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Process NMR Associates
Quantitative Small Mixture Analysis (SMA):
Quality of Aloe Vera,
Acid Profiles of Sour Beers,
PDE5i Adulteration of Male Enhancement Formulations
Presented By
John Edwards, Ph.D.
Process NMR Associates, LLC
Danbury, Connecticut
March 23, 2014
Mnova UM at 55th ENC, Boston MA
Process NMR Associates
Contract NMR Analysis
NMR Application Development
Solids -200
Liquids-300
60 MHz
# Chemical Characterization of the Immunomodulating Polysaccharide of Aloe Vera L., W.J.Goux, et al,
http://www.iasc.org/AloeStructure080604.pdf
Aloe Vera
b
z
c
y
x
d
a
w
w
m
m
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
Process NMR Associates
Commercial freeze-dried 200x aloe vera leaf juice powder
Process NMR Associates
Compound IASC Certification requirement
Acemannan ≥ 5% dry weight
Glucose Present
Aloin
10 ppm or less in 0.5% aloe vera solids solution, analysed by
HPLC or other fit for purpose methodology approved by IASC
Isocitrate ≤ 5% dry weight
Maltodextrin
Must be listed on label and analysis must meet label claims. If
undeclared, is considered an adulterant.
Solids
≥ 0.46% in single-strength juice (for example, a 10x
concentrate should have ≥ 4.6%)
Ash ≤ 40%
Aloe Vera Inner Leaf Juice Constituents and Additives that need to be
Analyzed and Reported for IASC Certification
Included in the American Herbal Pharmacopoeia Monograph on Aloe
Vera Leaf, Leaf Juice & Inner Leaf Juice
Process NMR Associates
Substance Signal Type and N Parameter Chemical shift, ppm
Acetylated Polysaccharides Broad Group of CH3 Singlets (N=3) 2.0-2.3
Isocitric acid CH, Doublet (N=1) 4.25
Malic acid CH, 4 peak multiplet (N=1) 4.45
-Glucose CH Doublet (N=1) 4.6
-Glucose CH Doublet (N=1) 5.2
Isocitric lactone CH Doublet (N=1) 5.05
Characteristic chemical shift values, peak multiplicity, protonated carbon type and N
values used for detection and quantitation of the major natural components of aloe
vera leaf juice
Compound Type of compound Signal type Chemical shift,
ppm
Propylene glycol Additive CH3, doublet (N=3) 1.1
Ethanol Degradation product or additive CH3, triplet (N=3) 1.15
Lactic acid Degradation product CH3, doublet (N=3) 1.33
Potassium sorbate Preservative CH3, doublet (N=3) 1.82
Acetic acid Degradation product CH3, singlet (N=3) 1.96
Pyruvic acid Degradation product CH3, singlet (N=3) 2.35
Citric acid Naturally present or added as pH
regulator or preservative
2 x CH2, Multiplet (N=4) 2.5-3.0
Succinic acid Degradation product 2 x CH2, singlet (N=4) 2.6
Glycerol Additive CH2 and CH, multiplet 3.5
Glycine Additive CH2, singlet (N=2) 3.51
Sucrose Additive CH, doublet (N=1) 5.4
Fumaric acid Degradation product 2 x CH, singlet (N=2) 6.5
Sodium benzoate Preservative 2 x CH, doublet (N=2) 7.95
Formic acid Degradation product CH, singlet (N=1) 8.2-8.3
Chemical shift values, peak and chemistry descriptions, molar conversion factors
that can be used for detection and quantitation of aloe vera leaf juice
preservatives, additives, and degradation products
Analysis of Aloe Sample 458 – Whole Leaf Aloe Powder
Starting Screen
 Add sample weight
 Add reference weights
 Add Metadata
 Choose Previously SavedLibrary
and Experiments
Launch SMA
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
Experiment Setup
Add Component Information Name,
Molecular Wt, # protons,
Shift Ranges of Component Peaks
Acceptable results can be specified, and
outliers will be flagged
Setup Calculation Formulas
Note: The Experimental and
Formula Setup are performed only
once and are then saved in a library
for further use
Formula Setup
Enter qNMR
calculations
Spectral Result - Sample 458
GSD Output is Used in Formula
Component shifts identified
XHTML Results
Output
Comparison of 1H qNMR calculations of
component wt% obtained from :
1) Mnova SMA
2) Manual Integration + Excel Method (validated)
Aloe Sample 42 :
Whole Leaf Powder with Maltodextrin Adulterant
Two Experiments Analyzed Simultaneously
For Aloe sample 42 the full analysis required
2 related samples, but the final analysis was
achieved in a single step.
