{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T23:49:36Z","timestamp":1792799376100,"version":"4.5.0"},"reference-count":153,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2025,1,24]],"date-time":"2025-01-24T00:00:00Z","timestamp":1737676800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Brazilian National Council for Scientific and Technological Development (CNPq)","award":["PROEP\/FAR 440023\/2022-0"],"award-info":[{"award-number":["PROEP\/FAR 440023\/2022-0"]}]},{"name":"Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior\u2013Brasil CAPES","award":["PROEP\/FAR 440023\/2022-0"],"award-info":[{"award-number":["PROEP\/FAR 440023\/2022-0"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Perillic acid (PA) is a limonene derivative in which the exocyclic methyl is oxidized to a carboxyl group. Although endowed with potential anticancer activity, PA has been much less explored regarding its biological properties than analogous compounds such as perillyl alcohol, perillaldehyde, or limonene itself. PA is usually described in mixture with alcohols and ketones produced in the oxidation of monoterpenes, with relatively few existing reports focusing on the PA molecule. This study provides a comprehensive review of PA, addressing its origin, the processes of obtaining it through organic synthesis and biotransformation, and the pharmacological tests in which it is either the lead compound or reference for in vitro efficacy in experimental models. Although feasible and generally poorly yielded, the synthesis of PA from limonene requires multiple steps and the use of unusual catalysts. The most economical process involves using (\u2212)-\u03b2-pinene epoxide as the starting material, ending up with (\u2212)-PA. On the other hand, some bacteria and yeasts are successful in producing, exclusively or at satisfactory purity level, PA from limonene or a few other monoterpenes, through environmentally friendly approaches. The compiled data revealed that, with few exceptions, most reports on PA bioactivity are related to its ability to interfere with the prenylation process of oncogenic proteins, an essential step for the growth and dissemination of cancer cells. The present survey reveals that there is still a vast field to disclose regarding the obtaining and scaling of PA via the fermentative route, as well as extending prospective studies on its properties and possible pharmacological applications, especially in the preclinical oncology field.<\/jats:p>","DOI":"10.3390\/molecules30030528","type":"journal-article","created":{"date-parts":[[2025,1,24]],"date-time":"2025-01-24T05:24:31Z","timestamp":1737696271000},"page":"528","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis, Bioproduction and Bioactivity of Perillic Acid\u2014A Review"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1517-9085","authenticated-orcid":false,"given":"Tha\u00eds de Souza","family":"Rolim","sequence":"first","affiliation":[{"name":"Institute of Drug Technology, Fiocruz, Sizenando Nabuco St. 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andr\u00e9 Luiz Franco","family":"Sampaio","sequence":"additional","affiliation":[{"name":"Institute of Drug Technology, Fiocruz, Sizenando Nabuco St. 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Luiz","family":"Mazzei","sequence":"additional","affiliation":[{"name":"Institute of Drug Technology, Fiocruz, Sizenando Nabuco St. 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3060-0395","authenticated-orcid":false,"given":"Davyson Lima","family":"Moreira","sequence":"additional","affiliation":[{"name":"Institute of Drug Technology, Fiocruz, Sizenando Nabuco St. 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil"},{"name":"Rio de Janeiro Botanical Garden Research Institute, Pacheco Le\u00e3o St. 915, Jardim Bot\u00e2nico, Rio de Janeiro 22460-030, RJ, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8108-2500","authenticated-orcid":false,"given":"Antonio Carlos","family":"Siani","sequence":"additional","affiliation":[{"name":"Institute of Drug Technology, Fiocruz, Sizenando Nabuco St. 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,1,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"6328","DOI":"10.1080\/10408398.2021.1900060","article-title":"Recent development in biological activities and safety concerns of perillaldehyde from perilla plants: A review","volume":"62","author":"Erhunmwunsee","year":"2021","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_2","first-page":"1","article-title":"Limonene: Natural monoterpene volatile compounds of potential therapeutic interest","volume":"7","author":"Soulimani","year":"2019","journal-title":"Am. J. Essent. Oils Nat. Prod."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"155826","DOI":"10.1016\/j.phymed.2024.155826","article-title":"Molecular pharmacology and therapeutic advances of monoterpene perillyl alcohol","volume":"132","author":"Zhang","year":"2024","journal-title":"Phytomedicine"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"013","DOI":"10.17352\/ojpp.000021","article-title":"On the anticancer clinical activity of perillyl alcohol and limonene: A critical assessment of the outcomes","volume":"7","author":"Santos","year":"2022","journal-title":"Open J. Pharmacol. Pharmacother."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1007\/BF01898448","article-title":"Perillartine and some derivatives: Clarification of structures","volume":"26","author":"Acton","year":"1970","journal-title":"Experientia"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"961","DOI":"10.1039\/D2FO02227C","article-title":"Perillartine protects against metabolic associated fatty liver in high-fat diet-induced obese mice","volume":"14","author":"Xiao","year":"2023","journal-title":"Food Funct."},{"key":"ref_7","first-page":"CASE22215","article-title":"Detection of perillyl alcohol and its metabolite perillic acid in postsurgical glioblastoma tissue after intranasal administration of neo100: Illustrative case","volume":"4","author":"Swenson","year":"2022","journal-title":"J. Neurosurg. Case Lessons"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/j.taap.2003.11.013","article-title":"Perillyl alcohol-mediated inhibition of lung cancer cell line proliferation: Potential mechanisms for its chemotherapeutic effects","volume":"195","author":"Xu","year":"2004","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"216","DOI":"10.1016\/j.canlet.2007.07.020","article-title":"Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non-small cell lung cancer cells","volume":"257","author":"Yeruva","year":"2007","journal-title":"Cancer Lett."},{"key":"ref_10","first-page":"34","article-title":"Bioactive plant compounds inhibited the proliferation and induced apoptosis in human cancer cell lines, in vitro","volume":"1","author":"Samaila","year":"2004","journal-title":"Trans. Integrated Biomed. Inform. Enabling Tech. Symp. J."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"925342","DOI":"10.1155\/2013\/925342","article-title":"A review on bioactivities of perilla: Progress in research on the functions of perilla as medicine and food","volume":"2013","author":"Igarashi","year":"2013","journal-title":"Evid.-Based Complement. Altern. Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/j.cbi.2018.02.007","article-title":"Limonene: Aroma of innovation in health and disease","volume":"283","author":"Vieira","year":"2018","journal-title":"Chem.-Biol. Interact."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Mukhtar, Y.M., Adu-Frimpong, M., Xu, X., and Yu, J. (2018). Biochemical significance of limonene and its metabolites: Future prospects for designing and developing highly potent anticancer drugs. Biosci. Rep., 38.","DOI":"10.1042\/BSR20181253"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1636","DOI":"10.1016\/j.bmc.2008.12.057","article-title":"Taste-guided identification of high potency TRPA1 agonists from Perilla frutescens","volume":"17","author":"Bassoli","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_15","first-page":"342","article-title":"Essential oil of Perilla nankinensis Decne","volume":"23","author":"Furukawa","year":"1920","journal-title":"J. Chem. Ind. Tokyo"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1007\/s11418-007-0213-0","article-title":"Perilla frutescens var. frutescens in northern Laos","volume":"62","author":"Ito","year":"2008","journal-title":"J. Nat. Med."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1016\/j.indcrop.2014.04.048","article-title":"Regional variation in components and antioxidant and antifungal activities of Perilla frutescens essential oils in China","volume":"59","author":"Tian","year":"2014","journal-title":"Ind. Crops Prod."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1080\/10412905.2015.1081415","article-title":"Chemical diversity in the volatiles of Perilla frutescens (L.) Britt. populations from Uttarakhand Himalaya (India)","volume":"28","author":"Gwari","year":"2016","journal-title":"J. Essent. Oil Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1080\/10412905.2012.755478","article-title":"Volatile oil composition of Indian Perilla [Perilla frutescens (L.) Britton] collected at different phenophases","volume":"25","author":"Verma","year":"2013","journal-title":"J. Essent. Oil Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"697","DOI":"10.1046\/j.1365-2745.1999.00391.x","article-title":"Can plasticity compensate for architectural constraints on reproduction? Patterns of seed production and carbohydrate translocation in Perilla frutescens","volume":"87","author":"Preston","year":"1999","journal-title":"J. Ecol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1007\/s42965-021-00195-w","article-title":"Morphology and physiology of Perilla frutescens (Linn.) Britt in relation to micro-climate and edaphic characteristics","volume":"63","author":"Sharma","year":"2022","journal-title":"Trop. Ecol."},{"key":"ref_22","first-page":"945","article-title":"Chemotype study of volatile components from Perillae Folium of different germplasms","volume":"12","author":"Chen","year":"2021","journal-title":"China Pharm."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"859","DOI":"10.1016\/0031-9422(86)80017-6","article-title":"Genetic control of the chemical composition of volatile oils in Perilla frutescens","volume":"25","author":"Koezuka","year":"1986","journal-title":"Phytochemistry"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1007\/PL00020530","article-title":"Genetic analysis of essential oil variants in Perilla frutescens","volume":"33","author":"Yuba","year":"1995","journal-title":"Biochem. Genet."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s00606-009-0152-1","article-title":"Essential oil variations in different Perilla L. accessions: Chemotaxonomic implications","volume":"281","author":"Zhang","year":"2009","journal-title":"Plant Syst. Evol."},{"key":"ref_26","unstructured":"(2025, January 01). Schimmel and Co. Oil of Perilla nankinensis. Semi-Annual Report 1910, Miltitz, Oct., pp. 146\u2013147. Available online: https:\/\/www.biodiversitylibrary.org\/page\/42014511#page\/158\/mode\/1up."