Physicochemical properties of dietary phytochemicals can predict their passive absorption in the human small intestine
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1 Physicochemical properties of dietary phytochemicals can predict their passive absorption in the human small intestine Sophie N.B. Selby-Pham 1,2, Rosalind B. Miller 3, Kate Howell 1, Frank Dunshea 1 and Louise E. Bennett 2,* 1 Faculty of Veterinary and Agricultural Science, The University of Melbourne, Parkville, 3010, Australia 2 CSIRO Agriculture and Food, 671 Sneydes Road, Werribee, 3030, Australia 3 CSIRO Data61, North Ryde, 2113, Australia * Louise.Bennett@csiro.au
2 S1 Table. The training dataset used for the development of the predictive model. Phytochemical Mr * LogP * Anthocyanins Cyanidin 3-Oarabinoside Cyanidin 3-Ogalactoside Cyanidin 3-Orutinoside Cyanidin 3-Orutinoside Cyanidin 3-Osambubioside Cyanidin 3-Oxylosyl-rutinoside PSA * (Å 2 ) No. freely rotatable bonds * No. H acceptor * No. H donor * Molecular volume * (Å 3 ) Intake # semi- (freeze-dried whole fruit made into a paste) semi- (freeze-dried whole fruit made into a paste) semi- (freeze-dried whole fruit made into a paste) semi- (freeze-dried whole fruit made into a paste) Tmax # (h) (mean ± SE) Reference # 3.5 ± ± ± ± ± ±
3 Delphinidin 3-Oglucoside Delphinidin 3-Orutinoside Malvidin 3-Oglucoside Peonidin 3-Oglucoside Flavanols ( )-Epicatechin 3- O-gallate ( )- Epigallocatechin 3-O-gallate ( )- Epigallocatechin 3-O-gallate Flavonols Isorhamnetin 3- O-glucuronide Quercetin aglycone Quercetin 3-Oglucuronide Quercetin 3'-Osulfate Hydroxybenzoic acids semi- (extract with yoghurt) semi- (extract with yoghurt) semi- (fried red onions) semi- (fried red onions) semi- (fried red onions) ± ± ± ± ± ± ± ± ±
4 Ellagic acid Ellagic acid Ellagic acid Ellagic acid Ellagic acid Ellagic acid Hydroxycinnamic acids 5-O- Caffeoylquinic acid Ocaffeoylquinic acid lactone-osulfate Ocaffeoylquinic acid lactone-osulfate O- Feruloylquinic acid (extract drink) semi- (freeze-dried whole fruit made into a paste) 0.65 ± ± ± ± ± ± ± ± ±
5 4-O- Feruloylquinic acid 5-O- Feruloylquinic acid Stilbenes trans-resveratrol trans-resveratrol trans-resveratrol trans-resveratrol Carotenoids Lycopene Lycopene Lycopene Lycopene Lycopene β-carotene β-carotene semi- (pure compound in emulsion) 0.8 ± ± ± ± ± ± ±
6 Astaxanthin Astaxanthin Canthaxanthin all-e-zeaxanthin all-e-zeaxanthin Lutein Vitamins Vitamin C (ascorbic acid) Vitamin B1 (thiamine) Vitamin B1 (thiamine) Vitamin B2 (riboflavin) Vitamin B2 (riboflavin) Vitamin B2 (riboflavin) Nicotiamide Nicotiamide Nicotiamide semi- 8 ± ± ± ± ± ± ± ± ± ±
7 Nicotiamide Nicotinic acid Nicotinuric acid Cobalamin (vitamin B12) R,R,R-α- Tocopherol α-tocotrienol γ-tocotrienol δ-tocotrienol Phylloquinone (vitamin K) * calculated using the Molinspiration Chemoinformatics calculator # collected from the literature (whole vegetable) 1.9 ± ± ± ± ± ± ± ±
8 S2 Table. The PCv dataset for validation of the predictive model. Family Phyto-chemical Source # LogP * M r * Liquid intake Anthocyanins Cyanidin 3-Oarabinoside Cyanidin 3-Oarabinoside Cyanidin 3-Ogalactoside Cyanidin 3-Ogalactoside Cyanidin 3-Orutinoside PSA * (Å 2 ) Predicted T max_ LogP ** (h) Predicted T max_ PSA ** (h) Measured T max# (h) Reference # Mean SE N Acai berry Black currant Elderberry Black currant
9 Cyanidin 3-Osambubioside Cyanidin 3-Osambubioside Delphinidin 3- O-glucoside Delphinidin 3- O-glucoside Delphinidin 3- O-glucoside Delphinidin 3- O-glucoside Delphinidin 3- O-rutinoside Delphinidin 3- O-sambubioside Malvidin 3-Oglucoside Malvidin 3-Oglucoside Malvidin 3-Oglucoside Malvidin 3-Oglucoside Peonidin 3-Oarabinoside Peonidin 3-Oarabinoside Peonidin 3-Ogalactoside Peonidin 3-Ogalactoside Elderberry Hibiscus Black currant Black currant Hibiscus
10 Flavanols Peonidin 3-Oglucoside Peonidin 3-Oglucoside Peonidin 3-Oglucoside Peonidin 3-Oglucoside Peonidin 3-Oglucoside Petunidin 3-Oglucoside Petunidin 3-Oglucoside Petunidin 3-Oglucoside Petunidin 3-Oglucoside Red wine Red wine Epicatechin Pure compound Epicatechin Epicatechin Epicatechin Epicatechin and catechin Epicatechin gallate Epigallocatechin Cocoa Cocoa NA NA
