scientific poster design, presentation, research, science

1. Lecturer: Assoc.Prof. Nguyen Thi Hiep
TA: Ms. Vo Ngoc Hai Chau
BIOMATERIALS
How to design a
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7. Samples

8. Method

9. Method

10. Phuc Vo1, Zhentian Lei23, Lloyd Sumner23, Van K. Ho1, Edward Huxel5, Anuradha Roy4 and Chung-Ho Lin1
1Center for Agroforestry, School of Natural Resources, University of Missouri
2MU Metabolomics Center, University of Missouri
3Department of Biochemistry, University of Missouri
4High-Throughput Screening Laboratory, University of Kansas
5Bois d’Arc BioProducts Company
Osage orange (Muclura pomifera), a native species was widely distributed in the
United States, is extremely durable and is considered one of the most decay resistant
woods.
Osage orange provides an abundant resource of the bioactive lipids and polyphenolics
(e.g., isoflavonoid and xanthones) that have not been systematically studied.
Osage orange is considered to be safe, therefore, a possibly good source of antioxidant
nutraceuticals and functional food ingredients, and active ingredients for personal care
products.
The compounds in Osage Orange were extracted and analyzed by Bruker Impact II Q-
Tof HRMS.
The ion chromatograms were submitted to XCMS platform operated by Center for
Metabolomics at the Scripps Research Institute.
The spectra were annotated and the compounds were identified and categorized by the
integration of the METLIN, the world's largest metabolite database.
The most potential bioactive compounds in SCG were quantify by Water ACQUITY
TQD LC-MS/MS.
The commercial application of the compounds will be immediately identified by
screening for their antioxidant, anti-inflammatory, anti-microbial and skin brightening
activities.
Compare the chemical profiles between different tissues (fruits and seeds).
Quantify and characterize the most promising bioactive compounds in Osage orange
using high performance liquid chromatography coupled with tandem mass
spectrometry (HPLC-MS/MS).
Perform an array of high-throughput screening bioassays to identify the commercial
applications.
Explore potential new uses and applications in cosmetic, personal care products and
pharmaceutical industries.
We have successfully identified approximately more than 200 polyphenols (Table 1) and quantify more than 28 compounds (Table
2). Many of them have antioxidant, anti-inflammatory, anti-cancer, antibiotic activities in fruit and seed extracted from Osage
orange.
Anti-microbial assay showed that the fruits and seeds of Osage orange could be an excellent source of phytochemicals for cosmetic,
personal care products and pharmaceutical industries.
We would like to acknowledge University of Missouri Center for Agroforestry (UMCA), University of Missouri Metabolomics Center,
and High-Throughput Screening Laboratory in University of Kansas.
Table 1. The annotations of peaks isolated from fruit and seed extracts
Osage orange was
extracted by Methanol
Bruker Impact II Q-Tof HRMS
Waters Acquity TQD LC-
MS/MS
High Throughput Screening
Laboratory at KU
Quantify potential
compounds
Explore potential
applications
Anti-microbial assay
Figure 1. Fruit and seed extracts of Osage Orange show
strong anti-microbial activities against Staphylococcus
aureus (MRSA) (Fruit: 28,29,30) (Seed: 31, 32, 33).