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1002\/cber.19110440107","article-title":"Zur Kenntnis der Bestandteile \u00e4therischer \u00d6le. (Konstitution des Perilla-Aldehyds, C10H14O)","volume":"44","author":"Semmler","year":"1911","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"127","DOI":"10.3839\/jabc.2021.019","article-title":"Variation in essential oil composition and antimicrobial activity among different genotypes of Perilla frutescens var. crispa","volume":"64","author":"Ju","year":"2021","journal-title":"J. Appl. Biol. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1002\/cber.191104401118","article-title":"Zur Kenntnis der Bestandteile \u00e4therischer \u00d6le. \u00dcber \u2018falsches Campherholz\u00f6l\u2019 (faux camphrier); \u00fcber das Vorkommen von Myrtenal und d-Perilla-Aldehyd in der Natur","volume":"44","author":"Semmler","year":"1911","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"ref_30","unstructured":"Miller, K.L. (1952). The Chemistry of Perillaldehyde and Certain of Its Derivatives. [Ph.D. Thesis, Oregon State College]."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"122","DOI":"10.1002\/ffj.1174","article-title":"Composition of the essential oil of Perilla frutescens (L.) Britton from Turkey","volume":"18","author":"Demirci","year":"2003","journal-title":"Flavour Fragr. J."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Bouzekri, O., Elgamouz, S., Ghaleb, A., Amechrouq, A., and El Idrissi, M. (2022). Valorization of perillaldehyde molecule contained in the essential oil of Ammodaucus leucotrichus Coss. from the Saharan zones of Morocco. J. Microbiol. Biotechnol. Food Sci., 11.","DOI":"10.55251\/jmbfs.4324"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"606","DOI":"10.3109\/09637480801993938","article-title":"Chemical composition and antimicrobial activity of the extracts of Kefe cumin (Laser trilobum L.) fruits from different regions","volume":"60","author":"Parlatan","year":"2009","journal-title":"Int. J. Food Sci. Nutr."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/j.foodchem.2010.08.043","article-title":"Comparison of HS-SPME with hydrodistillation and SFE for the analysis of the volatile compounds of Zisu and Baisu, two varietal species of Perilla frutescens of Chinese origin","volume":"125","author":"Huang","year":"2011","journal-title":"Food Chem."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Wei, M.C., Wang, C.S., Wei, D.H., and Yang, Y.C. (2021). Insights into the supercritical CO2 extraction of perilla oil and its theoretical solubility. Processes, 9.","DOI":"10.3390\/pr9020239"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"9963","DOI":"10.53730\/ijhs.v6nS6.12566","article-title":"Essential oil composition and biological activities of Hyssopus officinalis and Perilla frutescens","volume":"6","author":"Eldeghedy","year":"2022","journal-title":"Int. J. Health Sci."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1545","DOI":"10.1016\/S0031-9422(00)90843-4","article-title":"Monoterpene glucosides and other constituents from Perilla frutescens","volume":"34","author":"Fujita","year":"1993","journal-title":"Phytochemistry"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1684","DOI":"10.1021\/jo00949a014","article-title":"(+)-Limonene oxidation with selenium dioxide-hydrogen peroxide","volume":"38","author":"Shaw","year":"1973","journal-title":"J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1016\/0304-5102(93)87064-F","article-title":"Carbon monoxide as a building block in organic synthesis: Part II. One-step synthesis of esters by alkoxycarbonylation of naturally occurring allylbenzenes, propenylbenzenes and monoterpenes","volume":"78","author":"Chenal","year":"1993","journal-title":"J. Mol. Catal."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"7713","DOI":"10.1021\/acssuschemeng.1c01788","article-title":"Selective catalytic epoxide ring-opening of limonene dioxide with water","volume":"9","author":"Raupp","year":"2021","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/S1381-1169(97)00285-9","article-title":"Selective palladium-catalysed functionalization of limonene: Synthetic and mechanistic aspects","volume":"135","author":"Baqqa","year":"1998","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1016\/j.molcata.2006.02.021","article-title":"Palladium-catalyzed oxidation of monoterpenes: Highly selective syntheses of allylic ethers from limonene","volume":"252","author":"Bueno","year":"2006","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1869","DOI":"10.1039\/C4CY00087K","article-title":"Recent developments in liquid-phase selective oxidation using environmentally benign oxidants and mesoporous metal silicates","volume":"4","author":"Kholdeeva","year":"2014","journal-title":"Catal. Sci. Technol."},{"key":"ref_44","first-page":"11","article-title":"Oxidaci\u00f3n al\u00edlica de monoterpenos con metaloftalocianinas","volume":"13","author":"Villa","year":"2007","journal-title":"Sci. Tech."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1016\/0040-4020(89)80018-3","article-title":"Allyl-and benzylstannanes, new reagents in terpenic synthesis","volume":"45","author":"Adrianome","year":"1989","journal-title":"Tetrahedron"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1431","DOI":"10.1016\/j.tetlet.2014.01.039","article-title":"Synthesis of (+)-perillyl alcohol from (+)-limonene","volume":"55","author":"Geoghegan","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"925","DOI":"10.1016\/0040-4020(76)85050-8","article-title":"An efficient synthesis of juvabione and todomatuic acid via hydroboration-carbonylation","volume":"32","author":"Negishi","year":"1976","journal-title":"Tetrahedron"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"77","DOI":"10.3109\/00498257409049347","article-title":"Studies on the metabolism of d-limonene (p-mentha-1, 8-diene): I. the absorption, distribution and excretion of d-limonene in rats","volume":"4","author":"Igimi","year":"1974","journal-title":"Xenobiotica"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"20152","DOI":"10.1021\/acs.iecr.3c02633","article-title":"Versatile heterogeneous catalytic system for the selective synthesis of limonene epoxide and diepoxide","volume":"62","author":"Villa","year":"2023","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2381","DOI":"10.1021\/ja01162a009","article-title":"The action of t-butyl hypochlorite on \u03b1-pinene","volume":"72","author":"Ritter","year":"1950","journal-title":"J. Am. Chem. Soc."