Agilent Sample Preparation The Pesticide Analysis Workflow
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1 Agilent Sample Preparation The Pesticide Analysis Workflow Insights into Preparing your Cannabis Sample and Triple Quad Mass Spec Analysis Joan Stevens, Ph.D. Sample Preparation Application Specialist
2 Outline Introduction to Plant Material and Edibles Existing Sample Prep Techniques - Extraction, QuEChERS - SPE, dispersive SPE Evaluation of Extraction - Data from Initial Studies - Insights and observations Optimization Sample Preparation Techniques - Sample extraction, cleanup and dilution - EMR-Lipid dispersive SPE Future Investigations, Aspects and Considerations Agilent products and solutions are intended to be used for cannabis quality control and safety testing in laboratories where such use is permitted under state/country law.
3 Cannabis and Cannabis-Based Products: Pesticide Analysis No tolerances have been established for marijuana, because of its illegal federal status and because the pesticide companies have yet to embark on the lengthy and expensive process of testing their products on cannabis Cannabis Now Issue 19
4 Pesticide Analytes and their action levels in Oregon Range ppm or ppb
5 Constituents of Cannabis Plants: Complex Nitrogenous compounds (27 known) Amino acids (18), Proteins (3) Glycoproteins (6) Enzymes (2) Sugars and related compounds (34) Hydrocarbons (50) Simple alcohols (7) Aldehydes (13) Ketones (13) Simple acids (21) Fatty acids (22) Simple esters (12) Lactones (1) Steroids (11) Terpenes (120) Non-cannabinoid phenols (25) Cannabinoids (66) Flavonoids (21) Vitamins (1) [Vitamin A] Pigments (2) Elements (9).
6 Sample Preparation: Pesticide Analysis Complex matrix associated with cannabis plant material and edibles needs to be addressed CBDs are in large amounts (10-20%), THCA can interfere with analysis with broad interference (100, ,000 ppm) Terpenes and other non-cannabinoid compounds are also in large ppm quantities ( ppm) Pesticides in 500 ppb amounts ( % ) THC-A THC LC/MSMS analysis after QuEChERS and dspe cleanup (universal)
7 Sample Preparation Techniques: Pesticide Analysis Methanol extraction with C18 SPE Acetonitrile extraction with C18 SPE Acetonitrile extraction with both NH2 and C18 SPE QuEChERS extraction with SPE cleanup QuEChERS extraction with dispersive SPE cleanup Plant material and edibles considered dry matrix; < 60% water Addition of water required for QuEChERS extraction/partitioning: step 1 Use of Salts: Na Acetate, Citrates, NaCl with MgSO4 Super-saturates the water with the salts allowing separation of water from the ACN Analytes of interest extract/transfer into the ACN layer Clean-up of co-extractive matrix: step 2
8 Basic Protocol: Pesticide Analysis Add 15 ml water and 15 ml ACN (1% acetic acid), shake 30 minutes Add AOAC QuEChERS salts, shake 2 min, centrifuge 5000 rpm, 5 min Clean-up transfer aliquot to dispersive SPE Grind flower or plant material (weigh1.5 g) SPEX GenoGrinder, 2 Ceramic Homogenizers, 5 min at 1500 rpm Individual grinding in 50 ml disposable centrifuge tubes eliminates washing, carryover and cross contamination Add 15 ml ACN (1% acetic acid), shake 30 minutes, centrifuge 5000 rpm, 5 min Clean-up transfer aliquot to dispersive SPE 2 nd Cleanup transfer aliquot to dispersive SPE??? Dispersive SPE: Universal or All Food Types: (2 ml) 50 mg PSA, 50 mg C18, 7.5 mg GCB, 150 mg MgSO4 ( ) (15 ml) 400mg PSA, 400 mg C18, 45 mg GCB, 1200 MgSO4 ( )
