(3aR,4aS,5R,7R,8aS,9R,10aR)-Decahydro-5,7-dihydroxy-4a,9-dimethyl-3-methylenefuro[2′,3′:5,6]cyclohepta[1,2-c]pyran-2(3H)-one

282.33 g/mol

282.33

AYR8B2NT77

76 Ų

HYMENOVIN, A SESQUITERPENE LACTONE PREVIOUSLY REPORTED AS THE MAJOR TOXIC CONSTITUENT OF HYMENOXYS ODORATA, WAS ISOLATED FROM EXTRACTS OF HYMENOXYS RICHARDSONII AND DUGALDIA HOOPESII AND WAS SHOWN TO ACCOUNT FOR THE TOXICITY OF THESE PLANTS AS WELL. THE FINDING THAT THESE 3 POISONOUS RANGE PLANTS CONTAIN AN IDENTICAL TOXICANT IS CONSISTENT WITH PRIOR OBSERVATIONS OF VERY SIMILAR RESPONSES IN LIVESTOCK POISONED WITH THE WHOLE PLANTS.|HYMENOXYS ODORATA (BITTERWEED) IS A MAJOR POISONOUS RANGE PLANT THAT IS INDIGENOUS TO TEXAS, NEW MEXICO, COLORADO, OKLAHOMA, ARIZONA AND CALIFORNIA. HYMENOXON IS EXTRACTED FROM THIS PLANT. HYMENOXON WAS FOUND IN HYMENOXYS ODORATA, HELENIUM HOOPSII AND BAILEYA MULTIRADIATA, AND THE HYMENOXON CONTENT WAS RELATED TO THE RELATIVE TOXICITY (TO ANIMALS) OF THE 3 PLANTS.

THE SULFHYDRYL GROUP IS NOT THE PRIMARY REACTIVE SITE. HYMENOXON IS EXCRETED AS GLUCURONIDES VIA URINE AND BILE.

HYMENOVIN IS A MIXTURE OF EPIMERIC DIHEMIACETALS AND IS LETHAL TO SHEEP WHEN GIVEN ORALLY AT LEVELS AS LOW AS 100 MG/KG. HYMENOVIN PROBABLY EXERTS ITS TOXIC ACTION, AT LEAST IN PART, BY ALKYLATING SULFHYDRYL GROUPS OF KEY ENZYMES AND OTHER BODY CONSTITUENTS.

EXPTL THERAPY: ADMINISTRATION OF 2 ANTIOXIDANTS BUTYLATED HYDROXYANISOLE (BHA), ETHOXYQUIN (EQ) AND DL-METHIONINE WITH THE DIET FOR 7 DAYS PROTECTED MICE FROM ACUTE TOXICITY OF HYMENOXON.|EXPTL THERAPY: ANTIDOTAL EFFECTS OF ETHOXYQUIN (EQ) (2.5 G/SHEEP/DAY FOR 9 DAYS BEFORE POISONING) WERE SIGNIFICANT IN SHEEP POISONED WITH BITTERWEED, BUT THE PROTECTIVE EFFECTS OF BUTYLATED HYDROXYANISOLE (BHA) WERE INSIGNIFICANT. OF 6 SHEEP GIVEN EQ IN THE FEED, 5 SURVIVED 7 DOSES OF BITTERWEED (4 G/KG/DAY OR HIGHER FOR 7 DAYS), WHEREAS 5 OF 7 CONTROLS AND 4 OF 7 SHEEP GIVEN FEED WITH ADDED BHA DIED. THE ADDED EQ IN THE FEED DECREASED THE SERUM ALKALINE PHOSPHATASE ACTIVITY AND TOTAL PROTEIN, ALBUMIN, AND CALCIUM CONCENTRATIONS. SEEMINGLY, EQ IS THE FIRST PROTECTIVE AGENT WITH FIELD APPLICATION POTENTIAL FOR BITTERWEED TOXICITY.

hymenovin

HYMENOXON WAS SUCCESSFULLY EXTRACTED WITH ETHYL ACETATE FROM GROUND PLANT MATERIAL AND QUANTITATIVELY ANALYZED ON A 3% OV-17 GLC COLUMN.