},{"key":"ref_51","first-page":"46","article-title":"Composition of gum turpentines of pines. XVI. A report on Pinus oocarpa and P. pseudostrobus var. oaxacana from Chiapas and P. cooperi from Durango","volume":"42","author":"Illof","year":"1953","journal-title":"J. Am. Pharm. Assoc."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"3054","DOI":"10.1021\/ja01616a038","article-title":"Neighboring carbon and hydrogen. XVIII. Solvolysis of the nopinyl p-bromobenzenesulfonates","volume":"77","author":"Winstein","year":"1955","journal-title":"J. Am. Chem. Soc."},{"key":"ref_53","first-page":"1161","article-title":"Sur les reactions des derives des pinenes-alpha et pinenes-beta ayant une fonction alcool en alpha du cycle butanique","volume":"8\u20139","author":"Kergomard","year":"1957","journal-title":"Bull. Soc. Chim. Fr."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1032","DOI":"10.1021\/jo01050a503","article-title":"Acid-catalyzed rearrangements of nopinic acid","volume":"27","author":"Herz","year":"1962","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1039\/p19760000484","article-title":"Formation of ortho-menthenes by acid-catalysed ring opening of pin-2-ene derivatives","volume":"5","author":"Lander","year":"1976","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"668","DOI":"10.1039\/J29710000668","article-title":"Rearrangements of pinane derivatives. Part I. Products of acid catalysed hydration of \u03b1-pinene and \u03b2-pinene","volume":"4","author":"Williams","year":"1971","journal-title":"J. Chem. Soc. B Phys. Org."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1442","DOI":"10.1002\/hlca.201500125","article-title":"The First Synthesis of (4S, 5R, 6R)-5,6-Dihydroxy-4-(prop-1-en-2-yl) cyclohex-1-ene-1-carboxylic Acid","volume":"98","author":"Ardashov","year":"2015","journal-title":"Helv. Chim. Acta"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1747","DOI":"10.1039\/p19800001747","article-title":"Cyclobutane ring opening of pin-2 (10)-ene with mercury (II) salts. A new, high-yield synthesis of p-mentha-1,8-dien-7-ol","volume":"8","author":"Bluthe","year":"1980","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1039\/qr9662000373","article-title":"Rearrangements of pinane derivatives. Q","volume":"20","author":"Banthorpe","year":"1966","journal-title":"Rev. Chem. Soc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1016\/S0040-4020(01)86265-7","article-title":"Enantioselective synthesis of chiral liquid crystalline compounds from monoterpenes","volume":"49","author":"Wang","year":"1993","journal-title":"Tetrahedron"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1134\/S1070428008010016","article-title":"Acid-catalyzed transformations of pinane terpenoids. New prospects","volume":"44","author":"Volcho","year":"2008","journal-title":"Russ. J. Org. Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"2279","DOI":"10.1007\/s10562-020-03489-1","article-title":"Selective synthesis of perillyl alcohol from \u03b2-pinene epoxide over Ti and Mo supported catalysts","volume":"151","author":"Cruz","year":"2021","journal-title":"Catal. Lett."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1002\/open.202000318","article-title":"Selective Catalytic Isomerization of \u03b2-Pinene Oxide to Perillyl Alcohol Enhanced by Protic Tetraimidazolium Nitrate","volume":"10","author":"Li","year":"2021","journal-title":"ChemistryOpen"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1016\/j.micromeso.2019.05.053","article-title":"Ring-opening of \u03b2-pinene epoxide into high-added value products over Colombian natural zeolite","volume":"287","author":"Gelves","year":"2019","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1007\/s11144-016-0994-9","article-title":"The solvent effect in \u03b2-pinene oxide rearrangement","volume":"118","author":"Aho","year":"2016","journal-title":"React. Kinet. Mech. Catal."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"3971","DOI":"10.1007\/s11164-018-3335-y","article-title":"Perillyl alcohol preparation from \u03b2-pinene oxide using Fe-modified zeolite beta","volume":"44","author":"Krupka","year":"2018","journal-title":"Res. Chem. Intermed."},{"key":"ref_67","unstructured":"Hifzur, R.A., and Fido, P.E. (1976). Production of the Carboxylic Acid of Perillyl. (US3957856A), Alcohol. Patent."},{"key":"ref_68","unstructured":"Shen, M., Ma, S., and Ha, C. (2006). A Kind of Method for Preparing 4-Normenthane Formic. (CN1733683A), Acid. Patent."},{"key":"ref_69","unstructured":"Chastain, D.E., Mody, N., and Majetich, G. (1999). Method of Preparing Perillyl Alcohol and Perillyl. (US5994598A), Acetate. Patent."},{"key":"ref_70","unstructured":"Kolomeyer, G.G., and Ferone, D.A. (2010). Process for Making Perillyl. (US7851660B1), Alcohol. Patent."