HH IU th I ntel"n ational Conference on

Polyphenols Communications 2008 Volume I

Editors: M. Teresa Escribano-Bail6n Susana Gonzalez-Manzano Ana M. Gonzillez-Paramils Montserrat Duenas-Paton Celestino Santos-Buelga

Salamanca, 8th-l ph

July 2008

s 2008

d which III of the lerman:, ;:ntrancc e Figure

'or leule

'/lie :id.r I'll).

talyses the Icstigatlons bitar, in The lala for tliis !dded in the It modes of n belonging tat the most atom of the 7 c_tennin.! cot with tfie .tural X·'RilY ~alocatechin

polyphenols Communications 2008 Volume 11T1.02 -_ ... _-_ .... _-_ •......•.. _--. __ ... ----. . -. . _ ..... __ ...•..•..•............ -.-_ .. .•....•. __ ...•.. __ .. _._-_ .•. __ . __ ._-_.-.--_ .......• -_ ..• --_ ..

Phenolic composition of Cydollia oblollga Miller leaf

Branca M. Silval.~"', Andreia P. Oliveira l, Jose A. Pereira3, Patricia ValentBo\ Rosa M. Seabra!, Paula B. Andrade2•1CEBrMED, Faculdade de Ciencias da Saude, Universidnde Fernando Pessoa, R. Carlos da Maia, 296,4200-150 Porto, Portugal. *bsilva@ufp.pt; 2REQUlAlTE, Servic;o de Farmacognosia, Faculdade de Fannacia, Universidade do Porto, R. Anihal Cunha, 4050-047 Porto, Portugal; :lCIMD, Escola Superior Aer.iria, Instituto Politecnico de Brogan!;a, Campus de SantaApolonia, Apartado 1172,5301-855 Bragan!;a, p;rtugat.

Abstract. Phenolic profile of 36 Cydonia oblollga Miller leaf samples, from 3 different geographical origins of Portugal, harvested in 3 collection months, was determined by HPLC/DAD. Quince leaf presented a common profile composed by 9 constituents: 3-0-, 4-0- and 5-0-caffeoylquinic acids, 3,5-0-dicaffeoylquinic acid, quercetin-3-0-galactoside, quercetin-3-0-rutinoside, kaempferol-3-0-glycoside, kaempfcrol-3-0-g1ucoside and kaempferol-3-0-rutinoside. e. oblollga leaf total content varied from 4.9 to 16.5 glkg of dry maUer, indicating that this leaf can be used as a good and cheap source of bioactive constituents. 5-0-caffeoylquinic acid was the major phenolic compound (36.2%). Significantly differences were found in 3-0-caffeoylquinic and 3,5-0-dicaffeoylquinic acids coments, according to geographical provenience and harvesting month.

Introduction. The importance of many plants as natural sources of polyphenols and as nutrition promoting human health is well-established [I].

Nowadays, quince fruit is recognized as a good, cheap and important source of health promoting compounds, especially due to its antioxidant, antimicrobial and antiulcerative properties [2,3]. Several studies suggest that phenolic compounds are the main responsible for these activities and consequently by the possible health benefits associated [2]. - -

II has also been reported that the leaves and fruits of Cydonia oblollga Miller have some positive effects in the medical treatment of various conditions, including cardiovascular diseases, haemorrhoids, bronchial asthma, and cough [4].

As far as we know, for C. oblollga lenf, few phytochemical studies have been developed. So, in continuation of our-investigation on this plant species, the work herein represents a contribution to the chemical composition of quince leaf, concerning its phenolic profile. It \Vas also our purpose, to study the possii;Jle influence of factors, such as geographical origin and collection month, in the phenolics content.