Table 2. Concentrations of compounds in fruit and seed extracts
No. Compound Formula Part Biological function Application
1 Pomiferin C₂₅H₂₄O₆ Seed antioxidant, antimicrobial, anti-cancer -
2 Osajin C₂₅H₂₄O₅ Seed anticholinesterase, antimicrobial -
3 Butamirate C₁₈H₂₉NO₃ Seed anti-inflammatory A cough suppressant
4 (-)-Epicatechin C₁₅H₁₄O₆ Seed antioxidant, reduces Myostatin Functional foods
5 (+)-Taxifolin C₁₅H₁₂O₇ Fruit antioxidant, anti-cancer, anti-inflammtory, anti-mutagenic
Food industry, oil industry, cosmetics
industry
6 Rutin C₂₇H₃₀O₁₆ Fruit antioxidant, anti-inflammatory, antinociceptive Medicine, functional foods
7 Quercetin C₁₅H₁₀O₇ Fruit antioxidant, anti-inflammatory, antibacterial Medicine, functional foods
8 Apigenin C₁₅H₁₀O₅ Fruit, Seed anti-cancer, anti-inflammatory, anti-obesity Functional foods
9 Troxerutin C₃₃H₄₂O₁₉ Fruit anti-oxidative, anti-inflammatory, anti-thrombotic, anti-fibrinolytic Medicine
10 Shanciol C₂₅H₂₄O₆ Fruit, Seed anti-inflammatory Medicine
11 Artocarpesin C₂₀H₁₈O₆ Fruit, Seed antimicrobial, anti-cancer Medicine, cancer drugs
12 Justicidin A C₂₂H₁₈O₇ Fruit, Seed antitumor, neuroprotection Medicine
13 Justicidin B C₂₁H₁₆O₆ Fruit, Seed antifungal, antibacterial, antiviral, anti-inflammatory Pharmaceuticals
14 Morusin C₂₅H₂₄O₆ Seed antitumor, anti-nociceptive Medicine
15 Astragalin C₂₁H₂₀O₁₁ Fruit antioxidant, anti-allergic, anti-inflammatory Medicine
16 Oleic acid C₁₈H₃₄O₂ Seed antitumor Additives, Funtional foods
17 Lutein C₄₀H₅₆O₂ Seed antioxidant Functional foods
18 Quinic acid C₇H₁₂O₆ Fruit, Seed antioxidant Medicine
19 Ellagic acid C₁₄H₆O₈ Seed anti-inflammatory, anti-cancer Functional foods
20 Naringin C₂₇H₃₂O₁₄ Fruit blood lipid-lowering, antioxidant, anticarcinogenic Functional foods
21 Ferulic acid C₁₀H₁₀O₄ Seed anti-cancer, skin brightening Cosmetic industry
22 Chrysin C₁₅H₁₀O₄ Fruit, Seed skin protection, anti-inflammation, antioxidant Functional foods, cosmetic industry
23 Chlorogenic acid C₁₆H₁₈O₉ Fruit
anti-inflammatory, antioxidant, anti-aging, anti-skin cancer,
antimicrobial
Functional foods
24 Zeaxanthin C₄₀H₅₆O₂ Seed antioxidant Functional foods
25 Mureidomycin A C₃₈H₄₈N₈O₁₂S Fruit,Seed antibiotic Medicine
26 p-Coumaric acid C₉H₈O₃ Fruit,Seed anti-pigmentation, antioxidant, antimicrobial, anti-inflammatory -
27 Neochlorogenic acid C₁₆H₁₈O₉ Fruit anticarcinogenics, antioxidant -
28 Aescin C₅₅H₈₆O₂₄ Seed anti-inflammatory Medicine, functional foods
Global chemical profiling using XCMS metabolomics platform
mg/kg
No. Samples Fruit Seed
1 Chlorogenic acid 0.933±0.002 <LOD
2 Caffeic acid 10.708±0.062 <LOD
3 Rutin 14.798±0.167 <LOD
4 p-Hydroxybenzoic acid 0.606±0.025 15.715±0.363
5 Quinic acid 35.686±0.229 0.508±0.024
6 Ellagic acid <LOD 8.690±0.371
7 Neochlorogenic acid 126.029±1.888 <LOD
8 Quercetin-3-glucose 6.392±0.107 <LOD
9 p-Coumaric acid 0.210±0.005 0.380±0.005
10 Naringin 2.656±0.022 <LOD
11 Ferulic acid <LOD 0.188±0.020
12 Quercetin 0.546±0.020 <LOD
13 Chrysin 2.597±0.032 1.040±0.047
14 Gentiopicroside 0.847±0.001 <LOD
15 Rhoifolin 0.490±0.008 0.336±0.012
16 Aescin <LOD 14.989±0.227
17 Artesunate 0.022±0.001 <LOD
18 Eudesmic acid <LOD 3.533±0.054
Pomiferin Osajin
Figure 2. Two major bioactive chemicals. The anti-microbial Osajin and
Pomiferin also have potential value as antioxidants and pharmaceutical
precursors.
Figure 3. The pairwise job allowing for the comparison of two group (Osage orange
extracts and control) (A). An example of identification of pomiferin by XCMS Online
screen shot including results table (B), extracted ion chromatogram (C), mass spectrum
(D), and putative METLIN identification (E).
