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From Nature towards Nature: molecules, mechanisms and
processes for sustainability, energy, food quality and health
Istituto di Chimica Biomolecolare
UOS di CATANIA - Via Paolo Gaifami, 18
Phenomics, the concepts behind: monitoring the expression of selected secondary
metabolites for chemotaxonomy, traceability, quality and safety studies1
Sustainable processes for biodiesel production
(PCT/IB2014/058783)
1L.
Siracusa, G.Ruberto. Plant polyphenol profiles as a tool for traceability and valuable support to biodiversity.
Chapter II (15-33) In Polyphenols in Plants: Isolation, Purification and Extract Preparation , 1st Edition (April 2014) . Elsevier Books, ISBN 9780123979346.
Biodiesel is a non-toxic and biodegradable
alternative fuel obtained from renewable sources.
There are several key challenges arising with
biodiesel optimization processes which must still
be addressed efficiently. The main problem is the
inevitable production of glycerol as the co-product
(about 10% of produced biodiesel), which must be
removed and whose formation impacts on the
expense of the entire process.
The use of glycerol-derivatives that may be
exploited as biodiesel additives is being explored.
saffron
(C. sativus)
L.Siracusa, F.Gresta, G.Avola, E.Albertini, L.Raggi, G.Marconi, G.Ruberto. Agronomic, chemical and genetic variability of
saffron of different origin by LC-UV-VIS-DAD and AFLP analyses. Genetic Resources Crop Evolution 2013, 60, 711-721.
Soybean oil: 1.0 g
TBME: 3.2 mL (Oil/TBME 1:10)
Catalyst: 1.0% w/w
One-pot microwave assisted catalytic transformation of vegetable oil
into glycerol-free Biodiesel
R
O
“long storage” tomato
(L. esculentum)
MW: power/time
)))
O
O
O
R
+ CH OH
3
O
O
O
O
OH
O
R
O
O
OH
O
O
O
OH
O
O
acid-catalyst
O
O
70:30
O
O
O
MW: power/time
oregano (O.vulgare)
)))
O
MW: power/time
O
)))
+
+
CH3OH
3
acid-catalyst
T.Tuttolomondo,S. La Bella,M.Licata,G.Virga,C.Leto,A.Saija,D.Trombetta, M.Cristani, A.Speciale, E.M.
Napoli, L.Siracusa, A.Pasquale, G.Curcuruto, G.Ruberto. Biomolecular Characterization of Wild Sicilian
Oregano –Phytochemical Screening of Essential oils and Extracts And Evaluation of Their Antioxidant
Activities. Chemistry & Biodiversity 2013,10,411433.
Laura Siracusa, Cristina Patanè, Giovanni Avola, Giuseppe Ruberto. Polyphenols as chemotaxonomic markers in Italian
“long storage” tomato genotypes. J. Agric. Food Chem. 2012, 60, 309-314.
Isolation and characterization of new natural products and phytocomplexes endowed
with peculiar and interesting biological activities
A pool of polyphenols, namely dihydrostilbens and flavonoids,
have been isolated from the leaves of Sicilian liquorice
(Glycyrrhiza glabra L.). The lipid extract containing the aforesaid
components showed antioxidant and anti-inflammatory
properties, which have been associated to the polyphenol
compounds. In particular, both the extracts and the pure
compounds showed a selective anti-inflammatory activity
against COX-2 rather than COX-1, indicating these molecules
as potential new anti-inflammatory components with limited side
effects.
The figure shows the docking studies of one of the most active
dihydrostilbenes isolated from the leaves of liquorice with
COX-1 (A) and COX-2 (B)
O
O
R
O
The microwave assisted catalytic decomposition of
TBME gives methanol and isobutene which
participate to the transesterification of triglycerides
and the etherification of the obtained glycerol. The
three independent reactions occur simultaneously
and efficiently in presence of the same catalyst and
under the same reaction conditions.
