Embed Size (px)
Citation preview
Prof. Dr. Adriana Z. MercadanteDepartment of Food Science, FEAUNICAMP, Campinas - Brazile-mail: [email protected]
Bioactive compounds and antioxidant capacity from Brazilian fruits
May 12 and 13, 2015 – São Paulo
Principal investigator
Genipap(Genipa americana L.)
Guajiru(Chrysobalanus icaco L.)
Murici (Byrsonima crassifolia)
Umbu(Spondias tuberosa)
Umbu-cajá(Spondias spp)
açai
Acerola (Malpighia punicifolia L.)
Camu-camu
cashew apple (Anacardium occidentale L.)
Pupunha(Bactris gasipaes)
Tucumã (Astrocaryum aculeatum)
visible light absorptionlipophilic
4
5
67
8
1
2
3
9
10
11
12
13
14
15
15’
14’
13’
12’
11’
10’
9’
8’
7’
6’
5’ 4’
3’
2’
1’
4
5
67
8
1
2
3
9
10
11
12
13
14
15
15’
14’
13’
12’
11’
10’
9’
8’
7’
6’
5’ 4’
3’
2’
1’
1
2
3
9
10
11
12
13
14
151
2
3
1
2
3
9
10
11
12
13
14
15
15’
14’
13’
12’
11’
10’
9’
8’
7’
6’
5’ 4’
3’
2’
1’
-carotene
cyanidin-3-glucoside
hydrophilic
acid
alkaliOH
O
OHOH
OH
O
O+
OH
OH
OHOH
O
OH
OHOH
OH
O
OH
quercetin
Web of Science, May 2015
UV absorption
PHYSICAL-CHEMICAL PROPERTIES
diode array detector (DAD) MSn – ion-trap
ionization sources (APCI/ESI)
C30 column C18 columncarotenoids phenolic compounds
gradient of MeOH/MTBE/H2O gradient of MeOH/H2O/formic acid
piquiá
Carotenoids and phenolic compounds
12 carotenoids
17 phenolic compoundsgallic acid (182.4 μg/g pulp dw)ellagic acid rhamnoside (107 μg/g pulp dw)ellagic acid (104 μg/g pulp dw)
all-trans-antheraxanthin (3.4 μg/g pulp dw)all-trans-zeaxanthin (2.9 μg/g pulp dw)lutein-like carotenoid (2.8 μg/g pulp dw)
piquiá
saponified carotenoid extract
dimyristoyl lutein
O
O
O
Odipalmitoyl lutein
O
O
O
O distearoyl lutein
myristoyl lutein
OH
O
O palmitoyl lutein OH
O
Ostearoyl lutein
carotenoid esters are naturally found in fruits !!!
identical cromophore
different MW
similar MW to triacylglycerides
and many more combinations with different FA
Web of Science, May 2015
O
O
O
O
OH
O
O
0 5 10 15 20 25 30 35 40 45 50 55
0
100
200
300
400
500
600
700
Det
ecto
r res
pons
e (m
AU
)
Time (min)
** * *
all-t
rans
-zea
xant
hin
all-t
rans
-lute
in
all-t
rans
-zea
xant
hin
all-t
rans
-lute
in* cis isomers
total carotenoids (HPLC)
31.00 ± 2.24 g/g dw
lauroylm
iristoyl lutein
dimiristoyl lutein
miristoylpalmito
yl lutein
monoesters
total carotenoids (g/g dw)
saponified x non-saponified extract - murici
UV-vis: 100.7 ± 9.8
HPLC (all peaks): 117.0
HPLC (13 major peaks): 79.7
lutein
(results not yet published)
saponified x non-saponified extract – orange cv. Valencia
0 1 0 2 0 3 0 4 0 5 0 6 0 7 0
0
5 0
1 0 0
1 5 0
2 0 0
Det
ecto
r res
pons
e (m
AU
)
R e t e n t i o n t i m e ( m i n )Monoesters Diesters
saponified extract
93.67 ± 5.09 µg/g dw
total carotenoids (UV-Vis, violaxanthin)
132.09 ± 1.84 µg/g dw
29%0 1 0 2 0 3 0 4 0 5 0 6 0 7 0
0
5 0
1 0 0
1 5 0
2 0 0
2 5 0
Det
ecto
r res
pons
e (m
AU
)R e t e n t i o n t i m e ( m i n )
all‐trans‐lu
tein
all‐trans‐violaxanthin
9‐cis‐‐violaxanthin
(res
ults
not
yet
pub
lishe
d)
levels of these compounds are most probably overestimated in comparison to
the bioaccessible fraction
contents and the composition of bioactive compounds in foods does not consider the
changes occurred in the gastrointestinal tract
INFO
GES
T
in vitro bioaccessibility
mixed micelles
simulated gastrointestinal digestion
i-link FAPESP-CSIC project (2013/50789-0)Bioaccessibility of -cryptoxanthin vs -carotene from major food contributors to the provitamin A intake in Brazil, Panamá
and Spain
Final results are coming in 2016!
