LC-MS Analysis of Botanicals
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1 Botanical workshop UAB, Sept 11, 26 LC-MS Analysis of Botanicals Jeevan K. Prasain, Ph.D. Department of Pharmacology & Toxicology, UAB Purdue-UAB Botanicals Center for Age-related Disease
2 Applications of mass spectrometry in botanical research Identification, characterization and quantitation of chemical components by LC-MS and MS-MS Purity assessment and quality control of dietary supplements/neutraceuticals In vitro & in vivo metabolism, bioavailability, toxicity and pharmacokinetics of drugs and their metabolites in biological samples Molecular target profiling - proteomics/metabolomics and chemical imaging of analytes
3 Kudzu root (Radix Puerariae) as a dietary supplement Different brands are available CH 2 H H Puerarin (PN)
4 The fruit of the American cranberry is a rich source of dietary flavonoids and considered to be beneficial for Urinary Tract Infection H Quercetin
5 Grape seeds are one of the richest sources of Proanthocyanidins (B type) H H Catechin extension subunit H H H n terminal subunit H Catechin gallate
6 Isoflavonoids in Kudzu Dietary Supplements/root culture extract
7 TIC of reverse-phase LC-MS of kudzu dietary supplement (KDS) isoflavones 1 1 puerarin 2 daidzin 4 daidzein % 6 formononetin 3 genistin Time (min)
8 MS/MS spectra of protonated - and C- glycosides of daidzein (m/z 417) [A] Daidzein (-Glc) daidzin % -162 Da [B] % Daidzein (C-Glc) puerarin -12 Da Neutral losses of 162 and 12 Da are characteristics m/z
9 Proposed fragmentation mechanisms of protonated puerarin and daidzin H+ 297 H H CH 2 H H+ 269 H 8 m/z 297 m/z 417 Base Peak [M+H-12] + H+ Puerarin H+ H 2 C H H Yo + m/z 267 [M+H-15] + H+ H m/z 417 Daidzin Yo +
10 Possible product ions of puerarin in ESI-MS/MS in negative ion mode H H CH 2 H -12 Da H m/z m/z Da H -28 Da H H H - - m/z 325 m/z 267 Prasain et al. J Agric Food Chem. 51, 4213, 23.
11 Neutral loss scans 12 and 162 can be used to detect C-and -glycosides, respectively in a crude mixture [A] Rel. Int. (%) Full scan ESI-MS of kudzu extract [B] Rel. Int. (%) Neutral loss scan 12 LC-MS/MS [C] Rel. Int. (%) Neutral loss scan 162 LC-MS/MS m/z
12 Hydroxylated daidzein C-glucosides were detected in the kudzu root culture extract Rel. Int. (%) [A] 2.6 min Da Rel. Int. (%) [B] 3.5 min Da 431 Rel. Int. (%) [C] 6.5 min m/z Da 431 Prasain et al. Phytochemical Analysis, in press
13 LC-MS analysis of cranberry fruits/concentrate
14 Extraction Flow Chart of an ethyl acetate extract from cranberry fresh fruits MS analysis Cranberry fruits (1 g) Homogenised and extracted With acetone and filtered Residue Acetone soluble fraction Solvent Evaporated Under reduced pressure Acetone extract Extracted with EtAc Water sol. residue Ethyl acetate extract
15 LC-MS and HPLC chromatographic conditions: LC-MS column: 4.6 x 1 mm, RP-3 column Gradient A : 1% ACN + 1 mm NH4Ac B : 4% ACN + 1 mm NH4Ac Linear gradient increased of solvent B 1% over 4 min ESI-MS in the negative ion mode of a PE-Eciex API III Triple quadrupole mass spectrometer. HPLC analysis: Column : Brownlee (22 cm x 4.6 mm I.d.) C8-column Gradient A : 1% aq. ACN/.1% TFA B : 9% aq. ACN/.1% TFA Flow rate : 1.5 ml with a linear gradient increase of solvent B 1% over 35 min
16 LC-MS chromatogram of the EtAc extract obtained from Cranberry fresh fruits 1 Relative Intensity (%) 5 M/z 289 catachins QC-hexoside MC-hexoside QC-pentoside MC-pentoside QC m/z 31, MC m/z 317 QC = Quercetin MC = Myricetin Me-QC Time (min)
17 ESI-MS/MS spectra of the ions at m/z 31 and 317 in the cranberry extract Rel. Int. (%) H Quercetin 299 Rel. Int. (%) H m/z Myricetin
18 Pentose and hexose sugar derivative of Myricetin were detected the cranberry extract 1 315, 316 Rel. Int. (%) 5 Myricetin-hexoside Da ,316 Rel. Int. (%) 5 Myricetin-pentoside 132 Da , 448 m/z
19 HPLC Chromatogram of a commercially available cranberry concentrate mau mm of Quercetin.5. Cranberry concentrate Quercetin Time (min)
20 Conclusions Quercetin and its glycosides are the major flavonoids in the cranberry fresh fruit, and commercially available cranberry concentrates. Catechin was detected but its oligomers (proanthocyanidins) were not detected in the ethyl acetate extract of the samples. Quercetin, myricetin and their glycosides produced predominant radical anions in the ms/ms experiments.
