Chiroptical properties of ajugol investigated by quantum chemical calculation using time-dependent density functional theory.
The chiroptical properties of an iridoid glycoside ajugol were fully investigated by quantum chemical calculations of specific optical rotation at the sodium D line ([α]Dvalue), optical rotatory dispersion (ORD), and electronic circular dichroism (ECD) using time-dependent density functional theory...
| Publicado en: | Journal of Asian Natural Products Research Vol. 15; no. 6; pp. 670 - 680 |
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| Autores principales: | , , , |
| Formato: | pictorial research tables/charts Journal Article |
| Publicado: |
Taylor & Francis Ltd
Jun2013
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| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=ccm&AN=104185314&site=ehost-live header: @attributes: shortDbName: ccm uiTerm: 104185314 longDbName: CINAHL Complete uiTag: AN controlInfo: bkinfo: dissinfo: jinfo: jid: 10286020 J40 jtl: Journal of Asian Natural Products Research issn: 10286020 maglogo: Y pubinfo: dt: Jun2013 vid: 15 iid: 6 pid: 377 pub: Taylor & Francis Ltd place: Philadelphia, Pennsylvania artinfo: ui: 104185314 88353760 10.1080/10286020.2013.802691 NLM23777271 104185314 ppf: 670 ppct: 10 formats: tig: atl: Chiroptical properties of ajugol investigated by quantum chemical calculation using time-dependent density functional theory. aug: au: Li, Li Liu, Yan-Fei Si, Yi-Kang Yu, De-Quan affil: Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing , 100050 , China sug: subj: Plant Extracts Analysis Glycosides Analysis Molecular Structure Spectral Analysis Time Data Analysis Software Funding Source ab: The chiroptical properties of an iridoid glycoside ajugol were fully investigated by quantum chemical calculations of specific optical rotation at the sodium D line ([α]Dvalue), optical rotatory dispersion (ORD), and electronic circular dichroism (ECD) using time-dependent density functional theory (TDDFT). TDDFT calculations of the [α]Dvalue and ORD of ajugol over the range of 365–633 nm were in good agreement with the experimental data. The predicted ECD spectrum of ajugol was also consistent with the experiment, showing a strong negative Cotton effect (CE) at around 190 nm and a weak positive CE at around 220 nm. Our results unambiguously determined the absolute configuration (AC) of the aglycone part of ajugol as (1S, 5R, 6R, 8S, 9S) and supported the generally accepted AC assignments of iridoid glycosides. Semi-empirical rule for the enol ether chromophore, basis set selection, and effect of glucose group on ECD spectra were also discussed in the case of ajugol. pubtype: Academic Journal doctype: pictorial research tables/charts Journal Article ougenre: Article language: English refInfo: holdings: @attributes: islocal: N |
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