Abstract
Background: 3,4-dihydroisocoumarins are an important small group belonging to the class of naturally occurring lactones isolated from different bacterial strains, molds, lichens, and plants. The structures of these natural compounds show various types of substitution in their basic skeleton and this variability influences deeply their biological activities. These lactones are structural subunits of several natural products and serve as useful intermediates in the synthesis of different heterocyclic molecules, which exhibit a wide range of biological activities, such as anti-inflammatory, antiplasmodial, antifungal, antimicrobial, antiangiogenic and antitumoral activities, among others. Their syntheses have attracted attention of many researchers reporting many synthetic strategies to achieve 3,4-dihydroisocoumarins and other related structures.
Objective: In this context, the isolation of these natural compounds from different sources, their syntheses and biological activities are reviewed, adding the most recent advances and related developments.
Conclusion: This review aims to encourage further work on the isolation and synthesis of this class of natural products. It would be beneficial for synthetic as well as the medicinal chemists to design selective, optimized dihydroisocoumarin derivatives as potential drug candidates, since dihydroisocoumarin scaffolds have significant utility in the development of therapeutically relevant and biologically active compounds.
Keywords: Isocoumarins, dihydroisocoumarins, lactones, natural products, microorganisms, isolation.
Graphical Abstract
[1]
Braca, A.; Bader, A.; De Tommasi, N. In: Studies in Natural Products Chemistry,; Atta-ur-Rahman, Ed.; Elsevier Science B. V: Amsterdam, 2012; Vol. 37, pp. 191-215.
[2]
Tyurin, A.P.; Efimenko, T.A.; Prokhorenko, I.A.; Rogozhin, E.A.; Malanicheva, I.A.; Zenkova, V.A.; Efremenkova, O.V.; Korshun, V.A. In: Studies in Natural Products Chemistry,; Atta-ur-Rahman, Ed.; Elsevier Science B. V: Amsterdam, 2017; Vol 55, pp. 385-441.
[3]
Pal, S.; Chatare, V.; Pal, M. Isocoumarin and Its Derivatives: An Overview on their Synthesis and Applications. Curr. Org. Chem., 2011, 15, 782-800.
[4]
Saeed, A. Isocoumarins, miraculous natural products blessed with diverse pharmacological activities. Eur. J. Med. Chem., 2016, 116, 290-317.
[5]
Saddiqa, A.; Usman, M.; Çakmak, O. Isocoumarins and 3,4-dihydroisocoumarins, amazing natural products: a review. Turk. J. Chem., 2017, 41, 153-178.
[6]
Larsen, T.O.; Breinholt, J. Dichlorodiaportin, diaportinol, and diaportinic acid: three novel isocoumarins from Penicillium nalgiovense. J. Nat. Prod., 1999, 62, 1182-1184.
[7]
Isaka, M.; Yangchum, A.; Intamas, S.; Kocharin, K.; Jones, G.E.B.; Kongsaeree, P.; Prabpai, S. Aigialomycins and related polyketide metabolites from the mangrove fungus Aigialus parvus BCC 5311. Tetrahedron, 2009, 65, 4396-4403.
[8]
Sappapan, R.; Sommit, D.; Ngamrojanavanich, N.; Pengpreecha, S.; Wiyakrutta, S.; Sriubolmas, N.; Pudhom, K. 11-Hydroxymonocerin from the plant endophytic fungus Exserohilum rostratum. J. Nat. Prod., 2008, 71, 1657-1659.
[9]
Singh, B.; Parshad, R.; Khajuriac, R.K.; Gurud, S.K.; Pathania, A.S.; Sharma, R.; Chibe, R.; Aravind, S.; Guptag, V.K.; Khan, I.A.; Bhushan, S.; Bharate, S.B.; Vishwakarmaa, R.A. Saccharonol B, a new cytotoxic methylated isocoumarin from Saccharomonospora azurea. Tetrahedron Lett., 2013, 54, 6695-6699.
