€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****PLANT MOLECULAR BIOLOGY***** Clark IM Forde BG Hallahan DL Spatially distinct expression of two new cytochrome P450s in leaves of Nepeta racemosa: identification of a trichome-specific isoform. In: Plant Mol Biol (1997 Mar) 33(5):875-85 ISSN: 0167-4412 Using a PCR-based approach, two novel cytochrome P450 cDNAs were isolated from a catmint (Nepeta racemosa) leaf cDNA library. The cDNAs (pBSK3C7 and pBSK4C3) were 76.9% identical in their nucleotide sequences, indicating that they are the products of two closely- related genes. A comparison of the sequence of these cDNAs with database sequences indicated that they represent new members of the CYP71 gene family of plant cytochrome P450s. Clone pBSK3C7 contains the full-length coding sequence of a cytochrome P450, whilst pBSK4C3 lacks ca. 6 codons at the 5' end. The cytochromes P450 encoded by these clones were designated CYP71A5 and CYP71A6 (pBSK3C7 and pBSK4C3, respectively). Southern blot analysis indicated that the corresponding genes were present as single copies in the genome of N. racemosa. Northern blot analysis showed that a gene homologous with CYP71A5 was expressed in the related species N. cataria, but no homologue of CYP71A6 was detected in this species. Expression of CYP71A5 in N. racemosa was maximal in flowers, tissues within the apical bud, and young expanded leaves. That of CYP71A6 was maximal in older leaves. Expression of CYP71A5 occurred exclusively in trichomes present on the leaf surfaces, in contrast to that of CYP71A6, which occurred predominantly within the leaf blade tissues. Registry Numbers: 9035-51-2 (Cytochrome P-450) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****APPLIED AND ENVIRONMENTAL MICROBIOLOGY***** Saxena J Mathela CS Antifungal activity of new compounds from Nepeta leucophylla and Nepeta clarkei. In: Appl Environ Microbiol (1996 Feb) 62(2):702-4 ISSN: 0099-2240 Iridodial beta-monoenol acetate, isolated from the essential oil of Nepeta leucophylla Benth, and actinidine from N. clarkei Benth were screened for antifungal activities against Aspergillus flavus, Aspergillus ochraceus, Penicillium citrinum, and Penicillium viridicatum, all known mycotoxin-producing taxa, and Sclerotium rolfsii and Macrophomina phaseolina, potential soybean pathogens. Iridodial beta-monoenol acetate was most effective against S. rolfsii, while actinidine was highly active against M. phaseolina. Registry Numbers: 524-03-8 (actinidine) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS***** Hallahan DL West JM Wallsgrove RM Smiley DW Dawson GW Pickett JA Hamilton JG Purification and characterization of an acyclic monoterpene primary alcohol:NADP+ oxidoreductase from catmint (Nepeta racemosa). In: Arch Biochem Biophys (1995 Apr 1) 318(1):105-12 ISSN: 0003-9861 A soluble monoterpene primary alcohol:NADP+ oxidoreductase has been purified to apparent homogeneity from leaves of the catmint, Nepeta racemosa. The purified enzyme consisted of two polypeptides, with molecular masses of 42,000 and 40,000 Da, and contained zinc ions. A number of monoterpene alcohols (geraniol, nerol, citronellol, and their hydroxylated derivatives) were substrates, but the enzyme was inactive toward ethanol. The enzyme required NADP(H) as cofactor, with NAD(H) ineffective. Gas chromatographic and coupled mass spectrometric analysis of the reaction products showed that 10- hydroxygeraniol and 10-hydroxynerol were oxidized by the enzyme in the presence of NADP+, at both C-1 and C-10. These results are consistent with a role for this enzyme in the biosynthesis of iridoid monoterpenes. Registry Numbers: EC 1.1 (Alcohol Oxidoreductases) EC 1.1.1.- (acyclic monoterpene primary alcohol - NADP(+) oxidoreductase) 53-59-8 (NADP) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****BIOCHIMICA ET BIOPHYSICA ACTA***** Hallahan DL Lau SM Harder PA Smiley DW Dawson GW Pickett JA Christoffersen RE O'Keefe DP Cytochrome P-450-catalysed monoterpenoid oxidation in catmint (Nepeta racemosa) and avocado (Persea americana); evidence for related enzymes with different activities. In: Biochim Biophys Acta (1994 Sep 28) 1201(1):94-100 ISSN: 0006-3002 A cytochrome P-450 present in ripening avocado (Persea americana) fruit mesocarp (CYP71A1) had previously been shown to metabolize the monoterpenoids nerol and geraniol (Hallahan et al. (1992) Plant Physiol. 