Nepeta lactone

Cavill and his co-workers have reported stereospecific syntheses of the enantiomers of two naturally occurring cyclopentanoid monoterpenes, iridodial and nepeta-lactone, from the common precursor D-(+)-pulegone 219, Scheme 35).299 ... 

Diethyl ether extract of plant and nepeta-lactones have shown in vitro antibacterial and antifungal activities. ° Vapors of nepetalactone have shown repellent activity in 13 families of insects. The essential oil and the two isomers of nepetalactone have shown insect repellent activity to subterranean termites (Reticulitermes spp) and to male German cockroaches Blattella germanica) ,Z-nepe-talactone showed greater repellent activity than DEBT (A,V-diethyl-3-methylbenzamide). ... 

Content and composition of essential oils from Nepeta L. species, most of them containing diastereomeric nepetalactones, unsaturated 8-lactones with annelated cyclopentane ring 98KPS84. 

Nepetalactone (Fig. 11.5c), a monoterpene lactone (or iridoid) from the volatile oil of catmint, Nepeta cataria, excites domestic cats and other felids (Todd, 1962 Palen and Goddard, 1966 Hill etal, 1976). 

Coumarin 162 (Structure 4.49) is a naturally occurring lactone in crystal form found in hay and tonka beans. It is one of the most used fragrance materials and is responsible for spicy green notes. Dihydrocoumarine 163 is also present in various essential oils with a characteristic sweet herbal odour. Umbellif-erone 164, scopoletin 165, bergaptene 166 and coumarin are found in Rutaceae, Apiaceae, Lamiaceae and Asteraceae oils. Nepetalactones 167 are confined to the oils of Nepeta species [1,3, 21-23, 63]. 

Simple iridoids are volatile iridoids of which the best known is the cat-exciting nepetalactone (C5 C50L) from Nepeta cataria (catnip) (Lamiaceae). The lactone nepetalactone, the hemiacetal neomatatabiol (G51G50H), iridodiol (in the ring opened bi-aldehyde... 

Among the monoterpenoid lactones, derivatives of the iridane series 600) have acquired limited importance as aroma substances. Nepetalactone (143) occurs in quantities of up to 78% in American oil of catnip Nepeta cataria L.) 490), while epinepetalactone (144) is the major constituent (70%) of the essential oil of Nepeta mussini L. 490). The essential oil of this species was also found to contain neonepetalactone (146) as well as the two saturated compounds a- and 5-dihydronepetalactones (147) and (148) 490, 518) and 5,9-dehydronepetalactone (145) 528). Both dihydro compounds (147) and (148) are structurally closely related to the iri-domyrmecins from Actinidia polygama 515, 516). Lactones (143) to (150) are aroma compounds which have a strong odor and which exert an attracting effect on Felidae 518, 519). 

The feline attractant, nepetalactone, has been thoroughly studied as to structure, occurrence and metabolism by Waller and co-workers (16). The biological active component is a bicyclic monoterpene lactone found in Nepeta catarla with the common name catnip (17). 

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