~ii.terials nnd Methods. Samples.36 healthy quince leaf samples were collected in 3 geographical origins of.Portugai (Braganc;a, Carrazeda de Ansiues and Covilhii), in the beginning of June, August nod October af~OO6. ExtractiOIl of phenolic compoullds. Phenolics were extracted with methanol (40"C) and the extracts were.purified by using SPE C 18 columns, as previously reported [2).

~~~DAD system. 20 1-11 oflhe purified extracts were analyzed on an analytical HPLC unit, using a CIS P'1J~ns?rb OD52 column. The solvent system used was a gradient of water-ronnie acid (19: I) and methanol,

!SI!reVlOusly reported [2). Detection was achieved with a Diode Array Detector (DAD).

~Its and Discussion.TIle leafofe. oblollga presented a chemical profile composed by 9 phenolic compounds: ~.4{).. and 5-0-caffeoylquinic acids, 3,5-0-dicaffeoylquinic acid, quercetin-3-0-galactoside, quercetin-3-0-

kaempferol.)-O-glycoside, kaempferol·)-O·glucoside and kaempferol-)·O·rutinoside (Figure I). ';'i!!'P"in. this . profile with that of quince fruit there are some differences: pulp was characterized by

'~il~;~~,~f;~~~~16~~O~f;th~~es:~e compounds (3-0-, 4-0- and 5-0-caffeoylquinic acids, 3,5-0-dicaffeoylquinic acid, ~ ' quercetin-3-0-rutinoside); peel contained 13 phenolics, the compounds presented

• ... 1 ,T~:""''''· plus 4 not totally identified (2 quercetin glycosides ncylated with p-coumaric acid and 2 kaempferol

I , '.

.• j--

Volume 11T1.02 Polyphenols Communications 2008

glycosides acylated with p-coumaric acid); seed presented 11 phenolics, the 4 hydroxycynamic acid derivatives presented in leaves and 7 C-glycosil flnvones (Iucenin-2, vicenin-2, stellarin-2, isoschafioside, schaftoside, 6 C-pentasyl-8-C-glucasyl chrysaerial and 6-C-glucasyl-8-C-pentasyl cluysaerial) [2].

3 o~o

0.00

o "

4

tJ;nules

6 8

7 9

GO

Figure 1. HPLC phellolic profile of qlfince leaf DeleClioll at 350 11111. Peaks: (/J 3-0-caffeoylquillic acid; (2) 4-0-caffeoylquillic acid; (3) 5-0-caffeoylqllillic acid; (4) 3.5-0-dicaffeoylqllill;c aci4; (5) quercetin·J-O-galactoside; (6) qllercetill-3-0-nttilloside; (7) koempferol-3-0-glycoside: (8) kaempJerof­l-O-glucoside: (9) kaemp!erol-3-0-rutilloside.

C. ob/ollga leaf total phenolics content varied from 4.9 to 16.5 glkg of dry matter and the most abundant compound was 5-0-caffeoylquinic acid (36.2%), followed by quercetin-3-0-rutinoside (2 1.1 %), When compared with quince frui~, leaf is characterized by higher total phenolics content and relative concentrations ofkaempferol derivatives, especially in what concerns knempferoI-3-0-mtinoside (12.5%), Generally. in pulp and seed, the most abundant compound was also 5-0-cafTeoylquinic ac id , representing ca. 59% and 21 % of the total phenolics content, respectively, while the major compound in peel was quercetin-3-0-rutinoside (ca, 38%) [2] .

Significantly differences were found in 3-0-caffeoYlquinic and 3,5-0-dicaffeoylquinic acids contents, according to geographical origin and collection month, which indicates a possible use of these compounds as geographical provenience and/or maturiry markers.

So, in conclusion, this study suggests that leaf from C. oblollga can be used as a great and cheap source of bioactive compounds and may have relevance in the prevention of diseases in which free radicals arc implicated.

References

[I] Fattauch et al. (2007) J. Agric. Food CIr elll.55: 963-969. [2] Oliveira et al. (2007) J. Agric. Food Cir elli. 55: 7926-7930. [3] Oliveira et al. (2008) Foad Cirelli. (ill press). [4] Yildirim et 01. (2001) Tllrk .. f. Med. Sci.3 l : 23-27.

116

a u II

T d· ~

a It

Ie

1>1 c. cl co us SI sp as Bi SIr

R, U\ Cal

sar Nu

1.1a anri wit SlUI