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Raspberry Polyphenols: Synergies with Other Fruits

Navindra P. Seeram, PhD. UCLA Center for Human Nutrition David Geffen School of Medicine

Presentation Outline

Introduction UCLA

In vitro Berry Studies UCLA In vivo Berry Studies Raspberry Polyphenol Synergism

What are Phytochemicals?

Non-nutrient

plant compounds that may provide human health benefits against cancer, heart disease, neurodegenerative diseases etc. Produced by plants for defense against harmful UV radiation, herbivorous predators etc. or as attractants for pollination (bright colors) etc.

Polyphenols

are ubiquitous dietary phytochemicals

UCLA Polyphenol Studies

Polyphenols

Tea

Green tea Black tea Tea supplements

Pomegranates

Juice Extracts Pure compounds

Strawberries

Fresh fruits Extracts

Studies on Other Berries

Cranberries Blueberries Red

& Black Raspberries Blackberries Seeds, Seed-oils, Fiber & Other ByProducts

Red Raspberry Polyphenols

Flavonoids

· Anthocyanins · Flavonols

Ellagitannins

(and Ellagic acid)

HPLC-UV and LC-MS/MS Profiling of Red Raspberry

2 34000 32000 30000 28000 26000

24000 22000 20000 18000 uA U 16000 14000 12000 7 10000 8000 5 6000 10 4000 14 2000 12 0 4 8 0 5 10 15 20 25 9 30 35 T im e ( m in ) 40 45 11 17 13 15 18 16 50 55 60 65 70 1 6 3

Seeram NP et al; Blackberry, Black Raspberry, Blueberry, Cranberry, Red Raspberry and Strawberry extracts inhibit growth and stimulate apoptosis of human cancer cell in vitro, J. Agric. Food. Chem. 2006, 9329-39.

Structures of Raspberry Polyphenols

R OH HO O OH OH O OH HO O+ OH R OH

Flavonols Quercetin R = OH Kaempferol R = H

O HO HO O O O OH OH

Anthocyanidins Cyanidin R = OH Pelargonidin R = H

Ellagic acid

OH HO OH HO O HO HO HO OH C O C O O O HO HO OH OH OH O O O HO HO O O C HO HO O C O C O O O HO OH HO OH OH O

O O O O C O

OH OH OH OH

OH OH OH

Ellagitannin Sanguiin H-6

Biological Activities of Berry Polyphenols

Antioxidant Anti-inflammatory Anti-proliferative & Pro-apoptotic Anti-neurodegenerative

1. Seeram NP et al; Cycylooxygenase inhibitory and antioxidant cyanidin glycosides from cherries and berries; Phytomedicine, 2001,362-369. 2. Seeram NP et al; Inhibition of Proliferation of human tumor cell lines by anthocyanidins and catchins; Nutrition and Cancer, 2003,10-106. 3. Tall J et al; Tart cherry anthocyanins suppress inflammation induced pain behavior in the rat; Behavioral Brain Research,2004, 181-188. 4. Seeram NP et al; Blackberry, Black Raspberry, Blueberry, Cranberry, Red Raspberry and Strawberry extracts inhibit growth and stimulate apoptosis of human cancer cell in vitro, J. Agric. Food. Chem. 2006, 932939.

Inhibition of Lipid Peroxidation

raspberry

1.2 1 0.8

blueberry strawberry blackberry

Rel. fluorescence

Fe+2

0.6 0.4 0.2 0 0 3 6 9 12 15 18 21

bilberry elderberry cranberry tart cherry cv. Balaton sweet cherry

Time (min)

Seeram NP et al; Cyclo-oxygenase inhibitory and antioxidant cyanidin glycosides from cherries and berries; Phytomedicine, 2001, 362-9.

Anti-inflammatory Activity:

Inhibition of COX Enzymes

55 50

55

45

50 45 40

COX-1 % Inhibition

40

COX-2 % Inhibition

35 30 25 20 15 10 5 0

35 30 25 20 15 10 5 0 A B C D E F G H I J K L M N O P

A B

C

D E

F

G H

I

J

K

L M

N O

P

A = DMSO; B = cyanidin 4; C = anthocyanin 1; D = anthocyanin 2; E = tart cherry cv. BalatonTM; F = tart cherry cv. Montmorency; G = sweet cherry; H = blueberry var. Jersey; I = cranberry var. Early Black; J = bilberry; K = elderberry; L = strawberry var. Honeoye; M = blackberry; N = raspberry; O = naproxen; P = ibuprofen.

What happens when we consume Polyphenols?

Absorption Distribution Metabolism Excretion

Metabolism of Polyphenols

Oral Ingestion Peripheral Tissues

Small Intestine Small amounts Blood Circulation Formation of metabolites Colon Microflora Bile Liver Enterohepatic Circulation Urine (conjugates detected in urine) Kidneys

Phenolic Acid Metabolites

Feces

Pharmacokinetics and Metabolism of Ellagitannins (n = 18)

Day 1 Day 2 Day 3 Day 4 Day 5 Day 6

`phenolic-free diet'

180 mL PJC (312 mg ETs) spot urine 2 x 12 h urine

Blood Collection

(0, 0.5, 1, 2, 3, 4, 6 h)

Urine Collection

(2 x 12 h)

Ellagic Acid (EA) Pharmacokinetics

Tmax = 0.98 h ; Cmax = 0.06 µM; AUC = 0.17 µM

1) Seeram N.; Lee, R.; Heber, D. Clin. Chim. Acta. 2004, 348, 63-68. 2) Seeram N.; Henning, S.; Zhang, Y.; Suchard, M.; Li, Z.; Heber, D. J. Nutrition.,2006, 136,2481-5.

EA Urinary Metabolites Persist for 48 h

(observed Inter-individual variability in metabolite formation)

OH H 3C O O O O O H 3C O O O O OH

DM EAG M -H m /z 5 0 5

DM EA M -H m / z 3 2 9

O

(D a y 5 )

OCH OH

3

OC H3 O - g lu c u ro n id e OH

OH

HO

OH O O O OH O

O O O O

OH OH

OH

U r o l i th i n A M - H m /z 2 2 7

O

E l la g i c a c i d M - H m /z 3 0 1

O

U r o li t h in B M -H m / z 2 1 1

O -g l u c u r o n i d e

O

M -H m / z 4 0 3

(D a y 6 )

O O - g lu c u r o n id e

M + H m /z 3 8 9

(D ay 6 )

Seeram N.; Henning, S.; Zhang, Y.; Suchard, M.; Li, Z.; Heber, D. J. Nutrition.,2006, 136,2481-5.

Berrry Poylphenol Synergy Hypothesis

Multiple compounds (in a food or extract matrix) interact synergistically and/or additively to potentiate the bioactivity of major active ingredient (s)

Published Studies

Seeram N.P. et al. Total Cranberry Extract vs. its Phytochemical Constituents : Antiproliferative and synergistic effects against human tumor cell lines. J. Agric. Food Chem. 2004, 52, 2517-7. Seeram N.P. et al. In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice. J. Nutr. Biochem. 2005, 16, 360-7.

Red Raspberry Combined with Other Berries: ( e.g.Pomegranates)

Additivity

of ellagitannin-rich berries Enhanced taste profile of foods and beverages. Enhanced bioactivities in extracts Commercial Impact on Taste, Appearance, Health Appeal

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