PVD

(1S,4E,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

Metabolic Pathways

map00909

Structure

IUPAC Name

(1S,4E,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

PubChem CID

20831623

Synonymous Names

Formula

C15H24

Molecular Weight

204.35

Chemical Class

Sesquiterpenoid, Aliphatic, Olefin, Prenol

Reference Link

De Moraes, C. M., Mescher, M. C., and Tumlinson, J. H. 2001. Caterpillar-induced nocturnal plant volatiles repel conspecific females. Nature. 410:577–80.
Rodriguez-Saona, C. R., Rodriguez-Saona, L. E., and Frost, C. J. 2009. Herbivore-induced volatiles in the perennial shrub, Vaccinium corymbosum, and their role in inter-branch signaling. J Chem Ecol. 35:163–75.
Pare, P. W., and Tumlinson, J. H. 1997a. De Novo Biosynthesis of Volatiles Induced by Insect Herbivory in Cotton Plants. Plant Physiol. 114:1161–1167.
Jiménez-Martínez, E. S., Bosque-Pérez, N. A., Berger, P. H., Zemetra, R. S., Ding, H., and Eigenbrode, S. D. 2004. Volatile Cues Influence the Response of Rhopalosiphum padi (Homoptera: Aphididae) to Barley Yellow Dwarf Virus–Infected Transgenic and Untr
Frost, C. J., Appel, H. M., Carlson, J. E., De Moraes, C. M., Mescher, M. C., and Schultz, J. C. 2007. Within-plant signalling via volatiles overcomes vascular constraints on systemic signalling and primes responses against herbivores. Ecol Lett. 10:490–
Altenburger, R., and Matile, P. 1990. Further observations on rhythmic emission of fragrance in flowers. Planta. 180:194–7.
Rodriguez-Saona, C. R., Rodriguez-Saona, L. E., and Frost, C. J. 2009. Herbivore-induced volatiles in the perennial shrub, Vaccinium corymbosum, and their role in inter-branch signaling. J Chem Ecol. 35:163–75.
Buttery, R. G., Kamm, J. A., and Ling, L. C. 1982. Volatile components of alfalfa flowers and pods. J Agric Food Chem. 30:739–742
Huang, J., Cardoza, Y. J., Schmelz, E. A., Raina, R., Engelberth, J., and Tumlinson, J. H. 2003. Differential volatile emissions and salicylic acid levels from tobacco plants in response to different strains of Pseudomonas syringae. Planta. 217:767–75.
Eigenbrode, S. D., Ding, H., Shiel, P., and Berger, P. H. 2002. Volatiles from potato plants infected with potato leafroll virus attract and arrest the virus vector, Myzus persicae (Homoptera: Aphididae). Proc Biol Sci. 269:455–60.
Copolovici, L., Kännaste, A., Pazouki, L., and Niinemets, U. 2012. Emissions of green leaf volatiles and terpenoids from Solanum lycopersicum are quantitatively related to the severity of cold and heat shock treatments. J Plant Physiol. 169:664–72.
Degen, T., Dillmann, C., Marion-Poll, F., and Turlings, T. C. J. 2004a. High genetic variability of herbivore-induced volatile emission within a broad range of maize inbred lines. Plant Physiol. 135:1928–38.
Buttery, R. G., Kamm, J. A., and Ling, L. C. 1984. Volatile components of red clover leaves, flowers, and seed pods: possible insect attractants. J Agric Food Chem. 32:254–256. ers, and seed pods: possible insect attractants
Loughrin, J. H., Hamilton-Kemp, T. R., Andersen, R. A., and Hildebrand, D. F. 1990. Headspace compounds from flowers of Nicotiana tabacum and related species. J Agric Food Chem. 38:455–460.
Chen, P., Dai, C., Liu, H., and Hou, M. 2022. Identification of Key Headspace Volatile Compounds Signaling Preference for Rice over Corn in Adult Females of the Rice Leaf Folder Cnaphalocrocis medinalis. J Agric Food Chem. 70:9826–9833.
Giacomuzzi, V., Cappellin, L., Khomenko, I., Biasioli, F., Schütz, S., Tasin, M., et al. 2016. Emission of Volatile Compounds from Apple Plants Infested with Pandemis heparana Larvae, Antennal Response of Conspecific Adults, and Preliminary Field Trial.
Ángeles López, Y. I., Martínez-Gallardo, N. A., Ramírez-Romero, R., López, M. G., Sánchez-Hernández, C., and Délano-Frier, J. P. 2012. Cross-kingdom effects of plant-plant signaling via volatile organic compounds emitted by tomato (Solanum lycopersicum)
Vallat, A., Gu, H., and Dorn, S. 2005. How rainfall, relative humidity and temperature influence volatile emissions from apple trees in situ. Phytochemistry. 66:1540–50.
Michereff, M. F. F., Laumann, R. A., Borges, M., Michereff-Filho, M., Diniz, I. R., Neto, A. L. F., et al. 2011. Volatiles mediating a plant-herbivore-natural enemy interaction in resistant and susceptible soybean cultivars. J Chem Ecol. 37:273–85.
González-Mas, M. C., Rambla, J. L., López-Gresa, M. P., Blázquez, M. A., and Granell, A. 2019. Volatile Compounds in Citrus Essential Oils: A Comprehensive Review. Front Plant Sci. 10:12.
Strapasson, P., Pinto-Zevallos, D. M., Da Silva Gomes, S. M., and Zarbin, P. H. G. 2016. Volatile Organic Compounds Induced by Herbivory of the Soybean Looper Chrysodeixis includens in Transgenic Glyphosate-Resistant Soybean and the Behavioral Effect on
Hijaz, F., El-Shesheny, I., and Killiny, N. 2013. Herbivory by the insect diaphorina citri induces greater change in citrus plant volatile profile than does infection by the bacterium, Candidatus Liberibacter asiaticus. Plant Signal Behav. 8:doi: 10.4161
Fereres, A., Peñaflor, M. F. G. V, Favaro, C. F., Azevedo, K. E. X., Landi, C. H., Maluta, N. K. P., et al. 2016. Tomato Infection by Whitefly-Transmitted Circulative and Non-Circulative Viruses Induce Contrasting Changes in Plant Volatiles and Vector Be
Chamberlain, K., Briens, M., Jacobs, J. H., Clark, S. J., and Pickett, J. A. 2012. Use of honey bees (Apis mellifera L.) to detect the presence of Mediterranean fruit fly (Ceratitis capitata Wiedemann) larvae in Valencia oranges. J Sci Food Agric. 92:205
Jones, S. E., and Killiny, N. 2021. Influence of Rootstock on the Leaf Volatile Organic Compounds of Citrus Scion Is More Pronounced after the Infestation with Diaphorina citri. Plants (Basel). 10.
da Cruz, M. A., Plotto, A., Ferrarezi, R. S., Leite Junior, R. P., and Bai, J. 2023. Effect of Huanglongbing on the Volatile Organic Compound Profile of Fruit Juice and Peel Oil in “Ray Ruby” Grapefruit. Foods. 12.

