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A novel 16,24-dehydrobiladiene-ab system: The reaction of xanthobilirubic acid methyl ester with bromine (1995)

Ma, J. -S. ; Chen, Q. -Q. ; Wang, C. -Q. ; [et al.]

Springer

Monatshefte für Chemie 126 (1995), S. 201-209

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ISSN: 1434-4475

Keywords: 16,24-Dehydrobiladiene-ab ; Biladiene-ab ; Xanthobilirubic acid methyl ester ; Mesobilirubin-XIIIα ; Mesobiliverdin-XIIIα ; 14-Formyl-tripyrrinone ; 15,16-Dimethoxy-biladienes-ab

Source: Springer Online Journal Archives 1860-2000

Topics: Chemistry and Pharmacology

Description / Table of Contents: Zusammenfassung Der Umsatz von Xanthobilirubinsäuremethylester mit Brom in Methanol ergibt in 20-prozentiger Ausbeute ein rotes Pigment, für das die bislang nicht bekannte 16,24-Dehydrobiladien-ab-Konstitution abgeleitet wurde. Darüber hinaus konnte das entsprechende Mesobiliverdin-XIIIα, Mesobilirubin-XIIIα, 14-Formyltripyrrinon, und zwei diastereomere 15,16-Dimethoxybiladiene-ab aus der Reaktionsmischung isoliert werden. Die mechanistischen Aspekte dieser Reaktion werden diskutiert.

Notes: Summary On treating xanthobilirubic acid methyl ester with bromine in methanol, a red bile pigment, which was assigned the hitherto unknown 16,24-dehydrobiladiene-ab constitution, is obtained in 20% yield. In addition, the corresponding mesobiliverdin-XIIIα, mesobilirubin-XIIIα, 14-formyl-tripyrrinone, and two diastereomeric 15,16-dimethoxybiladienes-ab could be isolated from the reaction mixture. The mechanistic aspects of this reaction are discussed.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00812248

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Bone morphogenetic proteins inhibit adipocyte differentiation by bone marrow stromal cells (1995)

Gimble, J. M. ; Morgan, C. ; Kelly, K. ; [et al.]

New York, N.Y. : Wiley-Blackwell

Journal of Cellular Biochemistry 58 (1995), S. 393-402

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ISSN: 0730-2312

Keywords: adipocytes ; bone morphogenetic proteins ; differentiation ; bone marrow stromal cells ; transforming growth factor β ; Life and Medical Sciences ; Cell & Developmental Biology

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Biology , Chemistry and Pharmacology , Medicine

Notes: The bone morphogenetic proteins were originally identified based on their ability to induce ectopic bone formation in vivo and have since been identified as members of the transforming growth factor-β gene superfamily. It has been well established that the bone morphogenetic cytokines enhance osteogenic activity in bone marrow stromal cells in vitro. Recent reports have described how bone morphogenetic proteins inhibited myogenic differentiation of bone marrow stromal cells in vitro. In vivo, bone marrow stromal cells differentiate along the related adipogenic pathway with advancing age. The current work reports the inhibitory effects of the bone morphorphogenetic proteins on adipogenesis in a multipotent murine bone marrow stromal cell line, BMS2. When exposed to bone morphogenetic protein-2, the pre-adipocyte BMS2 cells exhibited the expected induction of the osteogenic-related enzyme, alkaline phosphatase. Following induction of the BMS2 cells with adipogenic agonists, adipocyte differentiation was assessed by morphologic, enzymatic, and mRNA markers. Flow cytometric analysis combined with staining by the lipophilic fluorescent dye, Nile red, was used to quantitate the extent of lipid accumulation within the BMS2 cells. By this morphologic criteria, the bone morphogenetic proteins inhibited adipogenesis at concentrations of 50 to 500 ng/ml. This correlated with decreased levels of adipocyte specific enzymes and mRNAs. The BMS2 pre-adipocytes constitutively expressed mRNA encoding bone morphogenetic protein-4 and this was inhibited by adipogenic agonists. Together, these findings demonstrate that bone morphogenetic proteins act as adipogenic antagonists. This supports the hypothesis that adipogenesis and osteogenesis in the bone marrow microenvironment are reciprocally regulated.

Additional Material: 4 Ill.