Quality control of Aloe vera (Aloe barbadensis) and Aloe ferox using band-selective quantitative heteronuclear single quantum correlation spectroscopy (bs-qHSQC)

被引:13
作者
Girreser, Ulrich [1 ]
Ugolini, Tommaso [2 ,3 ]
Cicek, Serhat Sezai [2 ]
机构
[1] Univ Kiel, Inst Pharm, Dept Pharmaceut & Med Chem, Gutenbergstr 76, D-24118 Kiel, Germany
[2] Univ Kiel, Inst Pharm, Dept Pharmaceut Biol, Gutenbergstr 76, D-24118 Kiel, Germany
[3] Univ Florence, Dept Chem Hugo Schiff, Via Lastruccia 3-13, I-50019 Florence, Italy
关键词
Barbados aloes; Cape aloes; Quantitative NMR; Aloin; Natural product; Band selective HSQC; RESOLUTION; QUANTIFICATION; ALOINOSIDE; ANTHRONES; PRODUCTS; ACIDS; HSQC; HMBC; PH;
D O I
10.1016/j.talanta.2019.07.004
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
In the present study, band-selective quantitative heteronuclear single quantum correlation spectroscopy (bs-qHSQC) was applied for the quality control of the two Aloe species present in the European Pharmacopeia. After development and validation of a complete spectral range (csr-) qHSQC assay, a specific pulse program with selective excitation was applied and the measuring time was reduced from 135 to 32 min, while maintaining the same resolution. This bs-qHSQC method (method I) showed slightly higher RSD values compared to the csr-qHSQC method (maximum RSD of 2.80%), but better recovery rates in comparison to the assay of the Pharmacopeia (97.3% for Aloe vera and 96.6% for Aloe ferox). Apart from quantifying the total anthranoid content, the method moreover allows the quantitation of aloin among other aloin derivatives, such as 7-hydroxyaloin, as well as the differentiation of the two investigated species. Additionally, a second bs-qHSQC method (method II) for the fast (4 min) determination of the aloin A/B ratio was developed and compared to C-13 qNMR measurements. Showing the same results in much less analysis time, the latter approach contributes to a general problem in natural product chemistry, the co-occurrence of structurally similar compounds and their analysis in complex matrices, e.g. plant extracts.
引用
收藏
页数:7
相关论文
共 32 条
[1]   RESOLUTION OF ALOIN INTO DIASTEREOMERS AND THEIR CHARACTERIZATION [J].
AUTERHOFF, H ;
GRAF, E ;
EURISCH, G ;
ALEXA, M .
ARCHIV DER PHARMAZIE, 1980, 313 (02) :113-120
[2]   Quantitative 1H NMR spectroscopy [J].
Bharti, Santosh Kumar ;
Roy, Raja .
TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 2012, 35 :5-26
[3]  
Bisset N. G., 2001, HERBAL DRUGS PHARM
[4]   Evaluation of Band-Selective HSQC and HMBC: Methodological Validation on the Cyclosporin Cyclic Peptide and Application for Poly(3-hydroxyalkanoate)s Stereoregularity Determination [J].
Caytan, Elsa ;
Ligny, Romain ;
Carpentier, Jean-Francois ;
Guillaume, Sophie M. .
POLYMERS, 2018, 10 (05)
[5]   Quantification of diterpene acids in Copaiba oleoresin by UHPLC-ELSD and heteronuclear two-dimensional qNMR [J].
Cicek, Serhat Sezai ;
Barbosa, Anna Lais Pfeifer ;
Girreser, Ulrich .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2018, 160 :126-134
[6]   Quantification of the total amount of black cohosh cycloartanoids by integration of one specific 1H NMR signal [J].
Cicek, Serhat Sezai ;
Girreser, Ulrich ;
Zidorn, Christian .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2018, 155 :109-115
[7]   Enhanced 13C resolution in semi-selective HMBC:: a band-selective, constant-time HMBC for complex organic structure elucidation by NMR [J].
Claridge, TDW ;
Pérez-Victoria, I .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (21) :3632-3634
[8]   Anthrones from Aloe microstigma [J].
Dagne, E ;
Bisrat, D ;
VanWyk, BE ;
Viljoen, A ;
Hellwig, V ;
Steglich, W .
PHYTOCHEMISTRY, 1997, 44 (07) :1271-1274
[9]   PROTON DETECTION OF LONG-RANGE COUPLINGS TO C-13 USING SEMISELECTIVE PULSES - A HIGH-RESOLUTION METHOD FOR ASSIGNING AMINO-ACIDS IN PEPTIDES [J].
DAVIS, DG .
JOURNAL OF MAGNETIC RESONANCE, 1989, 83 (01) :212-218
[10]  
Ding WJ, 2014, INT J FOOD SCI TECH, V49, P1773, DOI [10.1111/ijfs.12500, 10.1111/ijfs.125]