RSS-Feed abonnieren
DOI: 10.1055/s-0028-1088377
© Georg Thieme Verlag KG Stuttgart · New York
Bakkenolides from Petasites tricholobus and Their Neuroprotective Effects Related to Antioxidant Activities
Publikationsverlauf
Received: May 4, 2008
Revised: October 16, 2008
Accepted: October 21, 2008
Publikationsdatum:
15. Dezember 2008 (online)
Abstract
Four novel bakkenolides – bakkenolide-Ia (1), bakkenolide-IIa (2), bakkenolide-IIIa (3) and bakkenolide-IVa (4) – were isolated from the extract of the rhizome of Petasites tricholobus. The structures were characterized by using NMR (1H, 13C, 1H–1H COSY, HMQC, HMBC, and NOESY) and mass spectrometry. The neuroprotective activity of the compounds 1 – 4 was assayed with primary cultured neurons exposed to oxygen-glucose deprivation and oxidative insults. Antioxidant activity of the bakkenolides was evaluated by cell-free bioassays. The in vitro assay results showed that all these compounds exhibited significant neuroprotective and antioxidant activities. To our knowledge, this is the first report on the neuroprotective and antioxidant activities of bakkenolides.
Key words
Petasites tricholobus - Asteraceae - bakkenolide - neuroprotection
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Abe N, Onoda R, Ro K, Kurihara T. The structures of bakkenolides-B, -C and -D as determined by the use of a nuclear overhauser effect. Tetrahedron Lett. 1968; 9 1993-7
- 2 Wu T S, Kao M S, Wu P L, Lin F W, Shi L S, Liou M J. et al . The bakkenolides from the root of Petasites formosanus and their cytotoxicity. Chem Pharm Bull. 1999; 47 375-82
- 3 Wu T S, Kao M S, Wu P L, Lin F W, Shi LS ,Teng C M. Antiplatelet principles from the root of Petasites formosanus. . Phytochemistry. 1999; 52 901-5
- 4 Yaoita Y, Kikuchi M. Structures of new eremophilane derivatives from the rhizomes of Petasites japonicus Maxim. Chem Pharm Bull. 1995; 43 1738-43
- 5 Tori M, Kawahara M, Sono M. Eremophilane-type sesquiterpenes from fresh rhizomes of Petasites japonicus. . Phytochemistry. 1998; 47 401-9
- 6 Neuenschwander M, Neuenschwander A, Steinegger E, Engel P. Struktur der Sesquiterpene von Petasites hybridus CL.1 G.M. et SCH.: Petasol- und Isopetasol-Abkömmlinge. Helv Chim Acta. 1979; 62 609-26
- 7 Cheng J K. Study on structure of compound isolated from Petasites tricholobus France. J Chin Pharm. 1999; 34 734-6
- 8 Deng G H, Wei S L, Wei H X. Studies of the chemical constituent of Petasites tricholobus France. Nat Prod Res Dev. 2000; 12 52-6
- 9 Xie W D, Zhang Q, Li P L, Jia Z J. Two triterpenoids and other constituents from Petasites tricholobus. . Phytochemistry. 2005; 66 2340-5
- 10 Wang Y L, Guo M L, Zhang G, Xue Q. Chemical constituents in root of Petasites tricholobus France. and their anti-inflammatory activity. Acad J Sec Mil Med Univ. 2006; 27 1210-3
- 11 Ohgoh M, Kimura M, Ogura H, Katayama K, Nishizawa Y. Apoptotic cell death of cultured cerebral cortical neurons induced by withdrawal of astroglial trophicupport. Exp Neurol. 1998; 149 51-63
- 12 Jung Y S, Kang T S, Yoon J H, Joe B Y, Lim H J, Seong C M. et al . Synthesis and evaluation of 4-hydroxyphenylacetic acid amides and 4-hydroxycinnamamides as antioxidants. Bioorg Med Chem Lett. 2002; 12 2599-602
- 13 Dok-Go H, Lee K H, Kim H J, Lee E H, Lee J, Song Y S. et al . Neuroprotective effects of antioxidative flavonoids, quercetin, (+)-dihydroquercetin and quercetin 3-methyl ether, isolated from Opuntia ficus-indica var. saboten. . J Cho Brain Res. 2003; 965 130-6
- 14 Dave J R. Neuroprotection produced by the NAALADase inhibitor 2-PMPA in rat cerebellar neurons. Eur J Pharmacol. 2000; 402 31-7
- 15 Muyderman H, Nilsson M, Sims N R. Highly selective and prolonged depletion of mitochondrial glutathione in astrocytes markedly increases sensitivity to peroxynitrite. J Neur Sci. 2004; 24 8019-28
- 16 Cho J, Lee H K. Wogonin inhibits excitotoxic and oxidative neuronal damage in primary cultured rat cortical cells. Eur J Pharmacol. 2004; 485 105-10
- 17 Naya K, Hayashi M, Takagi I, Nakamura S, Kobayashi M. The structural elucidation of sesquiterpene lactones from Petasites japonicus Maxim. Bull Chem Soc Jpn. 1972; 45 3673-85
- 18 Torres P, Ayala J, Grande C, Macias M, Grande M. Furanoeremophilanes and a bakkenolide from Senecio auricula var. major. . Phytochemistry. 1998; 47 57-61
Mei-Li Guo
Department of Pharmacognosy
School of Pharmacy
Second Military Medical University
325 Guohe Road
Shanghai 200433
People’s Republic of China
Telefon: +86-021-2507-4576
Fax: +86-021-2507-4575
eMail: mlguo@smmu.edu.cn
- www.thieme-connect.de/ejournals/toc/plantamedica