Skip to main content

Advertisement

SpringerLink
Log in

Biosynthesis, natural distribution, and biological activities of acyclic monoterpenes and their derivatives

  • Published:
Phytochemistry Reviews Aims and scope Submit manuscript

Abstract

Monoterpenoids are C10 isoprenoid natural products with diverse functions as volatile and non-volatile secondary metabolites. Their biosynthesis from acyclic diphosphate precursors is often accompanied by one or more ring closures, which stabilize the linear, carbocationic intermediates generated during typical terpene synthase reaction sequences. The subset that remains uncyclized following the elimination of the diphosphate group correspondingly retains higher reactivity than their cyclized counterparts, a property that may explain the additional transformations that geraniol and other acyclics undergo to yield monoterpene aldehydes, acids, esters, glycosides, and iridoids, many of which possess allelochemical activity as pollinator attractants, feeding deterrents, or insect repellents. Essential oils of lemon grass (or citronella) (Cymbopogon), rose-scented geraniums (Pelargonium), and lemon-scented gums (Corymbia) are rich sources of the acyclic monoterpene alcohols we collectively refer to in this review as ‘citronelloids’. Their formation from geranyl diphosphate may be brought about by the tps-g or tps-b subclade of terpene synthases or, alternatively, by a subclade of Nudix hydrolases which act preferentially on prenyl diphosphate substrates, yielding monoterpene alcohols in a two step process that involves a monophosphate intermediate. In some members of the Lamiid and Campanulid clades, further oxidation of geraniol and a non-classical, reductive cyclization leads to the iridoids, a group of mostly non-volatile, bicyclic monoterpenes with potent anti-herbivory and anti-inflammatory properties. Here we review the recent literature on acyclic monoterpene biosynthesis, their natural distribution across the plant kingdom, and their emerging roles in medicine as biologically active natural products.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17

Similar content being viewed by others

Abbreviations

BAHD:

Benzyl alcohol/anthocyanin/N-hydroxycinnamoyl/deacetylvindoline

BAT:

BAHD acyl transferases

CMR1:

Human cold and menthol receptor

DEET:

N,N-Diethyl-m-toluamide

DMADP:

Dimethylallyl diphosphate

FDP:

Farnesyl diphosphate

FDS:

Farnesyl diphosphate synthase

GDP:

Geranyl diphosphate

GDS:

Geranyl diphosphate synthase

GES:

Geraniol synthase

GP:

Geranyl phosphate

HGO:

Hydroxygeraniol oxidoreductase

IDP:

Isopentenyl diphosphate

IG:

Iridoid glycoside

ISY:

Iridoid synthase

LDP:

Lavandulyl diphosphate

MIA:

Monoterpene indole alkaloid

NES/LIS:

Nerolidol/linalool synthase

Nudix:

Nucleotide diphosphate bound to X

TPS:

Terpene synthase

TRPA:

Transient receptor potential ankyrin channel

References

  • Abbas F, Ke Y, Zhou Y, Ashraf U, Li X, Yu Y, Yue Y, Ahmad KW, Yu R, Fan Y (2020) Molecular cloning, characterization and expression analysis of LoTPS2 and LoTPS4 involved in floral scent formation in oriental hybrid Lilium variety ‘Siberia.’ Phytochemistry 173:112294. https://doi.org/10.1016/j.phytochem.2020.112294

    Article  CAS  PubMed  Google Scholar 

  • Adal AM, Mahmoud SS (2020) Short-chain isoprenyl diphosphate synthases of lavender (Lavandula). Plant Mol Biol 102(4):517–535. https://doi.org/10.1007/s11103-020-00962-8

    Article  CAS  PubMed  Google Scholar 

  • Adam KP, Thiel R, Zapp J (1999) Incorporation of 1- 1-C-13 deoxy-D-xylulose in chamomile sesquiterpenes. Arch Biochem Biophys 369(1):127–132

    Article  CAS  PubMed  Google Scholar 

  • Adler LS, Schmitt J, Bowers MD (1995) Genetic variation in defensive chemistry in Plantago lanceolata (Plantaginaceae) and its effect on the specialist herbivore Junonia coenia (Nymphalidae). Oecologia 101(1):75–85. https://doi.org/10.1007/BF00328903

    Article  PubMed  Google Scholar 

  • Aguiar RWdS, Ootani MA, Ascencio SD, Ferreira TPS, Santos MMd, Santos GRd (2014) Fumigant antifungal activity of Corymbia citriodora and Cymbopogon nardus essential oils and citronellal against three fungal species. Sci World J 2014:492138. https://doi.org/10.1155/2014/492138

    Article  CAS  Google Scholar 

  • Aharoni A, Giri AP, Verstappen FWA, Bertea CM, Sevenier R, Sun Z, Jongsma MA, Schwab W, Bouwmeester HJ (2004) Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell 16(11):3110–3131. https://doi.org/10.1105/tpc.104.023895

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ahmed OM, Galaly SR, Mostafa M-AMA, Eed EM, Ali TM, Fahmy AM, Zaky MY (2022) Thyme oil and thymol counter doxorubicin-induced hepatotoxicity <i>via</i> modulation of inflammation, apoptosis, and oxidative stress. Oxid Med Cell Longev 2022:6702773. https://doi.org/10.1155/2022/6702773

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Akhila A (1986) Biosynthesis of monoterpenes in Cymbopogon winterianus. Phytochemistry 25(2):421–424. https://doi.org/10.1016/S0031-9422(00)85493-X

    Article  CAS  Google Scholar 

  • An S, Pae H, Oh G, Choi B, Jeong S, Jang S, Oh H, Kwon T, Song C, Chung H (2002) Inhibition of TNF-α, IL-1β, and IL-6 productions and NF-κB activation in lipopolysaccharide-activated RAW 264.7 macrophages by catalposide, an iridoid glycoside isolated from Catalpa ovata G. Don (Bignoniaceae). Int Immunopharmacol 2(8):1173–1181

  • Andrade P, Manzano D, Ramirez-Estrada K, Caudepon D, Arro M, Ferrer A, Phillips MA (2018) Nerolidol production in agroinfiltrated tobacco: Impact of protein stability and membrane targeting of strawberry (Fragraria ananassa) NEROLIDOL SYNTHASE1. Plant Sci 267:112–123

    Article  CAS  PubMed  Google Scholar 

  • Andreani S, Uehara A, Blagojević P, Radulović N, Muselli A, Baldovini N (2019) Key odorants of industrially-produced Helichrysum italicum subsp. italicum essential oil. Ind Crops Prod 132:275–282. https://doi.org/10.1016/j.indcrop.2019.02.008

    Article  CAS  Google Scholar 

  • Angioni A, Barra A, Arlorio M, Coisson JD, Russo MT, Pirisi FM, Satta M, Cabras P (2003) Chemical composition, plant genetic differences, and antifungal activity of the essential oil of Helichrysum italicum G. Don ssp. microphyllum (Willd) Nym. J Agric Food Chem 51(4):1030–1034. https://doi.org/10.1021/jf025940c

  • Ao H, Wang J, Chen L, Li S, Dai C (2019) Comparison of volatile oil between the fruits of Amomum villosum lour. and amomum villosum lour. var. xanthioides T L. Wu et Senjen based on GC-MS and chemometric techniques. Molecules 24 (9):1663

  • Arraché Gonçalves G, Eifler-Lima VL, von Poser GL (2021) Revisiting nature: a review of iridoids as a potential antileishmanial class. Phytochem Rev. https://doi.org/10.1007/s11101-021-09750-8