9 Basic Protocol: Pesticide Analysis Add 15 ml water and 15 ml ACN (1% acetic acid), shake 30 minutes Add AOAC QuEChERS salts, shake 2 min, centrifuge 5000 rpm, 5 min Clean-up transfer aliquot to dispersive SPE Grind flower or plant material (weigh1.5 g) SPEX GenoGrinder, 2 Ceramic Homogenizers, 5 min at 1500 rpm Individual grinding in 50 ml disposable centrifuge tubes eliminates washing, carryover and cross contamination Add 15 ml ACN (1% acetic acid), shake 30 minutes, centrifuge 5000 rpm, 5 min Clean-up transfer aliquot to dispersive SPE 2 nd Cleanup transfer aliquot to dispersive SPE??? Dispersive SPE: Universal or All Food Types: (2 ml) 50 mg PSA, 50 mg C18, 7.5 mg GCB, 150 mg MgSO4 ( ) (15 ml) 400mg PSA, 400 mg C18, 45 mg GCB, 1200 MgSO4 ( )
10 Basic Protocol: Pesticide Analysis Add 15 ml water and 15 ml ACN (1% acetic acid), shake 30 minutes Add AOAC QuEChERS salts, shake 2 min, centrifuge 5000 rpm, 5 min Clean-up transfer aliquot to dispersive SPE Grind flower or plant material (weigh1.5 g) SPEX GenoGrinder, 2 Ceramic Homogenizers, 5 min at 1500 rpm Individual grinding in 50 ml disposable centrifuge tubes eliminates washing, carryover and cross contamination Add 15 ml ACN (1% acetic acid), shake 30 minutes, centrifuge 5000 rpm, 5 min Clean-up transfer aliquot to dispersive SPE 2 nd Cleanup transfer aliquot to dispersive SPE??? Dispersive SPE: Universal or All Food Types: (2 ml) 50 mg PSA, 50 mg C18, 7.5 mg GCB, 150 mg MgSO4 ( ) (15 ml) 400mg PSA, 400 mg C18, 45 mg GCB, 1200 MgSO4 ( )
11 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
12 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
13 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
14 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
15 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
16 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
17 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
18 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
19 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
20 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
21 Optimization and Custom Dispersive SPE: Why is it Important Step 1: Step 2: QuEChERS Extraction/Partitioning or ACN (1% acetic acid) extraction Advantages or Disadvantages Addition of water Addition of 1% acetic acid Clean-up: Dispersive SPE Advantage over SPE, less steps, no manifold, vacuum Enhanced (custom) clean-up or additional clean-up
22 Cannabis mixture cleanup QuEChERS with 1x dspe vs. 2 x dspe custom dispersive steps 9 x Red 1x dspe Blue 2x dspe Counts vs. Acquisition Time (min) GC MS 7010 Triple Quad TIC Scan, 0.5 ul injection, Gain 10 Custom dispersive: Mixture of PSA, C18-EC, GCB, additional sorbent, and MgSO4
23 Sample Preparation: Insights and Observations Step 1: QuEChERS or ACN Extraction Addition of Water, vortex minutes Water 5 min 10 min 20 min with indicator ph range 5 min with indicator ph range 50 mm Na Acetate ph 3.5 Water/ACN (1:1 v/v) Addition of water to cannabis flower/plant turns basic almost immediately Why is this a concern degradation of base sensitive pesticides (fungicides) Captan, Folpet, Dichlofluanid, Chlorothalonil, Dicofol, Tolylfluanid
24 Recovery Recovery Comparison using Custom dspe with and Custom dspe Recovery Experimental Recovery Data without Water 1xdSPE EXP 1a 2xdSPE EXP 1b 1xdSPE EXP 2a 2xdSPE EXP 2b Pesticide EXP 1a: AOAC QuEChERS: ACN (1%AA) ml, dspe custom, 1xdSPE EXP 1b: AOAC QuEChERS: ACN (1%AA) ml, dspe custom, 2xdSPE EXP 2a: ACN (1%AA) ml only no QuEChERS salts and no H2O, dspe custom, 1xdSPE EXP 2b: ACN (1%AA) ml only no QuEChERS salts and no H2O, dspe custom, 2xdSPE