[10]
Schreck, I.; Deigendesch, U.; Burkhardt, B.; Marko, D.; Weiss, C. The Alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome P450 1A1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbon receptor. Archives . Toxicol., 2012, 86, 625-632.
[11]
Pero, R.W.; Owens, R.G.; Dale, S.W.; Harvan, D. Isolation and indentification of a new toxin, altenuene, from the fungus Alternaria tenuis. Biochimica Biophysica Acta (BBA)-. General Subj, 1971, 230, 170-179.
[12]
Xie, Y.; Wang, N.; Cheng, B.; Zhai, H. Total synthesis of (±)-cephalosol. Org. Lett., 2011, 14, 3-5.
[13]
Harunari, E.; Imada, C.; Igarashi, Y.; Fukuda, T.; Terahara, T.; Kobayashi, T. Hyaluromycin, a new hyaluronidase inhibitor of polyketide origin from marine Streptomyces sp. Mar. drugs, 2014, 12, 491-507.
[14]
Boonlarppradab, C.; Suriyachadkun, C.; Suphothina, S.; Tobwor, P. Bireticulol, a bioactive isocoumarin dimer from Streptomyces sp. BCC24731. J. Antibiot. , 2011, 64, 267-270.
[15]
Ayer, W.A.; Craw, P.A.; Nozawa, K. Two 1H-naphtho [2, 3-c] pyran-1-one metabolites from the fungus Paecilomyces variotii. Canad. J. Chem., 1991, 69, 189-191.
[16]
Hald, B.; Christensen, D.H.; Krogh, P. Natural occurrence of the mycotoxin viomellein in barley and the associated quinone-producing penicillia. Appl. Environ. Microbiol., 1983, 46, 1311-1317.
[17]
Wei, M.; Zhang, X.; Li, S.; Shao, C.; Wang, C.; She, Z.; Lin, Y. A new dihydroisocoumarin with an isoprenyl group from the endophytic fungus Cephalosporium sp. Chem. Nat. Compd., 2010, 46, 340-342.
[18]
Chen, M.; Shao, C-L.; Wang, K-L.; Xu, Y.; She, Z-G.; Wang, C-Y. Dihydroisocoumarin derivatives with antifouling activities from a gorgonian-derived Eurotium sp. fungus. Tetrahedron, 2014, 70, 9132-9138.
[19]
Wang, Q.X.; Bao, L.; Yang, X.L.; Guo, H.; Yang, R.N.; Ren, B.; Zhang, L.X.; Dai, H.Q.; Guo, L.D.; Liu, H.W. Polyketides with antimicrobial activity from the solid culture of an endolichenic fungus Ulocladium sp. Fitoterapia, 2012, 83, 209-214.
[20]
Bi, Y.M.; Bi, X.B.; Zhao, Q.R.; Chen, Y.T.; Xie, J.L. Four novel dihydroisocoumarin (3,4-dihydro-1H-2-benzopyran-1-one) Glucosides from the fungus Cephalosporium sp. AL031. Helv. Chim. Acta, 2004, 87, 2890-2895.
[21]
Oliveira, C.M.; Regasini, L.O.; Silva, G.H.; Pfenning, L.H.; Young, M.; Berlinck, R.G.; Bolzani, V.S.; Araujo, A.R. Dihydroisocoumarins produced by Xylaria sp. and Penicillium sp., endophytic fungi associated with Piper aduncum and Alibertia macrophylla. Phytochem. Lett., 2011, 4, 93-96.
[22]
Chinworrungsee, M.; Kittakoop, P.; Isaka, M.; Chanphen, R.; Tanticharoen, M.; Thebtaranonth, Y. Halorosellins A and B, unique isocoumarin glucosides from the marine fungus Halorosellinia oceanica. J. Chem. Soc., Perkin Trans. 1, 2002, 22, 2473-2476.