    Article  PubMed  PubMed Central  Google Scholar 

  • Babu KGD, Kaul VK (2005) Variation in essential oil composition of rose-scented geranium (Pelargonium sp.) distilled by different distillation techniques. Flavour Fragrance J 20(2):222–231. https://doi.org/10.1002/ffj.1414

  • Baden CU, Dobler S (2009) Potential benefits of iridoid glycoside sequestration in Longitarsus melanocephalus (Coleoptera, Chrysomelidae). Basic Appl Ecol 10(1):27–33. https://doi.org/10.1016/j.baae.2007.12.003

    Article  CAS  Google Scholar 

  • Beekwilder J, Alvarez-Huerta M, Neef E, Verstappen FWA, Bouwmeester HJ, Aharoni A (2004) Functional characterization of enzymes forming volatile esters from strawberry and banana. Plant Physiol 135(4):1865–1878. https://doi.org/10.1104/pp.104.042580

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Bergman ME, Davis B, Phillips MA (2019) Medically useful plant Terpenoids: biosynthesis, occurrence, and mechanism of action. Molecules 24(21):3961–3983

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Bergman ME, Chávez Á, Ferrer A, Phillips MA (2020) Distinct metabolic pathways drive monoterpenoid biosynthesis in a natural population of Pelargonium graveolens. J Exp Bot 71(1):258–271. https://doi.org/10.1093/jxb/erz397

    Article  CAS  PubMed  Google Scholar 

  • Bergman ME, Bhardwaj M, Phillips MA (2021) Cytosolic geraniol and citronellol biosynthesis require a Nudix hydrolase in rose scented geranium (Pelargonium graveolens). Plant J 107(2):493–510

    Article  CAS  PubMed  Google Scholar 

  • Bergman ME, Phillips MA (2020) Structural diversity and biosynthesis of plant derived p-menthane monoterpenes. Phytochem Rev, pp 1–27

  • Biere A, Marak HB, van Damme JMM (2004) Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs? Oecologia 140(3):430–441. https://doi.org/10.1007/s00442-004-1603-6

    Article  PubMed  Google Scholar 

  • Blerot B, Baudino S, Prunier C, Demarne F, Toulemonde B, Caissard JC (2016) Botany, agronomy and biotechnology of Pelargonium used for essential oil production. Phytochem Rev 15(5):935–960. https://doi.org/10.1007/s11101-015-9441-1

    Article  CAS  Google Scholar 

  • Blerot B, Martinelli L, Prunier C, Saint-Marcoux D, Legrand S, Bony A, Sarrabère L, Gros F, Boyer N, Caissard J-C, Baudino S, Jullien F (2018) Functional analysis of four terpene synthases in rose-scented Pelargonium Cultivars (Pelargonium × hybridum) and evolution of scent in the Pelargonium Genus. Front Plant Sci 9. https://doi.org/10.3389/fpls.2018.01435

  • Bohlmann J, Meyer-Gauen G, Croteau R (1998) Plant terpenoid synthases: molecular biology and phylogenetic analysis. Proc Natl Acad Sci 95(8):4126–4133

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Bohman B, Karton A, Flematti GR, Scaffidi A, Peakall R (2018) Structure-activity studies of semiochemicals from the Spider Orchid Caladenia plicata for sexual deception. J Chem Ecol 44(5):436–443. https://doi.org/10.1007/s10886-018-0946-0

    Article  CAS  PubMed  Google Scholar 

  • Boukhris M, Ben Nasri-Ayachi M, Mezghani I, Bouaziz M, Boukhris M, Sayadi S (2013) Trichomes morphology, structure and essential oils of Pelargonium graveolens L’Hér. (Geraniaceae). Ind Crops Prod 50:604–610. https://doi.org/10.1016/j.indcrop.2013.08.029

    Article  CAS  Google Scholar 

  • Bowers MD (2003) Hostplant suitability and defensive chemistry of the Catalpa Sphinx, Ceratomia catalpae. J Chem Ecol 29(10):2359–2367. https://doi.org/10.1023/A:1026234716785

    Article  CAS  PubMed  Google Scholar 

  • Carper AL, Enger M, Bowers MD (2019) Host plant effects on immune response across development of a specialist caterpillar. Front Ecol Evol 7:208

    Article  Google Scholar 

  • Chen W, Viljoen A (2010) Geraniol—a review of a commercially important fragrance material. S Afr J Bot 76(4):643–651

    Article  CAS  Google Scholar 

  • Chen F, Li W, Jiang L, Pu X, Yang Y, Zhang G, Luo Y (2016) Functional characterization of a geraniol synthase-encoding gene from Camptotheca acuminata and its application in production of geraniol in Escherichia coli. J Ind Microbiol Biotechnol 43(9):1281–1292. https://doi.org/10.1007/s10295-016-1802-2

    Article  CAS  PubMed  Google Scholar 

  • Chuah GK, Liu SH, Jaenicke S, Harrison LJ (2001) Cyclisation of citronellal to isopulegol catalysed by hydrous zirconia and other solid acids. J Catal 200(2):352–359. https://doi.org/10.1006/jcat.2001.3208

    Article  CAS  Google Scholar 

  • Collu G, Unver N, Peltenburg-Looman AMG, van der Heijden R, Verpoorte R, Memelink J (2001) Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis. FEBS Lett 508(2):215–220. https://doi.org/10.1016/S0014-5793(01)03045-9

    Article  CAS  PubMed  Google Scholar 

  • Conart C, Saclier N, Foucher F, Goubert C, Rius-Bony A, Paramita SN, Moja S, Thouroude T, Douady C, Sun P, Nairaud B, Saint-Marcoux D, Bahut M, Jeauffre J, Hibrand Saint-Oyant L, Schuurink RC, Magnard J-L, Boachon B, Dudareva N, Baudino S, Caissard J-C (2022) Duplication and specialization of NUDX1 in Rosaceae led to geraniol production in rose petals. Mol Biol Evol. https://doi.org/10.1093/molbev/msac002

    Article  PubMed  PubMed Central  Google Scholar 

  • Croteau R (1987) Biosynthesis and catabolism of Monoterpenoids. Chem Rev 87(5):929–954

    Article  CAS  Google Scholar 

  • Croteau RB, Davis EM, Ringer KL, Wildung MR (2005) (−)-Menthol biosynthesis and molecular genetics. Naturwissenschaften 92(12):562–562. https://doi.org/10.1007/s00114-005-0055-0

    Article  CAS  PubMed  Google Scholar 

  • D’Auria JC (2006) Acyltransferases in plants: a good time to be BAHD. Curr Opin Plant Biol 9(3):331–340. https://doi.org/10.1016/j.pbi.2006.03.016

    Article  CAS  PubMed  Google Scholar 

  • Damtoft S (1994) Biosynthesis of catalpol. Phytochemistry 35(5):1187–1189. https://doi.org/10.1016/S0031-9422(00)94819-2

    Article  CAS  Google Scholar 

  • Damtoft S, Jensen SR, Jessen CU, Knudsen TB (1993) Late stages in the biosynthesis of aucubin in Scrophularia. Phytochemistry 33(5):1089–1093

    Article  CAS  Google Scholar 

  • Damtoft S, Jensen SR, Weiergang I (1994) Early stages in the biosynthesis of aucubin and harpagide. Deuterium Labelling Stud Phytochem 35(3):621–622

    Article  CAS  Google Scholar 

  • De Deyn GB, Biere A, van der Putten WH, Wagenaar R, Klironomos JN (2009) Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L. Oecologia 160(3):433–442. https://doi.org/10.1007/s00442-009-1312-2

