Synthesis
A 5 mol% IMesCuCl (13.6 mg) catalyst was added to an anhydrous toluene (1 mL) solution of 1,1-disubstituted epoxide (0.2 mmol). The resulting reaction mixture was heated under reflux for several hours. DAM (0.3 mmol) was slowly added dropwise to the reaction system using a syringe pump over approximately 2 hours. The reaction vessel was then sealed, and the reaction was stirred under reflux for another 2 hours. After the reaction was complete, a saturated NH4Cl aqueous solution (1 mL) was added to the reaction mixture to quench the reaction. The reaction mixture was extracted twice with dichloromethane (3 × 2 mL). The organic layers were then combined, the organic components were washed with brine, and the organic layers were dried with anhydrous Na2SO4. The combined organic matter was filtered to remove the drying agent. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel (n-hexane/ethyl acetate = 10:1~3:1) column chromatography to obtain the target product, juniperene.
Figure: Synthetic Route of SABINENE
Description
Sabinene is a bicyclic monoterpene found in a variety of plants, including
Cannabis, that has antifungal and anti-inflammatory properties. It inhibits the growth of various fungi
in vitro, including several species of
Candida,
Trichophyton, and
Aspergillus (MICs = 0.16-5 μl/ml). Sabinene (0.32 μl/ml) prevents increases in nitrite production in RAW 264.7 macrophages stimulated by LPS and IFN-γ. It is cytotoxic to RAW 264.7 macrophages and HaCat keratinocytes when used at a concentration of 1.25 μl/ml. Formulations containing sabinene have been used as perfume additives.
Uses
Sabinene is an essential oil component, found to have bactericidal activity.
Definition
ChEBI: A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.
in vivo
Sabinene (6.4 mg/kg; p.o.; once daily; during the fasting for 2 d) attenuates skeletal muscle atrophy by regulating the activation mechanism of ROS-mediated MAPK/MuRF-1 pathways in starved myotubes, probably leading to the reverse of reduced muscle fiber size in fasted rats[2].
| Animal Model: | Fasted animal model in rat[2] |
| Dosage: | 6.4 mg/kg |
| Administration: | Oral gavage; once daily; during the fasting for 2 days |
| Result: | Reduced the levels of muscle fiber atrophy and MuRF-1 expression in gastrocnemius from fasted rats. |
References
[1] YUJIN CAO. Biosynthesis and production of sabinene: current state and perspectives[J]. Applied Microbiology and Biotechnology, 2017, 102 4: 1535-1544. DOI:
10.1007/s00253-017-8695-5[2] J. VALENTE . Antifungal, antioxidant and anti-inflammatory activities of Oenanthe crocata L. essential oil[J]. Food and Chemical Toxicology, 2013, 62: Pages 349-354. DOI:
10.1016/j.fct.2013.08.083
