Login Register Cart 0
Generic placeholder image

Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Genus Acronychia: An Extensive Review on Phytochemistry and Pharmacological Activities

Author(s): Ninh The Son*

Volume 20, Issue 8, 2023

Published on: 13 December, 2022

Page: [818 - 841] Pages: 24

DOI: 10.2174/1570193X20666221026162904

Price: $65

Abstract

Background: Acronychia is a genus of medicinal plants that were used traditionally to treat various ailments such as cough, asthma, sores, ulcers, itchy skin, fever, and rheumatism. Acronychia plants have a wide range of distribution, but they are mostly native to India, Siri Lanka, Australia, and Indochina since the 1950s Acronychia plants have been extensively used in phytochemical research and pharmacological examinations.

Objective: The goal of this study is to structurally compile almost secondary metabolites from the title plants, as well as coverage of full information on their biomedical actions.

Conclusion: Phytochemical profile of this genus is associated with the appearances of various chemical classes, including principal compounds type acetophloroglucinols and alkaloids, as well as other types coumarins, mono-phenols, flavonoids, phytosterols, lignans, xanthenes, and tocopherols. More than one hundred thirty secondary metabolites have been isolated. Naturally occurring acetophloroglucinols represented in both monomers and dimers, and most of them were new in nature. Phytochemical research based on GC-MS identification showed that Acronychia plants should be suitable for the cosmeceutical field and food chemistry due to the high content of volatiles. Acronychia extracts are safe in use, and they are increasingly exploited within pharmacological assays. In agreement with traditional properties, crude plant extracts, fractions, and their isolated compounds are well-known for antimicrobial, antioxidative, antiinflammatory, antiprotozal, antiarrhythmic, antinociceptive, antihistamine, and allelopathic activities, especially in terms of cytotoxicity. A sustainable use program should be established to aid the further studies of these medicinal plants.

