Antioxidative Phenylpropanoid-Substituted Epicatechin Glycosides from Parabarium huaitingii

Abstract

Three new phenylpropanoid-substituted epicatechin glycosides, namely parabarosides A – C (1–3), together with three known compounds, 5-caffeoylquinic acid (4), 5-caffeoylshikimic acid (5), and 3,4-dicaffeoylquinic acid (6), were obtained from the plant Parabarium huaitingii. Their structures were determined and full assignments of ¹H- and ¹³C‐NMR spectroscopic data were achieved by analyses of 1D- and 2D‐NMR, mass, and CD spectra. The oxygen radical absorbance capacity (ORAC) assay was applied to evaluate their antioxidative capacity in vitro, which revealed that 1–6 showed strong antioxidative properties.

Parabarium huaitingii - Apocynaceae - phenylpropanoid‐substituted epicatechin glycosides - natural polyphenols - antioxidative activities

References

• 1 Chinese Virtual Herbarium. Informational tips online. Available at www.cvh.org.cn/zhiwuzhi/list.asp. Accessed March 26, 2009
• 2 Han T, Li H L, Zhang Q Y, Zheng H C, Qin L P. New thiazinediones and other compounds from Xanthium strumarium.  Chem Nat Compd. 2006;  42 567-571
• 3 Maria P A, Marinella D L, Alesandra B. Phenolics of Arbutus unedo L. (Ericaceae) fruits: identification of anthocyanins and gallic acid derivatives.  J Agric Food Chem. 2006;  54 10234-10238
• 4 Huang M Z, Chen H S, Liu J G, Zou X H, Du J L, Xiang Z B. Studies on the chemical constituents of Bidens bipinnata.  Acad J Sec Mil Med Univ. 2006;  27 888-891
• 5 Nonaka G, Nishioka I. Tannins and related compounds. VII. Phenylpropanoid-substituted epicatechins, cinchonains from Cinchona succirubra.  Chem Pharm Bull. 1982;  30 4268-4276
• 6 Tang W X, Hioki H, Harada K, Fukuyama Y. Antioxidant phenylpropanoid-substituted epicatechins from Trichilia catigua. .  J Nat Prod. 2007;  70 2010-2013
• 7 Xiong Q B, Fan W Z, Tezuka Y, Adnyana I K, Stampoulis P, Hattori M, Namba T, Kadota S. Hepatoprotective effect of Apocynum venetum and its active constituents.  Planta Med. 2000;  66 127-133
• 8 Fan W Z, Tezuka Y, Xiong Q B, Hattori M, Namba T, Kadota S. Apocynins A–D: new phenylpropanoid-substituted flavan-3-ols isolated from leaves of Apocynum venetum (Luobuma-ye).  Chem Pharm Bull. 1999;  47 1049-1050
• 9 Chen H F, Tanaka T, Nonaka G, Fujioka T, Mihashi K. Tannins and related compounds. Part 121. Phenylpropanoid-substituted catechins from Castanopsis hystrix and structure revision of cinchonains.  Phytochemistry. 1993;  33 183-187
• 10 Zhang L Y, Ming D, Yu S S, Li J B, Luo Y M. A novel phenylpropanoid-substituted catechin glycoside and a new dihydrochalcone from Sarcandra glabra.  Chin Chem Lett. 2006;  17 207-210
• 11 Huang H L, Lu Z Q, Chen G T, Zhang J Q, Wang W, Yang M, Guo D A. Phenylpropanoid-substituted catechins and epicatechins from Smilax china.  Helv Chim Acta. 2007;  90 1751-1757
• 12 Gao H, Wang Z, Yang L, Yu Y, Yao Z H, Wang N L, Zhou G X, Ye W C, Yao X S. Five new bidesmoside triterpenoid saponins from Stauntonia chinensis.  Magn Reson Chem. 2008;  46 630-637
• 13 Davalos A, Gomez C C, Bartolome B. Extending applicability of the oxygen radical absorbance capacity (ORAC fluorescein) assay.  J Agric Food Chem. 2004;  52 48-54