Browse > Article

Phytochemical Studies on Paeoniae Radix (1);Monoterpene Glucosides  

Yean, Min-Hye (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Lee, Joo-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Publication Information
Korean Journal of Pharmacognosy / v.39, no.1, 2008 , pp. 19-27 More about this Journal
Abstract
From the polar fractions of 70% EtOH extract of Paeonia lactiflora roots (Paeoniaceae), ten monoterpene glucosides were isolated and identified as lactiflorin (1), benzoylpaeoniflorin (2), mudanpioside C (3), $1-O-{\beta}-D-glucosylpaeonisuffrone$ (4), paeonidanin (5), $1-O-{\beta}-D-glucosyl-8-O-benzoylpaeonisuffrone$ (6), paeoniflorin (7), albiflorin (8), oxypaeoniflorin (9) and mudanpioside E (10) by spectroscopic methods. Among these glucosides, 3-6 and 10 were isolated for the first time from this plant.
Keywords
Paeonia lactiflora; Paeoniaceae; monoterpene glucoside;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By SCOPUS : 5
연도 인용수 순위
1 Lee, S. M. Y., Li, M. L. Y., Tse, Y. C., Leung, S. C. L., Lee, M. M. S., Tsui, S. K. A., Fung, K. P., Lee, C. Y. and Waye, M. M. Y. (2002) Paeoniae Radix, a Chinese herbal extract, inhibit hepatoma cells growth by inducing apoptosis in a p53 independent pathway. Life Sci. 71: 2267-2277   DOI   ScienceOn
2 Zhang, G.-Q., Hao, X.-M., Chen, S.-Z., Zhou, P.-A., Cheng, H.-P. and Wu, C.-H. (2003) Blockade of paeoniflorin on sodium current in mouse hippocampal $CA_1$ neurons. Acta Pharmacol. Sin. 24: 1248-1252
3 Wang, H., Wei, W., Wang, N.-P., Wu, C.-Y., Yan, S.-X., Yue, L., Zhang, L.-L. and Xu, S.-Y. (2005) Effects of total glucosides of peony on immunological hepatic fibrosis in rats. World J. Gastroenterol. 11: 2124-2129   DOI
4 Kaneda, M., Iitaka, Y. and Shibata, S. (1972) Chemical studies on the oriental plant drugs - XXXIII. The absolute structures ofpaeoniflorin, albiflorin, oxypaeoniflorin and benzoyIpaeoniflorin isolated from Chinese Paeony Root. Tetrahedron 28: 4309-4317   DOI   ScienceOn
5 Yu, J., Elix, J. and Iskander, M. N. (1990) Lactiflorin, A monoterpene glycoside from Paeony Root. Phytochemistry 29: 3859-3863   DOI   ScienceOn
6 Yoshikawa, M., Harada, E., Kawaguchi, A Yamahara, J., Murakami, N. and Kitagawa, I. (1993) Absolute stereostructures of paeonisuffrone and paeonisuffral, two new labile monoterpenes, from Chinese Moutan Cortex. Chem. Pharm. Bull., 41: 630-632   DOI   ScienceOn
7 Yoo, M. Y., Lee, B. H., Choi, Y. H., Lee, J. W., Seo, J. H., Oh, K.-S., Koo, H.-N., Seo, H. W., Yon, G H., Kwon, D. Y., Kim, Y. S. and Ryu, S. Y. (2006) Vasorelaxant effect of the rootbark extract of Paeonia moutan on isolated rat thoracic aorta. Planta Med. 72: 1338-1341   DOI   ScienceOn
8 Ohta, H., Matsumoto, K., Watanabe, H. and Shimizu, M. (1993) Involvement of beta-adrenergic systems in the antagonizing effect of paeoniflorin on the scoploamine-induced deficit in renal maze performance in rats. Jpn. J. Pharmacal. 62: 345-349   DOI
9 Ohta, H., Ni, J.-W., Matsumoto, K., Watanabe, H. and Shimizu, M. (1993) Peony and its major constituent, Paeoniflorin, improve radial maze performance impaired by scopolamine in rats. Pharmacol. Biochem. Behav. 45: 719-723   DOI   ScienceOn
10 Ohta, H., Matsumoto, K., Shimizu, M. and Watanabe, H. (1994) Paeoniflorin attenuates learning impairment of aged rats in operant brightness discrimination task. Pharmacol. Biochem. Behav. 49: 213-217   DOI   ScienceOn