21 Analysis of Grape Seed Extracts (GSE)
22 Fractionation of monomeric catechins from oligomers Grape Seed Powder (2 g) Dissolved with 25 ml Me Precipitated with 125 ml CHCl3 Filtered through filter paper Filtrate Precipitate Dried under dessicator Dried GSP precipitate (1.35 g)
23 GSE is a complicated mixture of polyphenols And other secondary metabolites mau A, Sig=262,4 Ref=38,4 (6244A\47-81.D) DAD1 A, Sig=262,4 Ref=38,4 (6244A D) GSE HPLC slides Catechin min DAD1 A, Sig=262,4 Ref=38,4 (6244A D) mau 3 Catechin 25 GS-CHCl DAD1 A, Sig=262,4 Ref=38,4 (6244A D) mau 8 7 Catechin 6 5 GS-PPT proanthocyanidins min min min
24 MALDI-TF mass spectrum in positive linear mode showing a pronathocyanidin series [M+Na]+ from the dimer m/z 6 to oligomers % Intensity Mass (m/z)
25 % Intensity Equation to detect poly-galloyl-polyflavans in GSP c + 152g = mol wt. of the terminal catechin/epicatechin C = degree of plymerization G = unit of galloyl esters; 23 = weight of sodium Mass (m/z)
26 GSE precipitate in ESI-MS QTF % gallate gallate Hexo- Dimer- Trimer- Tetro Pento Mono m/z
27 LCMS and MSMS analysis of the methanolic extract of a Grape Seed Dietary Supplement with ionization polarity switch TIC Proanthocyanidin gallates Catechin monomer Negative survey scan in trap) Dimer Trimer Tetromer EPI (Enhanced Product Ion Scan of dimer m/z 577 in Trap)
28 Metal ion adducts are common in Positive Mode TIC EMS (positive survey scan in trap) Dimer [M+H]+ Dimer [M+Na]+ Trimer EPI (Enhanced Product Ion Scan of m/z 579 in Trap)
29 Negative ion mode provides better sensitivity for dimer than monomeric catechin 1 289/ / / / Time (min) Gradient: 1 min from -6% Me in 5 min in.1% HC
30 Monomeric catechin is better detected in positive ion mode 291/ / / / Time (min)
31 Conclusions A sensitive LC-MS/MS method was developed to analyze GSP in biological samples. In mass spectrometric analysis, monomeric catechins are more sensitive in positive ion mode, while catechins dimers are in negative ion mode. GSP is a complex mixture of catechins and nonpolyphenols.
32 Thanks to Dr. S. Barnes Dr. Mary Ann Lila Dr. E. Meezan Dr. J. M. Wyss Dr. N. Peng Dr. Connie Weaver Kenneth Jones Ray Moore Nancy Brissie M. Kirk Funding- NCCAM Sponsored Purdue-UAB Botanicals center for Age- Related Diseases P5 AT-477
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