Complete conversion into the corresponding methyl
esters and a mixture of mono- and di- tert-butyl
glycerol ether in a ratio 30:70. As desired, negligible
traces of glycerol were detected.
References:
1. M. L. Testa, V. La Parola, L. F. Liotta, A. M. Venezia; J. Mol. Catal. A-Chem., 2013, 367, 69
2. C. Drago, L. F. Liotta, V. La Parola, M. L. Testa and G. Nicolosi Fuel, 2013, 113, 707-711
Citrus genetic improvement
One of the most used procedures is the production of new varieties by crossing the best extant species. In
collaboration with the CNR Institute of Bioscience and Bioresources (Palermo) and CRA-ACM of Acireale we have
analysed the secondary metabolic profiles (polyphenols from the juices and the peel essential oils) of the new
fruits and those of the parents.
HPLC profiles of the flavonoid
content of a series of new hybrids
References:
Biondi, D.M.; Rocco, C.; Ruberto, G. New dihydrostilbene derivatives from the leaves of Glycyrrhiza glabra
and evaluation of their antioxidant activity. J. Nat. Prod., 2003, 66, 477-480.
Biondi, D.M.; Rocco, C.; Ruberto, G. Dihydrostilbene derivatives from Glycyrrhiza glabra L. leaves. J. Nat.
Prod. 2005, 68, 1099-1102.
Siracusa, L.; Saija, A.; Cristani, M.; Cimino, F.; D’Arrigo, M.; Trombetta, D.; Rao, F.; Ruberto, G.
Phytocomplexes from liquorice (Glycyrrhiza glabra L.) leaves: chemical characterization and evaluation of
their antioxidant, anti-genotoxic and anti-inflammatory activity. Fitoterapia 2011, 82, 546-556.
References:
Biocatalytic procedures to retrieve high added value molecules from fish wastes
1. Ruberto, G.; Rapisarda, P. Essential oils of new pigmented Citrus hybrids: Citrus sinensis L. Osbeck x C. clementina Hort ex Tanaka. J. Food Sci. 2002, 67, 2778-2780.
2. Tusa, N.; Abbate, L.; Renda, A.; Ruberto, G. Polyphenols distribution in juices from Citrus allotetraploid somatic hybrids and their sexual hybrids J. Agric. Food Chem. 2007, 55, 9089-9094.
3. Fabroni, S.; Ruberto, G.; Rapisarda, P. Essential oil profiles of new Citrus hybrids, a tool for genetic citrus improvement. J. Essent. Oil Res. 2012, 24(2), 159-169.
4. Abbate, L.; Tusa, N.; Fatta Del Bosco, S.; Strano, T.; Renda, A.; Ruberto, G. Genetic improvement of Citrus fruits: New somatic hybrids from Citrus sinensis (L.) Osb. and Citrus limon (L.)
Burm. F. Food Res. Int. 2012, 48, 284-290.
5. Fatta Del Bosco, S.; Abbate, L.; Tusa, N.; Strano, T. ; Renda, A.; Ruberto, G. Genetic improvement of Citrus fruits: The essential oil profiles in a Citrus limon backcross progeny derived from
somatic hybridization. Food Res. Int. 2013, 50, 344-350.
COOEt
Mechanism of antioxidant activity
Omega-3
ALA
Sequential Proton Loss Electron Transfer
CH3
EPA H 3C
CH3
COOEt
COOEt
DHA
We discovered that oxidant radicals (e.g. NO2, CO3•-, dpph, etc.) react with phenols in ionizing solvents through
electron-transfer from the phenoxide anions. This mechanism was baptized, “Sequential Proton Loss Electron
Transfer“ (SPLET). Quenching of radicals via SPLET can be very active in those cellular compartments at higher
pHs. The discovery of this mechanism was achieved by studying the reactivity of cinnamic acids (ACs) with dpph in
methanol. We observed that the bimolecular rate constants decreased as the concentration of ACs was increased
(see Fig. 2. This is because ionization of the carboxylic acid group represses the ionization of the phenolic OH and
reduces, therefore, the concentration of phenoxide anions in solution (see Fig. 3).
