Citrus essential oils and main terpenes: chemical composition and good litholytic activity on gallstones

, , ,


Research Articles | Published:

Print ISSN : 0970-4078.
Online ISSN : 2229-4473.
Website:www.vegetosindia.org
Pub Email: contact@vegetosindia.org
Doi: 10.1007/s42535-021-00251-9
First Page: 600
Last Page: 605
Views: 12297


Keywords: Moroccan citrus fruits, Essential oil, Terpenes, Gallstones, Litholytic activity


Abstract


We studied the gallstone dissolving capacity of Moroccan citrus (C) essential oils; C. clementina, C. aurantium, C. sinensis and C. paradisi. Their litholytic activity was compared to that of their main constituents revealed by a gas chromatography-mass spectrometry (GC–MS) analysis; limonene, linalool and γ-terpinene and to the Methyl tertbutyl ether (MTBE) standard as well. Gallstone sample was classified as a cholesterol type after a quantification analysis, using UV-spectrophotometer. The hydrocarbon compounds predominated the chemical composition of the oils, limonene was the commonly major identified compound, representing between 72.06 and 88.49 %. The citrus essential oils caused a deterioration in the morphological appearance of gallstone samples. The C. sinensis essential oil manifested with remarkable litholytic activity after a day of incubation, reached to a dissolution capacity of 95.78 ± 0.49 %, the same for C. clementina with 94.81 ± 1.30 % and C. aurantium with 92.99 ± 2.04 %. These oils were more effective than MTBE standard. In last position, C. paradisi essential oil exhibited the less high dissolution of 87.68 ± 1.82 %, comparing with other oils. Linalool showed a good litholytic activity, better than that of MTBE and similar to that of limonene. Therefore, in addition to limonene role, also the other constituents may have, as a natural mixture, an important additive effect in the gallstone dissolution of each essential oil.


Moroccan citrus fruits, Essential oil, Terpenes, Gallstones, Litholytic activity


*Get Access

(*Only SPR Members can get full access. Click Here to Apply and get access)

Advertisement

References


Adams RP (2007) Identification of essential oil components by gas chromatography/mass spectrometry. Allured publishing corporation Carol Stream, IL


Allen MJ, Borody TJ, Bugliosi TF, May GR, Larusso NF, Thistle JL (1985) Cholelitholysis Using Methyl Tertiary Butyl Ether. Gastroenterology 88:122–125. https://doi.org/10.1016/S0016-5085(85)80143-8


Bicchi C, Liberto E, Matteodo M, Sgorbini B, Mondello L, Zellner B, d’Acampora, Costa R, Rubiolo P (2008) Quantitative analysis of essential oils: a complex task. Flavour Fragr J 23(6):382–391. https://doi.org/10.1002/ffj.1905


Chaieb I, Zarrad K, Sellam R, Tayeb W, Hammouda AB, Laarif A, Bouhachem S (2017) Chemical composition and aphicidal potential of Citrus aurantium peel essential oils. Entomol Gen 37:63–75. https://doi.org/10.1127/entomologia/2017/0317


Choi H-S (2006) Lipolytic effects of citrus peel oils and their components. J Agric Food Chem 54:3254–3258


Choi HJ, Cho SJ, Kim O-H, Song JS, Hong H-E, Lee SC, Kim K-H, Lee SK, You YK, Hong TH, Kim EY, Park JH, Na GH, You D, Han D, Park JH, Kwak JW, Lee BJ, Ahn TY, J, … Kim, S.-J (2019) Efficacy and safety of a novel topical agent for gallstone dissolution: 2-methoxy-6-methylpyridine. J Transl Med 17:195. https://doi.org/10.1186/s12967-019-1943-y


Costa CARA, Cury TC, Cassettari BO, Takahira RK, Flório JC, Costa M (2013) Citrus aurantium L. essential oil exhibits anxiolytic-like activity mediated by 5-HT1A-receptors and reduces cholesterol after repeated oral treatment. BMC Complement Altern Med 13:42. https://doi.org/10.1186/1472-6882-13-42


Cox MR, Eslick GD, Padbury R (Éds.) (2018) The Management of Gallstone Disease: A Practical and Evidence-Based Approach. Springer International Publishing. https://doi.org/10.1007/978-3-319-63884-3


de Moraes Pultrini A, Almeida Galindo L, Costa M (2006) Effects of the essential oil from Citrus aurantium L. in experimental anxiety models in mice. Life Sci 78:1720–1725. https://doi.org/10.1016/j.lfs.2005.08.004


Doran J, Keighley MR, Bell GD (1979) Rowachol—a possible treatment for cholesterol gallstones. Gut 20:312–317. https://doi.org/10.1136/gut.20.4.312


Dugo G, Giacomo AD (2002) Citrus: The Genus Citrus, medicinal and aromatic plants-industrial profiles. CRC Press


Girometti R, Brondani G, Cereser L, Como G, Del Pin M, Bazzocchi M, Zuiani C (2010) Post-cholecystectomy syndrome: spectrum of biliary findings at magnetic resonance cholangiopancreatography. Br J Radiol 83:351–361. https://doi.org/10.1259/bjr/99865290


Hosni K, Zahed N, Chrif R, Abid I, Medfei W, Kallel M, Brahim NB, Sebei H (2010) Composition of peel essential oils from four selected Tunisian Citrus species: evidence for the genotypic influence. Food Chem 123:1098–1104. https://doi.org/10.1016/j.foodchem.2010.05.068


Igimi H, Ide H (1975) Gallstone solubilizer (United States Patent No US3882248A). https://patents.google.com/patent/US3882248A/en


