Biosynthesis of nepetalactone in Nepeta cataria

Bellesia, Franco; Grandi, Romano; Pagnoni, Ugo Maria; Pinetti, Adriano; Trave, R.

doi:10.1016/0031-9422(84)83082-4

Cited by 44 publications

(31 citation statements)

References 7 publications

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“…The compound occurs not only in T. marum, but in a number of insects, including ants and a walking stick (Meinwald et al 1962;Cavill et al 1976;Cornelius et al 1995). Similarly, nepetalactone, or catnip, the familiar active principle of the mint plant, Nepeta cataria (Meinwald 1954;Eisner 1964;Bellesia et al 1984), is produced for defense also by a walking stick (Smith et al 1979), and the isoprenoid alkaloid actinidine, a product of some plants (Torssell & Wahlberg 1967;Johnson & Waller 1971), occurs in ants (Wheeler et al 1977;Cavill et al 1982), walking sticks (Chow & Lin 1986;Ho & Chow 1993), and staphilinid beetles as well (Dettner & Schwinger 1990;Huth & Dettner 1990). Some methylcyclopentanoid monoterpenes occur without parallel representation in other species, as for instance, chrysomelidial from chrysomelid beetles (Meinwald et al 1977).…”

Section: Discussionmentioning

confidence: 99%

Chemical defense of the mint plant, Teucrium marum (Labiatae)

Eisner¹,

Eisner²,

Aneshansley³

et al. 2000

Chemoecology

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The mint plant, Teucrium marum (family Labiatae), sometimes called cat thyme, contains two methylcyclopentanoid monoterpenes, dolichodial and teucrein. The former compound is potently anti-insectan. It is repellent to ants (Monomorium pharaonis) and induces preening reflexes in flies (Phormia regina) and cockroaches (Periplaneta americana). Evidence is presented suggesting that dolichodial, which is presumed to be the plant's chief defensive agent, is stored in the tiny epidermal capsules that beset the leaves. It is only when the leaves are injured (and the capsules ruptured) that the leaves become repellent. Teucrein, in contrast, has no anti-insectan potency. It is present predominantly in the leaf buds, unlike dolichodial, which is present mostly in mature leaves. It is argued that teucrein is the storage compound from which dolichodial is generated during leaf development.

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Section: Discussionmentioning

confidence: 99%

Chemical defense of the mint plant, Teucrium marum (Labiatae)

Eisner¹,

Eisner²,

Aneshansley³

et al. 2000

Chemoecology

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“…Catmint (Nepeta racemosa, Lamiaceae) produces an essential oil containing nepetalactones (Regnier et al 1967;Clark et al 1997b); the biosynthesis of these iridoid monoterpenoids is initiated by the allylic hydroxylation of citronellol at C10 (Bellesia et al 1984). Microsomal preparations from N. racemosa leaves catalyze the C10-hydroxylation of nerol and geraniol (Hallahan et al 1994) and both enantiomers of citronellol (Hallahan and West 1996) (Fig.…”

Section: Other Monoterpene Hydroxylasesmentioning

confidence: 97%

Cytochrome P450 oxygenases of monoterpene metabolism

Mau

Croteau

2006

Phytochem Rev

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The cytochrome P450 monoterpene oxygenases are largely responsible for imparting structural and functional diversity to this family of natural products. In most cases, cytochrome P450-mediated allylic hydroxylation of a parental monoterpene olefin leads to a series of redox transformations and conjugation reactions which yield a family of structurally related derivatives and isomers. An overview is provided of the extant monoterpene oxygenases, with examples mainly from the mint (Lamiaceae) family of essential oil plants, and, where possible, information on the structure, mechanism, localization and regulation of these enzymes is described. The review concludes with a brief assessment of biotechnological applications and a view to future research in this area.

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“…The chemical composition of T. marum has been the subject of numerous studies in which phenylpropanoid, neo‐clerodane diterpenoids and iridoid cyclopentane monoterpenes have been reported. Iridoids such as dolichodial, teucrein and dolicholactone are volatile components of T. marum identified in the organic solvent extracts obtained by Soxhlet and simultaneous distillation–extraction .…”

Section: Introductionmentioning

confidence: 99%

Analysis of the volatile fraction of Teucrium marum L.

Djabou

Andreani

Varesi

et al. 2012

Flavour & Fragrance J

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Volatile components of Teucrium marum from Corsica were investigated using a combination of analytical techniques. Analysis of essential oils obtained by hydrodistillation was performed using capillary GC‐RI, GC‐MS and 13C NMR spectroscopy after fractionation on column chromatography. The emitted volatile fractions from full aerial parts and separated organs of fresh T. marum were investigated using HS‐SPME/GC‐RI and HS‐SPME/GC‐MS. The intra‐species variations of the chemical compositions of essential oils and volatile fractions from 25 Corsican sample locations were investigated using statistical analysis. The main essential oil components were caryophyllene oxide (0.4–20.5%), (E)‐β‐caryophyllene (0.9–18.9%), (E)‐α‐bergamotene (1.0–21.5%), (3Z,6E,10E)‐α‐springene (1.1–17.8%), β‐bisabolene (0.4–14.7%), β‐sesquiphellandrene (0.9–10.9%) and estragole (0.5–7.0%), while dolichodial (20.0–83.4%), (E)‐α‐bergamotene (0.2–20.6%), (E)‐β‐caryophyllene (0.3–23.1%), dolicholactone (0.4–20.9%), β‐bisabolene (0.2–10.0%), estragole (1.1–10.5%) and β‐sesquiphellandrene (0.2–8.3%) were the main volatiles emitted by the plant. The 13C‐NMR data of (3Z,6E,10E)‐α‐springene and its occurrence in T. marum essential oils are reported for the first time. The importance of the sample preparation step is discussed through the absence/occurrence of dolichodial in both liquid and gaseous matrices studied, respectively. Copyright © 2012 John Wiley & Sons, Ltd.

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Biosynthesis of nepetalactone in Nepeta cataria

Cited by 44 publications

References 7 publications

Chemical defense of the mint plant, Teucrium marum (Labiatae)

Chemical defense of the mint plant, Teucrium marum (Labiatae)

Cytochrome P450 oxygenases of monoterpene metabolism

Analysis of the volatile fraction of Teucrium marum L.

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