11 He, X. H., Xing, D. M., Ding, Y., Li, Y. P., Xu, L. Z. and Du, L. J. (2004) Effects of cerebral ischemia-reperfusion on pharmacokinetic fate of paeoniflom after intravenous adminstration of Paeoniae Radix extract in rats. J. Ethnopharmacol. 94: 339-344   DOI   ScienceOn
12 Tsai, H.-Y., Lin, Y.-T., Tsai, C.-H. and Chen, Y.-F. (2001) Effects of paeoniflorin on the formalin-induced nociceptive behaviour in mice. J. Ethnopharmacol. 75: 267-271   DOI   ScienceOn
13 Sakai, Y., Nagase, H., Ose, Y., Kito, H., Sata, T., Kawai, M. and Mizuno, M. (1990) Inhibitory action of peony root extract on the mutagenicity of benzo[a]pyrene. Mutat. Res. Lett. 244: 129-134   DOI   ScienceOn
14 Liu, D.-F., Wei, W. and Song, L.-H. (2006) Protective effect of paeoniflorin on immunological liver injury induced by Bacillus calmette-guerin plus lipopolysaccharide: Modulation of tumor necrosis $factor-{\alpha}$ and interleukin-6 mRNA. Clin. Exp. Pharmcol. Physiol. 33: 332-339   DOI   ScienceOn
15 Abdel-Hafez, A. A., Meselhy, M. R., Nakamura, N., Hattori, M., Watanabe, H., Murakami, Y., El-Gendy, M. A., Mahfouz, N. M. and Mohamed, T. A. (1998) Effects of paeoniflorin derivatives on scopolamine-induced amnesia using a passive avoidance task in mice; structure-activity relationship. Biol. Pharm. Bull. 21: 1174-1179   DOI
16 Yu, Y.-B., Jeong, I.-Y., Park, H.-R., Oh, H., Jung, U. and Jo, S.-K. (2004) Toxicological safety and stability of the components of an irradiated Korean medicinal herb, Paeoniae Radix. Rad. Phys. Chem. 71: 115-119
17 Liu, T. P., Liu, M., Tsai, C. C., Lai, T. Y., Hsu, F. L. and Cheng, J. T. (2002) Stimulatory effect of paeoniflorin on the release of noradrenaline from ileal synaptosomes of gineapig in vitro. J. Pharm. Pharmacol. 54: 81-88   DOI
18 Yen, P. H., Kiem, P. V., Nhiem, N. X., Tung, N. H., Quang, T. H., Minh, C. V., Kim, J. W, Choi, E. M. and Kim Y. H. (2007) A new monoterpene glycoside from the roots of Paeonia lactiflora increases the differentiation of osteoblastic MC3T3-E1 cells. Arch. Pharm. Res. 30: 1179-1185   과학기술학회마을   DOI
19 Mitova, M., Passov, St. and Handjieva, N. (1999) Paeoniflorin from Galium aegeum. Fitoterapia 70: 109-110   DOI   ScienceOn
20 Yang, H. O., Ko, W. K., Kim, J. Y. and Ro, H. S. (2004) Paeoniflorin: an antihyperlipidemic agent from Paeonia lactiflora. Fitoterapia 75: 45-49   DOI   ScienceOn
21 Dezaki, K., Kimura, I., Miyahara, K. and Kimura, M. (1995) Complementary effects of paeoniflorin and glycyrrhizin on intracellular $Ca^{2+}$ mobilization in the nerve-stimulated skeletal muscle of mice. Jpn. J. Pharmacol. 69: 281-284   DOI
22 Okubo, T., Nagai, F., Seto, T., Satoh, K., Ushiyama, K. and Kano, I. (2000) The inhibition of phenylhydroquinoneinduced oxidative DNA cleavage by constituents of Moutan Cortex and Paeoniae Radix. BioI. Pharm. Bull. 23: 199-203   DOI   ScienceOn
23 Yang, H. Y., Li, S. Z., Wang, H. B., Yu, D. Q. and Liang, X. T. (1990) The structure of lactiflorin, an artefact during isolation? Tetrahedron 46: 323-3128
24 Institute for Production Development Science (1983) 'Paeonone' Jpn Kokai Tokkyo Koho JP 58-18,398 pp. 949-954 [CA 99: 16561p (1983)]
25 Kostava, I. N., Simeonov, M. F. and Todorova, D. I. (1998) A monoterpene glucoside from Paeonia peregrina roots. Phytochemistry 47: 1303-1307   DOI   ScienceOn
26 Kobayashi, M., Ueda, C., Aoki, S., Tajima, K., Tanaka, N. and Yamahara, J. (1990) Anticholinergic action of Paeony Root and its active constituents. Yakugaku Zasshi 110: 964-968   DOI
27 Lang, H. Y. Li, S. Z., McCabe, T. and Clardy, J. (1984) A new monoterpene glycoside of Paeonia lactiflora. Planta Med. 50: 501-504   DOI   ScienceOn