« Previous Next »
Graphical Abstract

[1]
Son, N.T.; Mai Thanh, D.T.; Van Trang, N. Flavone norartocarpetin and isoflavone 2′-hydroxygenistein: A spectroscopic study for structure, electronic property and antioxidant potential using DFT (Density functional theory). J. Mol. Struct., 2019, 1193, 76-88.
[http://dx.doi.org/10.1016/j.molstruc.2019.05.016]
[2]
Son, N.T.; Oda, M.; Hayashi, N.; Yamaguchi, D.; Kawagishi, Y.; Takahashi, F.; Harada, K.; Cuong, N.M.; Fukuyama, Y. Antimicrobial activity of the constituents of Dalbergia tonkinensis and structural-bioactive highlights. Nat. Prod. Commun., 2018, 13(2), 157-161.
[http://dx.doi.org/10.1177/1934578X1801300212]
[3]
Brophy, J.J.; Goldsack, R.J.; Forster, P.I. Leaf essential oils of the Australian species of Acronychia (Rutaceae). J. Essent. Oil Res., 2004, 16(6), 597-607.
[http://dx.doi.org/10.1080/10412905.2004.9698807]
[4]
Miyake, K.; Morita, C.; Suzuki, A.; Matsushita, N.; Saito, Y.; Goto, M.; Newman, D.J.; O’Keefe, B.R.; Lee, K.H.; Nakagawa-Goto, K. Prenylated acetophloroglucinol dimers from Acronychia trifoliolata: Structure elucidation and total synthesis. J. Nat. Prod., 2019, 82(10), 2852-2858.
[http://dx.doi.org/10.1021/acs.jnatprod.9b00596] [PMID: 31550158]
[5]
Chen, N.H.; Li, W.; Zhong, Y.L.; Niu, Q.W.; Li, Y.Y.; Zhang, Y.B.; Li, M.M.; Li, Y.L.; Wang, G.C. New acetophenone derivatives from Acronychia oligophlebia and their anti-inflammatory and antioxidant activities. Chem. Biodivers., 2018, 15(5), e18000080.
[http://dx.doi.org/10.1002/cbdv.201800080] [PMID: 29624846]
[6]
Kouloura, E.; Halabalaki, M.; Lallemand, M.C.; Nam, S.; Jove, R.; Litaudon, M.; Awang, K.; Hadi, H.A.; Skaltsounis, A.L. Cytotoxic prenylated acetophenone dimers from Acronychia pedunculata. J. Nat. Prod., 2012, 75(7), 1270-1276.
[http://dx.doi.org/10.1021/np201007a] [PMID: 22708987]
[7]
Panyasawat, P.; Wisetsai, A.; Lekphrom, R.; Senawong, T.; Schevenels, F.T. Acroquinolones A and B, two polyphenolic isoprenylated acetophenone-quinolone hybrids with anti-proliferative activities from Acronychia pedunculata (L.). Miq. Nat. Prod. Res., 2022, 36, 2743-2752.
[http://dx.doi.org/10.1080/14786419.2021.1922405] [PMID: 33960228]
[8]
Epifano, F.; Fiorito, S.; Genovese, S. Phytochemistry and pharmacognosy of the genus Acronychia. Phytochemistry, 2013, 95, 12-18.
[http://dx.doi.org/10.1016/j.phytochem.2013.07.013] [PMID: 23920228]
[9]
Ito, C.; Matsui, T.; Ban, Y.; Wu, T.S.; Itoigawa, M. Acetophenones isolated from Acronychia pedunculata and their anti-proliferative activities. Nat. Prod. Commun., 2016, 11(1), 1934578X1601100.
[http://dx.doi.org/10.1177/1934578X1601100125] [PMID: 26996027]
[10]
Ito, C.; Hosono, M.; Tokuda, H.; Wu, T.S.; Itoigawa, M. Acetophenones from Acronychia pedunculata and their cancer chemopreventive activity. Nat. Prod. Commun., 2016, 11(9), 1934578X1601100.
[http://dx.doi.org/10.1177/1934578X1601100929] [PMID: 30807028]
[11]
Tanjung, M.; Nurmalasari, I.; Wilujeng, A.K.; Dewi Saputri, R.; Rachmadiarti, F.; Srie Tjahjandarie, T.; Acronyculatin, P. A new isoprenylated acetophenone from the stem bark of Acronychia pedunculata. Nat. Prod. Sci., 2018, 24(4), 284-287.
