Curcumin is a yellow dye in the crude drug "Turmeric" (Curcumae Rhizoma) from the rhizome of Curcuma longa L. (Zingiberaceae). Curcumin is reported to have anti-inflammatory, 1) anti-oxidative, 2) liver protective, 3) anti-spastic 4) and anti-tumor effects. 5) We reported that curcumin had an antiallergic effect using the type I and IV allergy model animals 6) and also that curcumin had an inhibitory effect on histamine release from rat peritoneal mast cells. 7)Several curcumin-related compounds occur in plants or biometabolites. Curcuminoids such as curcumin, monodemethoxycurcumin and bis-demethoxycurcumin are contained in the crude drug "Turmeric".2) Tetrahydrocurcumin (THC) is known to be an active metabolite of curcumin. 8,9) Curcuminoids are pharmacologically active agents of the crude drug "Turmeric" for multiple pharmacological activities.10) However, few, if any, reports have so far been concerned with which action of curcuminoids may be fundamental for exerting a variety of actions. Therefore, we focused our attention on the anti-oxidative and anti-allergic activities of curcumin-related compounds in order to see if the anti-allergic activities originate in anti-oxidative activities. Furthermore, we were very interested in the chemical features of curcumin or THC for exerting the anti-oxidative and anti-allergic activities.In the present study, we investigated anti-allergic and antioxidative effects of curcumin-related compounds (glycosides, reductants and bis-demethoxy analogs) in order to elucidate the chemical structural features of curcumin. The anti-allergic activities were assessed by measurement of histamine release from rat basophilic leukemia (RBL-2H3) cells. The anti-oxidative activities were evaluated by measurement of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in cell-free solution and superoxide anion in cells. Finally, we discussed the underlying mechanisms on anti-allergic activities of curcumin-related compounds with special reference to their anti-oxidative activities. MATERIALS AND METHODSMaterials Curcumin, concanavalin A (Con A) and phosphatidyl serine were purchased from Sigma Japan Co. (Tokyo, Japan). Histamine · 2HCl, 2,2-diphenyl-1-picrylhydrazyl (DPPH), phorbol-12-myristate-13-acetate (PMA), cytochrome c (from bovine heart), superoxide dismutase (SOD) and o-phthalaldehyde were purchased from Wako Pure Chemical Co. (Osaka, Japan). Calcium ionophore A23187 was purchased from Calbiochem Co. (CA, U.S.A.).0.05% BSA-Tyrode buffer (pH 7.4) was prepared in distilled water and consisted of NaCl (137 mM), KCl (2.7 mM), N-(2-hydroxyethyl)piperazine-NЈ-ethanesulfonic acid (HEPES) (10 mM), glucose (5.6 mM), CaCl 2 (1.0 mM), MgCl 2 (1.0 mM), NaH 2 PO 4 · 2H 2 O (0.4 mM) and bovine serum albumin (BSA) (0.05%). Phosphate buffer saline (PBS) (pH 6.8) was prepared in distilled water and consisted of NaCl (137 mM), KCl (2.7 mM), Na 2 HPO 4 · 12H 2 O (8.0 mM) and KH 2 PO 4 (1.5 mM). Preparation of Curcumin-Related CompoundsWe prepared fifteen curcumin-related compounds by chemical modification o...

ABSTRACT. In the canine liver with portosystemic shunts (PSS), focal lesions consisting of cells with cytoplasmic brown pigments and lipid vacuoles are often observed in the hepatic parenchyma. Termed lipogranulomas, their histopathological characteristics have been little studied. In the present study, we examined liver biopsy samples from 144 dogs (age: 3 months-16 years; 65 PSS and 79 non-PSS cases), and investigated the histopathological characteristics, incidence, and density of lipogranulomas. Lipogranulomas were detected histopathologically in 55.4% of PSS dogs. The lesions were then grouped into 3 types according to the amount of cytoplasmic lipid vacuoles and brown pigments. The pigments were positive for Berlin blue, PAS, and Sudan black B, but negative with the Hall method. The majority of the cells were immunohistochemically positive for macrophage scavenger receptor, class A (MSR-A), while no cells were positive for hepatocyte-antigen and albumin. The cytoplasmic pigments were recognized as electron-dense microgranular materials by electron microscopy. The incidence of lipogranulomas was significantly higher in the PSS group than non-PSS group when dogs less than 1 year old were excluded. The lipogranuloma density in the liver was significantly higher in the PSS group. It is concluded that lipogranulomas are frequently observed in liver biopsies of canine PSS especially in dogs more than 1 year old. The lesions consisted of Kupffer cells and/or macrophages, and the cytoplasmic brown pigments are ceroid and hemosiderin. The pathogenesis of lipogranuloma in PSS needs to be clarified.

Spontaneous progressive nephropathy dominated by glomerular lesions in common marmosets has been reported. However, the histopathologic characteristics, including the relationship between glomerular and tubulointerstitial lesions, have not been described in detail. In the present study, the authors examined the histopathologic characteristics of the background renal lesions in common marmosets (3 males and 9 females, 3 to 8 years old). The severity of glomerular lesions was graded into 3 classes: grade I, no alteration; grade II, hilar/focal increase of mesangial matrix; grade III, global/diffuse increase of mesangial matrix. Tubulointerstitial lesions (tubular regeneration and hyperplasia and interstitial inflammation and fibrosis) were scored according to the area of each lesion. The renal lesions were characterized by enlargement of glomeruli, expanded mesangial area with increase of periodic acid-Schiff reaction-positive matrix, tubular regeneration and hyperplasia, and interstitial inflammation and fibrosis. Glomerular lesions progressed with increasing mesangial matrix and aging. Additionally, the tubulointerstitial lesions became exacerbated with progressing glomerular lesions. Tubular hyperplasia was divided into 4 types according to the structure of the cell layer (simple or stratified-like), the area of increased lining cells (partial or entire), cytoplasmic staining (eosinophilic or basophilic), brush border and thickness of basement membrane, and the activity of cell proliferation. In conclusion, the background renal lesions in common marmosets were characterized by glomerular lesions with increase of mesangial matrix, which progressed with aging, and secondary tubulointerstitial lesions, including tubular hyperplasia. Those lesions were thus diagnosed as progressive glomerulonephropathy in common marmosets.

Condensation of glycosylated arylaldehyde with acetylacetone-B 2 O 3 complex gave a corresponding diglycosylcurcuminoid, and a similar reaction using a mixture of arylaldehyde and glycosylarylaldehyde gave an unsymmetrical monoglycosylcurcuminoid, both as boron-complexes. The boron was removed from the complexes by heating in methanol, thus achieving the synthesis of di-and mono-glycosylcurcuminoids.

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