25 QuEChERS AOAC Extraction/Partitioning with Custom dspe versus Universal dspe: Hops x GC/MSMS MS1 Scan x Counts vs. Acquisition Time (min) Universal dspe Custom B dspe Custom C dspe Custom D dspe Custom F dspe GC/MSMS x 15 m configuration mid-column backflush HP-5msUI (19091S-431UI), 15m x 250 µm x 0.25 µm Counts vs. Acquisition Time (min)
26 QuEChERS AOAC Extraction/Partitioning with Custom F dspe versus Universal dspe: Hops x GC/MSMS MS1 Scan GC/MSMS x 15 m configuration mid-column backflush HP-5msUI (19091S-431UI), 15m x 250 µm x 0.25 µm Counts vs. Acquisition Time (min)
27 Recovery Pesticide Recovery after QuEChERS AOAC with Custom F dspe or Universal dspe: Hops QuEChERS AOAC with Custom F dspe versus Universal dspe AOAC with Custom F AOAC with Universal dspe Concentration of spiked pesticides: 100 ppb Pesticide Daminozide is not extracted into the ACN layer after QuEChERS AOAC salt partitioning
28 Recovery Pesticide Recovery after QuEChERS AOAC with Custom F dspe or Universal dspe: Hops QuEChERS AOAC with Custom F dspe versus Universal dspe Custom Dispersive SPE Did Not Improve Matrix Removal in Cannabis AOAC with Custom F AOAC with Universal dspe Concentration of spiked pesticides: 100 ppb Pesticide Daminozide is not extracted into the ACN layer after QuEChERS AOAC salt partitioning
29 Recovery Pesticide Recovery after QuEChERS AOAC with Custom F dspe or Universal dspe: Hops QuEChERS AOAC with Custom F dspe versus Universal dspe Custom Dispersive SPE Did Not Improve Matrix Removal in Cannabis AOAC with Custom F AOAC with Universal dspe Concentration of spiked pesticides: 100 ppb Pesticide Daminozide is not extracted into the ACN layer after QuEChERS AOAC salt partitioning
30 Recovery Pesticide Recovery after QuEChERS AOAC with Custom F dspe or Universal dspe: Hops QuEChERS AOAC with Custom F dspe versus Universal dspe Custom Dispersive SPE Did Not Improve Matrix Removal in Cannabis AOAC with Custom F AOAC with Universal dspe Concentration of spiked pesticides: 100 ppb Pesticide Daminozide is not extracted into the ACN layer after QuEChERS AOAC salt partitioning
31 Recovery Pesticide Recovery after QuEChERS AOAC with Custom F dspe or Universal dspe: Hops QuEChERS AOAC with Custom F dspe versus Universal dspe Custom Dispersive SPE Did Not Improve Matrix Removal in Cannabis AOAC with Custom F AOAC with Universal dspe Log P Concentration of spiked pesticides: 100 ppb Pesticide Daminozide is not extracted into the ACN layer after QuEChERS AOAC salt partitioning
32 9 x10 Comparison of Cannabis Extract versus Extract with 20 x Dilution Full Scan GC/MSMS 1 gram material, 15 ml ACN total (Black trace) After 20 x dilution (Red trace) Counts vs. Acquisition Time (min)
33 x10 Comparison of Cannabis Extract versus Extract 20 x Dilution with Cleanup for GCMSMS gram material, 15 ml ACN total (Black trace) After 20 x dilution and cleanup for GC/MSMS (Blue trace) Counts vs. Acquisition Time (min)
34 Overlay of Cannabis Extracts Full Scan GC/MSMS 9 x gram material, 15 ml ACN total (Black trace) After 20 x dilution (Red trace) After 20 x dilution and cleanup for GC/MSMS (Blue trace) Counts vs. Acquisition Time (min)
35 Dilution better for Quantitation & Recovery? Compound recoveries in black pepper extremely complex matrix Agilent 6495B: LC/MSMS
36 Dilution better for Quantitation & Recovery? Compound recoveries in black pepper extremely complex matrix Agilent 6495B: LC/MSMS 1:100 dilution required for acceptable recoveries >90% of the compounds
37 Recovery of Problematic Pesticides from Cannabis Extraction with 20 x Dilution LC/MSMS N=5 Compound Recovery% Average ng/ml Abamectin Acephate Acequinocyl-Hydroxy Azoxystrobin Bifenazate Daminozide Hexythiazox Piperonyl butoxide Prallethrin Pyrethrin I Pyrethrin II Spinosyn A Spinosyn D Spirotetramat Spiroxamine