11 Flavonols Epigallocatechin Epigallocatechin gallate Epigallocatechin gallate Procyanidin B2 dimer Myricetin Quercetin 4- Hydroxybenzoic acid Protocatechuic acid Cocoa Montmorency tart cherry NA NA Hydroxybenzoic acids Protocatechuic acid Vanillic acid Vanillic acid Montmorency tart cherry Montmorency tart cherry NA NA Hydroxycinnamic acids Vanillic acid Caffeic acid Ferulic acid p-coumaric acid Sinapic acid Montmorency tart cherry NA
12 Hydroxyphenylacetic acids Stilbenes 3,4-Dihydroxyphenylacetic acid cis-piceid (cis- Resveratrol 3-Oglucoside) trans-piceid (trans- Resveratrol 3-Oglucoside) Red wine Red wine β-carotene Pure compound Fucoxanthinol Lutein Lycopene Kombu Marigold flower Tomato NA NA 5 65 Carotenoids Lycopene Tomato NA 5 65 Lycopene Tomato NA 5 65 Lycopene Tomato NA 5 65 Semi- intake Anthocyanins Acai berry (pulp)
13 Vitamins Solid intake Cyanidin 3-Oglucosylrutinosi de Cyanidin 3-Oglucosylrutinosi de Cyanidin 3-Orutinoside Cyanidin 3-Orutinoside Delphinidin 3- O-glucoside Malvidin 3-Oglucoside Peonidin 3-Oglucoside Petunidin 3-Oglucoside Ascorbic acid (juice and puree) Raspberry (homogenised whole fruit) Montmorency tart cherry (whole fruit) Montmorency tart cherry (whole fruit) Montmorency tart cherry (whole fruit) Montmorency tart cherry (whole fruit) (juice and puree) (juice and puree) (juice and puree) (juice and puree) Kiwi fruit (whole fruit) NA NA NA NA NA NA 9 63
14 Anthocyanins Pure compound Epicatechin Epicatechin NA Epicatechin gallate Flavanols Epicatechin NA gallate Epigallocatechin Epigallocatechin NA Epigallocatechin gallate Epigallocatechin gallate NA Pomegranate Ellagic acid Hydroxybenzoic acids Pomegranate Ellagic acid Resveratrol Pure compound trans- Resveratrol Pure compound Stilbenes cis-piceid (cis- Resveratrol 3-Oglucoside) Pure compound trans-piceid (trans- Resveratrol 3-Oglucoside) Pure compound Carotenoids β-carotene Pure compound NA 12 91
15 β-carotene Pure compound NA β-carotene Pure compound NA Crocetin Pure compound Crocetin Pure compound Crocetin Pure compound Lutein Pure compound Ascorbic acid Pure compound NA 9 63 Vitamins Calcitriol Pure compound NA Phenprocoumon Pure compound NA * calculated using the Molinspiration Chemoinformatics calculator ** calculated from the predictive model # collected from the literature Phylloquinone Pure compound
16 S3 Table. The PHv_fasted dataset for validation of the predictive model. All compounds were taken as form. Predicted Predicted Measured Pharmaceutical LogP * * PSA M T max_ T max_ T max# (h) r (Å compound ) LogP ** PSA ** Mean SE N (h) (h) Reference # Nadolol Nifedipine Odanacatib Tramadol Amisulpride Levofloxacin Mirodenafil Talinolol Aleglitazar Mitiglinide Risperidone Sonidegib Imidafenacin Olanzapine Imatinib Arbidol Ruxolitinib Risperidone Ritonavir Rosuvastatin Capravirine Proguanil CH RO Tinidazole Pantoprazole Moxifloxacin Tacrolimus Ethionamide
17 Metopimazine Sulfonamide Ketoconazole Miconazole Nifedipine Spironolactone Ciramadol Cyclosporin S MK Itraconazole Indinavir Celecoxib Rifampin Topiramate Ethambutol Isoniazid Cilostazol Febuxostat Apixaban Ziprasidone Cefprozil Eprosartan Amoxicillin Ampicillin Pyrazinamide Bosentan Telbivudine Tenoxicam Eltrombopag Fluconazole * calculated using the Molinspiration Chemoinformatics calculator ** calculated from the predictive model # collected from the literature
18 S4 Table. The Pharmaceutical fed dataset for validation of the predictive model. All compounds were taken as form. Predicted Predicted Measured Pharmaceutical LogP * * PSA M T max_ T max_ T max# (h) r (Å compound ) LogP ** PSA ** Mean SE N (h) (h) Reference # Odanacatib Amisulpride Mitiglinide Rosuvastatin Pantoprazole Moxifloxacin Tacrolimus Ethionamide Metopimazine Sulfonamide Ketoconazole Nifedipine Spironolactone Ciramadol S MK Itraconazole Indinavir Celecoxib Rifampin Ethambutol Isoniazid Cilostazol Febuxostat Apixaban Ziprasidone Cefprozil Eprosartan Artemisinin
19 Amoxicillin Ampicillin Pyrazinamide Bosentan Telbivudine Posaconazole Tenoxicam Eltrombopag Fluconazole * calculated using the Molinspiration Chemoinformatics calculator ** calculated from the predictive model # collected from the literature
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