Isocupressic acid

Catalogue number C101464
Chemical nameIsocupressic acid
CAS Number1909-91-7
Synonyms(1S,4aR,5S,8aR)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Molecular WeightC20H32O3
Formula320.5
Purity98%
Physical DescriptionOil
SolventChloroform, Dichloromethane,DMSO
StorageStored at 2-8°C, Protected from air and light, refrigerate or freeze
Applications

Isocupressic acid (ICA) induces abortion in pregnant cows when ingested primarily during the last trimester. The objective of this study was to investigate the effects of isocupressic acid on bovine oocyte maturation (in vitro maturation (IVM)-Experiment I) and preimplantation embryo development (in vitro culture (IVC)-Experiment II) using in vitro embryo production techniques and to subsequently evaluate viability and developmental competence of ICA-cultured embryos via embryo transfer to recipient heifers (Experiment III). A complete randomized block experimental design was used. In Experiment I and II, isocupressic acid was added to IVM or IVC media at 0 (TRT1, control), 1.3 (TRT2), and 2.6 microg/ml (TRT3) Results from Experiment I and II indicated that ICA did not inhibit oocyte maturation and did not adversely affect preinpiantation embryo development. Furthermore, results from Experiment II demonstrated that isocupressic acid enhanced bovine preimplantation embryo development in vitro in a dose dependent manner. Subsequently, all but two births were normal as evaluated by post natal veterinary examination. In conclusion, ICA showed no adverse effects on oocyte maturation and preimplantation embryo development in vitro or subsequent viability in vivo using the ICA concentrations and in vitro culture parameters of this study.

Isocupressic acid results in the decrease in progesterone secretion, which affects the angiogenesis of the female reproductive system. The decrease in blood flow and apoptosis of corpus luteum-derived endothelial cells of the uterine tissue results in abortion. However, a more detailed and in-depth study is needed to obtain strong supporting evidence for this hypothesis of Isocupressic acid-induced abortive mechanism in pregnant cows.

References1. J. Nat. Prod., 1998, 61(1), 51-56.
2. Anim Reprod Sci., 2004, 81(3-4), 237-244.
3. The American Journal of Chinese Medicine, 2002, 30(4), 533-541.
4. J. Agric. Food Chem., 1994, 42 (3), 756-761.
5. New Zealand Veterinary Journal, 1996, 44(3), 109-111.
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Isocupressic acid
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