38 THC and CBD High Fat Products
39 Cannabis-Based Products: Unique Dispersive SPE EMR-Lipid Innovative Sorbent! Avocado Extract dspe-psa, C18-EC EMR Lipid dspe 1.0 g EMR in 15 ml tube When activated by water EMR-Lipid Sorbent Selectively traps lipids. Size Exclusion: Unbranched hydrocarbon chains (lipids) enter the sorbent; bulky analytes do not. Sorbent Chemistry: Lipid chains that enter the sorbent are trapped by hydrophobic interactions.
40 Cannabis-Based Products: Unique Dispersive SPE EMR-Lipid Innovative Sorbent! Avocado Extract dspe-psa, C18-EC EMR Lipid dspe 1.0 g EMR in 15 ml tube When activated by water EMR-Lipid Sorbent Selectively traps lipids. Size Exclusion: Unbranched hydrocarbon chains (lipids) enter the sorbent; bulky analytes do not. Sorbent Chemistry: Lipid chains that enter the sorbent are trapped by hydrophobic interactions. EMR-Lipid Mechanism Size exclusion and hydrophobic interaction
41 and what does it do?
42 and what does it do? EMR sorbent removes LIPIDS it interacts with the long aliphatic chain NOT the functional groups What are Lipids? A class of naturally occurring hydrocarbon containing compounds commonly known as fats and oils Free Fatty Acids Triglycerides Sphingolipids Phospholipids
43 and what does it do? EMR sorbent removes LIPIDS it interacts with the long aliphatic chain NOT the functional groups What are Lipids? A class of naturally occurring hydrocarbon containing compounds commonly known as fats and oils Free Fatty Acids Triglycerides Sphingolipids Phospholipids
44 What Does EMR NOT Interact With? EMR does NOT remove analytes of interest Organophosphate Pesticides Insecticides and anthelmintics Imidazole pesticides Organochlorine Pesticides Fumonisin B2 Aflatoxins and Mycotoxins
45 Cannabis-Based Product: THC-Butter 1.5 g of THC-butter was added to a 50 ml centrifuge tube Add 15 ml of ACN (1%acetic acid) Vortex 30 minutes, centrifuge 5000 rpm, 5 min Add 5 ml water to EMR-Lipid, vortex immediately 1 min Add 5 ml of ACN (1% acetic acid) extract, vortex immediately 2 min Centrifuge 5000 rpm, 5 min Analyze by LCMSMS ACN (1%aa) extraction with dspe clean-up THC-A THC ACN (1%aa) extraction with EMR-Lipid dspe clean-up THC-A THC Pesticide Screened: Abamectin B1-a Abamectin B1-b Azoxystrobin Bifenazate Etoxazole Imazalil Imidacloprid Malathion Myclobutanil Permethrin-1 Permethrin-2 Spinosyn A Spinosyn D Spiromesifen Spirotetramat Tebuconazole
46 Extraction of Butter: MS1 Scan AOAC fatty dspe (PSA, C18-EC), blue EMR-Lipid dspe, green Blue Chromatogram: 1.5 g butter, AOAC fatty dspe (PSA and C18EC) Green Chromatogram: 1.5 g butter, AOAC salts, EMR-Lipid dispersive SPE
47 EMR-Lipid Cartridge Formate SPE format with gravity flow through design Accommodate mls of extract Very applicable to LC/MSMS work flow Continuing the work with high fat products for pesticide analysis Oils, cookies, chocolate based products Application work available at product release early fall
48 Insights and Observations :
49 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes
50 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes If QuEChERS AOAC method is being used you should add the ACN (1% acetic acid immediately after the addition of water, before vortexing for minutes
51 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes If QuEChERS AOAC method is being used you should add the ACN (1% acetic acid immediately after the addition of water, before vortexing for minutes Do not use QuEChERS EN method, water and ACN mix will be too basic for labile compounds based on the weaker buffering capacity of citrate salts used in the QuEChERS EN
