ABSTRACT
A review of our latest developments in the synthesis of sesquiterpenolides isolated from plants of the Umbelliferae family is presented.
Subject(s)
Apiaceae/metabolism , Sesquiterpenes/metabolism , Stereoisomerism , Thapsigargin/metabolismABSTRACT
A phenylpropanoid 1, a slovenolide 2, and two germacranes bearing a methylthiopropenoate moiety, 3 and 4, along with twenty known metabolites have been isolated from the roots of Thapsia villosa var. villosa L. The structures of two known phenylpropanoids 5 and 6 have been corrected. Compounds 7 and 8 showed activity as potential inhibitors of the sarco- and endoplasmic Ca(2+)-dependent ATPases (SERCA) pump. Compounds 9, 10 and 11 increased significantly the cytoplasmic free calcium concentration ([Ca(2+)](c)) in human platelets in a concentration-dependent manner.
Subject(s)
Blood Platelets/metabolism , Calcium-Transporting ATPases/antagonists & inhibitors , Calcium/blood , Enzyme Inhibitors/pharmacology , Plant Extracts/pharmacology , Thapsia/chemistry , Dose-Response Relationship, Drug , Enzyme Inhibitors/isolation & purification , Heterocyclic Compounds, 3-Ring/isolation & purification , Heterocyclic Compounds, 3-Ring/pharmacology , Humans , Lactones/isolation & purification , Lactones/pharmacology , Molecular Structure , Plant Extracts/chemistry , Plant Roots , Propanols/chemistry , Propanols/isolation & purification , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Sesquiterpenes, Germacrane/chemistry , Sesquiterpenes, Germacrane/isolation & purification , Sesquiterpenes, Germacrane/pharmacology , Sesquiterpenes, Guaiane/isolation & purification , Sesquiterpenes, Guaiane/pharmacology , Sulfhydryl Compounds/isolation & purification , SulfurABSTRACT
Nine new eudesmanolides (1-9), two new guaianolides (12 and 13), and a new germacrane (10), along with a previously reported guaianolide (11), have been isolated from the roots of Thapsia nitida var. meridionalis. Thapsia nitida var. nitida also afforded compound 13 along with a new guaianolide (14). The structure of 13 was confirmed by X-ray crystallographic analysis. Compounds 1, 2, and 11-14 have been tested as potential inhibitors of the sarco- and endoplasmic Ca2+-dependent ATPases (SERCA) pump. None of them showed significant activities.
Subject(s)
Plants, Medicinal/chemistry , Sarcoplasmic Reticulum Calcium-Transporting ATPases/antagonists & inhibitors , Sesquiterpenes/isolation & purification , Thapsia/chemistry , Crystallography, X-Ray , Molecular Conformation , Molecular Structure , Plant Roots/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , SpainABSTRACT
Four novel and unusual C-19 compounds from Thapsia transtagana, named transtaganolides A-D, have been isolated. Their structures were established by physical methods, including X-ray analysis of transtaganolides A and B. This is the first time that a 7-methoxy-4,5-dihydro-3H-oxepin-2-one ring has been found in a natural product. [structure: see text]