[23]
Li, C.; Yang, B.; Fenstemacher, R.; Turkson, J.; Cao, S. Lycopodiellactone, an unusual d-lactone-isochromanone from a Hawaiian plant-associated fungus Paraphaeosphaeria neglecta FT462. Tetrahedron Lett., 2015, 56, 1724-1727.
[24]
Cabras, A.; Mannoni, M.A.; Serra, S.; Andolfi, A.; Fiore, M.; Evidente, A. Occurrence, isolation and biological activity of phytotoxic metabolites produced in vitro by Sphaeropsis sapinea, pathogenic fungus of Pinus radiata. Eur. J. Plant Pathol., 2006, 115, 187-193.
[25]
Tian, J-F.; Yu, R-J.; Li, X-X.; Gao, H.; Hu, D.; Guo, L-D.; Tang, J-S.; Yao, X-S. Cyclohexenones and isocoumarins from an endophytic fungus of Sarcosomataceae sp. J. Asian Nat. Prod. Res., 2015, 17, 550-558.
[26]
Elsebai, M.F.; Ghabbour, H.A. Isocoumarin derivatives from the marine-derived fungus Phoma sp. 135. Tetrahedron Lett., 2016, 57, 354-356.
[27]
Kongsaeree, P.; Prabpai, S.; Sriubolmas, N.; Vongvein, C.; Wiyakrutta, S. Antimalarial Dihydroisocoumarins Produced by Geotrichum sp., an Endophytic Fungus of Crassocephalum crepidioides. J. Nat. Prod., 2003, 66, 709-711.
[28]
Kokubun, T.; Veitch, N.C.; Brisge, P.D.; Simmonds, M.S.J. Dihydroisocoumarins and a tetralone from Cytospora eucalypticola. Phytochemistry, 2003, 62, 779-782.
[29]
Ye, Y-Q.; Xia, C-F.; Yang, J-X.; Qin, Y.; Zhou, M.; Gao, X-M.; Du, G.; Yang, H-Y.; Li, X-M.; Hu, Q-F. Isocoumarins from the fermentation products of an endophytic fungus of Aspergillus versicolor. Phytochem. Lett., 2014, 10, 215-218.
[30]
Zhou, M.; Zhou, K.; He, P.; Wang, K.M.; Zhu, R.Z.; Wang, Y.D.; Dong, W.; Li, G.P.; Yang, H.Y.; Ye, Y.Q.; Du, G.; Li, X.M.; Hu, Q.F. Antiviral and cytotoxic isocoumarin derivatives from an endophytic fungus Aspergillus oryzae. Planta Medica., 2016, 82, 414-417.
[31]
Song, R-Y.; Wang, X-B.; Yin, G-P.; Liu, R.H.; Kong, L-Y.; Yang, M-H. Isocoumarin derivatives from the endophytic fungus, Pestalotiopsis sp. Fitoterapia, 2017, 122, 115-118.
[32]
Pan, C.; Shi, Y.; Auckloo, B.N.; Hassan, S.S.; Akhter, N.; Wang, K.; Ye, Y.; Chen, C-T.A.; Tao, X.; Wu, B. Isolation and Antibiotic Screening of Fungi from a Hydrothermal Vent Site and Characterization of Secondary Metabolites from a Penicillium Isolate. Mar. Biotechnol., 2017, 19, 469-479.
[33]
Pinchuk, I.V.; Bressollier, P.; Sorokulova, I.B.; Verneuil, B.; Urdaci, M.C. Amicoumacin antibiotic production and genetic diversity of Bacillus subtilis strains isolated from different habitats. Res. Microbiol., 2002, 153, 269-276.
[34]
Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M.; Iitaka, Y. (Studies on AI-77s, microbial products with pharmacological activity) structures and the chemical nature of AI-77s. Tetrahedron Lett., 1982, 23, 5435-5438.
[35]
Itoh, J.; Shomura, T.; Omoto, S.; Miyado, S.; Yuda, Y.; Shibata, U.; Inouye, S. Isolation, physicochemical properties and biological activities of amicoumacins produced by Bacillus pumilus. Agric. Biol. Chem., 1982, 46, 1255-1259.
[36]
Hashimoto, M.; Taguchi, T.; Nishida, S.; Ueno, K.; Koizumi, K.; Aburada, M.; Ichinose, K. Isolation of 80-phosphate ester derivatives of amicoumacins: structure-activity relationship of hydroxy amino acid moiety. J. Antibiot. , 2007, 60, 752-756.
[37]
Li, Y.; Xu, Y.; Liu, L.; Han, Z.; Lai, P.Y.; Guo, X.; Zhang, X.; Lin, W.; Qian, P-Y. Five new amicoumacins isolated from a marine-derived bacterium Bacillus subtilis. Mar. Drugs, 2012, 10, 319-328.
[38]
Sato, T.; Nagai, K.; Suzuki, K.; Morioka, M.; Saito, T.; Nohara, C.; Susaki, K.; Takebayashi, Y. A new isocoumarin antibiotic, Y-05460M-A. J. Antibiot., 1992, 45, 1949.
[39]
Canedo, L.M.; Puentes, J.L.F.; Baz, J.P.; Acebal, C.; De La Calle, F.; Garcia, D.Q.T.P.M. - 94128, a new isocoumarin antitumor agent produced by a marine bacterium. J. Antibiot., 1997, 50, 175-176.
[40]
Azumi, M.; Ogawa, K.I.; Fujita, T.; Takeshita, M.; Yoshida, R.; Furumai, T.; Igarashi, Y. Bacilosarcins A and B, novel bioactive isocoumarins with unusual heterocyclic cores from the marine-derived bacterium Bacillus subtilis. Tetrahedron, 2008, 64, 6420-6425.
[41]
Boya, C.A.; Herrera, L.; Guzman, H.M.; Gutierrez, M. Antiplasmodial activity of bacilosarcin A isolated from the octocoral-associated bacterium Bacillus sp. collected in Panama. J. Pharm. Bioallied Sci., 2012, 4, 66.
[42]
Liu, S.W.; Jin, J.; Chen, C.; Liu, J-M.; Li, J-Y.; Wang, F.F.; Jiang, Z.K.; Hu, J.H.; Gao, Z.X.; Yao, F. PJS, a novel isocoumarin with hexahydropyrimidine ring from Bacillus subtilis PJS. J. Antibiot. (Tokyo), 2013, 66, 281-284.
[43]
Liu, S.; Han, X.; Jiang, Z.; Wu, G.; Hu, X.; You, X.; Jiang, J.; Zhang, Y.; Sun, C. Hetiamacin B–D, new members of amicoumacin group antibiotics isolated from Bacillus subtilis PJS. J. Antibiot. (Tokyo), 2016, 69, 769-772.
[44]
Bai, J.; Liu, D.; Yu, S.; Proksch, P.; Lin, W. Amicoumacins from the marine-derived bacterium Bacillus sp. with the inhibition of NO production. Tetrahedron Lett., 2014, 55, 6286-6291.
[45]
Tang, H-L.; Sun, C-H.; Hu, X-X.; You, X-F.; Wang, M.; Liu, S-W. Damxungmacin A and B, Two New Amicoumacins with Rare Heterocyclic Cores Isolated from Bacillus subtilis XZ-7. Molecules, 2016, 21, 1601-1610.
[46]
McInerney, B.V.; Taylor, W.C.; Lacey, M.J.; Akhurst, R.J.; Gregson, R.P. Biologically active metabolites from Xenorhabdus spp., Part 2. Benzopyran-1-one derivatives with gastroprotective activity. J. Nat. Prod., 1991, 54, 785-795.
[47]
Reimer, D.; Pos, K.M.; Thines, M.; Grün, P.; Bode, H.B. A natural prodrug activation -mechanism in nonribosomal peptide synthesis. Nat. Chem. Biol., 2011, 7, 888-890.