1) All parameters except isocitrate were
calculated from the aloe sample dissolved
in D2O.
2) Isocitrate is calculated from the spectrum
of the same sample after acidification with
DCl, which shifts the isocitrate doublet to a
non-overlapping region at 4.7 ppm
Spectrum 1
Spectrum 2
DCl added
Spectrum 2
The single isocitrate
component is now clearly
quantifiable
Experimental Setup
Note reference to Spectrum 1
andSpectrum 2 in the
component listing. This allows
the majority of the component
concentrations to be calculated
from Spectrum 1 and the
isocitrate concentration from
Spectrum 2 which is of the
acidified aloe sample.
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
Validation
Comparison of qNMR calculations of
component wt% obtained from
1) Automated Mixture Analysis
2) Manual Integration + Excel Method
qNMR standard Parameters: concentration
reference mass (RW, in grams), sample volume
(in L), Molecular Weight (MW), and Hydrogen #
(NN1) are entered to determine the
Concentration Conversion Factor (CCF).
For each component, Integral (I#) is
automatically determined from GSD integration
based on specified peak ranges, and converted
to concentration using the CCF.
Concentrations of target metabolites are
calculated as a function of CCF, NN1, MW
& I#. The terminal coefficient (4285.71) is a
correction factor for sample dilution and
conversion to mg/L.
Global Spectral Deconvolution & Peak Picking automatically identifies
and integrates peaks based on entered peak ranges. Quantitation
results are immediately derived can be exported as XML & XHTML files,
copied to clipboard, or pasted onto the spectrum in Mnova.
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
Brewery Beer
Lactic
Acid
Acetic
Acid
Succinic
Acid
Citric
Acid
Lactic
Acid
Acetic
Acid
Succinic
Acid
Citric
Acid
Allagash Confluence 850.5 402.4 167.4 248.2 901.3 437.6 184.3 353.2
Budweiser Bud Light 93.9 38.1 35.8 82.7 117.1 17.7 34.2 62.6
Crooked Stave Surette 4699.2 564.9 195.7 265.5 4247.9 549.2 185.6 262.4
Drie Fonteinen Oude Gueuze 5137.6 865.9 234.6 0.0 4935.2 787.1 204.6 0.0
Drie Fonteinen Oude Gueuze 5389.9 917.7 228.9 0.0 5180.0 775.2 194.4 0.0
LoverBeer D'Uva Beer 3071.4 781.5 876.0 358.0 3302.8 759.9 842.4 377.3
Boone
Mariage Parfait
2009
4506.5 488.1 216.9 0.0 4591.8 403.2 193.1 0.0
Comparison of results obtained by manual integration (solid border,
left) and by automatic Mnova SMA (dotted border, right).
Units=mg/L
Manual Integration Mnova SMA
Ingredients : Oyster, Barberry,
Dextrose, Snow Lotus, Bombyx Mori L,
Ginger Root, Salfron Crocus.
Sample preparation:
Extract with 20:80 D2O:CD3CN
Centrifuge or Settle
Supernatant analyzed.
Answer:
Also contained ~10 wt% Sulfoaildenafil
A Viagra Analog
Question:
Why is this competitors product so good?