    Article  PubMed  Google Scholar 

  • De Luca V, Salim V, Thamm A, Masada SA, Yu F (2014) Making iridoids/secoiridoids and monoterpenoid indole alkaloids: progress on pathway elucidation. Curr Opin Plant Biol 19:35–42. https://doi.org/10.1016/j.pbi.2014.03.006

    Article  CAS  PubMed  Google Scholar 

  • De Pascual-T J, Caballero E, Caballero C, Anaya J, Gonzalez MS (1983) Four aliphatic esters of Chamaemelum fuscatum essential oil. Phytochemistry 22(8):1757–1759. https://doi.org/10.1016/S0031-9422(00)80265-4

    Article  Google Scholar 

  • de Santana MT, de Oliveira MGB, Santana MF, De Sousa DP, Santana DG, Camargo EA, de Oliveira AP, Almeida JRGdS, Quintans-Júnior LJ (2013) Citronellal, a monoterpene present in Java citronella oil, attenuates mechanical nociception response in mice. Pharm Biol 51(9):1144–1149. https://doi.org/10.3109/13880209.2013.781656

    Article  CAS  PubMed  Google Scholar 

  • de Sousa DP, Júnior GA, Andrade LN, Batista JS (2011) Spasmolytic activity of chiral monoterpene esters. Records Natural Products 5(2):117

    Google Scholar 

  • Demissie ZA, Erland LE, Rheault MR, Mahmoud SS (2013) The biosynthetic origin of irregular monoterpenes in Lavandula. J Biol Chem 288(9):6333–6341

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Dinda B, Dinda M, Kulsi G, Chakraborty A, Dinda S (2019) Therapeutic potentials of plant iridoids in Alzheimer’s and Parkinson’s diseases: a review. Eur J Med Chem 169:185–199. https://doi.org/10.1016/j.ejmech.2019.03.009

    Article  CAS  PubMed  Google Scholar 

  • Dobler S, Petschenka G, Pankoke H (2011) Coping with toxic plant compounds—the insect’s perspective on iridoid glycosides and cardenolides. Phytochemistry 72(13):1593–1604. https://doi.org/10.1016/j.phytochem.2011.04.015

    Article  CAS  PubMed  Google Scholar 

  • Docimo T, Davis AJ, Luck K, Fellenberg C, Reichelt M, Phillips M, Gershenzon J, D’Auria J (2015) Influence of medium and elicitors on the production of cocaine, amino acids and phytohormones by Erythroxylum coca calli. Plant Cell Tissue Organ Cult 120(3):1061–1075

    Article  CAS  Google Scholar 

  • Dong L, Miettinen K, Goedbloed M, Verstappen FWA, Voster A, Jongsma MA, Memelink J, Svd K, Bouwmeester HJ (2013) Characterization of two geraniol synthases from Valeriana officinalis and Lippia dulcis: Similar activity but difference in subcellular localization. Metab Eng 20:198–211. https://doi.org/10.1016/j.ymben.2013.09.002

    Article  CAS  PubMed  Google Scholar 

  • Dong L, Jongedijk E, Bouwmeester H, Van Der Krol A (2016) Monoterpene biosynthesis potential of plant subcellular compartments. New Phytol 209(2):679–690

    Article  CAS  PubMed  Google Scholar 

  • Du EJ, Ahn TJ, Choi MS, Kwon I, Kim H-W, Kwon JY, Kang K (2015) The mosquito repellent citronellal directly potentiates Drosophila TRPA1, facilitating feeding suppression. Mol Cells 38 (10):911–917. https://doi.org/10.14348/molcells.2015.0215

  • Dudareva N, Andersson S, Orlova I, Gatto N, Reichelt M, Rhodes D, Boland W, Gershenzon J (2005) The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. Proc Natl Acad Sci 102(3):933–938

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Feng L, Chen C, Li T, Wang M, Tao J, Zhao D, Sheng L (2014) Flowery odor formation revealed by differential expression of monoterpene biosynthetic genes and monoterpene accumulation in rose (Rosa rugosa Thunb.). Plant Physiol Biochem 75:80–88. https://doi.org/10.1016/j.plaphy.2013.12.006

    Article  CAS  PubMed  Google Scholar 

  • Frezza C, de Vita D, Toniolo C, Ventrone A, Tomassini L, Foddai S, Nicoletti M, Guiso M, Bianco A, Serafini M (2020) Harpagide: occurrence in plants and biological activities—a review. Fitoterapia 147:104764. https://doi.org/10.1016/j.fitote.2020.104764

    Article  CAS  PubMed  Google Scholar 

  • Georgiev MI, Ivanovska N, Alipieva K, Dimitrova P, Verpoorte R (2013) Harpagoside: from Kalahari Desert to pharmacy shelf. Phytochemistry 92:8–15. https://doi.org/10.1016/j.phytochem.2013.04.009

    Article  CAS  PubMed  Google Scholar 

  • Geu-Flores F, Sherden NH, Courdavault V, Burlat V, Glenn WS, Wu C, Nims E, Cui Y, O’Connor SE (2012) An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis. Nature 492(7427):138–142. https://doi.org/10.1038/nature11692

    Article  CAS  PubMed  Google Scholar 

  • Goodine T, Oelgemöller M (2020) Corymbia citriodora: a valuable resource from australian flora for the production of fragrances, repellents, and bioactive compounds. ChemBioEng Rev 7(6):170–192. https://doi.org/10.1002/cben.202000013

    Article  CAS  Google Scholar 

  • Guirimand G, Guihur A, Phillips MA, Oudin A, Glévarec G, Melin C, Papon N, Clastre M, St-Pierre B, Rodríguez-Concepción M, Burlat V, Courdavault V (2012) A single gene encodes isopentenyl diphosphate isomerase isoforms targeted to plastids, mitochondria and peroxisomes in Catharanthus roseus. Plant Mol Biol 79(4–5):443–459

    Article  CAS  PubMed  Google Scholar 

  • Gutensohn M, Orlova I, Nguyen TTH, Davidovich-Rikanati R, Ferruzzi MG, Sitrit Y, Lewinsohn E, Pichersky E, Dudareva N (2013) Cytosolic monoterpene biosynthesis is supported by plastid-generated geranyl diphosphate substrate in transgenic tomato fruits. Plant J 75(3):351–363. https://doi.org/10.1111/tpj.12212

    Article  CAS  PubMed  Google Scholar 

  • Hampel D, Mosandl A, Wüst M (2005) Biosynthesis of mono- and sesquiterpenes in carrot roots and leaves (Daucus carota L.): metabolic cross talk of cytosolic mevalonate and plastidial methylerythritol phosphate pathways. Phytochemistry 66(3):305–311

  • Hampel D, Swatski A, Mosandl A, Wüst M (2007) Biosynthesis of monoterpenes and norisoprenoids in raspberry fruits (Rubus idaeus L.): The role of cytosolic mevalonate and plastidial methylerythritol phosphate pathway. J Agricult Food Chem 55(22):9296–9304. https://doi.org/10.1021/jf071311x

  • Harassi Y, Tilaoui M, Idir A, Frédéric J, Baudino S, Ajouaoi S, Mouse HA, Zyad A (2019) Phytochemical analysis, cytotoxic and antioxidant activities of Myrtus communis essential oil from Morocco. J Complement Integrative Med 16(3). https://doi.org/10.1515/jcim-2018-0100

