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Dose of Fucoxanthin 3.5 Mg (5.6 Μmol)/Day/Mouse for 1 Month （Equal to 760 G Per Kg Bw of Raw Kombu)

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Dose of Fucoxanthin 3.5 Mg (5.6 Μmol)/Day/Mouse for 1 Month （Equal to 760 G Per Kg Bw of Raw Kombu) Searching for new functional properties in traditional foods of Japan and South America November 8, 2010 Kazuki Kanazawa Most of functional factors in food are non-nutrients. Nutrients (proteins, sugars and lipids) undergo decomposition to produce energy (catabolism) in liver. This indicates that nutrients cannot exhibit bio-functions. Contrarily, non-nutrients do not undergo catabolism, and therefore can exist in mostly their unchanged forms in food and can exhibit diverse bio-functions. However, most of non-nutrients undergo a different metabolism, conjugations, in intestinal surface cells. The conjugations occur on the functional groups, masking with glucuronic acid and/or sulfate, and then invalidate active non-nutrients. A strategy for finding out biofunctional factors To find out endogenously active functional non-nutrients, difficult forms to undergo the conjugations should be searched according to the following strategy: 1) Compounds retaining the activity even after the conjugations 2) A hard chemical to undergo conjugations 3) Unchanged chemical during absorption process 4) Metabolically activated chemicls when absorbed 5) Available chemicls after de-conjugation with endogenous β-glucuronidase 6) Compounds that can interact with intestinal surface cells and transfer immune signals without absorption The second idea Propolis includes a hard chemical to be conjugated, artepillin C Conjugate Bee collects from enzymes Baccharis dracunculifolia (chilca) Prenyls 5.0 1.0 Bioavailability of ● Free of ; □ 4.0 Apical side 0.8 Apical side ●; Naringenin artepillin C △ ○ ○ *** 3.0 0.6 ● ▲; Kaempferol *** *** *** △ ○ ○ ● in Caco-2 *** △ △ *** *** ■; Isosakuranetin ▼◆ ***● 2.0 ***□ 0.4 monolayers ***□ ◆; Chrysin ***□ ▲ *** ◆ *** 1.0 0.2 ■ ▼*** ◆ *** ▼; Kaempferide ▲*** *** ◆ ■ ▼▲■*** ▲*** ** *** ▼■*** N N N N N N*** 0 D D D 0 D D D 1.0 0.3 Free of ; In the cell In the cell ○; Ferulic acid 0.8 □ Conjugated of ; □ 0.2 △ □ ▼ ; p-Coumaric acid 0.6 Naringenin □; Artepillin C 0.4 ** Kaempferol 0.1 ▼ ** ▼ Isosakuranetin 0.2 ● ■ △ △ △ ***● **● Chrysin N N N N N N N N N N N N N N N N N NN Phenolics (nmol/well) Phenolics ■ ** 0 D ○ D D ○ D D D○ D 0 D ▲◆D D D D ▲◆D D D D ▲◆■D D D Kaempferide Conjugated of ; 1.5 0.5 Serosal Serosal ** Ferulic acid 1.2 0.4 ● *** □ p-Coumaric acid 0.9 0.3 △** *** ** ● Artepillin C 0.6 0.2 * ■ □ ** ◆ ● △** ** 0.3 0.1 ■ □ ◆*** △ ◆■ N N N N N N N N N 0 D ○ D ○ D ○ 0 ▼▲D D ▼▲D D ▼▲D D 0 30 60 90 120 0 30 60 90 120 Incubation time (min) Artepillin C can Enter HepG2 Cells and Suppress Oxidative Stress 3 - HepG2 cells Exposed to O2 cells) cells) ○ ○ 7 ○ ○ 