Abstract
Bioassay-guided fractionation of the MeOH extract of Thuja orientalis fruits using a DPPH (2,2-diphenyl-1-picrylhydrazyl) assay led to the isolation of 9 flavonoids: cupressuflavone (1), amentoflavone (2), robustaflavone (3), afzelin (4), (+)-catechin (5), quercitrin (6), hypolaetin 7-O-β-xylopyranoside (7), isoquercitrin (8) and myricitrin (9). Their chemical structures were determined by spectroscopic analyses. The free radical scavenging and human neutrophil elastase (HNE) inhibitory activities were evaluated for the isolated compounds. By DPPH scavenging assay, compounds 5, 6, 7, 8 and 9 showed anti-oxidant activities with IC50 values of 28.66, 31.19, 18.30, 26.63 and 15.10 μM, respectively. By ABTS [2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt] scavenging assay, these compounds also exhibited potent anti-oxidant activities with IC50 values of 6.77, 13.96, 6.97, 22.79 and 9.96 μM, respectively. Of note, compounds 1, 2 and 3 showed significant HNE inhibitory activities with IC50 values of 8.09, 1.27 and 1.33 μM, respectively.
Similar content being viewed by others
References
Agrawal, P. K., Carbon-13 NMR of flavonoids. Elsevier: Amsterdam, pp. 292–293 (1989).
Asili, J., Lambert, M., Ziegler, H. L., Stærk, D., Sairafianpour, M., Witt, M., Asghari, G., Ibrahimi, I. S., and Jaroszewski, J. W., Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells. J. Nat. Prod., 67, 631–637 (2004).
Bissett, D. L., An animal model of solar-aged skin: histological, physical, and visible changes in UV-irradiated hairless mouse skin. Photochem. Photobiol., 46, 367–378 (1987).
Braca, A., Politi, M., Sanogo, R., Sanou, H., Morelli, I., Pizza, C., and De Tommasi, N., Chemical composition and antioxidant activity of phenolic compounds from wild and cultivated Sclerocarya birrea (Anacardiaceae) leaves. J. Agric. Food Chem., 51, 6689–6695 (2003).
Chung, S. K., Kim, Y. C., Yoshiaki, T., Kenji, T., and Masatake, N., Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans and its antioxidant effect. J. Agric. Food Chem., 52, 4664–4668 (2004).
Cook, N. S. and Samman, S., Flavonoids-chemistry, metabolism, cardioprotective effects, and dietary sources. J. Nutr. Biochem., 7, 66–76 (1996).
Dora, G. and Edwards, J. M., Taxonomic status of Lanaria lanata and isolation of a novel biflavone. J. Nat. Prod., 54, 796–801 (1991).
Fernandez, J., Reyes, R., Ponce, H., Oropeza, M., VanCalsteren, M. R., Jankowski, C., and Campos, M., Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways. Eur. J. Pharmacol., 522, 108–115 (2005).
Inoue, M., Hasegawa, S., and Hirose, Y., Terpenoids from the seed of Platycladus orientalis. Phytochemistry, 24, 1602–1604 (1985).
Jung, S. J., Kim, D. H., Hong, Y. H., Lee, J. H., Song, H. N., Rho, Y. D., and Baek, N. I., Flavonoids from the flower of Rhododendron yedoense var. poukhanense and their antioxidant activities. Arch. Pharm. Res., 30, 146–150 (2007).
Khallouki, F., Haubner, R., Hull, W. E., Erben, G., Spiegelhalder, B., Bartsch, H., and Owen, R. W., Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br. Food Chem. Toxicol., 45, 472–485 (2007).
Krauze-Baranowska, M., Mardarowicz, M., and Wiwart, M., The chemical composition of Microbiota decussata. Z. Naturforsch., 57C, 998–1003 (2002).
Lee, C. W., Choi, H. J., Kim, H. S., Kim, D. H., Chang, I. S., Moon, H. T., Lee, S. Y., Oh, W. K., and Woo, E. R., Biflavonoids isolated from Selaginella tamariscina regulate the expression of matrix metalloproteinase in human skin fibroblasts. Bioorg. Med. Chem., 16, 732–738 (2008).
Lee, K. K., Kim, J. H., Cho, J. J., and Choi, J. D., Inhibitory effects of 150 plant extracts on elastase activity, and their anti-inflammatory effects. Int. J. Cosmet. Sci., 21, 71–82 (1999).
Lee, S. K., Mbwambo, Z. H., Chung, H., Luyengi, L., Gamez, E. J., Mehta, R. G., Kinghorn, A. D., and Pezzuto, J. M., Evaluation of the antioxidant potential of natural products. Comb. Chem. High T. Scr., 1, 35–46 (1998).
Liang, T., Qin, Y., and Liang, N., Study on the Anti-inflammatory effect of Biota orientalis. J. Chin. Pharm. Univ., 32,224–226 (2001).