A
B
C
D
E

11. Phuc Vo1, Jihyun Park2, Zhentian Lei34, Van K. Ho1, Lloyd Sumner34, and Chung-Ho Lin1
1Center for Agroforestry, School of Natural Resources, University of Missouri
2Korea Prime Pharm. Co., Ltd, South Korea
3MU Metabolomics Center, University of Missouri
4Department of Biochemistry, University of Missouri
We would like to acknowledge University of Missouri Center for Agroforestry (UMCA), University of Missouri Metabolomics Center for financial
support.
• The compounds in SCG were extracted with methanol and analyzed by
Bruker Impact II Q-Tof HRMS.
• The ion chromatograms were processed by XCMS Online in pairwise
job mode (compare SCG samples and MeOH control blank).
• The compounds were identified and categorized by the integration of
the METLIN, the world's largest metabolite database.
• The most potential bioactive compounds in SCG were quantify by
Water ACQUITY TQD LC-MS/MS.
• The commercial application of the compounds will be identified by
screening for their antioxidant, anti-inflammatory, anti-microbial and
skin brightening activities.
Figure 1. Identify the bioactive compounds (antioxidant, anti-
microbial) through bioassay-guided purification
• The results of the anti-microbial assay
indicated that fraction number 1-3, 8-9, and
13-43 showed no anti-bacterial activity
whereas fraction number 4-7 and 10-12 had
strong activity. The results are very
consistent among three plates in this test. It is
matched with antioxidant data result that
fraction 4 had the strongest activity.
• The results of the antioxidant assay
indicated that fraction number 4 from Flash
chromatography had the strongest activity.
The concentration of FeCl2 in each tubes
was calculated by standard curve. The
higher concentration or dark blue color
means stronger antioxidant activity. The
second assay using HPLC samples was
performed and showed that fraction number
10-13 had high activity.
Every day, there are about 4,000 tons of coffee consumed in the
United States and more than 6,000,000 tons of spent coffee grounds
(SCG) are generated worldwide. Whereas SCG has little commercial
value and has been treated as solid waste, the chemical profiles from
our previous metabolomics analysis suggested that SCG is a rich
source of bioactive compounds that have shown beneficial effects on
human health and can be reused as animal feed, biofuel, biodiesel, or
bioethanol production, adsorbent and activated carbon.
mg/kg
No. Samples Ethiopia coffee Costa Rican coffee Hawaiian coffee
1 Gallic acid 3.062±0.025 1.004±0.018 1.130±0.032
2 Chlorogenic acid 3.923±0.538 2.847±0.026 3.746±0.004
3 Syringic acid 31.275±0.435 32.065±0.649 <LOD
4 Caffeic acid 54.526±1.506 41.445±0.860 43.411±0.456
5 Vanillic acid 86.152±2.883 53.855±1.276 54.338±1.402
6 Rutin 12.843±1.427 2.449±0.935 <LOD
7 p-Hydroxybenzoic acid 27.886±0.322 1.913±0.236 2.151±0.116
8 Catechin 23.986±2.218 1.860±0.314 1.418±0.269
9 Epicatechin 37.167±1.489 <LOD <LOD
10 Quinic acid 207.383±0.459 238.306±0.462 218.796±0.288
11 Ellagic acid 67.088±0.035 <LOD <LOD
12 Neochlorogenic acid 338.086±1.742 236.697±1.517 293.482±1.782
13 Penta-O-galloyl-b-glucose 9.661±0.167 1.665±0.021 1.669±0.376
14 Epicatechin gallate 20.325±0.216 <LOD <LOD
15 Quercetin-3-glucose 28.548±0.880 <LOD <LOD
16 p-Coumaric acid 18.280±1.828 0.687±0.052 0.676±0.100
17 Naringin 15.664±0.256 <LOD <LOD
18 Ferulic acid 21.076±0.609 <LOD <LOD
19 Resveratrol 16.914±0.221 <LOD <LOD
20 Cinnamic acid 24.157±0.407 <LOD <LOD
21 Quercetin 17.646±0.218 <LOD <LOD
22 Chrysin 52.839±0.139 <LOD <LOD
• Compare the chemical profiles between the three coffee cultivars
(Ethiopia coffee (Yirgacheffe), Costa Rican coffee (Tarrazu), and
Hawaiian coffee (Kona Blend)).