},{"key":"ref_71","first-page":"137","article-title":"Processos de bioconvers\u00e3o aplicados \u00e0 obten\u00e7\u00e3o de f\u00e1rmacos e intermedi\u00e1rios","volume":"Volume 4","author":"Resende","year":"2017","journal-title":"Biotecnologia Aplicada \u00e0 Agro & Ind\u00fastria"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.cofs.2018.03.005","article-title":"Biogeneration of aroma compounds","volume":"19","author":"Sales","year":"2018","journal-title":"Curr. Opin. Food Sci."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1007\/s00253-003-1221-y","article-title":"Biotransformation of limonene by bacteria, fungi, yeasts, and plants","volume":"61","author":"Duetz","year":"2003","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"5507","DOI":"10.1021\/ja01529a060","article-title":"Microbial degradation of (+)-camphor","volume":"81","author":"Bradshaw","year":"1959","journal-title":"J. Am. Chem. Soc."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1016\/S0021-9258(18)97679-9","article-title":"Mixed function oxidation. II. Separation and properties of the enzymes catalyzing camphor lactonization","volume":"240","author":"Conrad","year":"1965","journal-title":"J. Biol. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"4029","DOI":"10.1016\/S0021-9258(18)97146-2","article-title":"Mixed function oxidation. III. An electron transport complex in camphor lactonization","volume":"240","author":"Conrad","year":"1965","journal-title":"J. Biol. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"689","DOI":"10.1038\/187689b0","article-title":"Microbiological transformation of terpenes: Hydroxylation of \u03b1-pinene","volume":"187","author":"Bhattacharyya","year":"1960","journal-title":"Nature"},{"key":"ref_78","unstructured":"Dhavalikar, R.S. (1964). Microbiological Transformation of Terpenes. [Ph.D. Thesis, University of Poona]."},{"key":"ref_79","first-page":"158","article-title":"Microbiological transformations of terpenes. IX. Pathways of degradation of limonene in a soil pseudomonad","volume":"3","author":"Dhavalikar","year":"1966","journal-title":"Indian J. Biochem."},{"key":"ref_80","first-page":"144","article-title":"Microbiological transformations of terpenes. 8. Fermentation of limonene by a soil pseudomonad","volume":"3","author":"Dhavalikar","year":"1966","journal-title":"Indian J. Biochem."},{"key":"ref_81","unstructured":"Shukla, O.P. (1965). Microbiological Transformation of Terpenes. [Ph.D. Thesis, University of Poona]."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"1429","DOI":"10.1139\/m84-228","article-title":"Metabolism of \u03b1-terpineol by Pseudomonas incognita","volume":"30","author":"Madyastha","year":"1984","journal-title":"Can. J. Microbiol."},{"key":"ref_83","first-page":"1507","article-title":"Terpene bioconversion\u2013how does its future look?","volume":"5","author":"Krings","year":"2010","journal-title":"Nat. Prod. Commun."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"1075","DOI":"10.1590\/S1517-83822014005000008","article-title":"Bioconversion of R-(+)-limonene to perillic acid by the yeast Yarrowia lipolytica","volume":"44","author":"Ferrara","year":"2013","journal-title":"Brazil. J. Microbiol."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"172","DOI":"10.4236\/gsc.2017.72013","article-title":"Synthesis of the prospective anticancer molecule perillic acid from orange essential oil by the yeast Yarrowia lipolytica","volume":"7","author":"Tappin","year":"2017","journal-title":"Green Sustain. Chem."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1016\/0006-291X(67)90448-2","article-title":"Perillyl aldehyde dehydrogenase from a soil pseudomonad","volume":"29","author":"Ballal","year":"1967","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1007\/BF00505828","article-title":"Microbial transformation of \u03b1-pinene","volume":"16","author":"Narushima","year":"1982","journal-title":"Eur. J. Appl. Microbiol. Biotechnol."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"1241","DOI":"10.1111\/j.1365-2621.1989.tb05964.x","article-title":"Bioconversion of (+)-limonene by Pseudomonas gladioli","volume":"54","author":"Cadwallader","year":"1989","journal-title":"J. Food Sci."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1007\/BF00058829","article-title":"Microbial metabolism of monoterpenes\u2014Recent developments","volume":"1","author":"Trudgill","year":"1990","journal-title":"Biodegradation"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1111\/j.1365-2621.1995.tb09824.x","article-title":"Cloning and expression of a limonene degradation pathway from Bacillus stearothermophilus in Escherichia coli","volume":"60","author":"Chang","year":"1995","journal-title":"J. Food Sci."},{"key":"ref_91","unstructured":"Pressler, U., Balkenhohl, F., Hauer, B., Ladner, W., Schnell, U., and Staudenmaier, H.R. (1994). Verfahren zur Biotechnologischen Herstellung von Alkoholen. (EP0707656B1), Aldehyden und Carbons\u00e4uren. Patent."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"300","DOI":"10.1021\/jf970142l","article-title":"Biotransformation of (+)-and (\u2212)-limonene by the larvae of common cutworm (Spodoptera litura)","volume":"46","author":"Miyazawa","year":"1998","journal-title":"J. Agric. Food Chem."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"538","DOI":"10.1007\/s002530051331","article-title":"Limonene bioconversion to high concentrations of a single and stable product, perillic acid, by a solvent-resistant Pseudomonas putida strain","volume":"50","author":"Speelmans","year":"1998","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1007\/s002530100625","article-title":"Bioconversion of limonene to increased concentrations of perillic acid by Pseudomonas putida GS1 in a fed-batch reactor","volume":"56","author":"Mars","year":"2001","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_95","unstructured":"Duetz, W.A., Witholt, B., and Jourdat, C. (2002). Process for the Preparation of Perillyl. (WO2002066662), Alcohol. Patent."