Ma, W., Wlaschek, M., Tantcheva-Poor, I., Schneider, L. A., Naderi, L., Razi-Wolf, Z., Schuller, J., and Kochanek, K. S., Chronological ageing and photoageing of the fibroblasts and the dermal connective tissue. Clin. Exp. Dermatol., 26, 592–599 (2001).
Mabry, T. J., Markham, K. R., and Thomas, M. B., The systematic identification of flavonoids. Springer: Berlin, pp. 35–250 (1970).
Markham, K. R., Franke, A., Molloy, B. P. J., and Webby, R. F., Flavonoid profiles of New Zealand Libocedrus and related genera. Phytochemistry, 29, 501–507 (1990).
Markham, K. R., Sheppard, C., and Geiger, H., 13C NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids. Phytochemistry, 26, 3335–3337 (1987).
Markham, K. R., Techniques of flavonoids identification. Academic Press: London, Chapter 3, pp. 36–51 (1982).
Melzig, M. F., Löser, B., and Ciesielski, S., Inhibition of neutrophil elastase activity by phenolic compounds from plants. Die Pharmazie, 56, 967–970 (2001).
Nakanishi, T., Iida, N., Inatomi, Y., Murata, H., Inada, A., Murata, J., Lang, F. A., Iinuma, M., and Tanaka, T., Neolignan and flavonoid glycosides in Juniperus communis var. depressa. Phytochemistry, 65, 207–213 (2004).
Natarajan, S., Murti, V. V. S., and Seshadri, T. R., Biflavones of some Cupressaceae plants. Phytochemistry, 9, 575–579 (1970).
Nishiyama, N., Chu, P. J., and Saito, H., Beneficial effects of biota, a traditional Chinese herbal medicine on learning impairment induced by basal forebrain-lesion in mice. Biol. Pharm. Bull., 18, 1513–1517 (1995).
Ohmoto, T. and Yamaguchi, K., Constituents of pollen. XV. Constituents of Biota orientalis (L.) Endl. (1). Chem. Pharm. Bull., 36, 807–809 (1988).
Pelter, A., Warren, R., Hameed, N., Khan, N. U., Ilyas, M., and Rahman, W., Biflavonyl pigments from Thuja orientalis (Cupressaceae). Phytochemistry, 9, 1897–1898 (1970).
Pietta, P. G., Flavonoids as antioxidants. J. Nat. Prod., 63, 1035–1042 (2000).
Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., and Rice-Evans, C., Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med., 26, 1231–1237 (1999).
Robert, L., Extracellular matrix and aging: a review of mechanisms and interventions. Cosmet. Toiletries, 116, 61–70(2001).
Siedle, B., Cisielski, S., Murillo, R., Löser, B., Castro, V., Klaas, C. A., Hucke, O., Labahn, A., Melzig, M. F., and Merfort, I. Sesquiterpene lactones as inhibitors of human neutrophil elastase. Bioorg. Med. Chem., 10, 2855–2861 (2002).
Strack, D., Heilemann, J., Mömken, M., and Wray, V., Cell wall-conjugated phenolics from coniferae leaves. Phytochemistry, 27, 3517–3521 (1988).
Sung, S. H., Koo, K. A., Lim, H. K., Lee, H. S., Cho, J. H., Kim, H. S., and Kim, Y. C., Diterpenes of Biota orientalis leaves. Kor. J. Pharmacog., 29, 347–352 (1998).
Tang, C., Jiang, T., and Zhuang, X., Action of Chinese arborvitae top tender leaves (Platycladus orientalis) on smooth muscle of guinea pig trachea. Chin. Tradit. Herb. Drugs, 30, 278–279 (1999).
Tomita, B., Hirose, Y., and Nakatsuka, T., Terpenoids. XVI new constituents of Biota orientalis. Tetrahedron Lett., 9,843–848 (1968).
Wiedow, O., Schroder, J. M., Gregory, H., Young, J. A., and Christophers, E., Elafin: an elastase-specific inhibitor of human skin. Purification, characterization, and complete amino acid sequence. J. Biol. Chem., 265, 14791–14795 (1990).
Yang, H. O., Suh, D. Y., and Han, B. H., Isolation and characterization of platelet-activating factor receptor binding antagonists from Biota orientalis. Planta Med., 61, 37–40 (1995).
Zhu, J. X., Ling, Y. W., Kong, D., Yang, C., and Zhang, X., Effects of Biota orientalis extract and its flavonoid constituents, quercetin and rutin on serum uric acid levels in oxonate-induced mice and xanthine dehydrogenase and xanthine oxidase activities in mouse liver. J. Ethnopharmacol., 93, 133–140 (2004).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Xu, GH., Ryoo, IJ., Kim, YH. et al. Free radical scavenging and antielastase activities of flavonoids from the fruits of Thuja orientalis . Arch. Pharm. Res. 32, 275–282 (2009). https://doi.org/10.1007/s12272-009-1233-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-009-1233-y