Carbon‐13 NMR spectra of nineteen (1<i>R</i>)‐(+)‐camphor derivatives

Crull, George B.; Garber, Albert R.; Kennington, John W.; Prosser, Christina M.; Stone, Phillip W.; Fant, James W.; Dawson, John H.

doi:10.1002/mrc.1260240822

Cited by 11 publications

(7 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…13 C-NMR (CDCl 3 ) δ: 219.0 (C-1), 57.7 (C-6), 46.8 (C-2), 43.3 (C-8), 40.1 (C-3), 30.0 (C-5), 27.1 (C-4), 19.8 (C-9) 19.1 (C-10), 9.3 (C-7). The data matched with the previous reports [ 47 , 48 , 49 ].…”

Section: Methodssupporting

confidence: 90%

Identification of Insecticidal Constituents of the Essential Oil of Curcuma wenyujin Rhizomes Active against Liposcelis bostrychophila Badonnel

et al. 2012

View full text Add to dashboard Cite

The aim of this research was to determine the chemical composition and insecticidal activity of the essential oil of Curcuma wenyujin Y.H. Chen et C. Ling rhizomes against the booklouse Liposcelis bostrychophila Badonnel and to isolate any insecticidal constituents from the essential oil. The essential oil of C. wenyujin rhizomes was obtained by hydrodistillation and analyzed by GC-MS. A total of 43 components of the essential oil were identified and the principal compounds in the essential oil were 1,8-cineole (15.26%), camphor (10.12%), germacrone (6.86%), β-elemene (6.33%), curzerene (6.70%), and β-elemenone (5.23%). followed by curzerenone (4.52%), curdione (4.45%) and linalool (4.43%). Based on bioactivity-guided fractionation, the two main active constituents were isolated from the essential oil and identified as 1,8-cineole and camphor. The essential oil of C. wenyujin rhizomes exhibited contact toxicity against L. bostrychophila with an LD50 value of 208.85 µg/cm2. Camphor (LD50 = 207.26 µg/cm2) exhibited stronger contact toxicity than 1,8-cineole (LD50 = 1048.75 µg/cm2) against booklouse. The essential oil of C. wenyujin (LC50 = 2.76 mg/L air) also possessed fumigant toxicity against L. bostrychophila, while the two constituents, camphor and 1,8-cineole had LC50 values of 1.03 mg/L air and 1.13 mg/L air, respectively. The results indicate that the essential oil of C. wenyujin rhizomes and its constituent compounds have potential for development as natural insecticides or fumigants for control of insects in stored grains.

show abstract

Section: Methodssupporting

confidence: 90%

Identification of Insecticidal Constituents of the Essential Oil of Curcuma wenyujin Rhizomes Active against Liposcelis bostrychophila Badonnel

et al. 2012

View full text Add to dashboard Cite

show abstract

“…Analysis and assignment of 13 C resonances were made using classical approaches (COSY, HSCQ, and HMBC) in combination with data from the literature. 47,48 Evaluation of scalar couplings, 1 J CH , and total spin-spin couplings, 1 T CH , of 5 were obtained by the analysis of 1 H coupled 13 C spectra and (T CH /4)-resolved experiments (see the ESI †).…”

Section: Anad 2d-nmrmentioning

confidence: 99%

“…As a model analyte, we focus our attention on a small chiral bicyclic molecule, (D)-(1R,4R)-(+)-camphor and (L)-(1S,4S)-(À)-camphor (denoted as R-(5) and S- (5), respectively), NMRspectroscopically well characterized, 47,48 for which the detection of ten pairs of monodeuterated enantiomeric isotopomers is expected (see Fig. 1b).…”

Section: Introductionmentioning

confidence: 99%

Study and quantification of the enantiodiscrimination power of four polymeric chiral LLCs using NAD 2D-NMR