Igimi H, Hisatsugu T, Nishimura M (1976) The use of d-limonene preparation as a dissolving agent of gallstones. Am J Dig Dis 21:926–939. https://doi.org/10.1007/BF01071903


Kelly E, Williams JD, Organ CH (2000) A history of the dissolution of retained choledocholithiasis. Am J Surg 180:86–98. https://doi.org/10.1016/S0002-9610(00)00428-1


Lota M-L, de Rocca Serra D, Tomi F, Casanova J (2001) Chemical variability of peel and leaf essential oils of 15 species of mandarins. Biochem Sys Ecol 29:77–104. https://doi.org/10.1016/S0305-1978(00)00029-6


Muhammad NO, Soji-Omoniwa O, Usman LA, Omoniwa BP (2013) Antihyperglycemic Activity of Leaf Essential Oil of Citrus sinensis (L.) Osbeck on Alloxan-Induced Diabetic Rats. Annu Res Rev Biol, 825–834


Njoroge SM, Koaze H, Karanja PN, Sawamura M (2005) Volatile Constituents of Redblush Grapefruit (Citrus paradisi) and Pummelo (Citrus grandis) Peel Essential Oils from Kenya. J Agric Food Chem 53:9790–9794. https://doi.org/10.1021/jf051373s


Okunowo WO, Oyedeji O, Afolabi LO, Matanmi E (2013) Essential Oil of Grape Fruit (Citrus paradisi) Peels and Its Antimicrobial Activities. Am J Plant Sci 04:1–9. https://doi.org/10.4236/ajps.2013.47A2001


Osadchuk MA, Mironova ED, Vasileva IN, Korzhenkov NP, Achkasov EE, Gulyaev PV, Osadchuk MM, Trushin MV (2019) Oral medical dissolution of gallstones in patients with gallstone disease. Prensa med argent 105:35–40


Osman A (2019) Citrus Oils. In M. F. Ramadan (Ed.), Fruit Oils: Chemistry and Functionality. Springer International Publishing. 521–540. https://doi.org/10.1007/978-3-030-12473-1_26


Thi Nguyen T-T, Tran T, Hua T-T, Diep T-M, Chau T-T, Duus D-KN, F., & Le TN (2016) Investigation of peel and leaf essential oils of Citrus clementina Hort. Ex Tan. Growing in the south of Vietnam. J Essent Oil Res 28:96–103. https://doi.org/10.1080/10412905.2015.1083491


Thistle JL, May GR, Bender CE, Williams HJ, LeRoy AJ, Nelson PE, Peine CJ, Petersen BT, McCullough JE (1989) Dissolution of Cholesterol Gallbladder Stones by Methyl Tert-Butyl Ether Administered by Percutaneous Transhepatic Catheter. N Engl J Med 320:633–639. https://doi.org/10.1056/NEJM198903093201004


Tritapepe R, Di Padova C, Pozzoli M, Rovagnati P, Montorsi W (1984) The treatment of retained biliary stones with monooctanoin: Report of 16 patients. Am J Gastroenterol 79:710–714


Vergunst H, Terpstra OT, Nijs HG, Steen G (1991) In vitro comparison of different gall stone dissolution solvents. Gut 32:211–214. https://doi.org/10.1136/gut.32.2.211


Yang S-A, Jeon S-K, Lee E-J, Shim C-H, Lee I-S (2010) Comparative study of the chemical composition and antioxidant activity of six essential oils and their components. Nat Prod Res 24:140–151. https://doi.org/10.1080/14786410802496598


You DD, Cho SJ, Kim O-H, Song JS, Hwang K-S, Lee SC, Kim K-H, Choi HJ, Hong H-E, Seo H, Hong TH, Park JH, Lee TY, Ahn J, Jung J-K, Jung K-Y, Kim S-J (2019) Superior gallstone dissolubility and safety of tert-amyl ethyl ether over methyl-tertiary butyl ether. World J Gastroenterol 25:5936–5952. https://doi.org/10.3748/wjg.v25.i39.5936


Zarrad K, Hamouda AB, Chaieb I, Laarif A, Jemâa JM-B (2015) Chemical composition, fumigant and anti-acetylcholinesterase activity of the Tunisian Citrus aurantium L. essential oils. Ind Crops Prod 76:121–127. https://doi.org/10.1016/j.indcrop.2015.06.039


Zlatkis A, Zak B, Boyle AJ (1953) A new method for the direct determination of serum cholesterol. The J Lab Clin Med 41:486–492. https://doi.org/10.5555/uri:pii:0022214353901255

 


Acknowledgements


We would like to thank Professor Ibrahim Sbai El Otmani from Faculty of Medicine and Pharmacy Casablanca, Hassan II University of Casablanca for enthusiastic help.


Author Information


Arrout Asma
Laboratory of Drugs Sciences, Biomedical Research and Biotechnology, Faculty of Medicine and Pharmacy, Hassan II University of Casablanca, Casablanca, Morocco

El Ghallab Yassine
Laboratory of Drugs Sciences, Biomedical Research and Biotechnology, Faculty of Medicine and Pharmacy, Hassan II University of Casablanca, Casablanca, Morocco
elghallabyassine@gmail.com

Lefriyekh Mohammed Rachid
Department General Surgery, Faculty of Medicine and Pharmacy, University Hospital Center Ibn Rochd, Hassan II University of Casablanca, Casablanca, Morocco


Ait Haj Said Amal
Laboratory of Drugs Sciences, Biomedical Research and Biotechnology, Faculty of Medicine and Pharmacy, Hassan II University of Casablanca, Casablanca, Morocco