28 Yamahara, J., Yamada, T., Kimura, H., Sawada, T. and Fujimura, H. (1982) Biologically active principles of crude drugs. II. Anti-allergic principles in 'Shosejryu-To' antiinflammatory properties of paeoniflorin and its derivatives. J. Pharmaco-Dynamics 5: 921-929   DOI
29 Aimi, N., Inaba, M., Watanabe, M. and Shibata, S. (1969) Chemical studies on the oriental plant drugs - XXIII. Paeoniflorin, a glucoside of Chinese Paeony Root. Tetrahedron 25: 1825-1838   DOI   ScienceOn
30 Ishida, H., Takamatsu, M., Tsuji, K. and Kosuge, T. (1987) Studies on active substances in herbs used for Oketsu ('Stagnant Blood') in Chinese Medicine. VI. On the anticoagulative principle in Paeoniae Radix. Chern. Pharm. Bull. 35: 849-852   DOI   ScienceOn
31 Kostava, I. N., Simeonov, M. F., Todorova, D. I. and Petkova, P. L. (1998) Two acylated monoterpene glucosides from Paeonia peregrina. Phytochemistry 48: 511-514   DOI   ScienceOn
32 Yan, D., Saito, K., Ohmi, Y., Fujie, N. and Ohtsyka, K. (2004) Paeoniflorin, a novel heat shock protein-inducing compound. Cell Stress Chaperones 9: 378-389   DOI
33 Kasai, R., Suzuo, M., Asakawa, 1.-1. and Tanaka, O. (1977) Carbon-13 chemical shifts of $isoprenoid-{\beta}-D-glucopyrano-sides$ and $-{\beta}-D-mannopyranosides$. Stereochemical influences of aglycone alcohols. Tetrahedron Lett. 18: 175-178   DOI   ScienceOn
34 Abdel-Hafez, A. A., Meselhy, M. R., Nakamura, N., Hattori, M., Watanabe, H., Mohamed, T. A., Mahfouz, N. M. and El-Gendy, M. A. (1998) Potent anticonvalsant paeonimetabolinI derivatives obtained by incubation of paeoniflorin and thiol compounds with Lactobacillus brevis. Chem. Pharm. Bull. 46: 1486-1487   DOI   ScienceOn
35 Tabata, K., Matsumoto, K., Murakami, Y. and Watanabe (2001) Ameliorative effects of paeoniflorin, a major constituent of Peony Root, on adenosine $A_1$ receptor-mediated impairment ofpassive aviodance performance and long-term potentiation in the hippocampus. BioI. Pharm. Bull. 24: 496-500   DOI   ScienceOn
36 Tsuboi, H., Hossain, K., Akhand, A. A., Takeda, K., Du, J., Rifa'i, M., Dai, Y., Hayakawa, A., Suzuki, H. and Nakashima, I. (2004) Paeoniflorin induces apoptosis of lymphocytes through a redox-linked mechanism. J. Cell Biochem. 93: 162-172   DOI   ScienceOn
37 Leem, K., Kim, H., Boo, Y., Lee, H. S., Kim, J. S., Yoo, Y. C., Ahn, H. J., Park, H. J., Seo, J. C., Kim, H. K., Jin, S. Y., Park, H. K., Chung, J. H. and Cho, J. J. (2004) Effects of Paeonia lactiflora root extracts on the secretions of monocyte chemotactic Protein-1 and -3 in human nasal fibroblasts. Phytother. Res. 18: 241-243   DOI   ScienceOn
38 Kang, S. S., Shin, K. H. and Chi, H. J. (1991) Galloylpaeoniflorin, A new acylated monoterpene glucoside from Paeony Root. Arch. Pharm. Res. 14: 52-54   DOI
39 Ye, J., Duan, H., Yang, X., Yan, W. and Zheng, X. (2001) Anti-thrombosis effect of paeoniflorin: evaluated in a photochemical reaction thrombosis model in vivo. Planta Med. 67: 766-767   DOI   ScienceOn
40 http://kfda.go.kr
41 Yamasaki, K., Kaneda, M. and Tanaka, O. (1976) Carbon-13 nmr spectral assignments of paeoniflorin homologues with the aid of spin-lattice relaxation time. Tetrahedron Lett. 17: 3965-3968   DOI   ScienceOn
42 Wei, W.-S., Wang, Y.-Q. and Wang, S.-Y. (1987) Immunoregulatory effects of total glucosides of paeony root in mice. Chin. Pharmacol. Bull. 3: 148-152
43 Zheng, Y.-Q. and Wei, W. (2005) Total glycosides ofpaeony suppresses adjuvant arthritis in rats and intervenes cytokinesignaling between different types of synoviocytes. Int. Immunopharmacol. 5: 1560-1573   DOI   ScienceOn