Berdagué

Gouilleux

Noll

et al. 2022

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

show abstract

“…Several studies in the literature describe T~ relaxation measurements investigating the manner of binding of substrates to the active sites of cytochromes P450 [1][2][3][4][5]. All of these studies report a stereoselective orientation of the substrate in the active site of the cytochrome P450, or even a link between the observed specific way of binding of the substrate and the regioselectivity of its hydroxylation by different P45o isozymes.…”

Section: Introductionmentioning

confidence: 99%

¹H NMR T₁ relaxation rate study on substrate orientation of fluoromethylanilines in the active sites of microsomal and purified cytochromes P₄₅₀ 1A1 and 2B1

et al. 1995

View full text Add to dashboard Cite

The present study describes tH NMR T1 relaxation rate studies on fluoromethylanilines bound to the active sites of microsomal and purified cytoehromes P45o IAI and 2B1. From the data obtained, insights into the average orientation of the substrates with respect to the paramagnetic Fe 3÷ centre in the cytochromes P4so could be derived. Particular attention was paid to a possible extra relaxation pathway for methyl protons compared to the aromatic protons, due to the rotational motion of the CH3 around the ~r-C-CH3 bond. However, this effect appeared to be minimal and to result in at most a few percent underestimation of the actual distance of the methyl protons to the Fe 3÷ centre. Furthermore, the data obtained demonstrate that all aromatic protons are at about the same average distance from the paramagnetic centre. The results also demonstrate that the fluoromethylanilines are bound to the active sites of cytochromes P45o 1A1 and 2B1 in a similar way. A time-averaged orientation of the substrate with the Fe 3+ above the aromatic ring, with the 7r-orbitals of the aromatic ring and those of the porphyrin rings in a parallel position, providing possibilities for energetically favourable ~t-~r interaction defines the orientation which best fits the results of the present study. Possibilities for a flip-flop rotation around an axis in the plane of the aromatic ring can be included in this picture, as such rotations would still result in a similar average distance of all aromatic protons to the Fe 3÷ paramagnetie centre. The results obtained also indicate that possible differences in metabolite patterns resulting from conversion of the fluoromethylanilines by different cytochromes P450, especially P45o IAI and 2B1, are unlikely to be caused by a specific orientation of the substrate imposed by the substrate binding site of the enzyme.

show abstract

Carbon‐13 NMR spectra of nineteen (1R)‐(+)‐camphor derivatives

Cited by 11 publications

References 11 publications

Identification of Insecticidal Constituents of the Essential Oil of Curcuma wenyujin Rhizomes Active against Liposcelis bostrychophila Badonnel

Identification of Insecticidal Constituents of the Essential Oil of Curcuma wenyujin Rhizomes Active against Liposcelis bostrychophila Badonnel

Study and quantification of the enantiodiscrimination power of four polymeric chiral LLCs using NAD 2D-NMR

¹H NMR T₁ relaxation rate study on substrate orientation of fluoromethylanilines in the active sites of microsomal and purified cytochromes P₄₅₀ 1A1 and 2B1

Contact Info

Product

Resources

About

Carbon‐13 NMR spectra of nineteen (1R)‐(+)‐camphor derivatives

Cited by 11 publications

References 11 publications

Identification of Insecticidal Constituents of the Essential Oil of Curcuma wenyujin Rhizomes Active against Liposcelis bostrychophila Badonnel

Identification of Insecticidal Constituents of the Essential Oil of Curcuma wenyujin Rhizomes Active against Liposcelis bostrychophila Badonnel

Study and quantification of the enantiodiscrimination power of four polymeric chiral LLCs using NAD 2D-NMR

1H NMR T1 relaxation rate study on substrate orientation of fluoromethylanilines in the active sites of microsomal and purified cytochromes P450 1A1 and 2B1

Contact Info

Product

Resources

About

¹H NMR T₁ relaxation rate study on substrate orientation of fluoromethylanilines in the active sites of microsomal and purified cytochromes P₄₅₀ 1A1 and 2B1