[http://dx.doi.org/10.20307/nps.2018.24.4.284]
[12]
Ali, N.D.; Latip, J.; Ismail, E. Pyranocoumarins from the roots of Acronychia pedunculata. Malays. J. Sci., 2005, 24, 149-153.
[13]
Funayama, S.; Cordell, G.A. Chemistry of acronycine IV. Minor constituents of acronine and the phytochemistry of the genus Acronychia. J. Nat. Prod., 1984, 47(2), 285-291.
[http://dx.doi.org/10.1021/np50032a009] [PMID: 6736969]
[14]
Nathabumroong, S.; Wisetsai, A.; Lekphrom, R.; Suebrasri, T.; Schevenels, F.T. A new polyphenolic isoprenylated acetophenone dimer from the stem bark of Acronychia pedunculata (L.) Miq. Nat. Prod. Res., 2021, 1-8.
[http://dx.doi.org/10.1080/14786419.2021.1989680] [PMID: 34632889]
[15]
Wisetsai, A.; Lekphrom, R.; Suebrasri, T.; Schevenels, F.T. Acroflavone A, a new prenylated flavone from the fruit of Acronychia pedunculata (L.) Miq. Nat. Prod. Res., 2021, 1-7.
[http://dx.doi.org/10.1080/14786419.2021.1938043] [PMID: 34126824]
[16]
Cui, B.; Chai, H.; Dong, Y.; Horgen, F.D.; Hansen, B.; Madulid, D.A.; Soejarto, D.D.; Farnsworth, N.R.; Cordell, G.A.; Pezzuto, J.M.; Kinghorn, A.D. Quinoline alkaloids from Acronychia laurifolia. Phytochemistry, 1999, 52(1), 95-98.
[http://dx.doi.org/10.1016/S0031-9422(99)00039-4] [PMID: 10466225]
[17]
Tran, T.D.; Olsson, M.A.; McMillan, D.J.; Cullen, J.K.; Parsons, P.G.; Reddell, P.W.; Ogbourne, S.M. Potent antibacterial prenylated acetophenones from the Australian endemic plant Acronychia crassipetala. Antibiotics (Basel), 2020, 9(8), 487.
[http://dx.doi.org/10.3390/antibiotics9080487] [PMID: 32781771]
[18]
Yang, X.; Zhang, Y.B.; Wu, Z.N.; Zhang, X.Q.; Jiang, J.W.; Li, Y.L.; Wang, G.C. Six new prenylated acetophenone derivatives from the leaves of Acronychia oligophlebia. Fitoterapia, 2015, 105, 156-159.
[http://dx.doi.org/10.1016/j.fitote.2015.07.002] [PMID: 26160157]
[19]
Su, C.R.; Kuo, P.C.; Wang, M.L.; Liou, M.J.; Damu, A.G.; Wu, T.S. Acetophenone derivatives from Acronychia pedunculata. J. Nat. Prod., 2003, 66(7), 990-993.
[http://dx.doi.org/10.1021/np030054x] [PMID: 12880321]
[20]
Ranaweera, C.B.; Karunathilaka, N.; Silva Niloshan, A.R.; Karunarathna, S.; Pathirana, R.; Ratnasooriya, W.D. Antibacterial activity of aqueous root, seed, flower and stem bark extracts of Acronychia pedunculata grown in Sri Lanka. Int. J. Pharm. Res. Allied Sci., 2016, 5, 21-25.
[21]
Raju, R.; Mathew, S.; Singh, A.; Reddell, P.; Munch, G. Acronyols A and B, new anti-inflammatory prenylated phloroglucinols from the fruits of Acronychia crassipetala. Nat. Prod. Res., 2021, 36(17), 4358-4364.
[http://dx.doi.org/10.1080/14786419.2021.1986711] [PMID: 34612780]
[22]
Pathmasiri, W.; El-Seedi, H.R.; Han, X.; Janson, J.C.; Huss, U.; Bohlin, L. Aryl ketones from Acronychia pedunculata with cyclooxygenase-2 inhibitory effects. Chem. Biodivers., 2005, 2(4), 463-469.
[http://dx.doi.org/10.1002/cbdv.200590026] [PMID: 17191994]
[23]
Han, X.; Pathmasiri, W.; Bohlin, L.; Janson, J.C. Isolation of high purity 1-[2′4′-dihydroxy-3′5′-di-(3″-methylbut-2″-enyl)-6′-meth-oxy] phenylethanone from Acronychia pedunculata (L.) Miq. by high-speed counter-current chromatography. J. Chromatogr. A, 2004, 1022(1-2), 213-216.