High added value molecules from Olive Mill Waste Water
Green routes
SPLET
Fig. 1
Fig. 2
Fig. 3
References
1. Litwinienko, G.; Ingold, K. U. J. Org. Chem. 2003, 68, 3433 – 3438 Abnormal Solvent Effects on Hydrogen Atom Abstractions. 1. The Reactions of Phenols with 2,2-Diphenyl-1-picrylhydrazyl (dpph•) in Alcohols
2. Foti, M. C.; Daquino, C.; Geraci, C. J. Org. Chem. 2004, 69, 2309 – 2314 Electron-Transfer Reaction of Cinnamic Acids and Their Methyl Esters with the DPPH Radical in Alcoholic Solutions
3. Litwinienko, G.; Ingold, K. U. J. Org. Chem. 2004, 69, 5888 – 5896 Abnormal Solvent Effects on Hydrogen Atom Abstraction. Resolution of the Curcumin Antioxidant Controversy. The Role of Sequential Proton
Loss Electron Transfer.
References:
PO FESR 2007/2013 “Valorizzazione di Biomasse Residuali per Applicazioni nel Settore Farmaceutico e Cosmetico”
PON02 “ Valorizzazione Biomolecolare ed Energetica di biomasse residuali del settore Agroindustriale ed Ittico “ (BIO4BIO)
Essential oils as therapeutic option in oncology
(Patent N° MI2014A000075)
Functional food: fruit and vegetable juice blends for health
Green Drink
Orange Drink 1
Orange Drink 2
celery
10%
strawberry
40%
golden apple
20%
pomegranate
30%
kiwi
70%
golden apple
30%
pomegranate
40%
white grape
40%
strawberry
50%
carrot
10%
pomegranate
30%
celery
10%
golden apple
20%
pomegranate
30%
white grape
40%
black grape
40%
carrot
15%
pomegranate
30%
kiwi
15%
golden apple
30%
Red Drink 1
Red Drink 2
Red Drink 3
For each «drink» and for single components of fruit and
vegetable, tests were carried out to define the antioxidant
profile (ABTS, DPPH, FRAP, RNS, and total phenols), the
hypoglycemic activity, and the content of biophenols
belonging to classes of phenolic acids, ellagitannins,
flavonoids, and anthocyanins. Among the 28 juice blends, six
have higher values ​of antioxidant activity compared to that
obtained by adding the contribution of individual components
in the mix (synergistic effect). This is in agreement with the
sensorial analysis.
Part of the benchtop prototype used for
making mixed “drinks”. This prototype has
the peculiarity of not providing any
preliminary processing of natural matrix used
(such as peeling or removing large seeds),
which makes it suitable for use in “Horeca”
(Hotel-Restaurant-Café) facilities.
References:
POR Regione Sicilia Obiettivo Operativo 4.1.1 Linea di Intervento 4.1.1.2 “Realizzazione di un prototipo di macchina automatica da banco di nuova concezione per la produzione istantanea di miscele di centrifugati di frutta e ortaggi freschi ad
elevato potere salutistico”
MTT
Lung cancer
Salvia officinalis
GC-FID-MS
Several essential oils are under study for their potential
use as anticancer agents1 alone or in combination with
conventional drugs. Moreover their antibiofilm2 activity is
under evaluation.
References:
1. Privitera G, Napoli E, Luca T, Ruberto G and Castorina S. In vitro Anti-Proliferative Effect of
Salvia officinalis Essential Oil and its Three Main Components on Human Lung Cancer Cells .
American Journal of Phytomedicine and Clinical Therapeutics , 2014 in press.
2. Schillaci D, Napoli, Cusimano M, Vitale M, and Ruberto G. Origanum vulgare subsp. Hirtum
Essential Oil Prevented Biofilm Formation and Showed Antibacterial Activity against Planktonic
and Sessile Bacterial Cells. J. Food Protection, 76 (10), 1747-1752, 2013.
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