Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-09-28
1997-10-28
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540103, C07J 7100, C07J 1700
Patent
active
056819501
ABSTRACT:
Withajardins A-D are new class of withanolides isolated from the leaves of Deprea orinocensis and characterized by having a bicyclic C-17.beta. system and hydroxyl group at C-14 and C-17. The bicyclic system consists of a lactone and a homocyclic ring with six carbon atoms unlike the acnistins which have a five-membered homocyclic ring. The two classes of compounds were differentiated and their structures were identified by a series of HMQC, HMBC and finally X-ray diffraction experiments. Withajardins and acnistins would seem to evolve along quite dissimilar biosynthetic pathways although both types of compound show a marked immunosupressive effect on in vitro cultures of human lymphocytes.
REFERENCES:
patent: 5494668 (1996-02-01), Patwardhan
Kirson et al. "Recent Developments in Naturally Occurring Ergostane-Type Steroids", Jnl. of Natural Products, 44:633-647 (1981).
Glotter "Withanolides and Related Ergostane-type Steroids", Natural Product Reports, 8:415-440 (1991).
Ksebati et al. "Minabeolides: A Group of Withanolides from a Soft Coral, Minabea sp.", Jnl. Org. Chem., 53:3926-3929 (1988).
Kupchan et al. "Tumor Inhibitors. XXXIX. Active Principles of Acnistus arborescens. Isolation and Structural and . . . ", Jnl. Org. Chem., 34:3858-3866 (1969).
Suffness et al. "Current Status of the NCl Plant and Animal Product Program", Jnl. of Natural Products, 45:1-14 (1982).
Shohat et al. "Immunosuppressive Activity of Two Plant Steriodal Lactones Withaferin A and Withanolide E", Biomedicine, 28:18-24 (1978).
Budhiraja et al. "Anti-inflammatory Activity of 3 .beta.-Hydroxy-2,3-dihydro-withanolide F", Planta Medica, 134-136 (1984).
Budhiraja et al. "Protective Effect of 3 .beta.-Hydroxy-2,3-dihydrowithanolide F Against CCl.sub.4 -induced Hepatotoxicity", Planta Medica 28-29 (1986).
Kawai et al. "Physalins N and O From Physalis Alkekengi", Phytochemistry, 31:4299-4302 (1992).
Luis et al. "Withajardins, Withanolides with a New Type of Skeleton Structure of Withajardins A, B, C and D Absolute Configuration of Withajardin C", Tetrahedron, 50:1217-1226 (1994).
Gutierrez et al. Abstract--"The Structure of Withajardins B, C, D and E".
Echeverri et al. Abstract--"Immunomodulatory Activity of Withajardin A".
Echeverri et al., Structure of Withajardin B, Spectroscopy, vol. 7 (5-6), pp. 345-352 (1989).
Echeverri et al., Withajardin: A new type of withanolides, Spectroscopy Internation Journal, vol. 6, pp. 137-146 (1988).
Cardona-Rendon Gloria
Echeverri-Lopez Luis F.
Garcia-Moreno Luis F.
Gonzalez-Gonzalez Antonio
Gutierrez-Luis Javier
Colciencias
Rao Deepak R.
Shah Mukund J.
Universidad De Antioquia
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