98, 1290-1297). Using DNA encoding CYP71A1 as a hybridization probe, we have shown by Southern analysis that a related gene is present in the catmint, Nepeta racemosa. RNA blot analysis, together with Western analysis of catmint leaf polypeptides using avocado cyt P-450 antiserum, showed that a closely related gene is expressed in catmint leaves. Cytochrome P-450 in catmint microsomes catalysed the specific hydroxylation of nerol and geraniol at C-10, whereas avocado CYP71A1, in either avocado microsomes or heterologously expressed in yeast, catalysed 2,3- or 6,7-epoxidation of these substrates. These results suggest that orthologous genes of the CYP71 family are expressed in these two plant species, but catalyse dissimilar reactions with monoterpenoid substrates. Registry Numbers: 624-15-7 (geraniol) 9035-51-2 (Cytochrome P-450) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****CHEMICAL AND PHARMACEUTICAL BULLETIN***** Murai F Tagawa M Damtoft S Jensen SR Nielsen BJ (1R,5R,8S,9S)-Deoxyloganic acid from Nepeta cataria. In: Chem Pharm Bull (Tokyo) (1984 Jul) 32(7):2809-14 ISSN: 0009-2363 [No Abstract Available] €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****DRUG METABOLISM AND DRUG INTERACTIONS***** Hallahan DL West JM Cytochrome P-450 in plant/insect interactions: geraniol 10- hydroxylase and the biosynthesis of iridoid monoterpenoids. In: Drug Metabol Drug Interact (1995) 12(3-4):369-82 ISSN: 0792-5077 The interactions between plant secondary metabolites (particularly monoterpenes) and insects are discussed. Such metabolites are likely to have influenced the evolution of cyt P450-linked detoxification systems in animals, through animal/plant coevolution. The biosynthesis of many classes of plant secondary metabolites involves cyt P450 enzymes. Of these, one of the best characterised is the geraniol/nerol 10-hydroxylase which catalyses a key step in the biosynthesis of the iridoid class of plant terpenes. It would appear that these monoterpenoids are synthesised (via cyt P450 hydroxylation) from different precursors in different plant species, namely geraniol, its isomer nerol, or the related monoterpenoid, citronellol. We show that cyt P450 from the plants Catharanthus roseus and Nepeta racemosa are capable of hydroxylating geraniol, nerol and citronellol, and thus do not impose precursor specificity on iridoid biosynthesis in plants. Registry Numbers: EC 1.14. (Hydroxylases) EC 1.14.- (geraniol 10-hydroxylase) 9035-51-2 (Cytochrome P-450) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****EXPERIENTIA***** Sherry CJ Hunter PS The effect of an ethanol extract of catnip (Nepeta cataria) on the behavior of the young chick. In: Experientia (1979 Feb 15) 35(2):237-8 ISSN: 0014-4754 The alcohol extract of catnip has a biphasic effect on the behavior of young chicks. Low and moderate dose levels (25--1800 mg/kg) cause increasing numbers of chicks to sleep, while high dose levels (i.e. above 2 g/kg) cause a decreasing number of chicks to sleep. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF ETHNOPHARMACOLOGY***** Panizzi L Flamini G Cioni PL Morelli I Composition and antimicrobial properties of essential oils of four Mediterranean Lamiaceae. In: J Ethnopharmacol (1993 Aug) 39(3):167-70 ISSN: 0378-8741 Essential oils from Satureja montana L., Rosmarinus officinalis L., Thymus vulgaris L., and Calamintha nepeta (L.) Savi, were chemically analysed and their antimicrobial and fungicide activities evaluated on the basis of their minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). All four oils have a biotoxic effect, the most active being those from Calamintha and Thymus. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF NATURAL PRODUCTS***** Mathela CS Gupta A Upreti P Pant AK Olmstead MM Hope H Bottini AT Coleon U 12-methyl ether from Nepeta leucophylla. In: J Nat Prod (1991 May-Jun) 54(3):910-2 ISSN: 0163-3864 [No Abstract Available] Registry Numbers: 65714-80-9 (coleon U 12 methyl ether) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****LLOYDIA***** Harney JW Barofsky IM Leary JD Behavioral and toxicological studies of cyclopentanoid monoterpenes from Nepeta cataria. In: Lloydia (1978 Jul-Aug) 41(4):367-74 ISSN: 0024-5461 Two samples of catnip oil were analyzed by tic, gc, and hplc; the results indicated the presence of 23 components. Fractionation of the commercial sample of catnip oil by either distillation or gc yielded 40% nepetalactone and 43% nepetalic acid. Catnip oil, nepetalic acid, and a nepetalactone-enriched fraction were evaluated for toxicological and behavioral effects in mice and rats. The LD50 of catnip oil, the nepetalactone-enriched fraction, and nepetalic acid were found in mice to be: 1300 mg/kg, 1550 mg/kg and 1050 mg/kg, respectively. Catnip oil (500 mg/kg) and nepetalic acid (62.5 mg/kg) were found to significantly increase hexobarbital sleeping time in mice. Rats trained on a Sidman avoidance schedule showed a significant decrease in performance following intraperitoneal injections of catnip oil (500--750 mg/kg), nepetalic acid (125--250 mg/kg), and the nepetalactone-enriched fraction (500--750 mg/kg). Rats trained on the same avoidance schedule developed behavioral tolerance after daily injections of 750 mg/kg catnip oil. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****VETERINARY AND HUMAN TOXICOLOGY***** Massoco CO Silva MR Gorniak SL Spinosa MS Bernardi MM Behavioral effects of acute and long-term administration of catnip (Nepeta cataria) in mice. In: Vet Hum Toxicol (1995 Dec) 37(6):530-3 ISSN: 0145-6296 Catnip or catmint (Nepeta cataria) is a plant used extensively to treat human diseases and in toys for pets. We investigated the effects of acute and long-term administration of the plant on some behaviors of mice. The plant was fed as 10% of the normal diet for 2 h/d for 1 or 7 d. Acute and long-term dosing increased both rearing and locomotion frequencies observed in an open field. Acute exposure to catnip increased stereotyped behavior and susceptibility to seizures, did not interfere with haloperidol-induced catalepsy, and decreased sleeping time after sodium pentobarbital administration. Long-term exposure induced tolerance to stereotypic behavior, catalepsy and sleeping time, and increased the susceptibility to seizures induced by picrotoxin and strychnine. An amphetamine-like effect of catnip was suggested to explain the acute effects, while dispositional and functional adaptative changes were considered involved with the long-term effects. Registry Numbers: 124-87-8 (Picrotoxin) 57-24-9 (Strychnine) 76-74-4 (Pentobarbital) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****ZEITSCHRIFT FUR NATURFORSCHUNG. SECTION C. JOURNAL OF BIOSCIENCES***** Kaufmann M Wink M Molecular systematics of the nepetoideae (family Labiatae): phylogenetic implications from rbcL gene sequences. In: Z Naturforsch [C] (1994 Sep-Oct) 49(9-10):635-45 ISSN: 0341-0382 Total DNA was extracted from 41 species (20 genera) of the subfamily Nepetoideae (family Labiatae). Using rbcL-specific primers, the rbcL gene wsa amplified by polymerase chain reaction (PCR) and sequenced directly. RbcL sequences were evaluated with character state (maximum parsimony; PAUP) and distance methods (neighbour-joining; MEGA). In agreement with classical systematics all taxa studied cluster within the Nepetoideae and are clearly distinguished from members of the subfamily Lamioideae. A number of distinctive clades are apparent within the Nepetoideae: I-Collinsonia, II-Lavandula, III-Agastache, Glechoma, IV-Satureja, Hyssopus, Dracocephalum, V-Nepeta, VI-Hormium, VII-Prunella, VIII-Melissa, Ocimum, IX-Monarda, Mentha, X-Origanum, Thymus, XI-Salvia, XII-Rosmarinus, and XIII-Perovskia. At least five main branches representing the clades I, II, III to VII, VIII, and IX to XIII respectively, can be distinguished within the Nepetoideae studied. They might be considered representing the tribes (according to Cantino, 1992) Elsholtzieae (I). Lavanduleae (II), and Mentheae (III-XIII). The tribe Mentheae needs to be subdivided into at least three main groups (clades III-VII, VIII and IX-XIII). Majorana hortensis which is often classified as Origanum hortensis does not cluster with Origanum and deserves a genetic status of its own. Registry Numbers: EC 4.1.1.39 (Ribulosebiphosphate Carboxylase) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€