• Quantify and characterize the most promising bioactive compounds in
SCG using high performance liquid chromatography coupled with
tandem mass spectrometry (HPLC-MS/MS).
• Explore potential new applications in cosmetic, personal care products
and pharmaceutical industries.
• More than 150 potential compounds (Table 1) have been identified by using XCMS metabolomics platform including several classes of antioxidant,
anti-inflammatory, skin brightening, and anti-aging compounds in SCG.
• We have successfully developed the methods to quantify more than 28 compounds in SCG (Table 2).
• We expect that the low cost SCG can become a new resource materials in the future for nutritional supplements, pharmaceutical, and cosmetics
applications.
Global chemical profiling using XCMS metabolomics platform
No. Compound Formula
Molecular
Weight
Biological function Application
1 Rutin C₂₇H₃₀O₁₆ 610.521 Antioxidant, anti-inflammatory, antinociceptive Medicine, functional foods
2 Quercetin C₁₅H₁₀O₇ 302.238 Antioxidant, anti-inflammatory, antibacterial Medicine, functional foods
3 Quinic acid C₇H₁₂O₆ 192.167 Antioxidant Medicine
4 Ellagic acid C₁₄H₆O₈ 302.194 Anti-inflammatory, anti-cancer Functional foods
5 p-Coumaric acid C₉H₈O₃ 164.16
Anti-pigmentation, antioxidant, antimicrobial, anti-
inflammatory
-
6 Naringin C₂₇H₃₂O₁₄ 580.539 Blood lipid-lowering, antioxidant, anticarcinogenic Functional foods
7 Ferulic acid C₁₀H₁₀O₄ 194.186 Anticancer, skin brightening Cosmetic industry
8 Chrysin C₁₅H₁₀O₄ 254.241 Skin protection, anti-inflammation and antioxidant Functional foods, Cosmetic industry
9 Resveratrol C₁₄H₁₂O₃ 228.247 Anti-inflammatory, antioxidant, anti-aging, photo protection Cosmetic industry
10 Eugenol C₁₀H₁₂O₂ 164.204
Anti-microbial, anti-inflammatory, antioxidant and
anticancer
Dental, Medicine
11 Caffeine C₈H₁₀N₄O₂ 194.194 Antioxidant, anti-skin cancer, antimicrobial, emollient Food industry, Cosmetic industry
12 Daidzein C₁₅H₁₀O₄ 254.241 Anti-inflammatory, anti-carcinogenic Functional foods
13 Chlorogenic acid C₁₆H₁₈O₉ 354.311 Anti-inflammatory, antioxidant, anti-aging, anti-skin cancer Functional foods
14 E-Cinnamic acid C₉H₈O₂ 148.161 Anti-tyrosinase, antioxidant, antimicrobial Cosmetics, dyes, pharmaceuticals
15 Hesperetin C₁₆H₁₄O₆ 302.282 Anti-inflammatory, antioxidant, antitumor
Health care products, pharmaceuticals,
food field
16 Guaiacol C₇H₈O₂ 124.139 Antioxidant Medicine
17 3,5-Di-O-Caffeoylquinic acid C₂₅H₂₄O₁₂ 516.455 Antioxidant, cytoprotective -
18
8-C-Ascorbyl epigallocatechin
3-gallate
C₂₈H₂₄O₁₇ 632.483 Antitumor, antioxidative, and antimicrobial Cosmetic industry
19 (-)-Epicatechin C₁₅H₁₄O₆ 290.271 Antioxidant, reduces Myostatin Functional foods
20 Apigenin C₁₅H₁₀O₅ 270.24 Anti-cancer, anti-inflammatory, anti-obesity Functional foods
21 Neochlorogenic acid C₁₆H₁₈O₉ 354.311 Anticarcinogenics, antioxidant -
22 Catechin C₁₅H₁₄O₆ 290.27 Antioxidant, antiangiogenic, antitumor Cosmetic industry
23 α-Fenchone C₁₀H₁₆O 152.237 Anti-inflammatory, antimicrobial Cosmetic industry
Table 1. The annotations of peaks isolated from SCG extracts Table 2. Concentrations of compounds in SCG extracts
Spent Coffee
Grounds
Bruker Impact II
Q-Tof HRMS
Waters Acquity
TQD LC-MS/MS
Flash
Chromatography
XCMS online
Quantify potential
compounds
Antioxidant,
microbial assay
Figure 2. The pairwise job allowing for the comparison of two group (SCG extracts and
control) (A). An example of identification of ferulic acid by XCMS Online screen shot
including results table (B), extracted ion chromatogram (C), mass spectrum (D), and
putative METLIN identification (E).