44 Abdel-Hafez, A. A., Meselhy, M. R., Nakamura, N., Hattori, M., Watanabe, H., Murakami, Y., El-Gendy, M. A., Mahfouz, N. M. and Mohamed, T. A. (1999) Anticonvalsant activity of paeonimetabolin-I adducts obtained by incubation of paeoniflorin and thiol compounds with Lactobacillus brevis. Biol. Pharm. Bull. 22: 491-497   DOI   ScienceOn
45 Zhu, L., Wei, W., Zheng, Y.-Q. and Jia, X.-Y. (2005) Effects and mechanisms of total glucosides of paeony on joint damage in rat collagen-induced arthritis. Injlamm. Res. 54: 211-220   DOI
46 Hong, J.-A, Chung, S.-H., Lee, J.-S., Kim, S.-S., Shin, H.D., Kim, H., Jang, M.-H., Lee, T.-H., Lim, B.-V., Kim, Y.-P. and Kim, C.-J. (2003) Effects of Paeonia Radix on 5-hydroxytryptamine synthesis and tryptophan hydroxylase expression in the dorsal raphe of exercised rats. BioI. Pharm. Bull. 26: 166-169   DOI   ScienceOn
47 Watanabe, H. (1997) Candidates for cognitive enhancer extracted from medicinal plants: paeoniflorin and tetramethylpyrazine. Behav. Brain Res. 83: 135-141   DOI   ScienceOn
48 Lemmich, J. (1996) Monoterpene and coumarin glucosides of Cnidium silaifolium. Phytochemistry 41: 1337-1340   DOI   ScienceOn
49 Hsu, F. L., Lai, C. W. and Cheng, J. T. (1997) Antihy-perglycemic effects of paeoniflorin and 8-debenzoylpaeon-iflorin, glucosides from the root of Paeonia lactiflora. Planta Med. 63: 323-325   DOI   ScienceOn
50 Lai, C.-W., Hsu, F.-L. and Cheng, J.-T. (1998) Stimulatory effect of paeoniflorin on adenosine A-1 receptors to increase the translocation of protein kinase C (PKC) and glucose transporter (GLUT 4) in isolated rat white adipocytes. Life Sci. 62: 1591-1595   DOI   ScienceOn
51 Zhang, X.-Y., Gao, C.-K, Wang, J.-H. and Li, X. (2002) A new monoterpene glycoside from Paeonia lactiflora Pall. Acta Pharm. Sin. 37: 705-708
52 Kitagawa, I., Yoshikawa, M., Tsunaga, K. and Tani, T. (1979) Studies on Moutan Cortex (II) On the chemical constituents. Shoyalatgalat Zasshi 33: 171-177
53 Kang, S. S., Shin, K. H. and Chi, H. J. (1989) Galloylpaeoniflorin, A new monoterpene glucoside from Paeony Roots. Kor. J. Pharmacogn. 20: 48-49   과학기술학회마을
54 배기환 (2000) 한국의 약용식물, 168. 교학사, 서울
55 Liu, D.-Z., Zhao, F.-L., Liu, J., Ji, X.-Q., Ye, Y. and Zhu, X.-Z. (2006) Potentiation of adenosine $A_1$ receptor agonist CPA-induced antinociception by paeoniflorin in mice. BioI. Pharm. Bull. 29: 1630-1633   DOI   ScienceOn
56 Shibata, S., Aimi, N. and Watanabe, M. (1964) Paeoniflorin, a monoterpene glucoside of Chinese Paeony Root. Tetrahedron Lett. 5: 1991-1995   DOI   ScienceOn
57 Kim, J. S., Yean, M. H., Lee, J. Y., Kim, Y. J., Lee, E. J., Lee, S. Y. and Kang, S. S. (2008) A new monoterpene glucoside from the roots of Paeonia lactiflora. Helv. Chim. Acta 91: 101-105
58 Murakami, N., Saka, M., Shimada, H., Matsuda, H., Yamahara, J. and Yoshikawa, M. (1996) New bioactive monoterpene glycosides from Paeoniae Radix. Chem. Pharm. Bull. 44: 1279-1281   DOI   ScienceOn
59 Lin, H.-C., Ding, H.-Y., Wu, T.-S. and Wu, P.-L. (1996) Monoterpene glycosides from Paeonia suffruticosa. Phytochemistry 41: 237-242   DOI   ScienceOn
60 Yoshikawa, M., Ohta, T., Kawaguchi, A. and Matsuda, H. (2000) Bioactive constituents of Chinese natural medicines. V. Radical scavenging effect ofMoutan Cortex. (1): Absolute stereostructures of two monoterpenes. paeonisuffrone and paeonisuffral. Chern. Pharm. Bull., 48: 1327-1331   DOI   ScienceOn
61 Kritsanida, M., Magiatis, P., Skaltsounis, A.-L. and Stables, J. P. (2006) Phytochemical investigation and anticonvulsant activity of Paeonia parnassica Radix. Nat. Prod Commun. 2: 351-356