Three New Acylated Glycosides from the Stems of Casearia velutina and their Protective Effect Against H₂O₂-Induced Impairment in PC12 Cells

Abstract

Chemical investigation of the stems of Casearia velutina led to the isolation and structural elucidation of three new acylated glycosides, casearicosides A–C (1–3), together with 13 known compounds. The structures of the new compounds were established by spectroscopic and chemical methods. These isolates were evaluated for protective effects against H₂O₂-induced impairment in PC12 cells and inhibitory activity against snake venom phosphodiesterase I. A brief chemotaxonomy of the genus Casearia is also discussed.

Key words

Casearia velutina Blume - Salicaceae - casearicosides A–C - Flacourtiaceae - chemotaxonomy

References

• 1 The Angiosperm Phylogeny Group . An update of the angiosperm phylogeny group classification for the orders and families of flowering plants: APG II.  Bot J Linn Soc. 2003;  141 399-436
• 2 Editorial Board of Flora Reipublicae Popularis Sinicae of Chinese Science Academy .Flora Reipublicae Popularis Sinicae, Vol. 52. Beijing; Beijing Scientific Press 2005: 73
• 3 Li F F, Chai X Y, Xu Z R, Ren H Y, Tu P F. Chemical constituents from stems of Casearia velutina.  Chin J Chin Mater Med. 2008;  39 984-986
• 4 Chai X Y, Lu Y N, Ren H Y, Tu P F. Advances in studies on chemical constituents and bioactivities of plants from Flacourtiaceae.  Chin J Chin Mater Med. 2006;  31 271-279
• 5 Kitajima J, Suzuki N, Ishikawa T, Tanaka Y. New hemiterpenoid pentol and monoterpenoid glycoside of Torillis japonica fruit and consideration of the origin of apiose.  Chem Pharm Bull. 1998;  46 1583-1586
• 6 Otsuka H, Takeuchi M, Inoshiri S, Sato T, Yamasaki K. Phenolic compounds from Coix lachrymal-jobi var. ma-yuen.  Phytochemistry. 1989;  28 883-886
• 7 Seidel V, Bailleul F, Waterman P G. Novel oligorhamnosides from the stem bark of Cleistopholis glauca.  J Nat Prod. 2000;  63 6-11
• 8 Masataka S, Masao K. Studies on the constituents of Osmanthus species. X. Structures of phenolic glucosides from the leaves of Osmanthus asiaticus.  Chem Pharm Bull. 1992;  40 325-326
• 9 Seigler D S, Pauli G F, Nahrstedt A, Leen R. Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya.  Phytochemistry. 2002;  60 873-882
• 10 Towers G HN, Mcinnes A G, Neish A C. The absolute configuration of the phenolic cyanogenic glucosides taxiphyllin and dhurrin.  Tetrahedron. 1964;  20 71-77
• 11 Nahrstedt A, Rockenbach J. Occurrence of the cyanogenic glucoside prunasin and its corresponding mandelic acid amide glucoside in Olinia species (Oliniaceae).  Phytochemistry. 1993;  34 433-436
• 12 Abrosca B D, DellaGreca M, Fiorentino A, Monaco P, Previtera L, Simonet A M, Zarreli A. Potential allelochemicals from Sambucus nigra.  Phytochemistry. 2001;  58 1073-1081
• 13 Zhong X N, Otsuka H, Ide T, Hirata E, Takeda Y. Hydroquinone diglycoside acyl esters from the leaves of Myrsine seguinii.  Phytochemistry. 1999;  52 923-927
• 14 Kanchanapoom T, Kasai R, Yamasaki K. Iridoid and phenolic diglycosides from Canthium berberidifolium.  Phytochemistry. 2002;  61 461-464
• 15 Kim H J, Woo E R, Park H. A novel lignan and flavonoids from Polygonum aviculare.  J Nat Prod. 1994;  57 581-586
• 16 Smite E, Pan H, Lundgren L N. Lignan glycosides from inner bark of Betula pendula.  Phytochemistry. 1995;  40 341-343
• 17 Kaneda N, Kinghorn A D, Farnsworth N R, Tuchinda P, Udchachon J, Santisuk T, Reutrakul V. Two diarylheptanoids and a lignan from casuarina junghuhniana.  Phytochemistry. 1990;  29 3366-3368
• 18 Hiroyuki F, Tetsuya S, Nobutoshi T. Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii.  Chem Pharm Bull. 1995;  43 1937-1942
• 19 Lu Y, Sun Y, Foo L Y, McNabb W C, Molan A L. Phenolic glycosides of forage legume Onobrychis viciifolia.  Phytochemistry. 2000;  55 67-75
• 20 Soltis D E, Soltis P S, Chase M W, Mort M E, Albach D C, Zanis M, Savolainen V, Hahn W H, Hoot S B, Fay M F, Axtell M, Swensen S M, Prince L M, Kress W J, Nixon K C, Farris J A. Angiosperm phylogeny inferred from 18S rDNA, rbcL, and atpB sequences.  Bot J Linn Soc. 2000;  133 381-461
• 21 Chase M W, Zmartzty S, Lledó M D, Wurdack K J, Swensen S M, Fay M F. When in doubt, put it in Flacourtiaceae: a molecular phylogenetic analysis based on plastid rbcL DNA sequences.  Kew Bull. 2002;  57 141-181
• 22 Mosaddik M A, Forster P I, Booth R, Waterman P G. Phenolic glycosides from some Australian species of Flacourtiaceae (Salicaceae sensu lato).  Biochem Syst Ecol. 2007;  35 166-168
• 23 Chai X Y, Song Y L, Xu Z R, Shi H M, Bai C C, Bi D, Wen J, Li F F, Tu P. Itosides J–N from Itoa orientalis and the structure-anti-COX‐2 activity relationship of phenolic glycosides.  J Nat Prod. 2008;  71 814-819
• 24 Denizot F LR. Rapid colorimetric assay for cell growth and survival modifications to the tetrazolium dye procedure giving improved sensitivity and reliability.  J Immunol Methods. 1986;  89 271-277
• 25 Chai X Y, Ren H Y, Xu Z R, Bai C C, Zhou F R, Ling S K, Pu X P, Li F F, Tu P F. Investigation of two Flacourtiaceae plants: Bennettiodendroon leprosipes and Flacourtia ramonchi. .  Planta Med. , advance online publication 2009;  DOI: 10.1055/s-0029-1185542