Calotropin

532.6

532.26723285

3XK21U1BZS

DTXSID10173613

RECTANGULAR PLATELETS FROM ALCOHOL OR ETHYL ACETATE

223 °C WITH DECOMPOSITION

SOL IN WATER, ALCOHOL; PRACTICALLY INSOL IN ETHER

CALOTROPIS PROCERA, A SHRUB NATIVE TO AFRICA, WAS THE FIRST SOURCE FOR ISOLATION OF THE CYCLIC BRIDGED GLYCOSIDES. FROM CALOTROPIS LATEX...WERE SEPARATED CALOTROPIN, CALACTIN, CALOTOXIN, USCHARIDIN, USCHARIN AND VORUSCHARIN -A NEW SERIES OF CARDENOLIDES WITH A COMMON GENIN, CALOTROPAGENIN.

EARLY STUDIES ON CARDENOLIDE SEQUESTRATION FROM MILKWEEDS WERE CARRIED OUT WITH THE GRASSHOPPER, POEKILOCERUS BUFONIUS. THIS APOSEMATIC NORTH AFRICAN SPECIES, WHICH PROBABLY FEEDS EXCLUSIVELY UPON MILKWEEDS IN NATURE, HAS A POISON GLAND FROM WHICH THE CONTENTS MAY BE EJECTED AS SPRAY DURING THE IMMATURE HOPPER STAGE, OR AS A FOAMY FROTH IN THE ADULT STAGE. THE SECRETION CONTAINS HISTAMINE AND ONE CAT-LETHAL DOSE OF CARDENOLIDE. WHEN REARED ON CALOTROPIS PROCERA OR ASCLEPIAS CURASSAVICA, THE GRASSHOPPERS SECRETION CONTAINED ONLY CALACTIN AND CALOTROPIN IN APPRECIABLE QUANTITIES OF THE SEVEN OR SO RELATED CARDENOLIDES PRESENT IN THE PLANT.|SELECTIVE STORAGE OF SOME CARDENOLIDES FROM AMONG SEVERAL IN THE FOOD PLANT WAS CONFIRMED /IN MONARCH LARVAE/... THAT METABOLIC CONVERSION MIGHT BE INVOLVED IN THIS SELECTIVITY WAS PROVEN BY SEPARATE ADMIN OF GRADED DOSES OF INDIVIDUAL CARDENOLIDES TO MONARCH LARVAE, WITH SUBSEQUENT ANALYSIS OF THE CARDENOLIDE CONTENT OF THE LARVAE & ADULTS. CALACTIN & CALOTROPIN WERE STORED INTACT, BUT USCHARIDIN WAS METABOLIZED TO A MIXTURE OF CALACTIN & CALOTROPIN, WHICH WERE THE CARDENOLIDES STORED. THIS CONVERSION, A REDUCTION, OCCURRED VERY RAPIDLY DURING FEEDING, APPARENTLY IN THE GUT. REASONS OFFERED FOR THE STOREABILITY OF CALACTIN & CALOTROPIN, BUT NOT USCHARIDIN, INCL CHEMICAL INSTABILITY OF THE LATTER IN THE GUT MILIEU, POLARITY (CALACTIN & CALOTROPIN ARE MORE POLAR THAN USCHARIDIN), & THE POSSIBILITY THAT THE C-3'OH IN THE CALACTIN & CALOTROPIN WAS NEEDED FOR BINDING TO A CARRIER AND/OR TISSUE STORAGE SITE.

(NA+,K+)-ATPASE PRESENT IN CARDIAC MUSCLE HAS BEEN PROPOSED AS THE PHARMACOLOGICAL RECEPTOR FOR CARDIAC GLYCOSIDES. INHIBITION OF THIS ENZYME SYSTEM IS THOUGHT TO BE RESPONSIBLE FOR THE THERAPEUTIC OR TOXIC EFFECTS OF CARDIAC GLYCOSIDES ON THE HEART OF VERTEBRATES. THE ABILITY OF NATURAL AND SEMISYNTHETIC CARDIAC GLYCOSIDES TO INHIBIT (NA+,K+)-ATPASE PREPARATIONS HAS BEEN USED TO PREDICT THE EXTENT OF THEIR EFFECT ON THE MYOCARDIUM. ... THE EVIDENCE CITED...INDICATES THAT ALL CARDENOLIDES MAY BE REGARDED AS HIGHLY TOXIC, THAT SENSITIVITY TO CARDENOLIDES MAY VARY CONSIDERABLY AMONG SPECIES AND THAT THE PRINCIPAL TOXIC EFFECTS ARE ASSOCIATED WITH THE MYOCARDIUM.

calotropin

CALOTROPIN CONCENTRATIONS IN CALOTROPIS PROCERA WERE MEASURED TO EVALUATE EXTRACTION TECHNIQUES & DETERMINE THE LEVELS IN DIFFERENT PLANT COMPONENTS. CONCN FROM UNEXTRACTED COMPONENTS: WHOLE PLANT 569 UG/G; STEMS 734 UG/G; LEAVES 275 UG/G; PODS 313 UG/G. CONCN FROM HEXANE EXTRACTION: WHOLE PLANT 749 UG/G; STEMS 565 UG/G; LEAVES 325 UG/G; PODS 263 UG/G. TRACE AMOUNTS WERE NOT DETECTED IN PLANT COMPONENTS FROM HEXANE AND METHANOL EXTRACTION. THE PRESUMPTIVE NUTRIENT VALUE OF EXTRACTED RESIDUE FROM CALOTROPIS PROCERA SUPPORTS CULTIVATION OF THIS PLANT SPECIES AS A POTENTIAL FUEL AND FEED RESOURCE.|...OF PARTICULAR INTEREST ARE INSECTS THAT ARE NOT ONLY TOLERANT OF THE /MILKWEED/ POISONS, BUT ADDITIONALLY HAVE THE CAPABILITY TO SEQUESTER THEM FROM THEIR PLANT HOST AND STORE THEM FOR DEFENSE AGAINST THEIR PREDATORS. ... THE MOST THOROUGHLY STUDIED WITH...MILKWEEDS /ARE/ MONARCH BUTTERFLIES, WHICH FEED UPON ASCLEPIAS DURING LARVAL DEVELOPMENT; AND BLUEJAYS, EXPERIMENTAL PREDATORS OF MONARCHS. /CARDENOLIDES/

THE TOTAL AMOUNT OF CARDENOLIDE IS GENERALLY DETERMINED BY SPECTROPHOTOMETRIC ASSAY OF A COLORED DERIVATIVE BASED ON CONVERSION OF THE STEROID OR BUTENOLIDE RINGS. ... IDENTIFICATION...BY INFRARED, NUCLEAR RESONANCE, AND MASS SPECTROMETRY MEASUREMENT. QUANTITATION IS ACHIEVED BY COMPARING A...HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY PEAK WITH THAT OF A STANDARD. /CARDENOLIDES/|...ASCLEPIAS CURASSAVICA BUTTERFLIES SEQUESTERED...CALOTROPIN... DETECTABILITY WITH HIGH PRESSURE LIQUID CHROMATOGRAPHY WAS ABOUT 0.1 UG, PERMITTING ANALYSIS OF THE MAJOR CARDENOLIDES IN A PORTION OF A SINGLE BUTTERFLY & IN AS LITTLE AS 0.1 G OF DRIED PLANT.