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"764","DOI":"10.1016\/j.procbio.2009.03.013","article-title":"Integrated bioprocess for the oxidation of limonene to perillic acid with Pseudomonas putida DSM 12264","volume":"44","author":"Mirata","year":"2009","journal-title":"Process Biochem."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"1282","DOI":"10.1002\/bit.24801","article-title":"Whole-cell-based CYP153A6-catalyzed (S)-limonene hydroxylation efficiency depends on host background and profits from monoterpene uptake via AlkL","volume":"110","author":"Cornelissen","year":"2013","journal-title":"Biotechnol. Bioeng."},{"key":"ref_98","first-page":"217","article-title":"Biotransformation of \u03943-carene by Penicillium nigricans","volume":"74","author":"Muddapur","year":"2015","journal-title":"J. Sci. Ind. Res."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"636","DOI":"10.4236\/ajac.2017.810046","article-title":"Determination of Perillic Acid in Bioconversion Supernatants by Gas Chromatography","volume":"8","author":"Carvalho","year":"2017","journal-title":"Am. J. Anal. Chem."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1002\/bit.26071","article-title":"Continuous multistep synthesis of perillic acid from limonene by catalytic biofilms under segmented flow","volume":"114","author":"Willrodt","year":"2017","journal-title":"Biotechnol. Bioeng."},{"key":"ref_101","unstructured":"Yang, D., Gao, S., and Yang, K. (2021). Method for Converting Limonene into Perillic Acid by Yarrowia. (CN113801899A), lipolytica. Patent."},{"key":"ref_102","doi-asserted-by":"crossref","unstructured":"Voicea, S.A., and Tudorache, M. (2022). Biocatalytic Preparation of Perillic Derivatives as an Alternative to Limonene Valorization. Chem. Proc., 7.","DOI":"10.3390\/chemproc2022007052"},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"2663","DOI":"10.1007\/s42770-023-01108-w","article-title":"Production of perillic acid from orange essential oil by Yarrowia lipolytica using a top-aerated bioreactor","volume":"54","author":"Knopp","year":"2023","journal-title":"Brazil. J. Microbiol."},{"key":"ref_104","first-page":"1934578X1200700401","article-title":"Determination of the Absolute Stereochemistry of Limonene and \u03b1-Santalol by Raman Optical Activity Spectroscopy","volume":"7","author":"Sakamoto","year":"2012","journal-title":"Nat. Prod. Commun."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"806","DOI":"10.1016\/j.biortech.2016.05.006","article-title":"Citrus Waste as Feedstock for Bio-Based Products Recovery: Review on Limonene Case Study and Energy Valorization","volume":"214","author":"Negro","year":"2016","journal-title":"Bioresour. Technol."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1007\/s10545-011-9445-y","article-title":"Protein farnesylation and disease","volume":"35","author":"Novelli","year":"2012","journal-title":"J. Inherit. Metab. Dis."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1016\/B978-0-12-420146-0.00008-1","article-title":"Recent progress in developing small molecule inhibitors designed to interfere with ras membrane association: Toward inhibiting K-Ras and N-Ras functions","volume":"34 Pt B","author":"Tamanoi","year":"2013","journal-title":"Enzymes"},{"key":"ref_108","unstructured":"Surana, K.R., Pawar, R.B., Khairnar, R.A., and Mahajan, S.K. (2022). Protein Prenylation and Their Applications. Modifications in Biomacromolecules, IntechOpen."},{"key":"ref_109","doi-asserted-by":"crossref","unstructured":"Marchwicka, A., Kami\u0144ska, D., Monirialamdari, M., B\u0142a\u017cewska, K.M., and Gendaszewska-Darmach, E. (2022). Protein prenyltransferases and their inhibitors: Structural and functional characterization. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23105424"},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1080\/14789450.2017.1332998","article-title":"Exploring the Biochemistry of the Prenylome and Its Role in Disease through Proteomics: Progress and Potential","volume":"14","author":"Brioschi","year":"2017","journal-title":"Expert Rev. Proteom."},{"key":"ref_111","doi-asserted-by":"crossref","unstructured":"Ashok, S., and Rao, S.R. (2024). Updates on protein-prenylation and associated inherited retinopathies. Front. Ophthalmol., 4.","DOI":"10.3389\/fopht.2024.1410874"},{"key":"ref_112","doi-asserted-by":"crossref","unstructured":"Jung, D., and Bachmann, H.S. (2023). Regulation of protein prenylation. Biomed. Pharmacother., 164.","DOI":"10.1016\/j.biopha.2023.114915"},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"814","DOI":"10.1038\/42961","article-title":"C-terminal binding domain of Rho GDP-dissociation inhibitor directs N-terminal inhibitory peptide to GTPases","volume":"387","author":"Gosser","year":"1997","journal-title":"Nature"},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"775","DOI":"10.1038\/nrc3151","article-title":"Targeting Protein Prenylation for Cancer Therapy","volume":"11","author":"Berndt","year":"2011","journal-title":"Nat. Rev. Cancer"},{"key":"ref_115","first-page":"e57082","article-title":"The Rat Sarcoma Virus (RAS) Family of Proteins in Sarcomas","volume":"16","author":"Unat","year":"2024","journal-title":"Cureus"},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"828","DOI":"10.1038\/nrd4389","article-title":"Drugging the Undruggable Ras: Mission Possible?","volume":"13","author":"Cox","year":"2014","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1002\/iub.2418","article-title":"Structure, catalysis, and inhibition mechanism of prenyltransferase","volume":"73","author":"Chang","year":"2021","journal-title":"IUBMB Life"},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"vdab005","DOI":"10.1093\/noajnl\/vdab005","article-title":"Phase I trial of intranasal NEO100, highly purified perillyl alcohol, in adult patients with recurrent glioblastoma","volume":"3","author":"Peereboom","year":"2021","journal-title":"Neuro-Oncol. Adv."