Plants/Microbial Species and Abiotic/Biotic Stimuli

Plant/Microbial Species	Abiotic/Biotic Stimuli
Lycopersicon esculentum (Tomato)	Heat - High Temperature
Solanum tuberosum (Potato)	Virus - Potato leaf roll virus (PLRV)
Vaccinium corymbosum (Blueberry)	Insect - Lymantina dispar
Nicotiana tabacum (Tobacco)	Insect - Heliothios virescens
Nicotiana tabacum (Tobacco)	Insect - Heliothis zea
Nicotiana tabacum (Tobacco)	Insect - Manduca sexta
Zea mays	Insect - Spodoptera littoralis
Nicotiana tabacum (Tobacco)	Bacteria - Pseudomonas syringae
Gossypium kirsutum (Cotton)	Insect - Spodoptera exigua Hubner
Triticum aestivum (Wheat)	Virus - Barley yellow dwarf virus (BYDV)
Ulmus americana (American Elm)	Insect - Lymantina dispar
Odontoglossum constrictum Lindl	None
Cypripedium calceolus (Lady's slipper orchid)	None
Trifolium pratense (Red clover)	None
Medicago sativa (Alfalfa)	None
Nicotiana sylvestris	None
Malus domestica (Apple)	Insect - Pandemis heparana
Lycopersicon esculentum (Tomato)	Insect - Trialeurodes vaporariorum - Whitefly
Glycine max (Soybean)	Insect - Chrysodeixis includens - Soybean Looper
Citrus grandis (Pummelo)	None
Citrus limon (Lemon)	None
Citrus aurantifolia (Lime)	None
Citrus aurantium (Bitter orange)	None
Citrus bergamia (Bergamot orange)	None
Citrus junos (Yuzu)	None
Citrus medica (Citron)	None
Citrus paradisi (Grapefruit)	Bacteria - Candidatus Liberibacter - asiaticus
Citrus sinensis (Sweet orange)	Insect - Diaphorina citri - Asian Citrus Psyllid
Lycopersicon esculentum (Tomato)	Virus - Tomato chlorosis virus (ToCV)
Citrus sinensis (Sweet orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Citrus reticulata (Mandarin orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Citrus paradisi (Grapefruit)	Insect - Diaphorina citri - Asian Citrus Psyllid

Confirmed/Hypothesized Functions

Circadian rhythm

Plant-Associated Volatile Organic Compound (VOC) Database (PVD)

(1S,4E,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene