Antihyperglycemic sesquiterpenes from Psacalium decompositum

Psacalium decompositum was investigated for antihyperglycemic compounds using diabetic ob/ob mice as a model for type 2 diabetes. In vivo bioassay-guided fractionation of an aqueous extract from the roots of P. decompositum led to the isolation of two new eremophilanolides, 3-hydroxycacalolide (1a)...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1999-08, Vol.62 (8), p.1088-1092
Main Authors: Inman, W.D, Luo, J, Jolad, S.D, King, S.R, Cooper, R
Format: Article
Language:English
Subjects:
Animals
Asteraceae
Asteraceae - chemistry
Biological and medical sciences
Blood Glucose - metabolism
Body Weight - drug effects
chemical constituents of plants
chemical structure
Chromatography, High Pressure Liquid
Diabetes Mellitus, Type 2 - blood
Diabetes Mellitus, Type 2 - drug therapy
Eating - drug effects
General pharmacology
hyperglycemia
hypoglycemic agents
Hypoglycemic Agents - isolation & purification
Hypoglycemic Agents - pharmacology
Magnetic Resonance Spectroscopy
Medical sciences
medicinal plants
Mice
Mice, Inbred C57BL
Mice, Obese
Molecular Conformation
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
roots
Sesquiterpenes - isolation & purification
Sesquiterpenes - pharmacology
sesquiterpenoids
spectral analysis
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Summary:Psacalium decompositum was investigated for antihyperglycemic compounds using diabetic ob/ob mice as a model for type 2 diabetes. In vivo bioassay-guided fractionation of an aqueous extract from the roots of P. decompositum led to the isolation of two new eremophilanolides, 3-hydroxycacalolide (1a) and epi-3-hydroxycacalolide (1b). A 1:1 mixture of 1a/1b exhibited antihyperglycemic activity when tested at 1.09 mmol/kg in ob/ob mice. The known furanoeremophilanes, cacalone (2a) and epicacalone (2b), were also isolated from the aqueous extract and were inactive. The known furanoeremophilane, cacalol (3), was isolated from a CH2Cl2 extract of P. decompositum roots and possessed antihyperglycemic activity. The relative stereochemistry in 1a and 1b was assigned 3R,5S and 3S,5S, respectively, based on ROESY data, 3J H-H values, and molecular mechanics calculations. Complete 13C and 1H NMR chemical shifts were assigned for 1a, 1b, 2a, 2b, and 3, and several revisions in 13C NMR assignments for 2a and 3 were made. Results from the conformational analysis of 1a, 1b, 2a, and 2b indicate that each compound exists in one major conformation in solution with H3-12 in a pseudoaxial position.
ISSN:0163-3864
1520-6025
DOI:10.1021/np990023v