A
B
C
D
E
Antioxidant and anti-microbial assay

12. Phuc Vo1, Jihyun Park2, Zhentian Lei34, Van K. Ho1, Lloyd Sumner34, and Chung-Ho Lin1
1Center for Agroforestry, School of Natural Resources, University of Missouri
2Korea Prime Pharm. Co., Ltd, South Korea
3MU Metabolomics Center, University of Missouri
4Department of Biochemistry, University of Missouri
• The compounds in SCG were extracted with methanol and analyzed by
Bruker Impact II Q-Tof HRMS.
• The ion chromatograms were processed by XCMS Online in pairwise
job mode (compare SCG samples and MeOH control blank).
• The compounds were identified and categorized by the integration of
the METLIN, the world's largest metabolite database.
• The most potential bioactive compounds in SCG were quantify by
Water ACQUITY TQD LC-MS/MS.
• The commercial application of the compounds will be identified by
screening for their antioxidant, anti-inflammatory, anti-microbial and
skin brightening activities.
Figure 1. Identify the bioactive compounds (antioxidant, anti-
microbial) through bioassay-guided purification
• The results of the anti-microbial assay
indicated that fraction number 1-3, 8-9, and
13-43 showed no anti-bacterial activity
whereas fraction number 4-7 and 10-12 had
strong activity. The results are very
consistent among three plates in this test. It is
matched with antioxidant data result that
fraction 4 had the strongest activity.
• The results of the antioxidant assay
indicated that fraction number 4 from Flash
chromatography had the strongest activity.
The concentration of FeCl2 in each tubes
was calculated by standard curve. The
higher concentration or dark blue color
means stronger antioxidant activity. The
second assay using HPLC samples was
performed and showed that fraction number
10-13 had high activity.
Every day, there are about 4,000 tons of coffee consumed in the
United States and more than 6,000,000 tons of spent coffee grounds
(SCG) are generated worldwide. Whereas SCG has little commercial
value and has been treated as solid waste, the chemical profiles from
our previous metabolomics analysis suggested that SCG is a rich
source of bioactive compounds that have shown beneficial effects on
human health and can be reused as animal feed, biofuel, biodiesel, or
bioethanol production, adsorbent and activated carbon.
mg/kg
No. Samples Ethiopia coffee Costa Rican coffee Hawaiian c
1 Gallic acid 3.062±0.025 1.004±0.018 1.130±0.
2 Chlorogenic acid 3.923±0.538 2.847±0.026 3.746±0.
3 Syringic acid 31.275±0.435 32.065±0.649 <LOD
4 Caffeic acid 54.526±1.506 41.445±0.860 43.411±0
5 Vanillic acid 86.152±2.883 53.855±1.276 54.338±1
6 Rutin 12.843±1.427 2.449±0.935 <LOD
7 p-Hydroxybenzoic acid 27.886±0.322 1.913±0.236 2.151±0.
8 Catechin 23.986±2.218 1.860±0.314 1.418±0.
9 Epicatechin 37.167±1.489 <LOD <LOD
10 Quinic acid 207.383±0.459 238.306±0.462 218.796±0
11 Ellagic acid 67.088±0.035 <LOD <LOD
12 Neochlorogenic acid 338.086±1.742 236.697±1.517 293.482±1
13 Penta-O-galloyl-b-glucose 9.661±0.167 1.665±0.021 1.669±0.
14 Epicatechin gallate 20.325±0.216 <LOD <LOD
15 Quercetin-3-glucose 28.548±0.880 <LOD <LOD
16 p-Coumaric acid 18.280±1.828 0.687±0.052 0.676±0.