Typical Herbal Extracts
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
60 MHz
300 MHz
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
Adulteration of Acacia senegal – aka Gum Arabic
Emulsifier in Many Food, Beverage, Pharmaceutical and Cosmetic Products
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
ENC 2014  - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14
Acknowledgments
Aloe Project Work – Adam Dicaprio and Daniel Edwards at PNA
Beer Project Work – Adam Dicaprio
ED Herbal Project – Kristie Adams and Anton Bzhelyanky - USP
Chris Berliner – ISC (Provided Gums)

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ENC 2014 - MNova Users Meeting Presentation Aloe Vera, Beer, PDE5i Adulterants in Dietary SupplementsAcacia Gum - 3-23-14

  • 1. Process NMR Associates Quantitative Small Mixture Analysis (SMA): Quality of Aloe Vera, Acid Profiles of Sour Beers, PDE5i Adulteration of Male Enhancement Formulations Presented By John Edwards, Ph.D. Process NMR Associates, LLC Danbury, Connecticut March 23, 2014 Mnova UM at 55th ENC, Boston MA
  • 2. Process NMR Associates Contract NMR Analysis NMR Application Development Solids -200 Liquids-300 60 MHz
  • 3. # Chemical Characterization of the Immunomodulating Polysaccharide of Aloe Vera L., W.J.Goux, et al, http://www.iasc.org/AloeStructure080604.pdf Aloe Vera
  • 6. Process NMR Associates Commercial freeze-dried 200x aloe vera leaf juice powder
  • 7. Process NMR Associates Compound IASC Certification requirement Acemannan ≥ 5% dry weight Glucose Present Aloin 10 ppm or less in 0.5% aloe vera solids solution, analysed by HPLC or other fit for purpose methodology approved by IASC Isocitrate ≤ 5% dry weight Maltodextrin Must be listed on label and analysis must meet label claims. If undeclared, is considered an adulterant. Solids ≥ 0.46% in single-strength juice (for example, a 10x concentrate should have ≥ 4.6%) Ash ≤ 40% Aloe Vera Inner Leaf Juice Constituents and Additives that need to be Analyzed and Reported for IASC Certification Included in the American Herbal Pharmacopoeia Monograph on Aloe Vera Leaf, Leaf Juice & Inner Leaf Juice
  • 8. Process NMR Associates Substance Signal Type and N Parameter Chemical shift, ppm Acetylated Polysaccharides Broad Group of CH3 Singlets (N=3) 2.0-2.3 Isocitric acid CH, Doublet (N=1) 4.25 Malic acid CH, 4 peak multiplet (N=1) 4.45 -Glucose CH Doublet (N=1) 4.6 -Glucose CH Doublet (N=1) 5.2 Isocitric lactone CH Doublet (N=1) 5.05 Characteristic chemical shift values, peak multiplicity, protonated carbon type and N values used for detection and quantitation of the major natural components of aloe vera leaf juice
  • 9. Compound Type of compound Signal type Chemical shift, ppm Propylene glycol Additive CH3, doublet (N=3) 1.1 Ethanol Degradation product or additive CH3, triplet (N=3) 1.15 Lactic acid Degradation product CH3, doublet (N=3) 1.33 Potassium sorbate Preservative CH3, doublet (N=3) 1.82 Acetic acid Degradation product CH3, singlet (N=3) 1.96 Pyruvic acid Degradation product CH3, singlet (N=3) 2.35 Citric acid Naturally present or added as pH regulator or preservative 2 x CH2, Multiplet (N=4) 2.5-3.0 Succinic acid Degradation product 2 x CH2, singlet (N=4) 2.6 Glycerol Additive CH2 and CH, multiplet 3.5 Glycine Additive CH2, singlet (N=2) 3.51 Sucrose Additive CH, doublet (N=1) 5.4 Fumaric acid Degradation product 2 x CH, singlet (N=2) 6.5 Sodium benzoate Preservative 2 x CH, doublet (N=2) 7.95 Formic acid Degradation product CH, singlet (N=1) 8.2-8.3 Chemical shift values, peak and chemistry descriptions, molar conversion factors that can be used for detection and quantitation of aloe vera leaf juice preservatives, additives, and degradation products
  • 10. Analysis of Aloe Sample 458 – Whole Leaf Aloe Powder Starting Screen  Add sample weight  Add reference weights  Add Metadata  Choose Previously SavedLibrary and Experiments Launch SMA
  • 12. Experiment Setup Add Component Information Name, Molecular Wt, # protons, Shift Ranges of Component Peaks Acceptable results can be specified, and outliers will be flagged Setup Calculation Formulas
  • 13. Note: The Experimental and Formula Setup are performed only once and are then saved in a library for further use Formula Setup Enter qNMR calculations
  • 14. Spectral Result - Sample 458 GSD Output is Used in Formula Component shifts identified
  • 15. XHTML Results Output Comparison of 1H qNMR calculations of component wt% obtained from : 1) Mnova SMA 2) Manual Integration + Excel Method (validated)
  • 16. Aloe Sample 42 : Whole Leaf Powder with Maltodextrin Adulterant Two Experiments Analyzed Simultaneously For Aloe sample 42 the full analysis required 2 related samples, but the final analysis was achieved in a single step. 1) All parameters except isocitrate were calculated from the aloe sample dissolved in D2O. 2) Isocitrate is calculated from the spectrum of the same sample after acidification with DCl, which shifts the isocitrate doublet to a non-overlapping region at 4.7 ppm Spectrum 1 Spectrum 2 DCl added Spectrum 2 The single isocitrate component is now clearly quantifiable
  • 17. Experimental Setup Note reference to Spectrum 1 andSpectrum 2 in the component listing. This allows the majority of the component concentrations to be calculated from Spectrum 1 and the isocitrate concentration from Spectrum 2 which is of the acidified aloe sample.
