Nanoformulations of quercetin: a potential phytochemical for the treatment of uv radiation induced skin damages

Tripathi, Nancy; Verma, Surajpal; Vyas, Manish; Yadav, Narendra Singh; Gain, Subhajit; Khatik, Gopal Lal

doi:10.1590/s2175-97902020000118744

Nancy Tripathi

School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, Punjab, India

Surajpal Verma ^**Correspondence: S. Verma. School of Pharmaceutical Sciences. Lovely Professional University. Phagwara, Punjab, India. E-mail: surajpal_1982@ yahoo.co.in

School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, Punjab, India

School of Pharmaceutical Sciences, Delhi Pharmaceutical Sciences & Research University (DPSRU), Mehrauli-Badarpur Road, Puspvihar, Sector-3, New Delhi-110017, India

http://orcid.org/0000-0002-4357-2995

Manish Vyas

School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, Punjab, India

Narendra Singh Yadav

French Associates Institute for Agriculture and Biotechnology of Drylands, Jacob Blaustein Institutes for Desert Research, Ben-Gurion University of the Negev, Midreshet Ben Gurion 84990, Israel

Subhajit Gain

School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, Punjab, India

Gopal Lal Khatik

School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, Punjab, India

*Correspondence: S. Verma. School of Pharmaceutical Sciences. Lovely Professional University. Phagwara, Punjab, India. E-mail: surajpal_1982@ yahoo.co.in

Authors declared that no conflicts of interest.

Figures (3)
Tables (3)

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FIGURE 1
General structure of flavonoid.

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FIGURE 2
General mechanism of action of flavonoids.

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FIGURE 3
Structure of quercetin.

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TABLE I
Classification of flavonoids, their chemical constituents and sources (Panche et al. 2016Panche AN, Diwan AD, Chandra SR. Flavonoids: an overview. J Nutr Sci. 2016;5: e47. doi:10.1017/jns.2016.41.
https://doi.org/10.1017/jns.2016.41... ); (Ugazio et al. 2016Ugazio E, Gastaldi L, Brunella V, Scalarone D, Jadhav SA, Oliaro-Bosso S, et al. Thermoresponsive mesoporous silica nanoparticles as a carrier for skin delivery of quercetin. Int J Pharm. 2016;511(1):446-454. doi:10.1016/j.ijpharm.2016.07.024.
https://doi.org/10.1016/j.ijpharm.2016.0... )

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TABLE II
Physicochemical properties of quercetin (Kumar et al. 2014Kumar A, Kushwaha V, Sharma PK. Pharmaceutical microemulsion: Formulation, characterization and drug deliveries across skin. Int J Drug Dev Res. 2014;6(1):1-21.)

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TABLE III
Comparative study of different formulations of Quercetin for topical application (Ichihashi et al. 2003Ichihashi M, Ueda M, Budiyanto A, Bito T, Oka M, Fukunaga M, et al. UV-induced skin damage. Toxicology. 2003;189(1-2):21-39. doi:10.1016/S0300-483X(03)00150-1.
https://doi.org/10.1016/S0300-483X(03)00... ); (Guo et al. 2012Guo CY, Yang CF, Li QL, Tan Qi, Xi YW, Liu WN, et al. Development of a Quercetin-loaded nanostructured lipid carrier formulation for topical delivery. Int J Pharm. 2012;430(1-2):292-298. doi:10.1016/j.ijpharm.2012.03.042.
https://doi.org/10.1016/j.ijpharm.2012.0... ); (Manca et al. 2014aManca ML, Castangia I, Caddeo C, Pando D, Escribano E, Valenti D, et al. Improvement of quercetin protective effect against oxidative stress skin damages by incorporation in nanovesicles. Colloids Surfaces B Biointerfaces. 2014a;123:566-574. doi:10.1016/j.colsurf b.2014.09.059.
https://doi.org/10.1016/j.colsurf b.2014... ); (Ugazio et al. 2016Ugazio E, Gastaldi L, Brunella V, Scalarone D, Jadhav SA, Oliaro-Bosso S, et al. Thermoresponsive mesoporous silica nanoparticles as a carrier for skin delivery of quercetin. Int J Pharm. 2016;511(1):446-454. doi:10.1016/j.ijpharm.2016.07.024.
https://doi.org/10.1016/j.ijpharm.2016.0... ); (Gao et al. 2011Gao L, Liu G, Wang X, Liu F, Xu Y, Ma J. Preparation of a chemically stable quercetin formulation using nanosuspension technology. Int J Pharm. 2011;404(1-2):231-237. doi:10.1016/j. ijpharm.2010.11.009.
https://doi.org/10.1016/j. ijpharm.2010.... ); (Sapino et al. 2015Sapino S, Ugazio E, Gastaldi L, Miletto I, Berlier G, Zonari D, et al. Mesoporous silica as topical nanocarriers for quercetin: Characterization and in vitro studies. Eur J Pharm Biopharm. 2015;89(December):116-125. doi:10.1016/j.ejpb.2014.11.022.
https://doi.org/10.1016/j.ejpb.2014.11.0... ); (Park et al. 2013Park SN, Lee MH, Kim SJ, Yu ER. Preparation of quercetin and rutin-loaded ceramide liposomes and drug-releasing effect in liposome-in-hydrogel complex system. Biochem Biophys Res Commun. 2013;435(3):361-366. doi:10.1016/j. bbrc.2013.04.093.
https://doi.org/10.1016/j. bbrc.2013.04.... ); (Wu et al. 2008Wu TH, Yen FL, Lin LT, Tsai TR, Lin CC, Cham TM. Preparation, physicochemical characterization, and antioxidant effects of quercetin nanoparticles. Int J Pharm. 2008;346(1-2):160-168. doi:10.1016/j.ijpharm.2007.06.036.
https://doi.org/10.1016/j.ijpharm.2007.0... ) and (Yuri et al. 2015)