  • Hassan M, Maarof ND, Ali ZM, Noor NM, Othman R, Mori N (2012) Monoterpene alcohol metabolism: identification, purification, and characterization of two geraniol dehydrogenase isoenzymes from Polygonum minus leaves. Biosci Biotechnol Biochem 76(8):1463–1470. https://doi.org/10.1271/bbb.120137

    Article  CAS  PubMed  Google Scholar 

  • Hemmerlin A, Rivera SB, Erickson HK, Poulter CD (2003) Enzymes encoded by the farnesyl diphosphate synthase gene family in the big sagebrush Artemisia tridentata ssp. spiciformis. J Biol Chem 278 (34):32132–32140

  • Henry LK, Thomas ST, Widhalm JR, Lynch JH, Davis TC, Kessler SA, Bohlmann J, Noel JP, Dudareva N (2018a) Contribution of isopentenyl phosphate to plant terpenoid metabolism. Nature Plants 4(9):721–729. https://doi.org/10.1038/s41477-018-0220-z

    Article  CAS  PubMed  Google Scholar 

  • Ho Y, Suphrom N, Daowtak K, Potup P, Thongsri Y, Usuwanthim K (2020) Anticancer effect of Citrus hystrix DC. leaf extract and its bioactive constituents citronellol and, citronellal on the triple negative breast cancer MDA-MB-231 cell line. Pharmaceuticals 13 (12):476

  • Iijima Y, Gang DR, Fridman E, Lewinsohn E, Pichersky E (2004) Characterization of Geraniol Synthase from the Peltate Glands of Sweet Basil. Plant Physiol 134(1):370–379. https://doi.org/10.1104/pp.103.032946

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Iijima Y, Koeduka T, Suzuki H, Kubota K (2014) Biosynthesis of geranial, a potent aroma compound in ginger rhizome (Zingiber officinale): Molecular cloning and characterization of geraniol dehydrogenase. Plant Biotechnology Advpub. https://doi.org/10.5511/plantbiotechnology.14.1020a

    Article  Google Scholar 

  • Ito M, Honda G (2007) Geraniol synthases from perilla and their taxonomical significance. Phytochemistry 68(4):446–453. https://doi.org/10.1016/j.phytochem.2006.11.006

    Article  CAS  PubMed  Google Scholar 

  • Jacob RG, Perin G, Loi LN, Pinno CS, Lenardão EJ (2003) Green synthesis of (−)-isopulegol from (+)-citronellal: application to essential oil of citronella. Tetrahedron Lett 44(18):3605–3608. https://doi.org/10.1016/S0040-4039(03)00714-7

    Article  CAS  Google Scholar 

  • Jamieson MA, Bowers MD (2010) Iridoid glycoside variation in the invasive plant Dalmatian toadflax, Linaria dalmatica (Plantaginaceae), and sequestration by the biological control agent, Calophasia lunula. J Chem Ecol 36(1):70–79

    Article  CAS  PubMed  Google Scholar 

  • Jassbi AR, Zamanizadehnajari S, Baldwin IT (2010) Phytotoxic volatiles in the roots and shoots of Artemisia tridentata as detected by headspace solid-phase microextraction and gas chromatographic-mass spectrometry analysis. J Chem Ecol 36(12):1398–1407. https://doi.org/10.1007/s10886-010-9885-0

    Article  CAS  PubMed  Google Scholar 

  • Jiang S-Y, Jin J, Sarojam R, Ramachandran S (2019) A comprehensive survey on the terpene synthase gene family provides new insight into its evolutionary patterns. Genome Biol Evol 11(8):2078–2098. https://doi.org/10.1093/gbe/evz142

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Jones DT, Taylor WR, Thornton JM (1992) The rapid generation of mutation data matrices from protein sequences. Bioinformatics 8(3):275–282

    Article  CAS  Google Scholar 

  • Kikukawa Y, Yamaguchi S, Nakagawa Y, Uehara K, Uchida S, Yamaguchi K, Mizuno N (2008) Synthesis of a dialuminum-substituted silicotungstate and the diastereoselective cyclization of citronellal derivatives. J Am Chem Soc 130(47):15872–15878. https://doi.org/10.1021/ja8014154

    Article  CAS  PubMed  Google Scholar 

  • Kim C-W, Choi K-C (2021) Potential roles of iridoid glycosides and their underlying mechanisms against diverse cancer growth and metastasis: Do they have an inhibitory effect on cancer progression? Nutrients 13(9):2974

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kim J-K, Kang C-S, Lee J-K, Kim Y-R, Han H-Y, Yun HK (2005) Evaluation of repellency effect of two natural aroma mosquito repellent compounds, citronella and citronellal. Entomol Res 35(2):117–120. https://doi.org/10.1111/j.1748-5967.2005.tb00146.x

    Article  CAS  Google Scholar 

  • Kongkaew C, Sakunrag I, Chaiyakunapruk N, Tawatsin A (2011) Effectiveness of citronella preparations in preventing mosquito bites: systematic review of controlled laboratory experimental studies. Tropical Med Int Health 16(7):802–810. https://doi.org/10.1111/j.1365-3156.2011.02781.x

    Article  CAS  Google Scholar 

  • König WA, Krebber R, Evers P, Bruhn G (1990) Stereochemical analysis of constituents of essential oils and flavor compounds by enantioselective capillary gas chromatography. J High Resolut Chromatogr 13(5):328–332. https://doi.org/10.1002/jhrc.1240130507

    Article  Google Scholar 

  • Kouda R, Yakushiji F (2020) Recent advances in iridoid chemistry: Biosynthesis and chemical synthesis. Chemistry – An Asian Journal 15 (22):3771–3783. https://doi.org/10.1002/asia.202001034

  • Kreis P, Mosandl A (1994) Chiral compounds of essential oils. Part XVII. Simultaneous stereoanalysis of Cymbopogon oil constituents. Flavour Fragrance J 9(5):257–260

  • Kries H, Caputi L, Stevenson CEM, Kamileen MO, Sherden NH, Geu-Flores F, Lawson DM, O’Connor SE (2016) Structural determinants of reductive terpene cyclization in iridoid biosynthesis. Nat Chem Biol 12(1):6–8. https://doi.org/10.1038/nchembio.1955

    Article  CAS  PubMed  Google Scholar 

  • Kulagina N, Méteignier L-V, Papon N, O’Connor SE, Courdavault V (2022) More than a Catharanthus plant: a multicellular and pluri-organelle alkaloid-producing factory. Curr Opin Plant Biol 67:102200

    Article  PubMed  Google Scholar 

  • Kumar S, Stecher G, Li M, Knyaz C, Tamura K (2018) MEGA X: molecular evolutionary genetics analysis across computing platforms. Mol Biol Evol 35(6):1547–1549

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kwon Y, Kim SH, Ronderos DS, Lee Y, Akitake B, Woodward OM, Guggino WB, Smith DP, Montell C (2010) Drosophila TRPA1 channel is required to avoid the naturally occurring insect repellent citronellal. Curr Biol 20(18):1672–1678. https://doi.org/10.1016/j.cub.2010.08.016

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lange BM (2015) Biosynthesis and biotechnology of high-value P-menthane monoterpenes, including menthol, carvone, and limonene. Adv Biochem Eng Biotechnol 148:319–353. https://doi.org/10.1007/10_2014_289

    Article  CAS  PubMed  Google Scholar 

  • Laule O, Furholz A, Chang HS, Zhu T, Wang X, Heifetz PB, Gruissem W, Lange BM (2003) Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana. Proc Natl Acad Sci 100(11):6866–6871