  • 19. Validation Comparison of qNMR calculations of component wt% obtained from 1) Automated Mixture Analysis 2) Manual Integration + Excel Method
  • 20. qNMR standard Parameters: concentration reference mass (RW, in grams), sample volume (in L), Molecular Weight (MW), and Hydrogen # (NN1) are entered to determine the Concentration Conversion Factor (CCF). For each component, Integral (I#) is automatically determined from GSD integration based on specified peak ranges, and converted to concentration using the CCF.
  • 21. Concentrations of target metabolites are calculated as a function of CCF, NN1, MW & I#. The terminal coefficient (4285.71) is a correction factor for sample dilution and conversion to mg/L.
  • 22. Global Spectral Deconvolution & Peak Picking automatically identifies and integrates peaks based on entered peak ranges. Quantitation results are immediately derived can be exported as XML & XHTML files, copied to clipboard, or pasted onto the spectrum in Mnova.
  • 24. Brewery Beer Lactic Acid Acetic Acid Succinic Acid Citric Acid Lactic Acid Acetic Acid Succinic Acid Citric Acid Allagash Confluence 850.5 402.4 167.4 248.2 901.3 437.6 184.3 353.2 Budweiser Bud Light 93.9 38.1 35.8 82.7 117.1 17.7 34.2 62.6 Crooked Stave Surette 4699.2 564.9 195.7 265.5 4247.9 549.2 185.6 262.4 Drie Fonteinen Oude Gueuze 5137.6 865.9 234.6 0.0 4935.2 787.1 204.6 0.0 Drie Fonteinen Oude Gueuze 5389.9 917.7 228.9 0.0 5180.0 775.2 194.4 0.0 LoverBeer D'Uva Beer 3071.4 781.5 876.0 358.0 3302.8 759.9 842.4 377.3 Boone Mariage Parfait 2009 4506.5 488.1 216.9 0.0 4591.8 403.2 193.1 0.0 Comparison of results obtained by manual integration (solid border, left) and by automatic Mnova SMA (dotted border, right). Units=mg/L Manual Integration Mnova SMA
  • 25. Ingredients : Oyster, Barberry, Dextrose, Snow Lotus, Bombyx Mori L, Ginger Root, Salfron Crocus. Sample preparation: Extract with 20:80 D2O:CD3CN Centrifuge or Settle Supernatant analyzed. Answer: Also contained ~10 wt% Sulfoaildenafil A Viagra Analog Question: Why is this competitors product so good?
  • 32. Adulteration of Acacia senegal – aka Gum Arabic Emulsifier in Many Food, Beverage, Pharmaceutical and Cosmetic Products
  • 36. Acknowledgments Aloe Project Work – Adam Dicaprio and Daniel Edwards at PNA Beer Project Work – Adam Dicaprio ED Herbal Project – Kristie Adams and Anton Bzhelyanky - USP Chris Berliner – ISC (Provided Gums)