52 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes If QuEChERS AOAC method is being used you should add the ACN (1% acetic acid immediately after the addition of water, before vortexing for minutes Do not use QuEChERS EN method, water and ACN mix will be too basic for labile compounds based on the weaker buffering capacity of citrate salts used in the QuEChERS EN QuEChERS methodology: Salting/Partitioning and dspe may negatively affect recovery; e.g. Daminozide
53 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes If QuEChERS AOAC method is being used you should add the ACN (1% acetic acid immediately after the addition of water, before vortexing for minutes Do not use QuEChERS EN method, water and ACN mix will be too basic for labile compounds based on the weaker buffering capacity of citrate salts used in the QuEChERS EN QuEChERS methodology: Salting/Partitioning and dspe may negatively affect recovery; e.g. Daminozide Promising results with ACN (1% acetic acid) extraction, no QuEChERS salts
54 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes If QuEChERS AOAC method is being used you should add the ACN (1% acetic acid immediately after the addition of water, before vortexing for minutes Do not use QuEChERS EN method, water and ACN mix will be too basic for labile compounds based on the weaker buffering capacity of citrate salts used in the QuEChERS EN QuEChERS methodology: Salting/Partitioning and dspe may negatively affect recovery; e.g. Daminozide Promising results with ACN (1% acetic acid) extraction, no QuEChERS salts Dispersive SPE or SPE will remove some of the matrix co-extractives
55 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes If QuEChERS AOAC method is being used you should add the ACN (1% acetic acid immediately after the addition of water, before vortexing for minutes Do not use QuEChERS EN method, water and ACN mix will be too basic for labile compounds based on the weaker buffering capacity of citrate salts used in the QuEChERS EN QuEChERS methodology: Salting/Partitioning and dspe may negatively affect recovery; e.g. Daminozide Promising results with ACN (1% acetic acid) extraction, no QuEChERS salts Dispersive SPE or SPE will remove some of the matrix co-extractives Dilution had the greatest effect on removing matrix inferences, consider incorporating in your protocol, require very sensitive triple quadrupole
56 Insights and Observations : The active ingredients can cause interference and instrument issues: cannabinoids and terpenes If QuEChERS AOAC method is being used you should add the ACN (1% acetic acid immediately after the addition of water, before vortexing for minutes Do not use QuEChERS EN method, water and ACN mix will be too basic for labile compounds based on the weaker buffering capacity of citrate salts used in the QuEChERS EN QuEChERS methodology: Salting/Partitioning and dspe may negatively affect recovery; e.g. Daminozide Promising results with ACN (1% acetic acid) extraction, no QuEChERS salts Dispersive SPE or SPE will remove some of the matrix co-extractives Dilution had the greatest effect on removing matrix inferences, consider incorporating in your protocol, require very sensitive triple quadrupole Is the existing clean-up techniques enough for long term analysis, issues with analysis and instrument maintenance, check you sample prep methodology by full scan both LC and GC/MSMS
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