Aglycone geniposidic acid, a naturally occurring crosslinking agent, and its application for the fixation of collagenous tissues.

A natural compound, aglycone geniposidic acid (aGSA), originated from the fruits of Gardenia jasminoides ELLIS was used for the fixation of collagenous tissues. The presumed crosslinking reaction mechanism of collagenous tissues with aGSA was inferred by reacting aGSA with a bifunctional amine, 1,6-hexanediamine, using a series of (1)H NMR, FT-IR, and UV/Vis spectra analyses. aGSA reacted with 1,6-hexanediamine by a nucleophilic attack on the olefinic carbon atom at C-2 of deoxyloganin aglycone, followed by opening the dihydropyran ring to form heterocyclic amine compounds. It is inferred that aGSA may form intramolecular and intermolecular crosslinks with a heterocyclic structure within collagen fibers in tissues. The degrees of tissue fixation by aGSA at different pH values were investigated by examining the fixation indices and denaturation temperatures of test samples. It was found that the fixation indices and denaturation temperatures of test samples fixed at neutral or basic pH (pH 7.4 or pH 8.5) were significantly greater than at acidic pH (pH 4.0). The results obtained in this study may be used to elucidate the crosslinking mechanism and optimize the fixation process for developing bioprostheses fixed by aGSA.

[1]  Rohit Srivastava,et al.  Stable encapsulation of active enzyme by application of multilayer nanofilm coatings to alginate microspheres. , 2005, Macromolecular bioscience.

[2]  Yen Chang,et al.  Construction of varying porous structures in acellular bovine pericardia as a tissue-engineering extracellular matrix. , 2005, Biomaterials.

[3]  F. Noyes,et al.  Meniscal material properties are minimally affected by matrix stabilization using glutaraldehyde and glycation with ribose , 2005, Journal of orthopaedic research : official publication of the Orthopaedic Research Society.

[4]  Edward J. Wood,et al.  Biochemistry (3rd ed.) , 2004 .

[5]  Yen Chang,et al.  Effects of crosslinking degree of an acellular biological tissue on its tissue regeneration pattern. , 2004, Biomaterials.

[6]  S. Hsu,et al.  Biocompatibility and biodegradation of a bone composite containing tricalcium phosphate and genipin crosslinked gelatin. , 2004, Journal of biomedical materials research. Part A.

[7]  Songjun Li,et al.  Sustained release of BSA from a novel drug delivery matrix -- bullfrog skin collagen film. , 2004, Macromolecular bioscience.

[8]  Mario Guerra,et al.  Biocompatibility of collagen membranes crosslinked with glutaraldehyde or diphenylphosphoryl azide: an in vitro study. , 2003, Journal of biomedical materials research. Part A.

[9]  J. Revilla,et al.  Recovery of Metal Ions by Chitosan: Sorption Mechanisms and Influence of Metal Speciation , 2003 .

[10]  Young Ha Kim,et al.  A novel chemical modification of bioprosthetic tissues using L-arginine. , 2003, Biomaterials.

[11]  Hsing-Wen Sung,et al.  Crosslinking of biological tissues using genipin and/or carbodiimide. , 2003, Journal of biomedical materials research. Part A.

[12]  T. Hahn,et al.  Isolation and characterization of water-soluble intermediates of blue pigments transformed from geniposide of Gardenia jasminoides. , 2002, Journal of agricultural and food chemistry.

[13]  J. Turnay,et al.  Gelatinases in soft tissue biomaterials. Analysis of different crosslinking agents. , 2002, Biomaterials.

[14]  Yen Chang,et al.  Biocompatibility study of biological tissues fixed by a natural compound (reuterin) produced by Lactobacillus reuteri. , 2002, Biomaterials.

[15]  H. Sung,et al.  In vivo evaluation of cellular and acellular bovine pericardia fixed with a naturally occurring crosslinking agent (genipin). , 2002, Biomaterials.

[16]  H. Sung,et al.  Stability of a biological tissue fixed with a naturally occurring crosslinking agent (genipin). , 2001, Journal of biomedical materials research.

[17]  H. Sung,et al.  In vitro evaluation of the genotoxicity of a naturally occurring crosslinking agent (genipin) for biologic tissue fixation. , 2000, Journal of biomedical materials research.

[18]  Yen Chang,et al.  Fixation of biological tissues with a naturally occurring crosslinking agent: fixation rate and effects of pH, temperature, and initial fixative concentration. , 2000, Journal of biomedical materials research.

[19]  H. Sung,et al.  In vitro surface characterization of a biological patch fixed with a naturally occurring crosslinking agent. , 2000, Biomaterials.

[20]  H. Sung,et al.  Biocompatibility study of a biological tissue fixed with a naturally occurring crosslinking reagent. , 1998, Journal of biomedical materials research.

[21]  H. Sung,et al.  Feasibility study of a natural crosslinking reagent for biological tissue fixation. , 1998, Journal of biomedical materials research.

[22]  D. Lin,et al.  Crosslinking characteristics of an epoxy-fixed porcine tendon: effects of pH, temperature, and fixative concentration. , 1996, Journal of biomedical materials research.

[23]  Y. Ikada,et al.  In vitro evaluation of cytotoxicity of diepoxy compounds used for biomaterial modification. , 1995, Journal of biomedical materials research.

[24]  J. Feijen,et al.  Changes in the mechanical properties of dermal sheep collagen during in vitro degradation. , 1995, Journal of biomedical materials research.

[25]  K. Kobashi,et al.  Enzymic studies on the animal and intestinal bacterial metabolism of geniposide. , 1994, Biological & pharmaceutical bulletin.

[26]  D. Lin,et al.  Fixation of bioprosthetic tissues with monofunctional and multifunctional polyepoxy compounds. , 1994, Journal of biomedical materials research.

[27]  T. Hahn,et al.  Physical stability of the blue pigments formed from geniposide of gardenia fruits: effects of pH, temperature, and light. , 2001, Journal of agricultural and food chemistry.