2 Artepillin C (µM) Lipid peroxides ○ Artepillin C (nmol/mg protein) △Conjugated Artepillin C 1 0 0.468+0.013 5 0.426+0.010* Artepillin C (nmol/10 Artepillin 10 0.446+0.006* 0 E △ △ △ △ 0 30 60 90 120 150 20 0.392+0.013* Incubation time (min) 8-OHdG/2’-dG X 10-5 0 8.22+1.089 H O O 5 7.14+0.411 10 5.35+0.724* 20 5.23+0.176* O H Mixed Polyphenols 7.18+0.815 Mixed polyphenol + 10 µM of Artepillin C 4.86+0.481* Speculation Artepillin C daily P. O. ddY mice (♂) 6-weeks old 1st day 8th day 28th day Azoxymethane (AOM) 10 mg/kg subcutaneously Artepillin C inhibits formation of aberrant crypt foci Treatment Number of ACF % of Control ACS/Focus Negative control (non-treatment) 0 0 0 Positive control (vehicle alone) 63.25 + 16.5 100 1.50 + 0.18 80 mg/Kg propolis 38.4 + 14.5* 60.8 1.40 + 0.20 160 mg/Kg propolis 35.6 + 6.8* 56.3 1.57 + 0.14 10 mg/Kg artepillin C 35.8 + 15.2* 56.6 1.49 + 0.19 n=5, p<0.05 Artepillin C Induces G0/G1 Arrest in WiDr Proliferation G0/G1 (%) G0/G1 ■ 0.1% DMSO ● 25 µM 250 ■ S ▲ 50 µM ■ ● 200 ◆ 75 µM ● G2/M ▼ 100 µM ▲ ■ ▲ ◆ ■ ▲● ●▲ ◆ ◆ ▼ 100 ◆ ▼ ▼ Artepillin C ▼◆●▲■ ▼ (µM) G0/G1 (%) S (%) G2/M (%) 0 h 0 61.6 ±0.8 33.0 ±1.7 5.4 ±1.0 0 0 24 48 72 24 h 0 61.6 ±4.8 29.0 ±4.3 9.4 ±2.2 Incubation time (h) 25 62.5 ±1.7 27.8 ±0.6 9.7 ±1.0 50 68.8 ±0.4 22.1 ±0.4 9.1 ±0.5 100 82.1 ±3.2 13.4 ±2.3 4.5 ±1.0 48 h 0 63.2 ±1.4 29.9 ±1.3 6.9 ±0.1 25 77.9 ±0.6 17.1 ±0.5 5.0 ±0.5 50 80.3 ±0.2 14.4 ±0.5 5.3 ±0.7 100 86.9 ±0.2 6.7 ±0.3 6.4 ±0.1 TGF-β DNA oxidation Growth factor Rac ATR ATM P Ras proteosome GF-receptor P P P MAPkinase PI3K （JNK） MAP kinase cascade P Smad2/3 P （ERK） P Ser15 P Thr68 P cascade Smad4 P P PIP3 MDM2 Chk2 P Smad2/3 p53 P Ser20 P P FKHR P P PDK P Ser473 Thr308 P Akt Bax INK4 family p15 p21Cip1 p27Kip1 p18 p19 P P Bad GSK-3β p16 Apoptosis Thr14 P P Cyclin D Thr160 P CDK2 Tyr15 P P Ser123 Apoptosis CDK4/6 Cyclin E cdc25A De-phospjorylation Proteosome INK family Retinoblastoma Proteosome DP E2F Gene expression P P P P Check point Retinoblastoma G1 phase S phase Artepillin C Regulates Cell-Cycle Related Proteins Artepillin C 48 h 0 25 50 100 (µM) P Rb-C fusion protein (Ser 780) P Rb-C fusion protein (Ser 807/811) 0 h 24 h 48 h 0 25 50 75 100 0 25 50 75 100 (µM) Cyclin D1 Cyclin D2 Cyclin D3 CDK4 β-actin In up-stream signals Artepillin C 48 h Control (0.1% DMSO) 50 µM Artepillin C 0 25 50 100 (µM) 0 6 12 24 36 48 6 12 24 36 48 (h) Cip1/p21 Cip1/p21 1.0 1.73 1.89 2.78 Kip1/p27 Fold (BAS/28S) 0 h 24 h 48 h Kip1/p27 0 25 50 75 100 0 25 50 75 100 (µM) 1.0 1.28 1.27 0.67 Fold (BAS/28S) Cip1/p21 Kip1/p27 28S β-actin 18S In Cip1/p21-deleted cells 80 Vehicle alone 50 µM artepillin C 60 100 µM artepillin C 40 Distribution (%) Distribution 20 0 G0/G1 S G2/M Regulatory events by Artepillin in Colon p21waf p19 p18 ink4a kip1 p16 p15 p57 p27 CDK4 CDK2 Cyclin D Cyclin E Phosphorylation p p E2F Rb Rb active E2F p p G0/G1 arrest G0 phase G1 phase G1/S transition