[http://dx.doi.org/10.1016/j.chroma.2003.09.046] [PMID: 14753789]
[24]
Kouloura, E.; Halabalaki, M.; Lallemand, M.C.; Tillequin, F.; Skaltsounis, A.L. Alkaloids and phenolic compounds from Acronychia laurifolia. Planta Med., 2008, 74(9), PB78.
[http://dx.doi.org/10.1055/s-0028-1084423]
[25]
Kozaki, S.; Takenaka, Y.; Mizushina, Y.; Yamaura, T.; Tanahashi, T. Three acetophenones from Acronychia pedunculata. J. Nat. Med., 2014, 68(2), 421-426.
[http://dx.doi.org/10.1007/s11418-013-0803-y] [PMID: 24129772]
[26]
Kumar, V.; Karunaratne, V.; Sanath, M.R.; Meeegalle, K. 1-[2′4′-dihydroxy-3′5′-di-(3″-methylbut-2″-enyl)-6′-methoxy] phenylethanone from Acronychia pedunculata root bark. Phytochemistry, 1989, 28(4), 1278-1279.
[http://dx.doi.org/10.1016/0031-9422(89)80234-1]
[27]
Matsui, T.; Ito, C.; Kato, A.; Wu, T.S.; Itoigawa, M. Acrofolione A and B, acetophenone dimers from Acronychia pendunculata, induce an apoptotic effect on human NALM-6 pre-B cell leukaemia cells. J. Pharm. Pharmacol., 2019, 71(3), 348-361.
[http://dx.doi.org/10.1111/jphp.13035] [PMID: 30362134]
[28]
Miyake, K.; Suzuki, A.; Morita, C.; Goto, M.; Newman, D.J.; O’Keefe, B.R.; Morris-Natschke, S.L.; Lee, K.H.; Nakagawa-Goto, K. Acetophenone monomers from Acronychia trifoliolata. J. Nat. Prod., 2016, 79(11), 2883-2889.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00645] [PMID: 27797192]
[29]
Niu, Q.W.; Chen, N.H.; Wu, Z.N.; Luo, D.; Li, Y.Y.; Zhang, Y.B.; Li, Q.G.; Li, Y.L.; Wang, G.C. Isolation and identification of new prenylated acetophenone derivatives from Acronychia oligophlebia. Nat. Prod. Res., 2019, 33(15), 2230-2235.
[http://dx.doi.org/10.1080/14786419.2018.1490902] [PMID: 30379092]
[30]
Oyama, M.; Bastow, K.F.; Tachibana, Y.; Shirataki, Y.; Yamaguchi, S.; Cragg, G.M.; Wu, T.S.; Lee, K.H. Antitumor agents 225. Acrofoliones A and B, two novel cytotoxic acetophenone dimers, from Acronychia trifoliolata. J. Chin. Pharm. Sci., 2003, 55, 239-245.
[31]
Robertson, L.P.; Lucantoni, L.; Duffy, S.; Avery, V.M.; Carroll, A.R. Acrotrione: An oxidized xanthene from the root of Acronychia pubescens. J. Nat. Prod., 2019, 82(4), 1019-1023.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00956] [PMID: 30865443]
[32]
Sy, L.K.; Brown, G.D. 1-[2′4′-Dihydroxy-3′-(3″-Methylbut-2″-enyl)-5′-(1‴-ethoxy-3‴-methylbutyl)-6′-methoxy]phenylethanone from Acronychia pedunculata. Phytochemistry, 1999, 52(4), 681-683.
[http://dx.doi.org/10.1016/S0031-9422(99)00252-6]
[33]
Wu, T.S.; Wang, M.L.; Jong, T.T.; McPhail, A.T.; McPhail, D.R.; Lee, K.H. X-ray crystal structure of acrovestone, a cytotoxic principle from Acronychia pedunculata. J. Nat. Prod., 1989, 52(6), 1284-1289.
[http://dx.doi.org/10.1021/np50066a014] [PMID: 2614422]
[34]
Bissoue, A.N.; Muyard, F.; Regnier, A.; Bevalot, F.; Vaquette, J.; Hartley, T.G.; Waterman, P.G. Alkaloids and coumarins from two species of Acronychia (Rutaceae). Biochem. Syst. Ecol., 1996, 24(7-8), 805.
[http://dx.doi.org/10.1016/S0305-1978(96)00067-1]
[35]
Bowen, I.H.; Dennis, R.; Osborne, S.J. The alkaloids of Acronychia pedunculata (L.) Miq. (Rutaceae). J. Pharm. Pharmacol., 2011, 37(Suppl. 12), 138P.
[http://dx.doi.org/10.1111/j.2042-7158.1985.tb14208.x]
