structure | [H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC([H])([H])C(\[H])=C(/C([H])([H])[H])[C@]([H])(O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] InChI=1S/C16H28O7/c1-9(2)4-5-11(18)10(3)6-7-22-16-15(21)14(20)13(19)12(8-17)23-16/h4,6,11-21H,5,7-8H2,1-3H3/b10-6+/t11-,12-,13-,14+,15-,16-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C16H28O7 |
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Average Mass | 332.3930 Da |
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Monoisotopic Mass | 332.18350 Da |
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IUPAC Name | (2R,3R,4S,5S,6R)-2-{[(2E,4R)-4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol |
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Traditional Name | (2R,3R,4S,5S,6R)-2-{[(2E,4R)-4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol |
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CAS Registry Number | Not Available |
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SMILES | [H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC([H])([H])C(\[H])=C(/C([H])([H])[H])[C@]([H])(O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] |
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InChI Identifier | InChI=1S/C16H28O7/c1-9(2)4-5-11(18)10(3)6-7-22-16-15(21)14(20)13(19)12(8-17)23-16/h4,6,11-21H,5,7-8H2,1-3H3/b10-6+/t11-,12-,13-,14+,15-,16-/m1/s1 |
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InChI Key | PBPYEEMQIFDGSQ-LABKNWELSA-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, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, 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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Classification | Not classified |
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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 | - Langeder J, Grienke U: A supercritical fluid workflow for the quality assessment of herbal drugs and commercial preparations from Rhodiola rosea. Phytochem Anal. 2021 Feb 26. doi: 10.1002/pca.3040. [PubMed:33638206 ]
- Langeder J, Grienke U, Doring K, Jafari M, Ehrhardt C, Schmidtke M, Rollinger JM: High-performance Countercurrent Chromatography to Access Rhodiola rosea Influenza Virus Inhibiting Constituents. Planta Med. 2020 Aug 11. doi: 10.1055/a-1228-8473. [PubMed:32781473 ]
- Carrero-Carralero C, Rodriguez-Sanchez S, Calvillo I, Martinez-Castro I, Soria AC, Ramos L, Sanz ML: Gas chromatographic-based techniques for the characterization of low molecular weight carbohydrates and phenylalkanoid glycosides of Sedum roseum root supplements. J Chromatogr A. 2018 Oct 5;1570:116-125. doi: 10.1016/j.chroma.2018.07.071. Epub 2018 Jul 27. [PubMed:30098734 ]
- Mudge E, Lopes-Lutz D, Brown PN, Schieber A: Purification of Phenylalkanoids and monoterpene glycosides from Rhodiola rosea L. roots by high-speed counter-current chromatography. Phytochem Anal. 2013 Feb;24(2):129-34. doi: 10.1002/pca.2391. Epub 2012 Jul 19. [PubMed:22811209 ]
- Ma YC, Wang XQ, Hou FF, Ma J, Luo M, Lu S, Jin P, Terevsky N, Chen A, Xu I, Patel AV, Gorecki D: Rapid resolution liquid chromatography (RRLC) analysis for quality control of Rhodiola rosea roots and commercial standardized products. Nat Prod Commun. 2011 May;6(5):645-50. [PubMed:21615025 ]
- Ma YC, Wang XQ, Hou F, Ma J, Luo M, Lu S, Jin P, Chen A, Xu I, Patel AV, Gorecki D: Simultaneous quantification of polyherbal formulations containing Rhodiola rosea L. and Eleutherococcus senticosus Maxim. using rapid resolution liquid chromatography (RRLC). J Pharm Biomed Anal. 2011 Jul 15;55(5):908-15. doi: 10.1016/j.jpba.2011.03.013. Epub 2011 Mar 12. [PubMed:21466940 ]
- van Diermen D, Marston A, Bravo J, Reist M, Carrupt PA, Hostettmann K: Monoamine oxidase inhibition by Rhodiola rosea L. roots. J Ethnopharmacol. 2009 Mar 18;122(2):397-401. doi: 10.1016/j.jep.2009.01.007. Epub 2009 Jan 9. [PubMed:19168123 ]
- Yoshikawa M, Nakamura S, Li X, Matsuda H: Reinvestigation of absolute stereostructure of (-)-rosiridol: structures of monoterpene glycosides, rosiridin, rosiridosides A, B, and C, from Rhodiola sachalinensis. Chem Pharm Bull (Tokyo). 2008 May;56(5):695-700. doi: 10.1248/cpb.56.695. [PubMed:18451561 ]
- Wiedenfeld H, Dumaa M, Malinowski M, Furmanowa M, Narantuya S: Phytochemical and analytical studies of extracts from Rhodiola rosea and Rhodiola quadrifida. Pharmazie. 2007 Apr;62(4):308-11. [PubMed:17484290 ]
- Akgul Y, Ferreira D, Abourashed EA, Khan IA: Lotaustralin from Rhodiola rosea roots. Fitoterapia. 2004 Sep;75(6):612-4. doi: 10.1016/j.fitote.2004.06.002. [PubMed:15351122 ]
- Tolonen A, Hohtola A, Jalonen J: Comparison of electrospray ionization and atmospheric pressure chemical ionization techniques in the analysis of the main constituents from Rhodiola rosea extracts by liquid chromatography/mass spectrometry. J Mass Spectrom. 2003 Aug;38(8):845-53. doi: 10.1002/jms.497. [PubMed:12938105 ]
- Fan, W., et al. (2001). Fan, W., et al, Chem. Pharm. Bull. 49, 396 (2001). Chem. Pharm. Bull..
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