17 Naringin 15.664±0.256 <LOD <LOD
18 Ferulic acid 21.076±0.609 <LOD <LOD
19 Resveratrol 16.914±0.221 <LOD <LOD
20 Cinnamic acid 24.157±0.407 <LOD <LOD
• Compare the chemical profiles between the three coffee cultivars
(Ethiopia coffee (Yirgacheffe), Costa Rican coffee (Tarrazu), and
Hawaiian coffee (Kona Blend)).
• Quantify and characterize the most promising bioactive compounds in
SCG using high performance liquid chromatography coupled with
tandem mass spectrometry (HPLC-MS/MS).
• Explore potential new applications in cosmetic, personal care products
and pharmaceutical industries.
Global chemical profiling using XCMS metabolomics platform
No. Compound Formula
Molecular
Weight
Biological function Application
1 Rutin C₂₇H₃₀O₁₆ 610.521 Antioxidant, anti-inflammatory, antinociceptive Medicine, functional foods
2 Quercetin C₁₅H₁₀O₇ 302.238 Antioxidant, anti-inflammatory, antibacterial Medicine, functional foods
3 Quinic acid C₇H₁₂O₆ 192.167 Antioxidant Medicine
4 Ellagic acid C₁₄H₆O₈ 302.194 Anti-inflammatory, anti-cancer Functional foods
5 p-Coumaric acid C₉H₈O₃ 164.16
Anti-pigmentation, antioxidant, antimicrobial, anti-
inflammatory
-
6 Naringin C₂₇H₃₂O₁₄ 580.539 Blood lipid-lowering, antioxidant, anticarcinogenic Functional foods
7 Ferulic acid C₁₀H₁₀O₄ 194.186 Anticancer, skin brightening Cosmetic industry
8 Chrysin C₁₅H₁₀O₄ 254.241 Skin protection, anti-inflammation and antioxidant Functional foods, Cosmetic industry
9 Resveratrol C₁₄H₁₂O₃ 228.247 Anti-inflammatory, antioxidant, anti-aging, photo protection Cosmetic industry
10 Eugenol C₁₀H₁₂O₂ 164.204
Anti-microbial, anti-inflammatory, antioxidant and
anticancer
Dental, Medicine
11 Caffeine C₈H₁₀N₄O₂ 194.194 Antioxidant, anti-skin cancer, antimicrobial, emollient Food industry, Cosmetic industry
12 Daidzein C₁₅H₁₀O₄ 254.241 Anti-inflammatory, anti-carcinogenic Functional foods
13 Chlorogenic acid C₁₆H₁₈O₉ 354.311 Anti-inflammatory, antioxidant, anti-aging, anti-skin cancer Functional foods
14 E-Cinnamic acid C₉H₈O₂ 148.161 Anti-tyrosinase, antioxidant, antimicrobial Cosmetics, dyes, pharmaceuticals
15 Hesperetin C₁₆H₁₄O₆ 302.282 Anti-inflammatory, antioxidant, antitumor
Health care products, pharmaceuticals,
food field
16 Guaiacol C₇H₈O₂ 124.139 Antioxidant Medicine
17 3,5-Di-O-Caffeoylquinic acid C₂₅H₂₄O₁₂ 516.455 Antioxidant, cytoprotective -
18
8-C-Ascorbyl epigallocatechin
3-gallate
C₂₈H₂₄O₁₇ 632.483 Antitumor, antioxidative, and antimicrobial Cosmetic industry
19 (-)-Epicatechin C₁₅H₁₄O₆ 290.271 Antioxidant, reduces Myostatin Functional foods
20 Apigenin C₁₅H₁₀O₅ 270.24 Anti-cancer, anti-inflammatory, anti-obesity Functional foods
21 Neochlorogenic acid C₁₆H₁₈O₉ 354.311 Anticarcinogenics, antioxidant -
Table 1. The annotations of peaks isolated from SCG extracts Table 2. Concentrations of compounds in SCG extracts
Spent Coffee
Figure 2. The pairwise job allowing for the comparison of two group (SCG extracts and
control) (A). An example of identification of ferulic acid by XCMS Online screen shot
including results table (B), extracted ion chromatogram (C), mass spectrum (D), and
putative METLIN identification (E).