Proliferation In Human trial 10 Artepillin C 20.4 µmol (6.12 mg) 8 Ferulic acid 0.3 µmol p-Coumaric acid 3.4 µmol Kaempferol 8.6 µmol x dG 5 6 Naringenin 1.8 µmol 4 3 Capsules per day 8-OHdG/10 For 3 month 2 0 Basal Final Basal Final n=15 n=15 n=15 n=15 Placebo Propolis Dosed amounts were too small 3) Unchanged chemical during absorption process OCOCH fucoxanthin HO 3 . Japanese kelp Kombu O O HO In intestinal surface cells OH fucoxanthinol HO . O Fucoxanthin Contents O In liver of animal Fucoxanthin per HO Brown algae not human 100 g fresh Wakame (Undaria pinnatifida) 11.1 mg OH amarouciaxanthin A HO Arame (Eisenia bicyclis) 7.7 mg . Hondawara (Sargassum fulvellum) 6.5 mg O Kombu (Laminalia japonica) 17.7 mg OH Hijiki (Hizikia fusiformis) 2.2 mg O Single dose of fucoxanthin 0.1 mg (160 nmol)/mouse 800 600 300 liver lung serum 600 400 200 400 200 100 200 (nmol/g) (nmol/g) (nmol/l) 0 0 0 0 5 10 15 20 25 0 5 10 15 20 25 0 5 10 15 20 25 300 300 80 kidney heart Red 60 200 200 blood 40 cells 100 100 20 (nmol/g) (nmol/g) (nmol/l) 0 0 0 0 5 10 15 20 25 0 5 10 15 20 25 0 5 10 15 20 25 Time after dose (hr) 300 60 spleen Adipose 200 40 tissue 100 20 (nmol/g) (nmol/g) 0 0 0 5 10 15 20 25 0 20 40 60 80 Time after dose (hr) Time after dose (hr) Fucoxanthinol（●） Amarouciaxanthin A（○） Hashimoto et al., Br. J. Nutr. Fucoxanthin was not detectable. Fucoxanthin Fucoxanthinol 8 80 Amarouciaxanthin A Fucoxanthin-fed mouse 6 60 4 40 mol/l mol/l mol/l mol/l µ µ 2 20 Control 0 0 Serum Liver Lung Kidney Heart Spleen Adipose Dose of fucoxanthin 3.5 mg (5.6 µmol)/day/mouse for 1 month （equal to 760 g per kg bw of raw kombu) In another experiments (20 times more), F344 fed rats on 0, 17.5, 35, 70 mg/day/mouse of fucoxanthin for 90 days and found NOAEL was more than 70 mg/day/mouse. 60 No abnormality; more than 8 mg/day for 5 weeks in humans 40 Pharmaceutical parameter in human 20 Cmax 44.2 nml/L 0 Tmax 4 h 0 5 10 15 20 25 t1/2 7.0 h Time after ingestion (h) AUC(∞) 663.7 nmol/L・h Fucoxanthinol (nmol/l) Fucoxanthinol (nmol/l) NoA bloodaccumulation profile of 18 volunteers indicates with 31 mg that produces no side effects and no toxicity. Amarouciaxanthin A Fucoxanthin cis-isomer of fucoxanthinol Fucoxanthinol Internal Standard chemicals standard In humans fucoxanthin and amarouciaxanthin A were In mouse 4 h after dose under the detection limits In human 4 h after dose In human before ingestion 0 10 20 30 Fucoxanthin in drinking water ddY mice (♂) 1st day 8th day 28th day 6-weeks old Subcutaneous injection of AOM treatment ACF % Negative control 0 0 Positive control 85 + 26 100 Fucoxanthin 50 ppm 60 + 10 70 Fucoxanthin 100 ppm 55 + 21* 65 Two step skin cancer 100 Spontaneous hepatic cancer 80 60 40 20 Detectable tumor % tumor Detectable 0 Fucoxanthin showed the strongest activity to prevent form colon, skin and hepatic cancers among carotenoids.
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