Piperitone oxide

The two diastereomers of cis- and rmws-piperitone oxide are 1,2-epoxy-3-keto-p-menthanes, which have been found in various plant species. The most abundant natural sources of these compounds are plants belonging to the Lamiaceae family, especially Mentha and Calamintha In many publications, the authors gave no details on the diastereomeric composition of piperitone oxides, probably because of their very similar retention times on a non-polar column. 

S,2S,AS) —)-trans-V vpcntonc oxide (dihydro rotundifolone) has been isolated for the first time from Mentha longifolia by Reitsema and Varnis. The presence of the (15,25,4i )(—l-ar-isomer was reported in aAf. spicata mutant. Only enantiomerically pure levorotatory piperitone oxides, (15,25, AS)-trans piperitone oxide and (15,25, AR)-cis piperitone oxide, were detected by chiral GC analysis of Micromeria fruticosa and Mentha longifolia The occurrence of the cis- and trans- piperitone oxides was dependent on the population of the species. In most cases, the enantiomeric composition of trans- and cis- piperitone oxides detected in various essential oils is unknown. 

The antimicrobial activity of piperitone oxide rich Mentha rotundifolia M. suaveolens) oil was investigated by Oumzil et al., who found it less significant than that of pulegone or piperitone rich oils. The biosynthesis of the two levorotatory diastereomers from (15,25)(+)-piperitenone oxide... 

Larkov O, Matasyoh JC, Dudai N, Lewinsohn E, Mayer AA, Ravid U, Distribution of piperitone oxide stereoisomers in Mentha and Micromeria species and their chemical syntheses. Flavour Fragr/22 328—333, 2007. 

Reitsema RN, Varnis JV, The isolation of piperitone oxide from Mentha sylvestris, JAm Chem 5oc 78 3792-3794, 1956. 

The chemical constituents of H. suaveolens comprise of essential oils and a few triterpenes (49, 50, 51, 52). Iwu et al. (53) identified in the steam distilled oil 32 terpenoid compounds. The major compounds were limonene thujane, a.-pinene, a.-phellandrine, 3-cyclohexen-l-ol, 4-methyl-l-(l-methylethyl)-3-cyclohexen-1 -ol, 3 -cyclohexen-1 -carboxyaldehyde, elemene, 4,11,11 -trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene, octahydro-l,4-dimethylazulene, 5.a., 8.p.,H-9.p.,H-10.a.-labd-14-ene 5.a-androst-9(ll)-en-12-one and 5.a.-androstan-2,ll-dione. Fun et al. (54) showed by GC analysis that the oil has high contents of 1,8-cineole (27-38%) and sabinene (12-18%). Analysis of the oil by Thoppil and Jose (55) showed the presence of citronellyl acetate, fl-caryophyllene, piperitone oxide and geranyl acetate. Zollo et al. (56) reported that the most abundant compounds in the oil collected from Cameroon were hydrocarbons (> 58%). Tchoumbougnang et al. (57) reported the presence of sabinene (20.6%), yff -caiyophyllene (17.5%) and bergamotol (10.9%) as the... 

Phytochemistry Aboveground parts contain essential oil with menthol, menthone, carvacrol, and pulegone (Khalmatov 1964 Gulluce et al. 2007). Thirty-seven componnds were characterized representing 97 % of the total components detected. The major constituents of the oil were trans-piperitone oxide (64.51 %) and piperitenone oxide (12.34 % Baser et al. 1997a). The seeds contain a variety of different fatty acids (Gusakova et al. 1976). 

Methylnona-2,3-dienoic acid, X1.9 Iridodial, T13.13 traAW-Pulegenic acid, A38.2 Piperitone oxide, T4.2 c -Chrysanthemic acid, A35.10, T"10 tran -Chrysanthemic acid, A35.6, T"20... 

Lahlou, S., Carneiro-Leao, R. F. L., Leal-Cardaso, J. H., Toscano, C. F. 2001. Cardiovascular effects of the essential oil of Mentha x villosa and its main constituent, piperitone oxide, in normotensive anaesthe tised rats Role of the autonomic nervous system, 67(7) 638-643. 

Miyazawa, M., H. Kakita, M. Hyakumachi, K. Umemoto, and H. Kameoka, 1991d. Microbiological conversion of piperitone oxide by plant pathogenic fungi Rhizoctonia solani. Proceedings of the 35th TEAC, pp. 276-277. 

Gyanchandani [85] has thus chromatographed caraway seed oil and dill oil under standard conditions and determined the position of the limonene epoxide (1,2) which had been formed by autoxidation of limonene. Nigam, Sahasrabudhe and Levi [185] have detected piperitone oxide in peppermint oils in a similar way. Attention has been drawn repeatedly to the bisabolene oxides I, II and III along with chamazulene in the assessment of camomile oils [78, 224, 305, 306]. 

Piperinic acid, T1 Piperitenone oxide, T4 Piperitols, T4 Piperitone, T2 Piperitone oxide, T4 Pipitzols, T1 Pisatin, Y3 Piscidic acid, A30 Plathyterpol, T39 Platicodigenin, T45 Platydesmine, K31 Platynecine, K22 Plicatic acid, Y7 Plinols, T3 Plumericin, T16 Plumieride, T16 Pluviine, K6 Podocarpic acid, T33 Podolactones, T38 Polyether antibiotics, Yll Polyporenic acid A, T50 Ponasterone, T48 Porantherine, K29 Porphyrins, Y23 Portentol, Y15 Portulal T40 Preisocalamendiol, T22 Pretoxin, T31 Pristimerin, T45 Pristimerol, T45 Proaporphine alkaloids, K3 Proline, All Prolinol, A17 Pronuciferine, K3 19-propylthevinol, K4 Prostaglandins, Y16 Protoaphins, YIO Protoemetine, K2 Protostanes, T50... 

Piperinic acid, T1 Piperitenone oxide, T4 Piperitols, T4 Piperitone, T2 Piperitone oxide, T4 Pipitzols, T1 Piptamine, K6 ... 

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