A
B
C
D
E
Antioxidant and anti-microbial assay

13. Phuc Vo1, Zhentian Lei23, Lloyd Sumner23, Van K. Ho1, Edward Huxel5, Anuradha Roy4 and Chung-Ho Lin1
1Center for Agroforestry, School of Natural Resources, University of Missouri
2MU Metabolomics Center, University of Missouri
3Department of Biochemistry, University of Missouri
4High-Throughput Screening Laboratory, University of Kansas
5Bois d’Arc BioProducts Company
Osage orange (Muclura pomifera), a native species was widely distributed in the
United States, is extremely durable and is considered one of the most decay resistant
woods.
Osage orange provides an abundant resource of the bioactive lipids and polyphenolics
(e.g., isoflavonoid and xanthones) that have not been systematically studied.
Osage orange is considered to be safe, therefore, a possibly good source of antioxidant
nutraceuticals and functional food ingredients, and active ingredients for personal care
products.
The compounds in Osage Orange were extracted and analyzed by Bruker Impact II Q-
Tof HRMS.
The ion chromatograms were submitted to XCMS platform operated by Center for
Metabolomics at the Scripps Research Institute.
The spectra were annotated and the compounds were identified and categorized by the
integration of the METLIN, the world's largest metabolite database.
The most potential bioactive compounds in SCG were quantify by Water ACQUITY
TQD LC-MS/MS.
The commercial application of the compounds will be immediately identified by
screening for their antioxidant, anti-inflammatory, anti-microbial and skin brightening
activities.
Compare the chemical profiles between different tissues (fruits and seeds).
Quantify and characterize the most promising bioactive compounds in Osage orange
using high performance liquid chromatography coupled with tandem mass
spectrometry (HPLC-MS/MS).
Perform an array of high-throughput screening bioassays to identify the commercial
applications.
Explore potential new uses and applications in cosmetic, personal care products and
pharmaceutical industries.
We have successfully identified approximately more than 200 polyphenols (Table 1) and quantify more than 28 compounds (Table
2). Many of them have antioxidant, anti-inflammatory, anti-cancer, antibiotic activities in fruit and seed extracted from Osage
orange.
Anti-microbial assay showed that the fruits and seeds of Osage orange could be an excellent source of phytochemicals for cosmetic,
personal care products and pharmaceutical industries.
We would like to acknowledge University of Missouri Center for Agroforestry (UMCA), University of Missouri Metabolomics Center,
and High-Throughput Screening Laboratory in University of Kansas.
Table 1. The annotations of peaks isolated from fruit and seed extracts
Osage orange was
extracted by Methanol
Bruker Impact II Q-Tof HRMS
Waters Acquity TQD LC-
MS/MS
High Throughput Screening
Laboratory at KU
Quantify potential
compounds
Explore potential
applications
Anti-microbial assay
Figure 1. Fruit and seed extracts of Osage Orange show
strong anti-microbial activities against Staphylococcus
aureus (MRSA) (Fruit: 28,29,30) (Seed: 31, 32, 33).