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lee S-Y, Lee D-S, Kim J-C, Park M-J, Choi I-G (2021) Antioxidant properties of 7 domestic essential oils and identification of physiologically active components of essential oils against Candida albicans. J Korean Wood Sci Technol 49(1):23–43. https://doi.org/10.5658/WOOD.2021.49.1.23

    Article  Google Scholar 

  • Leisner CP, Kamileen MO, Conway ME, O’Connor SE, Buell CR (2017) Differential iridoid production as revealed by a diversity panel of 84 cultivated and wild blueberry species. PLoS ONE 12(6):e0179417

    Article  PubMed  PubMed Central  Google Scholar 

  • Lewinsohn E, Dudai N, Tadmor Y, Katzir I, Ravid UZI, Putievsky ELI, Joel DM (1998) Histochemical localization of citral accumulation in lemongrass leaves (Cymbopogon citratus (DC.) Stapf., Poaceae). Annals of Botany 81 (1):35–39. https://doi.org/10.1006/anbo.1997.0525

  • Li X, Xu Y, Shen S, Yin X, Klee H, Zhang B, Chen K (2017) Transcription factor CitERF71 activates the terpene synthase gene CitTPS16 involved in the synthesis of E-geraniol in sweet orange fruit. J Exp Bot 68(17):4929–4938. https://doi.org/10.1093/jxb/erx316

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Li W, Lybrand DB, Xu H, Zhou F, Last RL, Pichersky E (2020) A trichome-specific, plastid-localized Tanacetum cinerariifolium nudix protein hydrolyzes the natural pyrethrin pesticide biosynthetic intermediate trans-chrysanthemyl diphosphate. Frontiers in Plant Science 11 (482). https://doi.org/10.3389/fpls.2020.00482

  • Lichman BR, Kamileen MO, Titchiner GR, Saalbach G, Stevenson CEM, Lawson DM, O’Connor SE (2019) Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis. Nat Chem Biol 15(1):71–79. https://doi.org/10.1038/s41589-018-0185-2

    Article  CAS  PubMed  Google Scholar 

  • Lichman BR, Godden GT, Hamilton JP, Palmer L, Kamileen MO, Zhao D, Vaillancourt B, Wood JC, Sun M, Kinser TJ, Henry LK, Rodriguez-Lopez C, Dudareva N, Soltis DE, Soltis PS, Buell CR, O’Connor SE (2020) The evolutionary origins of the cat attractant nepetalactone in catnip. Sci Adv 6 (20):eaba0721. https://doi.org/10.1126/sciadv.aba0721

  • Lin S, Chen T, Liu X-H, Shen Y-H, Li H-L, Shan L, Liu R-H, Xu X-K, Zhang W-D, Wang H (2010) Iridoids and Lignans from Valeriana jatamansi. J Nat Prod 73(4):632–638. https://doi.org/10.1021/np900795c

    Article  CAS  PubMed  Google Scholar 

  • Liu X, Wang J (2011) Anti-inflammatory effects of iridoid glycosides fraction of Folium syringae leaves on TNBS-induced colitis in rats. J Ethnopharmacol 133(2):780–787

    Article  CAS  PubMed  Google Scholar 

  • Liu M, Chen C-C, Chen L, Xiao X, Zheng Y, Huang J-W, Liu W, Ko T-P, Cheng Y-S, Feng X, Oldfield E, Guo R-T, Ma Y (2016) Structure and function of a “head-to-middle” prenyltransferase: Lavandulyl diphosphate synthase. Angew Chem Int Ed 55(15):4721–4724. https://doi.org/10.1002/anie.201600656

    Article  CAS  Google Scholar 

  • Liu X, Qiu Y, Liu Y, Huang N, Hua C, Wang Q, Wu Z, Lu J, Song P, Xu J, Li P, Yin Y (2021) Citronellal ameliorates doxorubicin-induced hepatotoxicity via antioxidative stress, antiapoptosis, and proangiogenesis in rats. J Biochem Mol Toxicol 35(2):e22639. https://doi.org/10.1002/jbt.22639

    Article  CAS  PubMed  Google Scholar 

  • Luciana N, Batista JS, de Sousa DP (2011) Spasmolytic activity of p-menthane esters. J Med Plants Res 5(32):6995–6999

    Google Scholar 

  • Lupien S, Karp F, Wildung M, Croteau R (1999) Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (−)-4S-limonene-3-hydroxylase and (−)-4S-limonene-6-hydroxylase. Arch Biochem Biophys 368(1):181–192

    Article  CAS  PubMed  Google Scholar 

  • Ma X, Koepke J, Panjikar S, Fritzsch G, Stöckigt J (2005) Crystal structure of Vinorine synthase, the first representative of the BAHD superfamily. J Biol Chem 280(14):13576–13583. https://doi.org/10.1074/jbc.m414508200

    Article  CAS  PubMed  Google Scholar 

  • Magedans YVdS, Phillips MA, Fett-Neto AG (2021) Production of plant bioactive triterpenoid saponins: from metabolites to genes and back. Phytochem Rev 20(2):461–482

    Article  Google Scholar 

  • Magnard J-L, Roccia A, Caissard J-C, Vergne P, Sun P, Hecquet R, Dubois A, Hibrand-Saint Oyant L, Jullien F, Nicolè F, Raymond O, Huguet S, Baltenweck R, Meyer S, Claudel P, Jeauffre J, Rohmer M, Foucher F, Hugueney P, Bendahmane M, Baudino S (2015) Biosynthesis of monoterpene scent compounds in roses. Science 349(6243):81–83. https://doi.org/10.1126/science.aab0696

    Article  CAS  PubMed  Google Scholar 

  • Mannschreck A, von Angerer E (2011) The scent of roses and beyond: molecular structures, analysis, and practical applications of Odorants. J Chem Educ 88(11):1501–1506. https://doi.org/10.1021/ed100629v

    Article  CAS  Google Scholar 

  • Maßberg D, Simon A, Häussinger D, Keitel V, Gisselmann G, Conrad H, Hatt H (2015) Monoterpene (−)-citronellal affects hepatocarcinoma cell signaling via an olfactory receptor. Arch Biochem Biophys 566:100–109. https://doi.org/10.1016/j.abb.2014.12.004

    Article  CAS  PubMed  Google Scholar 

  • Masumoto N, Korin M, Ito M (2010) Geraniol and linalool synthases from wild species of perilla. Phytochemistry 71(10):1068–1075. https://doi.org/10.1016/j.phytochem.2010.04.006

    Article  CAS  PubMed  Google Scholar 

  • Melo MS, Sena LCS, Barreto FJN, Bonjardim LR, Almeida JRGS, Lima JT, De Sousa DP, Quintans-Júnior LJ (2010) Antinociceptive effect of citronellal in mice. Pharm Biol 48(4):411–416. https://doi.org/10.3109/13880200903150419

    Article  CAS  PubMed  Google Scholar 

  • Miettinen K, Dong L, Navrot N, Schneider T, Burlat V, Pollier J, Woittiez L, van der Krol S, Lugan R, Ilc T, Verpoorte R, Oksman-Caldentey K-M, Martinoia E, Bouwmeester H, Goossens A, Memelink J, Werck-Reichhart D (2014) The seco-iridoid pathway from Catharanthus roseus. Nat Commun 5(1):3606. https://doi.org/10.1038/ncomms4606