},{"key":"ref_119","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1007\/s002800050793","article-title":"Phase I and pharmacokinetic study of D-limonene in patients with advanced cancer","volume":"42","author":"Vigushin","year":"1998","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref_120","doi-asserted-by":"crossref","first-page":"17679","DOI":"10.1016\/S0021-9258(19)47425-5","article-title":"Selective inhibition of isoprenylation of 21-26-kDa proteins by the anticarcinogen d-limonene and its metabolites","volume":"266","author":"Crowell","year":"1991","journal-title":"J. Biol. Chem."},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1007\/BF00685549","article-title":"Identification of metabolites of the antitumor agent d-limonene capable of inhibiting protein isoprenylation and cell growth","volume":"31","author":"Crowell","year":"1992","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1042\/bj2950031","article-title":"Modulation of insulin secretion from normal rat islets by inhibitors of the post-translational modifications of GTP-binding proteins","volume":"295","author":"Metz","year":"1993","journal-title":"Biochem. J."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"787","DOI":"10.1093\/carcin\/15.4.787","article-title":"Growth inhibition of rat liver epithelial tumor cells by monoterpenes does not involve Ras plasma membrane association","volume":"15","author":"Ruch","year":"1994","journal-title":"Carcinogenesis"},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1002\/eji.1830240204","article-title":"Prenylated proteins and lymphocyte proliferation: Inhibition by d-limonene and related monoterpenes","volume":"24","author":"Schulz","year":"1994","journal-title":"Eur. J. Immunol."},{"key":"ref_125","first-page":"67","article-title":"Human mononuclear cell proliferation, but not interleukin-6 production, is dependent on isoprenoid products of mevalonate metabolism","volume":"10","author":"Atluru","year":"1994","journal-title":"Biochem. Arch."},{"key":"ref_126","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/0304-3835(95)03747-K","article-title":"The inhibition of protein prenyltransferases by oxygenated metabolites of limonene and perillyl alcohol","volume":"91","author":"Gelb","year":"1995","journal-title":"Cancer Lett."},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1097\/00001813-199606000-00008","article-title":"Inhibition of tumor cell growth by monoterpenes in vitro: Evidence of a Ras-independent mechanism of action","volume":"7","author":"Karlson","year":"1996","journal-title":"Anti-Cancer Drugs"},{"key":"ref_128","doi-asserted-by":"crossref","first-page":"962","DOI":"10.1038\/ki.1997.418","article-title":"HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture","volume":"52","author":"Iimura","year":"1997","journal-title":"Kidney Int."},{"key":"ref_129","doi-asserted-by":"crossref","first-page":"720","DOI":"10.1006\/bbrc.1997.7884","article-title":"Perillic acid inhibits Ras\/MAPkinase-driven IL-2 production in human T lymphocytes","volume":"241","author":"Schulz","year":"1997","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_130","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/01635589809514708","article-title":"Monoterpenes inhibit cell growth, cell cycle progression, and cyclin D1 gene expression in human breast cancer cell lines","volume":"32","author":"Bardon","year":"1998","journal-title":"Nutr. Cancer"},{"key":"ref_131","doi-asserted-by":"crossref","first-page":"1352","DOI":"10.1152\/jn.1998.80.3.1352","article-title":"Involvement of Ras\/MAP kinase in the regulation of Ca2+ channels in adult bullfrog sympathetic neurons by nerve growth factor","volume":"80","author":"Lei","year":"1998","journal-title":"J. Neurophysiol."},{"key":"ref_132","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1161\/01.RES.83.5.490","article-title":"3-Hydroxy-3-methylglutaryl coenzyme A reductase and isoprenylation inhibitors induce apoptosis of vascular smooth muscle cells in culture","volume":"83","author":"Guijarro","year":"1998","journal-title":"Circ. Res."},{"key":"ref_133","doi-asserted-by":"crossref","first-page":"801","DOI":"10.1016\/S0006-2952(98)00349-9","article-title":"Inhibition of protein prenylation by metabolites of limonene","volume":"57","author":"Hardcastle","year":"1999","journal-title":"Biochem. Pharmacol."},{"key":"ref_134","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1006\/taap.2000.8988","article-title":"Cytotoxicity and biotransformation of the anticancer drug perillyl alcohol in PC12 cells and in the rat","volume":"167","author":"Boon","year":"2000","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"ref_135","doi-asserted-by":"crossref","first-page":"1637","DOI":"10.1016\/S0006-2952(01)00808-5","article-title":"Effect of S (\u2212) perillic acid on protein prenylation and arterial smooth muscle cell proliferation","volume":"62","author":"Ferri","year":"2001","journal-title":"Biochem. Pharmacol."},{"key":"ref_136","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/S0304-3835(02)00047-2","article-title":"Monoterpenes inhibit proliferation of human colon cancer cells by modulating cell cycle-related protein expression","volume":"181","author":"Bardon","year":"2002","journal-title":"Cancer Lett."