Table 2. Concentrations of compounds in fruit and seed extracts
No. Compound Formula Part Biological function Application
1 Pomiferin C₂₅H₂₄O₆ Seed antioxidant, antimicrobial, anti-cancer -
2 Osajin C₂₅H₂₄O₅ Seed anticholinesterase, antimicrobial -
3 Butamirate C₁₈H₂₉NO₃ Seed anti-inflammatory A cough suppressant
4 (-)-Epicatechin C₁₅H₁₄O₆ Seed antioxidant, reduces Myostatin Functional foods
5 (+)-Taxifolin C₁₅H₁₂O₇ Fruit antioxidant, anti-cancer, anti-inflammtory, anti-mutagenic
Food industry, oil industry, cosmetics
industry
6 Rutin C₂₇H₃₀O₁₆ Fruit antioxidant, anti-inflammatory, antinociceptive Medicine, functional foods
7 Quercetin C₁₅H₁₀O₇ Fruit antioxidant, anti-inflammatory, antibacterial Medicine, functional foods
8 Apigenin C₁₅H₁₀O₅ Fruit, Seed anti-cancer, anti-inflammatory, anti-obesity Functional foods
9 Troxerutin C₃₃H₄₂O₁₉ Fruit anti-oxidative, anti-inflammatory, anti-thrombotic, anti-fibrinolytic Medicine
10 Shanciol C₂₅H₂₄O₆ Fruit, Seed anti-inflammatory Medicine
11 Artocarpesin C₂₀H₁₈O₆ Fruit, Seed antimicrobial, anti-cancer Medicine, cancer drugs
12 Justicidin A C₂₂H₁₈O₇ Fruit, Seed antitumor, neuroprotection Medicine
13 Justicidin B C₂₁H₁₆O₆ Fruit, Seed antifungal, antibacterial, antiviral, anti-inflammatory Pharmaceuticals
14 Morusin C₂₅H₂₄O₆ Seed antitumor, anti-nociceptive Medicine
15 Astragalin C₂₁H₂₀O₁₁ Fruit antioxidant, anti-allergic, anti-inflammatory Medicine
16 Oleic acid C₁₈H₃₄O₂ Seed antitumor Additives, Funtional foods
17 Lutein C₄₀H₅₆O₂ Seed antioxidant Functional foods
18 Quinic acid C₇H₁₂O₆ Fruit, Seed antioxidant Medicine
19 Ellagic acid C₁₄H₆O₈ Seed anti-inflammatory, anti-cancer Functional foods
20 Naringin C₂₇H₃₂O₁₄ Fruit blood lipid-lowering, antioxidant, anticarcinogenic Functional foods
21 Ferulic acid C₁₀H₁₀O₄ Seed anti-cancer, skin brightening Cosmetic industry
22 Chrysin C₁₅H₁₀O₄ Fruit, Seed skin protection, anti-inflammation, antioxidant Functional foods, cosmetic industry
23 Chlorogenic acid C₁₆H₁₈O₉ Fruit
anti-inflammatory, antioxidant, anti-aging, anti-skin cancer,
antimicrobial
Functional foods
24 Zeaxanthin C₄₀H₅₆O₂ Seed antioxidant Functional foods
25 Mureidomycin A C₃₈H₄₈N₈O₁₂S Fruit,Seed antibiotic Medicine
26 p-Coumaric acid C₉H₈O₃ Fruit,Seed anti-pigmentation, antioxidant, antimicrobial, anti-inflammatory -
27 Neochlorogenic acid C₁₆H₁₈O₉ Fruit anticarcinogenics, antioxidant -
28 Aescin C₅₅H₈₆O₂₄ Seed anti-inflammatory Medicine, functional foods
Global chemical profiling using XCMS metabolomics platform
mg/kg
No. Samples Fruit Seed
1 Chlorogenic acid 0.933±0.002 <LOD
2 Caffeic acid 10.708±0.062 <LOD
3 Rutin 14.798±0.167 <LOD
4 p-Hydroxybenzoic acid 0.606±0.025 15.715±0.363
5 Quinic acid 35.686±0.229 0.508±0.024
6 Ellagic acid <LOD 8.690±0.371
7 Neochlorogenic acid 126.029±1.888 <LOD
8 Quercetin-3-glucose 6.392±0.107 <LOD
9 p-Coumaric acid 0.210±0.005 0.380±0.005
10 Naringin 2.656±0.022 <LOD
11 Ferulic acid <LOD 0.188±0.020
12 Quercetin 0.546±0.020 <LOD
13 Chrysin 2.597±0.032 1.040±0.047
14 Gentiopicroside 0.847±0.001 <LOD
15 Rhoifolin 0.490±0.008 0.336±0.012
16 Aescin <LOD 14.989±0.227
17 Artesunate 0.022±0.001 <LOD
18 Eudesmic acid <LOD 3.533±0.054
Pomiferin Osajin
Figure 2. Two major bioactive chemicals. The anti-microbial Osajin and
Pomiferin also have potential value as antioxidants and pharmaceutical
precursors.
Figure 3. The pairwise job allowing for the comparison of two group (Osage orange
extracts and control) (A). An example of identification of pomiferin by XCMS Online
screen shot including results table (B), extracted ion chromatogram (C), mass spectrum
(D), and putative METLIN identification (E).
A
B
C
D
E