    Article  CAS  PubMed  Google Scholar 

  • Narnoliya LK, Jadaun JS, Singh SP (2019) The phytochemical composition, biological effects and biotechnological approaches to the production of high-value essential oil from Geranium. In: Malik S (ed) Essential oil research: trends in biosynthesis, analytics, industrial applications and biotechnological production. Springer International Publishing, Cham, pp 327–352. https://doi.org/10.1007/978-3-030-16546-8_12

  • Nhu-Trang T-T, Casabianca H, Grenier-Loustalot M-F (2006) Authenticity control of essential oils containing citronellal and citral by chiral and stable-isotope gas-chromatographic analysis. Anal Bioanal Chem 386(7):2141–2152. https://doi.org/10.1007/s00216-006-0842-2

    Article  CAS  PubMed  Google Scholar 

  • Nikolic M, Markovic T, Markovic D, Calhelha R, Fernandes Â, Ferreira I, Stojkovic D, Ciric A, Glamoclija J, Sokovic M (2021) Chemical composition and biological properties of Pelargonium graveolens, Leptospermum petersonii and Cymbopogon martinii var. motia essential oils and of Rosa centifolia absolute. J Serb Chem Soc 00:96–96. https://doi.org/10.2298/jsc210729096n

    Article  CAS  Google Scholar 

  • Önder DG, Önder S, Karakurt Y (2021) Identification and molecular characterization of geraniol and linalool synthase genes related to monoterpene biosynthesis in Damask Rose (Rosa damascena Mill.), Several Genes for Little Scent. J Essential Oil Bearing Plants 24 (4):910–924. https://doi.org/10.1080/0972060X.2021.1977721

  • Oshikiri H, Watanabe B, Yamamoto H, Yazaki K, Takanashi K (2020) Two BAHD acyltransferases catalyze the last step in the shikonin/alkannin biosynthetic pathway. Plant Physiol 184(2):753–761. https://doi.org/10.1104/pp.20.00207

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • OuYang Q, Okwong RO, Chen Y, Tao N (2020) Synergistic activity of cinnamaldehyde and citronellal against green mold in citrus fruit. Postharvest Biol Technol 162:111095. https://doi.org/10.1016/j.postharvbio.2019.111095

    Article  CAS  Google Scholar 

  • OuYang Q, Liu Y, Oketch OR, Zhang M, Shao X, Tao N (2021) Citronellal exerts its antifungal activity by targeting ergosterol biosynthesis in Penicillium digitatum. J Fungi 7(6):432

    Article  Google Scholar 

  • Pan Q, Mustafa NR, Tang K, Choi YH, Verpoorte R (2016) Monoterpenoid indole alkaloids biosynthesis and its regulation in Catharanthus roseus: a literature review from genes to metabolites. Phytochem Rev 15(2):221–250

    Article  CAS  Google Scholar 

  • Pankoke H, Bowers MD, Dobler S (2010) Influence of iridoid glycoside containing host plants on midgut β-glucosidase activity in a polyphagous caterpillar, Spilosoma virginica Fabricius (Arctiidae). J Insect Physiol 56(12):1907–1912. https://doi.org/10.1016/j.jinsphys.2010.08.013

    Article  CAS  PubMed  Google Scholar 

  • Pankoke H, Buschmann T, Müller C (2013) Role of plant β-glucosidases in the dual defense system of iridoid glycosides and their hydrolyzing enzymes in Plantago lanceolata and Plantago major. Phytochemistry 94:99–107. https://doi.org/10.1016/j.phytochem.2013.04.016

    Article  CAS  PubMed  Google Scholar 

  • Paolini J, Costa J, Bernardini A-F (2005) Analysis of the essential oil from aerial parts of Eupatorium cannabinum subsp. corsicum (L.) by gas chromatography with electron impact and chemical ionization mass spectrometry. J Chromatography A 1076 (1):170–178. https://doi.org/10.1016/j.chroma.2005.03.131

  • Pazouki L, Niinemets Ü (2016) Multi-substrate terpene synthases: their occurrence and physiological significance. Front Plant Sci 7. https://doi.org/10.3389/fpls.2016.01019

  • Pereira FdO, Mendes JM, Lima IO, Mota KSdL, Oliveira WAd, Lima EdO (2015) Antifungal activity of geraniol and citronellol, two monoterpenes alcohols, against Trichophyton rubrum involves inhibition of ergosterol biosynthesis. Pharm Biol 53(2):228–234. https://doi.org/10.3109/13880209.2014.913299

    Article  CAS  PubMed  Google Scholar 

  • Phillips MA, D’Auria JC, Gershenzon J, Pichersky E (2008) The Arabidopsis thaliana type I isopentenyl diphosphate isomerases are targeted to multiple subcellular compartments and have overlapping functions in isoprenoid biosynthesis. Plant Cell 20(3):677–696

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Qi F, Yan Q, Zheng Z, Liu J, Chen Y, Zhang G (2018) Geraniol and geranyl acetate induce potent anticancer effects in colon cancer Colo-205 cells by inducing apoptosis, DNA damage and cell cycle arrest. JBUON 23(2):346–352

    PubMed  Google Scholar 

  • Quintans-Júnior L, Rocha RFd, Caregnato FF, Moreira JCF, Silva FAd, Araújo AAdS, Santos JPAd, Melo MS, de Sousa DP, Bonjardim LR, Gelain DP (2011) Antinociceptive action and redox properties of citronellal, an essential oil present in lemongrass. J Med Food 14(6):630–639. https://doi.org/10.1089/jmf.2010.0125

    Article  CAS  PubMed  Google Scholar 

  • Raina VK, Srivastava SK, Aggarwal KK, Syamasundar KV, Khanuja SPS (2003) Essential oil composition of Cymbopogon martinii from different places in India. Flavour Fragr J 18(4):312–315. https://doi.org/10.1002/ffj.1222

    Article  CAS  Google Scholar 

  • Ramezani H, Singh HP, Batish DR, Kohli RK, Dargan JS (2002) Fungicidal effect of volatile oils from Eucalyptus citriodora and its major constituent citronellal. New Zealand Plant Protection 55 (0):327–330. https://doi.org/10.30843/nzpp.2002.55.3900

  • Ravid U, Putievsky E, Katzir I, Ikan R, Weinstein V (1992) Determination of the enantiomeric composition of citronellol in essential oils by chiral GC analysis on a modified γ-cyclodextrin phase. Flavour Fragr J 7(4):235–238

    Article  CAS  Google Scholar 

  • Rodríguez-López CE, Jiang Y, Kamileen MO, Lichman BR, Hong B, Vaillancourt B, Buell CR, O'Connor SE (2022) Phylogeny-aware chemoinformatic analysis of chemical diversity in Lamiaceae enables iridoid pathway assembly and discovery of aucubin synthase. Molecular Biol Evolut 39(4). https://doi.org/10.1093/molbev/msac057

  • Sakulku U, Nuchuchua O, Uawongyart N, Puttipipatkhachorn S, Soottitantawat A, Ruktanonchai U (2009) Characterization and mosquito repellent activity of citronella oil nanoemulsion. Int J Pharm 372(1):105–111. https://doi.org/10.1016/j.ijpharm.2008.12.029

    Article  CAS  PubMed  Google Scholar 

  • Sharma S, Sangwan NS, Sangwan RS (2003) Developmental process of essential oil glandular trichome collapsing in menthol mint. Curr Sci 84(4):544–550

    CAS  Google Scholar 

  • Sharma PK, Sangwan NS, Mishra BN, Sangwan RS (2008) Coherent ontogenic dynamics of geraniol acetyltransferase activity and geranyl acetate concentration in flowers and leaves of aroma grass Cymbopogon martinii var. Motia Plant Growth Regulation 57(2):103. https://doi.org/10.1007/s10725-008-9328-x