[36]
Wen-Hao, X.; Zhi, X. Chemical studies on alkaloids in the root of Acronychia oligophlebia Merr. Huaxue Xuebao, 1984, 2, 66-73.
[37]
Lahey, F.N.; McCamish, M. Acrophylline and acrophyllidine two new alkaloids from Acronychia haplophylla. Tetrahedron Lett., 1968, 9(12), 1525-1527.
[http://dx.doi.org/10.1016/S0040-4039(01)98992-0] [PMID: 5640105]
[38]
Lahey, F.N.; Thomas, W.C. Alkaloids of the Autralian Rutaceae: Acronychia baueri. I. The isolation of the alkaoids. Aust. J. Sci. Res, 1949, 2, 423-426.
[39]
Lamberton, J.A.; Price, J.R. Alkaloids of the Australian Rutaceae: Acronychia baueri Schott. IV. Alkaloids present in the leaves. Aust. J. Chem., 1953, 6(1), 66-77.
[http://dx.doi.org/10.1071/CH9530066]
[40]
Prager, R.H.; Thredgold, H.M. Some neutral constituents of Acronychia baueri. Aust. J. Chem., 1966, 19(3), 451-454.
[http://dx.doi.org/10.1071/CH9660451]
[41]
de Silva, L.B.; de Silva, U.L.L.; Mahendran, M.; Jennings, R. Kokusaginine and evolitrine from Acronychia pedunculata. Phytochemistry, 1979, 18(7), 1255-1256.
[http://dx.doi.org/10.1016/0031-9422(79)80162-4]
[42]
Svoboda, G.H.; Poore, G.A.; Simpson, P.J.; Boder, G.B. Alkaloids of Acronychia baueri Schott I. Isolation of the alkaloids and a study of the antitumor and other biological properties of acronycine. J. Pharm. Sci., 1966, 55(8), 758-768.
[http://dx.doi.org/10.1002/jps.2600550803] [PMID: 5975286]
[43]
Svoboda, G.H. Alkaloids of Acronychia Baueri (Bauerella australiana). II. Extraction of the alkaloids and studies of structure-activity relationships. J. Nat. Prod., 1966, 29, 206-224.
[44]
Epifano, F.; Fiorito, S.; Taddeo, V.A.; Paciotti, R.; Patruno, A.; Genovese, S.; Coletti, C. Studies on the interaction of 4′-geranyloxyferulic acid and nelumal A with pro-inflammatory enzymes. Planta Med., 2016, 81(S 01), S1-S381.
[http://dx.doi.org/10.1055/s-0036-1596940]
[45]
Lichius, J.J.; Thoison, O.; Montagnac, A.; Païs, M.; Guéritte-Voegelein, F.; Sévenet, T.; Cosson, J.P.; Hadi, A.H.A. Antimitotic and cytotoxic flavonols from Zieridium pseudobtusifolium and Acronychia porteri. J. Nat. Prod., 1994, 57(7), 1012-1016.
[http://dx.doi.org/10.1021/np50109a024] [PMID: 7964782]
[46]
Davenport, J.B.; Sutherland, M.D. Asarinin in Acronychia muelleri W.D. Francis. Aust. J. Chem., 1954, 7(4), 384-386.
[http://dx.doi.org/10.1071/CH9540384]
[47]
The Son, N. Secondary metabolites of genus Pandanus-An aspect of phytochemistry. Mini Rev. Org. Chem., 2019, 16(7), 689-710.
[http://dx.doi.org/10.2174/1570193X16666181206102740]
[48]
Son, N.T. A mini-review of the tropical plant Cratoxylum fomosum ssp. pruniflorum: Phytochemical and pharmacological aspects. Lett. Org. Chem., 2020, 17(5), 327-339.
[http://dx.doi.org/10.2174/1570178616666190902111630]
[49]
Son, N.T.; Linh, N.T.T.; Tra, N.T.; Ha, N.T.T.; Tu Anh, L.T.; Cham, B.T.; Tuyet Anh, D.T.; Tuyen, N.V. Genus Styrax: A resource of bioactive compounds. In: Study in Natural Product Chemistry; Atta-ur-Rahman, Ed. Elsevier Science B. V: Amsterdam, 2021; 69, pp. 299-347.
[50]
Linh, N.T.T.; Son, N.T. Biologically active constituents from plants of genus Desmos. In: Progress in the Chemistry of Organic Natural Products; Douglas, K. Ed. Springer: Germany, 2021; 116, pp. 211-261.