Generic structure	Flavonoid	Dietary Source	Applications
Flavane
	(+)-catechin		Anioxidant and antimicrobial agent
	(-)-epicatechin
	Epigallocatechin gallate
Flavanone
	Narigin	Citrus, grapefruit	Antioxidant, antiinflammatory, and cholesterollowering effect
	Narigenin
	Taxifolin
	Eriodictyol	Lemons
	Hesperidin	Oranges
Flavone
	Chrysin	Fruit skins	Gout and kidney stones treatment as xanthine oxidase modulators
	Apigenin	Parsley, celery
	Luteolin	Red wine, buckwheat
	Luteolin glucosides	Citrus, tomato skin,
	Diosmetin	Red pepper
Flavonol	Kaempferol
		Leek, broccoli, endives
	Rutin	grapefruit, black tea
		Onion, lettuce, broccoli,	Antioxidant potential,
		tomato, tea, red wine,	lower dementia
	Quercetin	apples, Ginkgo biloba	and reduced risk of
		Berries, olive oil, apple skin	vascular disease
	Myricetin	Cranberry grapes, red wine
	Tamarixetin
Isoflavone
	Genistin
	Genistein
	Daidzin	Soyabean	Estrogenic activity,
	Daidzein		metabolic diseases
Neoflavone


	Calophyllolide	Calophyllum inophyllum seeds	Estrogen-like activity

Quercetin physicochemical properties	Values
Chemical formula	C₁₅H₁₀O₇
Chemical name (IUPAC)	2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
Solubility in MilliQ water	0.48 ± 0.1 μg/mL
Solubility in PBS¹ pH 3	0.44 ± 0.1 μg/m
Solubility in DMSO²	30 mg/mL
Solubility in ethanol	2 mg/mL
Partition coefficient (log P)	1.82 ± 0.3
Polymorphism	Three polymorphic forms