    Article  CAS  Google Scholar 

  • Sharma PK, Sangwan NS, Bose SK, Sangwan RS (2013) Biochemical characteristics of a novel vegetative tissue geraniol acetyltransferase from a monoterpene oil grass (Palmarosa, Cymbopogon martinii var. Motia) leaf. Plant Sci 203–204:63–73. https://doi.org/10.1016/j.plantsci.2012.12.013

    Article  CAS  PubMed  Google Scholar 

  • Sharma A, Cooper R, Bhardwaj G, Cannoo DS (2021) The genus Nepeta: traditional uses, phytochemicals and pharmacological properties. J Ethnopharmacol 268:113679. https://doi.org/10.1016/j.jep.2020.113679

    Article  CAS  PubMed  Google Scholar 

  • Sharma Y, Schaefer J, Streicher C, Stimson J, Fagan J (2020) Qualitative analysis of essential oil from French and Italian Varieties of Rosemary (Rosmarinus officinalis L.) Grown in the Midwestern United States. Anal Chem Lett 10 (1):104–112. https://doi.org/10.1080/22297928.2020.1720805

  • Sherden NH, Lichman B, Caputi L, Zhao D, Kamileen MO, Buell CR, O’Connor SE (2018) Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry. Phytochemistry 145:48–56

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Shieh J-P, Cheng K-C, Chung H-H, Kerh Y-F, Yeh C-H, Cheng J-T (2011) Plasma glucose lowering mechanisms of catalpol, an active principle from roots of Rehmannia glutinosa, in streptozotocin-induced diabetic rats. J Agric Food Chem 59(8):3747–3753

    Article  CAS  PubMed  Google Scholar 

  • Shishido H, Miyamoto Y, Ozawa R, Taniguchi S, Takabayashi J, Akimitsu K, Gomi K (2012) Geraniol synthase whose mRNA is induced by host-selective ACT-toxin in the ACT-toxin-insensitive rough lemon (Citrus jambhiri). J Plant Physiol 169(14):1401–1407. https://doi.org/10.1016/j.jplph.2012.05.003

    Article  CAS  PubMed  Google Scholar 

  • Simkin AJ, Miettinen K, Claudel P, Burlat V, Guirimand G, Courdavault V, Papon N, Meyer S, Godet S, St-Pierre B (2013) Characterization of the plastidial geraniol synthase from Madagascar periwinkle which initiates the monoterpenoid branch of the alkaloid pathway in internal phloem associated parenchyma. Phytochemistry 85:36–43

    Article  CAS  PubMed  Google Scholar 

  • Singh Sangwan R, Singh-Sangwan N, Luthra R (1993) Metabolism of acyclic monoterpenes: partial purification and properties of geraniol dehydrogenase from lemongrass (Cymbopogon flexuosus stapf.) leaves. J Plant Physiol 142 (2):129–134. https://doi.org/10.1016/S0176-1617(11)80952-1

  • Songkro S, Hayook N, Jaisawang J, Maneenuan D, Chuchome T, Kaewnopparat N (2012) Investigation of inclusion complexes of citronella oil, citronellal and citronellol with β-cyclodextrin for mosquito repellent. J Incl Phenom Macrocycl Chem 72(3):339–355. https://doi.org/10.1007/s10847-011-9985-7

    Article  CAS  Google Scholar 

  • Steinhaus M (2015) Characterization of the major odor-active compounds in the leaves of the curry tree Bergera koenigii l. by aroma extract dilution analysis. J Agric Food Chem 63(16):4060–4067. https://doi.org/10.1021/acs.jafc.5b01174

  • Stull GW, Schori M, Soltis DE, Soltis PS (2018) Character evolution and missing (morphological) data across Asteridae. Am J Bot 105(3):470–479

    Article  PubMed  Google Scholar 

  • Sun P, Schuurink RC, Caissard J-C, Hugueney P, Baudino S (2016) My way: noncanonical biosynthesis pathways for plant volatiles. Trends Plant Sci 21(10):884–894. https://doi.org/10.1016/j.tplants.2016.07.007

    Article  CAS  PubMed  Google Scholar 

  • Sun P, Dégut C, Réty S, Caissard J-C, Hibrand-Saint Oyant L, Bony A, Paramita SN, Conart C, Magnard J-L, Jeauffre J, Abd-El-Haliem AM, Marie-Magdelaine J, Thouroude T, Baltenweck R, Tisné C, Foucher F, Haring M, Hugueney P, Schuurink RC, Baudino S (2020) Functional diversification in the Nudix hydrolase gene family drives sesquiterpene biosynthesis in Rosa × wichurana. Plant J 104(1):185–199. https://doi.org/10.1111/tpj.14916

    Article  CAS  PubMed  Google Scholar 

  • Talalay P, Long MJD, Prochaska HJ (1988) Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc Natl Acad Sci 85(21):8261–8265. https://doi.org/10.1073/pnas.85.21.8261

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tang Y, Liu X, Yu B (2002) Iridoids from the rhizomes and roots of Valeriana jatamansi. J Nat Prod 65(12):1949–1952. https://doi.org/10.1021/np0203335

    Article  CAS  PubMed  Google Scholar 

  • Thamm AM, Qu Y, De Luca V (2016) Discovery and metabolic engineering of iridoid/secoiridoid and monoterpenoid indole alkaloid biosynthesis. Phytochem Rev 15(3):339–361

    Article  CAS  Google Scholar 

  • The Angiosperm Phylogeny G, Chase MW, Christenhusz MJM, Fay MF, Byng JW, Judd WS, Soltis DE, Mabberley DJ, Sennikov AN, Soltis PS, Stevens PF (2016) An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG IV. Bot J Linn Soc 181(1):1–20. https://doi.org/10.1111/boj.12385

    Article  Google Scholar 

  • Theodoratus DH, Bowers MD (1999) Effects of sequestered iridoid glycosides on prey choice of the prairie wolf spider, Lycosa carolinensis. J Chem Ecol 25(2):283–295. https://doi.org/10.1023/A:1020894729188

    Article  CAS  Google Scholar 

  • Tundis R, Loizzo MR, Menichini F, Statti GA, Menichini F (2008) Biological and pharmacological activities of iridoids: recent developments. Mini Rev Med Chem 8(4):399–420

    Article  CAS  PubMed  Google Scholar 

  • Ueoka H, Sasaki K, Miyawaki T, Ichino T, Tatsumi K, Suzuki S, Yamamoto H, Sakurai N, Suzuki H, Shibata D, Yazaki K (2020) A Cytosol-Localized Geranyl Diphosphate Synthase from Lithospermum erythrorhizon and Its Molecular Evolution1 [OPEN]. Plant Physiol 182(4):1933–1945. https://doi.org/10.1104/pp.19.00999

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Unno H, Ichimaida F, Suzuki H, Takahashi S, Tanaka Y, Saito A, Nishino T, Kusunoki M, Nakayama T (2007) Structural and Mutational Studies of Anthocyanin Malonyltransferases Establish the Features of BAHD Enzyme Catalysis. J Biol Chem 282(21):15812–15822. https://doi.org/10.1074/jbc.m700638200

    Article  CAS  PubMed  Google Scholar 

  • Vaičiulytė V, Ložienė K, Švedienė J, Raudonienė V, Paškevičius A (2021) α-Terpinyl acetate: occurrence in essential oils bearing Thymus pulegioides, phytotoxicity, and antimicrobial effects. Molecules 26(4):1065