},{"key":"ref_137","doi-asserted-by":"crossref","first-page":"2123","DOI":"10.1080\/1042819031000116652","article-title":"Farnesyl transferase inhibitors enhance death receptor signals and induce apoptosis in multiple myeloma cells","volume":"44","author":"Beaupre","year":"2003","journal-title":"Leuk. Lymphoma"},{"key":"ref_138","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1081\/IPH-120020476","article-title":"Immunomodulatory activity of naturally occurring monoterpenes carvone, limonene, and perillic acid","volume":"25","author":"Raphael","year":"2003","journal-title":"Immunopharmacol. Immunotoxicol."},{"key":"ref_139","first-page":"419","article-title":"Effect of naturally occurring monoterpenes carvone, limonene and perillic acid in the inhibition of experimental lung metastasis induced by B16F-10 melanoma cells","volume":"22","author":"Raphael","year":"2003","journal-title":"J. Exp. Clin. Cancer Res."},{"key":"ref_140","first-page":"3089","article-title":"Monoterpenes enhanced the sensitivity of head and neck cancer cells to radiation treatment in vitro","volume":"24","author":"Samaila","year":"2004","journal-title":"Anticancer Res."},{"key":"ref_141","doi-asserted-by":"crossref","first-page":"829","DOI":"10.1016\/j.intimp.2004.12.012","article-title":"Effect of D-limonene on immune response in BALB\/c mice with lymphoma","volume":"5","year":"2005","journal-title":"Int. Immunopharmacol."},{"key":"ref_142","doi-asserted-by":"crossref","first-page":"3887","DOI":"10.1016\/j.bpj.2010.11.009","article-title":"Interaction of salicylate and a terpenoid plant extract with model membranes: Reconciling experiments and simulations","volume":"99","author":"Khandelia","year":"2010","journal-title":"Biophys. J."},{"key":"ref_143","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1615\/JEnvironPatholToxicolOncol.v29.i3.40","article-title":"Protective role of perillic acid against radiation-induced oxidative stress, cytokine profile, DNA damage, and intestinal toxicity in mice","volume":"29","author":"Pratheeshkumar","year":"2010","journal-title":"J. Environ. Pathol. Toxicol. Oncol."},{"key":"ref_144","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.cellimm.2012.09.002","article-title":"D-Limonene modulates T lymphocyte activity and viability","volume":"279","author":"Lappas","year":"2012","journal-title":"Cell. Immunol."},{"key":"ref_145","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1021\/np200713q","article-title":"Influence of the active compounds of Perilla frutescens leaves on lipid membranes","volume":"75","author":"Duelund","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_146","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1186\/s12943-015-0374-5","article-title":"Na\/K-ATPase as a target for anticancer drugs: Studies with perillyl alcohol","volume":"14","author":"Garcia","year":"2015","journal-title":"Mol. Cancer"},{"key":"ref_147","unstructured":"Siani, A.C., Ferrara, M.A., Lacerda, P.S.B., Silva-L\u00f3pez, R.E., Sampaio, A.L.F., Tappin, M.R.R., and Bon, E.P.S. (2017). Compound, Process for Preparing a Compound, Pharmaceutical Composition, Use of a Compound and Method for Treating. (US20170260121A1), Cancer. Patent."},{"key":"ref_148","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1111\/iju.13516","article-title":"Perilla extract improves frequent urination in spontaneously hypertensive rats with enhancement of the urothelial presence and anti-inflammatory effects","volume":"25","author":"Kitamura","year":"2018","journal-title":"Int. J. Urol."},{"key":"ref_149","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3851\/IMP3315","article-title":"Perillyl alcohol and perillic acid exert efficient action upon HSV-1 maturation and release of infective virus","volume":"25","author":"Mello","year":"2020","journal-title":"Antiviral Ther."},{"key":"ref_150","doi-asserted-by":"crossref","first-page":"516","DOI":"10.54085\/ap.2023.12.2.61","article-title":"In vitro antidiabetic and antioxidant assessment of Hydrocharis laevigata (Hump. & Bonl. ex Willd.) Byng & Christenh","volume":"12","author":"Bhavani","year":"2023","journal-title":"Ann. Phytomed."},{"key":"ref_151","doi-asserted-by":"crossref","first-page":"11349","DOI":"10.1039\/D3DT01876H","article-title":"Platinum (IV) combo prodrugs containing cyclohexane-1R, 2R-diamine, valproic acid, and perillic acid as a multiaction chemotherapeutic platform for colon cancer","volume":"52","author":"Gabano","year":"2023","journal-title":"Dalton Trans."},{"key":"ref_152","doi-asserted-by":"crossref","unstructured":"Jiang, L., Hao, Y., Li, Q., and Dai, Z. (2024). Cinnamic acid, perillic acid, and tryptophan metabolites differentially regulate ion transport and serotonin metabolism and signaling in the mouse ileum in vitro. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms25126694"},{"key":"ref_153","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1007\/s10989-023-10583-6","article-title":"Design and self-assembly of tri-terpene peptide conjugates and their interactions with EGFR and EGFR mutant receptors: An in silico and in vitro study","volume":"30","author":"Rico","year":"2023","journal-title":"Int. J. Pept. Res. Ther."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/3\/528\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T10:35:19Z","timestamp":1759919719000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/3\/528"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,24]]},"references-count":153,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2025,2]]}},"alternative-id":["molecules30030528"],"URL":"https:\/\/doi.org\/10.3390\/molecules30030528","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,1,24]]}}}