Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596326
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Phenylpropanoid amides of Solanum paniculatum fruits

V Soares
1   Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Avenida Carlos Chagas Filho, 373, Edifício do CCS, 21941902, Rio de Janeiro, RJ, Brazil
,
JR Machado
1   Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Avenida Carlos Chagas Filho, 373, Edifício do CCS, 21941902, Rio de Janeiro, RJ, Brazil
,
AJR da Silva
1   Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Avenida Carlos Chagas Filho, 373, Edifício do CCS, 21941902, Rio de Janeiro, RJ, Brazil
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

Also available at
 

Phenylpropanoid amides are a class of natural compounds where cinnamic acid derivatives and 2-phenyletylamine are connected by an amide bond. According to Sun et al, [1] phenylpropanoid amides occurence was reported for 19 species in the Solanaceae family, including genera as Capsicum, Datura, Lycianthes, Lycium, Lycopersicon, Solanum, and Withania. These compounds are recognized to display interesting medicinal properties, such as anti-inflammatory, antiviral, anti-cancer and anti-coagulant activities [2].

The roots, stems, leaves and fruits of Solanum paniculatum are used in folk medicine as well as in culinary. This species is the only Solanum recognized as phytotherapic by Brazilian Ministry of Health who included S. paniculatum among the herbal medicines available for basic pharmaceutical care in Brazil. The root and stems of S. paniculatum are indicated in the treatment of anemia and liver and digestive disorders. The S. paniculatum fruits are used for the preparation of pickles, in oil or vinegar and are also consumed after cooking with rice. Here we report the isolation of two isomeric glicosilated phenylpropanoid amides from the fruits of S. Paniculatum.

100 g of lyophillized S. Paniculatum fruits were homogeneized in a laboratory blender and successively extracted with hexane and ethyl acetate. The residue was then subjected to ultrasound assisted extraction with methanol. The methanol was evaporated and the residue was fractionated in a Sephadex LH20 column. The initial fractions from the Sephadex column were further subjected to semipreparative HPLC yielding 1(2.9 mg): HRESIMS (negative ion mode), deprotonated molecular ion at m/z 504.1875 [M-H]- (C25H30NO10), calcd. 504.1869; and m/z 342.1347 [(M- H)- – Hexose], (C19H20NO5)), calcd 342.1341, and 2(1.1 mg): HRESIMS (negative ion mode), deprotonated molecular ion at m/z 504.1875 [M-H]- (C25H30NO10), calcd. 504.1869; and m/z 342.1343 [(M- H)- – Hexose], calcd. 342.1341. Based on 1H, 13C, 1 and 2D NMR data, 1 and 2 were identified as N-trans-feruloyl-3-methoxytyramine-4-O-β-D-glucopyranoside and N-trans-feruloyl-3-methoxytyramine-4'-O-β-D-glucopyranoside, respectively. The aglycones of these two compounds were previously isolated by Sun et al (2015) from the roots of S. melongena. This is the first report on the occurrence of these compounds in S. paniculatum.

Acknowledgements: The authors acknowledge the support from CNPq, CAPES and FAPERJ.

Keywords: Phenylpropanoid amides, Solanum, Solanum paniculatum.

References:

[1] Sun J, Huo HX, Zhang J, Huang Z, Zheng J, Zhang Q, Zhao YF, Li J, Tu PF. Phenylpropanoid amides from the roots of Solanum melongena L. (Solanaceae). Biochem Syst Ecol 2015; 58:265 – 269

[2] Lee YT, Hsieh YL, Yeh YH, Huang CY. Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo. RSC Adv 2015; 5: 85806 – 85815