    Article  PubMed  PubMed Central  Google Scholar 

  • Vernin GA, Parkanyi C, Cozzolino F, Fellous R (2004) GC/MS analysis of the volatile constituents of Corymbia citriodora Hook. from Réunion Island. Journal of Essential Oil Research 16 (6):560–565. https://doi.org/10.1080/10412905.2004.9698798

  • Viljoen A, Mncwangi N, Vermaak I (2012) Anti-inflammatory iridoids of botanical origin. Curr Med Chem 19(14):2104–2127

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wang C, Li J, Ma M, Lin Z, Hu W, Lin W, Zhang P (2021) Structural and biochemical insights into two BAHD acyltransferases (AtSHT and AtSDT) involved in phenolamide biosynthesis. Front Plant Sci 11. https://doi.org/10.3389/fpls.2020.610118

  • Wang P-p, Wang Z-k, Guan L, Haider MS, Nasim M, Yuan Y-b, Liu G-s, Leng X-p (2022) Versatile physiological functions of the Nudix hydrolase family in berry development and stress response in grapevine. J Integr Agric 21(1):91–112. https://doi.org/10.1016/S2095-3119(20)63490-6

    Article  CAS  Google Scholar 

  • Wany A, Jha S, Nigam VK, Pandey DM (2013) Chemical analysis and therapeutic uses of citronella oil from Cymbopogon winterianus: A short review. Int J Adv Res 1(6):504–521

    Google Scholar 

  • Williams DC, McGarvey DJ, Katahira EJ, Croteau R (1998) Truncation of limonene synthase preprotein provides a fully active “pseudomature” form of this monoterpene cyclase and reveals the function of the amino-terminal arginine pair. Biochemistry 37(35):12213–12220

    Article  CAS  PubMed  Google Scholar 

  • Willinger G, Dobler S (2001) Selective sequestration of iridoid glycosides from their host plants in Longitarsus flea beetles. Biochem Syst Ecol 29(4):335–346. https://doi.org/10.1016/S0305-1978(00)00082-X

    Article  CAS  PubMed  Google Scholar 

  • Wink M (2003) Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 64(1):3–19. https://doi.org/10.1016/S0031-9422(03)00300-5

    Article  CAS  PubMed  Google Scholar 

  • Wu Y, OuYang Q, Tao N (2016) Plasma membrane damage contributes to antifungal activity of citronellal against Penicillium digitatum. J Food Sci Technol 53(10):3853–3858. https://doi.org/10.1007/s13197-016-2358-x

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wu T, Li S, Zhang B, Bi C, Zhang X (2018) Engineering Saccharomyces cerevisiae for the production of the valuable monoterpene ester geranyl acetate. Microb Cell Fact 17(1):85. https://doi.org/10.1186/s12934-018-0930-y

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Xu H, Bohman B, Wong DCJ, Rodriguez-Delgado C, Scaffidi A, Flematti GR, Phillips RD, Pichersky E, Peakall R (2017) Complex sexual deception in an orchid is achieved by co-opting two independent biosynthetic pathways for pollinator attraction. Curr Biol 27(13):1867-1877.e1865. https://doi.org/10.1016/j.cub.2017.05.065

    Article  CAS  PubMed  Google Scholar 

  • Yahyaa M, Ibdah M, Marzouk S, Ibdah M (2018) Profiling of the Terpene Metabolome in Carrot Fruits of Wild (Daucus carota L. ssp. carota) Accessions and Characterization of a Geraniol Synthase. J Agric Food Chem 66 (10):2378–2386. https://doi.org/10.1021/acs.jafc.6b03596

  • Yan X, Qin X, Li W, Liang D, Qiao J, Li Y (2020) Functional characterization and catalytic activity improvement of BAHD acyltransferase from Celastrus angulatus Maxim. Planta 252(1):6. https://doi.org/10.1007/s00425-020-03413-2

    Article  CAS  PubMed  Google Scholar 

  • Yang T, Li J, Wang H-X, Zeng Y (2005) A geraniol-synthase gene from Cinnamomum tenuipilum. Phytochemistry 66(3):285–293

    Article  CAS  PubMed  Google Scholar 

  • Zeng X, Guo F, Ouyang D (2020) A review of the pharmacology and toxicology of aucubin. Fitoterapia 140:104443

    Article  CAS  PubMed  Google Scholar 

  • Zhang H, Xie Y, Liu C, Chen S, Hu S, Xie Z, Deng X, Xu J (2017) Comprehensive comparative analysis of volatile compounds in citrus fruits of different species. Food Chem 230:316–326. https://doi.org/10.1016/j.foodchem.2017.03.040

    Article  CAS  PubMed  Google Scholar 

  • Zhang X-M, Zhu J-L, Sun Y, Dai Y-L, Chen X, Cao J-H, Yang R-C, Chen C, Ma C-Y, Zhang T-E, Chen Y-H, Yan Z-Y (2018) Anxiolytic potency of iridoid fraction extracted from Valeriana jatamansi Jones and its mechanism: a preliminary study. Nat Prod Res 32(17):2071–2075. https://doi.org/10.1080/14786419.2017.1360881

    Article  CAS  PubMed  Google Scholar 

  • Zhang X, Liu K, Shi M, Xie L, Deng M, Chen H, Li X (2021a) Therapeutic potential of catalpol and geniposide in Alzheimer’s and Parkinson’s diseases: asnapshot of their underlying mechanisms. Brain Res Bull 174:281–295

    Article  CAS  PubMed  Google Scholar 

  • Zhang X, Teixeira da Silva JA, Niu M, Zhang T, Liu H, Zheng F, Yuan Y, Li Y, Fang L, Zeng S, Ma G (2021b) Functional characterization of an Indian sandalwood (Santalum album L.) dual-localized bifunctional nerolidol/linalool synthase gene involved in stress response. Phytochemistry 183:112610. https://doi.org/10.1016/j.phytochem.2020.112610

  • Zhao C, Yu Z, Silva JATd, He C, Wang H, Si C, Zhang M, Zeng D, Duan J (2020) Functional characterization of a Dendrobium officinale Geraniol Synthase DoGES1 involved in floral scent formation. Int J Mol Sci 21(19):7005

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhou F, Pichersky E (2020) The complete functional characterisation of the terpene synthase family in tomato. New Phytol 226(5):1341–1360. https://doi.org/10.1111/nph.16431

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Funding

This work was supported by a Discovery grant provided by the Natural Sciences and Engineering Research Council of Canada (RGPIN-2017–06400) to M.A.P. M.E.B. enjoyed the support of an NSERC CGSD scholarship, and A.E.F. was supported by a University of Toronto Excellence Award.

Author information

Authors and Affiliations

  1. Department of Cell and Systems Biology, University of Toronto, Toronto, ON, Canada

    Matthew E. Bergman & Michael A. Phillips

  2. Department of Biology, University of Toronto – Mississauga, Mississauga, ON, Canada

    Anya E. Franks & Michael A. Phillips

Authors
  1. Matthew E. Bergman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anya E. Franks
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Michael A. Phillips
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

MB, AF and MP wrote the manuscript, MP revised the manuscript, and MB and AF designed figures. Photo credits: MP.

Corresponding author

Correspondence to Michael A. Phillips.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bergman, M.E., Franks, A.E. & Phillips, M.A. Biosynthesis, natural distribution, and biological activities of acyclic monoterpenes and their derivatives. Phytochem Rev 22, 361–384 (2023). https://doi.org/10.1007/s11101-022-09849-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11101-022-09849-6

Keywords

Search

Navigation