[48]
Qadeer, G.; Rama, N.H.; Hussain, S.J. A new total synthesis of natural isocoumarin, thunberginol B. ARKIVOC, 2007, 14, 12-19.
[49]
Enomoto, M.; Kuwahara, S. Total Synthesis of Bacilosarcins A and B. Angew. Chem. Int. Ed., 2009, 48, 1144-1148.
[50]
Kurasawa, K.; Kuwahara, S.; Enomoto, M. Synthesis of bacilosarcins B and C. Tetrahedron Lett., 2016, 57, 4997-4999.
[51]
Suzuki, T.; Nagasawa, T.; Enomoto, M.; Kuwahara, S. Stereoselective total synthesis of amicoumacin C. Tetrahedron, 2015, 71, 1992-1997.
[52]
Rao, M.V.; Rao, B.V.; Ramesh, B. Total synthesis of AI-77-B. Tetrahedron Lett., 2014, 55, 5921-5924.
[53]
Uchida, K.; Fukuda, T.; Iwao, M. Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl) oxazoline. Tetrahedron, 2007, 63, 7178-7186.
[54]
Mali, R.G.; Badu, K.N. 3-Aryl-8-bydroxy-3,4-dihydroisocoumarins: Synthesis of aglycooes of macrophyllosides A, B and C. J. Indian Inst. Sci., 2001, 81, 103-110.
[55]
Duan, J.; Cheng, Y.; Cheng, J.; Li, R.; Li, P. Organocatalytic Asymmetric Benzylation and Aldol-Hemiacetalization of α,β-Unsaturated Trifluoromethyl Ketones: Efficient Enantioselective Construction of 3,4-Dihydroisocoumarins. Chemistry, 2017, 23, 519-523.
[56]
Abid, O.R.; Khalid, M.; Hussain, M.T.; Hanif, M.; Qadeer, G.; Rama, N.H.; Kornienko, A.; Khan, K.M. Synthesis and anti-cancer, anti-metastatic evaluation of some new fluorinated isocoumarins and 3,4-dihydroisocoumarins. J. Fluor. Chem., 2012, 135, 240-245.
[57]
Sanchez-Mangas, J.; Busto, E.; Gotor, V.; Gotor-Fernandez, V. One-Pot Synthesis of Enantiopure 3,4-Dihydroisocoumarins through Dynamic Reductive Kinetic Resolution Processes. Org. Lett., 2013, 15, 3872-3875.
[58]
Cheng, G.; Li, T-J.; Yu, J-Q. Practical Pd(II)-Catalyzed C−H Alkylation with Epoxides: One-Step Syntheses of 3,4-Dihydroisocoumarins. J. Am. Chem. Soc., 2015, 137, 10950-10953.
[59]
Zhang, X.; Huang, B.; Yang, C.; Xia, W. Photoinduced Regioselective Lactonization of ortho-Iodobenzoic Acids with Alkenes: Synthesis of 3,4-Dihydroisocoumarin Derivatives. Synlett, 2018, 29, 131-135.
[60]
Li, W.; Wiesenfeldt, M.P.; Glorius, F. Ruthenium−NHC−Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins. J. Am. Chem. Soc., 2017, 139, 2585-2588.
[61]
Guimaraes, K.G.; de Freitas, R.P.; Ruiz, A.L.T.G.; Fiorito, G.F.; Carvalho, J.E.; da Cunha, E.F.F.; Ramalho, T.C.; Alves, R.B. Synthesis, antiproliferative activities, and computational evaluation of novel isocoumarin and 3,4-dihydroisocoumarin derivatives. Eur. J. Med. Chem., 2016, 111, 103-113.
[62]
Ullah, I.; Sher, M.; Khera, R.A.; Ali, A.; Ibad, M.F.; Villinger, A.; Fischer, C.; Langer, P. Chelation-control in the formal [3þ3] cyclization of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones. One pot synthesis of 3-aryl-3,4-dihydroisocoumarins. Tetrahedron, 2010, 66, 1874-1884.
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