colon microbial community
Simulator of the Human Intestinal Microbial Ecosystem (SHIME®)
Prof. Katia Sivieri (FCF-UNESP) and Prof. Christian Hoffmann (FCF-USP)
interaction carotenoids/phenolics
SHIME-adaptedincr
easi
ng s
yste
m c
ompl
exity
15 carotenoidstandards
conflicting resultsin literature
bufferMethods availableOu et al. (2001)Huang et al. (2002)Zulueta et al. (2009)Müller et al. (2011)
generator: AAPHprobe: fluorescein
caro
teno
id
N
N
CH3CH3
N
CH3 CH3
N41°C
CH3 CH3
N
OO
generator(438 mM)
solvent medium
DMSO/MTBE (10:1, v/v)
Peroxylradical
C11-BODIPY581/591
Excitação = 540 nmEmissão = 600 nm
N+
B-N
F F (CH2)10O
OHH
H
H
H
Non-fluorescentproducts
probe(0.4 M)
carotenoiddissolved
AIBN
Synergy Mx
New method to measure the peroxyl scavenger capacity of carotenoids
4x
15 carotenoid standards
peach palm: 7.83 ± 0.21 (-tocopherol relative)mamey: 6.90 ± 0.44mana cubiu: 9.80 ± 0.80
Carotenoids: structure vs ROO scavenger capacity
Liposomes
PROBE FLUORESCENTEC11-BODIPY581/591
λexcitação= 540 nmλemissão= 596 nm
Unilamelar liposome mimicking cellular membrane
-caroteneastaxanthinlycopene
cantaxanthinfucoxanthinzeaxanthin
incorporation
incorporation
N+
B-N
F F (CH2)10
O
OH
CC
CC H
H
H
H
Carotenoids
ROO, OH, HOCl -carotene + efficientastaxanthin + efficient
ONOO-
ROO HOClOH ONOO-
Final remarks
bioactive compounds and nutrientscomposition and consumption data of regional and local foods are prerequisite to investigate the contribution of biodiversity to nutrition and health
bioacessibilityassessment the physical state of bioactive compounds and their location within the cellsassessment food/meals as they are eatenin vitro models allow one to test different hypothesis to understand the nature of the potential interaction between bioactive compounds and nutrients in foods.
ROS and RNS scavenging capacitymovement from organic media to systems mimicking biological systems
CollaborationsAntonio Meléndez-Martínez (Universidad de Sevilla, Spain)Antonio Pérez-Gálvez (CSIC-Sevilla, Spain)Beatriz Cordenunsi (FCF-USP, Brazil)Begoña Olmedilla (CSIC-Madrid, Spain)Claudio Borsarelli (UNSE, Argentina)Eduarda Fernandes (Universidade do Porto - Portugal) Fábio Yamashita (UEL, Brazil)Lusânia Antunes (FCFRP-USP, Brazil) Marta T. Benassi (UEL, Brazil)
Adriana Z. Mercadante (FEA-UNICAMP, Brazil)
PhD students - ongoing supervision :Daniele Bobrowski RodriguesFabiane Cristina PetryFelipe Rodrigues NogueiraGilsandro Alves da CostaMarcella C. Marques
Dr. Ana Augusta XavierDr. Lilian M.R. Mariutti
THANKS!