TABLE III Comparative study of different formulations of Quercetin for topical application (**Ichihashi et al. 2003Ichihashi M, Ueda M, Budiyanto A, Bito T, Oka M, Fukunaga M, et al. UV-induced skin damage. Toxicology. 2003;189(1-2):21-39. doi:10.1016/S0300-483X(03)00150-1.
https://doi.org/10.1016/S0300-483X(03)00... ); (Guo et al. 2012Guo CY, Yang CF, Li QL, Tan Qi, Xi YW, Liu WN, et al. Development of a Quercetin-loaded nanostructured lipid carrier formulation for topical delivery. Int J Pharm. 2012;430(1-2):292-298. doi:10.1016/j.ijpharm.2012.03.042.
https://doi.org/10.1016/j.ijpharm.2012.0... ); (Manca et al. 2014aManca ML, Castangia I, Caddeo C, Pando D, Escribano E, Valenti D, et al. Improvement of quercetin protective effect against oxidative stress skin damages by incorporation in nanovesicles. Colloids Surfaces B Biointerfaces. 2014a;123:566-574. doi:10.1016/j.colsurf b.2014.09.059.
https://doi.org/10.1016/j.colsurf b.2014... ); (Ugazio et al. 2016Ugazio E, Gastaldi L, Brunella V, Scalarone D, Jadhav SA, Oliaro-Bosso S, et al. Thermoresponsive mesoporous silica nanoparticles as a carrier for skin delivery of quercetin. Int J Pharm. 2016;511(1):446-454. doi:10.1016/j.ijpharm.2016.07.024.
https://doi.org/10.1016/j.ijpharm.2016.0... ); (Gao et al. 2011Gao L, Liu G, Wang X, Liu F, Xu Y, Ma J. Preparation of a chemically stable quercetin formulation using nanosuspension technology. Int J Pharm. 2011;404(1-2):231-237. doi:10.1016/j. ijpharm.2010.11.009.
https://doi.org/10.1016/j. ijpharm.2010.... ); (Sapino et al. 2015Sapino S, Ugazio E, Gastaldi L, Miletto I, Berlier G, Zonari D, et al. Mesoporous silica as topical nanocarriers for quercetin: Characterization and in vitro studies. Eur J Pharm Biopharm. 2015;89(December):116-125. doi:10.1016/j.ejpb.2014.11.022.
https://doi.org/10.1016/j.ejpb.2014.11.0... ); (Park et al. 2013Park SN, Lee MH, Kim SJ, Yu ER. Preparation of quercetin and rutin-loaded ceramide liposomes and drug-releasing effect in liposome-in-hydrogel complex system. Biochem Biophys Res Commun. 2013;435(3):361-366. doi:10.1016/j. bbrc.2013.04.093.
https://doi.org/10.1016/j. bbrc.2013.04.... ); (Wu et al. 2008**Wu TH, Yen FL, Lin LT, Tsai TR, Lin CC, Cham TM. Preparation, physicochemical characterization, and antioxidant effects of quercetin nanoparticles. Int J Pharm. 2008;346(1-2):160-168. doi:10.1016/j.ijpharm.2007.06.036.
https://doi.org/10.1016/j.ijpharm.2007.0... ) and (Yuri et al. 2015)

Formulation	Preparation technique	Excipients	Particle size (nm)	PDI	Surface charge (mV)	Entrapment Efficiency (%)	Antioxidant activity (%)
Lipid based nanosystems	Probe Ultra Sonication	Compritol 888, Glyceryl dibehenate, Olic acid	281.9 ± 2.9	0.31 ± 0.1	-36.57 ± 2.67	NS	NS
Nanovesicles Glycerosomes	Thin film hydration method	Lecithin, Glycerol	80 ± 3.0	0.26 ± 0.2	-67.0 ± 3.0	81.0 ± 1.0	95 ± 1.0
Liposomes	Thin film hydration method	Lecithin, Glycerol	102 ± 3.0	0.32 ± 0.1	-78.0 ± 2.0	88.0 ± 3.0	87 ± 2.0
Thermoresponsive mesoporous silica nanoparticles (MSN)	Q/copoly-MSN Big	CTAB, TEOS, NaOH TMB	328 ± 33.0	NS	-20.6 ± 0.7	32.4 (Q-loading)	53 ± 4.0
Thermoresponsive mesoporous silica nanoparticles (MSN)	Q/copoly-MSN small	CTAB, TEOS, NaOH TMB	200 ± 19.0	NS	-21.3 ± 0.5	33.5 (Q-loading)	72 ± 2.0
Nanosuspension	EPAS	Ethanol, Pluronic F68, Lecithin	251.56 ± 24.6	0.23 ± 0.1	-21.12 ± 2.7	NS	NS
Nanosuspension	HPH	Ethanol, Pluronic F68, Lecithin	192.47 ± 31.8	0.21 ± 0.1	-22.48 ± 4.6	NS	NS
Aminopropyl functionalized mesoporous silica nanoparticles (NH₂-MSN)	Sol-gel method	N-cetyltrimethylammonium bromide, Tetraethyl orthosilicate	250 ± 50.0	NS	+13.6 ± 0.2	8 (drug loading %)	NS
Ceramide liposomes-inhydrogel complex system	Thin film hydration method	Egg PC, Ceramide, Cholesterol, Oleic acid	NS	NS	NS	41.5	NS
Polymeric nanoparticle	Nanoprecipitation technique	PVA, Eudragit-E	82 ± 5.0	0.22 ± 0.1	NS	99.9 ± 0.6	NS
Deformable liposomes	Ethanol injection method	Lecithin, Cholesterol, Tween-80	132 ± 14.0	NS	21.1 ± 8.0	80.4 ± 4.2	NS

[1] *Correspondence: S. Verma. School of Pharmaceutical Sciences. Lovely Professional University. Phagwara, Punjab, India. E-mail: surajpal_1982@ yahoo.co.in

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Nanoformulations of quercetin: a potential phytochemical for the treatment of uv radiation induced skin damages

Abstract