[51]
Linh, N.T.T.; Son, N.T.; Ha, N.T.T.; Tra, N.T.; Tu Anh, L.T.; Chen, S.; Tuyen, N.V. Biologically active constituents from plants of the genus Xanthium. In: Progress in the Chemistry of Organic Natural Products; Douglas, K. Ed. Springer: Germany, 2021; 116, pp. 135-209.
[52]
Lesueur, D.; De Rocca Serra, D.; Bighelli, A.; Minh Hoi, T.; Huy Thai, T.; Casanova, J. Composition and antimicrobial activity of the essential oil of Acronychia pedunculata (L.) Miq. from Vietnam. Nat. Prod. Res., 2008, 22(5), 393-398.
[http://dx.doi.org/10.1080/14786410701475636] [PMID: 18404559]
[53]
Phung, T.T.; Ma, M.N.; Pham, T.H.; Nguyen, N.N. Antioxidant, allelopathic acitivities of leaf extracts and essential oil compositions of Acronychia pedunculata (L.). Miq. Vietnam J. Sci. Technol. Engineer, 2021, 63, 12-18.
[54]
Horgen, F.D.; Edrada, R.A.; de los Reyes, G.; Agcaoili, F.; Madulid, D.A.; Wongpanich, V.; Angerhofer, C.K.; Pezzuto, J.M.; Soejarto, D.D.; Farnsworth, N.R. Biological screening of rain forest plot trees from Palawan Island (Philippines). Phytomedicine, 2001, 8(1), 71-81.
[http://dx.doi.org/10.1078/0944-7113-00019] [PMID: 11292242]
[55]
Bagyawantha, N.M.Y.; Panagoda, G.J.; Bandara, B.M.R. Anticandidal activity of Acronychia pedunculata .Proceedings of the Peradeniya Univ. International Research Sessions, Sri Lanka, 2014, 324.
[56]
Gireesha, J.; Raju, N.S. Phytochemical analysis, antibacterial and antioxidant potential of Acronychia pedunculata (L.). Miq. Ann. Phytomed., 2016, 5(2), 147-151.
[http://dx.doi.org/10.21276/ap.2016.5.2.20]
[57]
Wright, M.H.; Wood, A.; Greene, A.C.; Cock, I.E. Growth inhibitory activity of Acronychia acidula F. Meull. Fruit extracts towards malodiur-forming bacteria. Pharmacogn. Commun., 2020, 10(2), 95-101.
[http://dx.doi.org/10.5530/pc.2020.2.18]
[58]
Ratnayake, W.M.K.M.; Suresh, T.S.; Abeysekera, A.M.; Salim, N.; Chandrika, U.G. Acute anti-inflammatory and anti-nociceptive activities of crude extracts, alkaloid fraction and evolitrine from Acronychia pedunculata leaves. J. Ethnopharmacol., 2019, 238, 111827.
[http://dx.doi.org/10.1016/j.jep.2019.111827] [PMID: 30910582]
[59]
Billo, M.; Fournet, A.; Cabalion, P.; Waikedre, J.; Bories, C.; Loiseau, P.; Prina, E.; Rojas de Arias, A.; Yaluff, G.; Fourneau, C.; Hocquemiller, R. Screening of new caledonian and vanuatu medicinal plants for antiprotozoal activity. J. Ethnopharmacol., 2005, 96(3), 569-575.
[http://dx.doi.org/10.1016/j.jep.2004.10.006] [PMID: 15619580]
[60]
Chang, G.J.; Wu, M.H.; Chen, W.P.; Kuo, S.C.; Su, M.J. Electrophysiological characteristics of antiarrhythmic potential of acrophyllidine, a furoquinoline alkaloid isolated from Acronychia halophylla. Drug Dev. Res., 2000, 50(2), 170-185.
[http://dx.doi.org/10.1002/1098-2299(200006)50:2<170:AID-DDR7>3.0.CO;2-W]
[61]
Rodrigo, S.K.; Jayasinghe, U.L.B.; Bandara, B.M.R. Antifungal, antioxidant and cytotoxic activity of Acronychia pedunculata and Adenanthera pavonina.Proceedings of the Peradeniya University Research Sessions, University of Peradeniya, Sri Lanka, 2007, 94-95.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy