Lignan and Neolignan Glycosides from the Roots of Glehnia littoralis

Abstract

A new lignan glycoside [glehlinoside G (1)] and three new neolignan glycosides [glehlinosides H (2), I (3) and J (4)] were isolated from the roots of Glehnia littoralis. Their structures were elucidated on the basis of spectroscopic data. The above glehlinosides (1–4), together with the other lignan and neolignan glycosides (5–12) from this plant, were evaluated for their prolyl oligopeptidase inhibitory activities, and a caffeoyled lignan glycoside (glehlinoside F, 8) exhibited a noticeable activity (IC₅₀ = 14.5 µM).

Umbelliferae - Glehnia littoralis - lignan glycosides - neolignan glycosides - glehlinosides - prolyl oligopeptidase inhibitory activity

References

• 1 Jiangsu New Medical College .Dictionary of Chinese Materia Medica. Shanghai; Shanghai Science and Technology Publisher 1977: 644
• 2 Yuan Z, Tezuka Y, Fan W, Li X, Kadota S. Constituent of the underground parts of Glehnia littoralis.  Chem Pharm Bull. 2002;  50 73-77
• 3 Kong W X, Yuan Z. New lignan glycosides from Glehnia littoralis.  Chin Chem Lett. 2008;  19 1459-1461
• 4 Wang L L, Kong W X, Yuan Z. A new 8-O-4′ neolignan from Glehnia littoralis.  Acta Pharma Sin. 2008;  43 1036-1039
• 5 Cunningham D F, O'Connor B. Proline specific peptidases.  Biochim Biophys Acta. 1997;  1343 160-186
• 6 Schneider J, Giardiniere M, Morain P. Effects of the prolyl endopeptidase inhibitor S17092 on cognitive deficits in chronic low dose MPTP-treated monkeys.  Neuropsychopharmacology. 2002;  26 176-182
• 7 Li W, Asada Y, Koike K, Furuya T, Yoshikawa T. Bellisosides A–F, six novel acylated triterpenoid saponins from Bellis perennis (Compositae).  Tetrahedron. 2005;  61 2921-2929
• 8 Wallen E A A, Christiaans J A M, Saarinen T J, Jarho E M, Forsberg M M, Venalainen J I, Mannisto P T, Gynther J. Conformationally rigid N-acyl-5-alkyl-L-prolylpyrrolidines as prolyl oligopeptidase inhibitors.  Bioorg Med Chem. 2003;  11 3611-3619
• 9 Sugahara T, Yamauchi S, Kondo A, Ohno F, Tominaga S, Yuki, Kishida T, Akiyama K, Maruyama M. First stereoselective synthesis of meso-secoisolariciresinol and comparison of its biological activity with (+)- and (−)-secoisolariciresinol.  Biosci Biotechnol Biochem. 2007;  71 2962-2968
• 10 Wallis A F A. Oxidation of (E)- and (Z)-2,6-dimethoxy-4-propenylphenol with ferric chloride – a facile route to the 2-aryl ethers of 1-arylpropane-1,2-diols.  Aust J Chem. 1973;  26 585-595
• 11 Wang C J, Jia Z J. Neolignan glycosides from Pedicularis longiflora.  Planta Med. 1997;  63 241-244
• 12 Machida K, Sakamoto S, Kikuchi M. Two new neolignan gycosides from leaves of Osmanthus heterophyllus.  J Nat Med. 2009;  63 227-231
• 13 Yoshikawa K, Kinoshita H, Kan Y, Arihara S. Neolignans and phenylpropanoids from the rhizomes of Coptis japonica.  Chem Pharm Bull. 1995;  43 578-581
• 14 Kimura K, Kanou F, Yamashita Y, Yoshimoto T. Prolyl endopeptidase inhibitors derived from Actinomycetes.  Biosci Biotechnol Biochem. 1997;  61 1754-1756
• 15 Wallen E A A, Christiaans J A M, Forsberg M M, Venalainen J I, Mannisto P T, Gynther J. Dicarboxylic acid bis(L-prolyl-pyrroldine) amides as prolyl oligopeptidase inhibitors.  J Med Chem. 2002;  45 4581-4584
• 16 Fan W, Tezuka Y, Ni K M, Kadota S. Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis.  Chem Pharm Bull. 2001;  49 396-401
• 17 Teresa T, Nessim K, Birgit C, Roger P, Meritxell T, Ernest G. Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor.  Bioorg Med Chem. 2008;  16 7516-7524
• 18 Lee J H, Lee S Y, Lee K S, Jang H J, Lee K H, Hahn T R, Paik R S. Prolyl endopeptidase inhibitors from the leaves of Ginkgo biloba.  Planta Med. 2004;  70 1228-1230
• 19 Lee S H, Jun M, Choi J Y, Yang E J, Hur J M, Bae K H, Seong Y H, Huh T L, Song K S. Plant phenolics as prolyl endopeptidase inhibitors.  Arch Pharm Res. 2007;  30 827-833