Abstract
β-Resorcylic acid lactones (RALs) are one of the major polyketides produced by fungi, and some of them have a diverse array of biological activities. Most RALs feature a 14-membered macrocyclic ring fused to β-resorcylic acid (2,4-dihydroxybenzoic acid). In this review, more than 100 RAL-type of compounds are structurally classified into three groups; 14-membered RALs with 17R configuration, 14-membered RALs with 17S configuration, and benzopyranones/benzofuranones, and they are reviewed comprehensively in terms of chemistry, biological activities, and biosynthetic pathways.
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References
Abid-Essefi S, Baudrimont I, Hassen W, Ouanes Z, Mobio TA, Creppy EE, Bacha H (2003) DNA fragmentation, apoptosis and cell cycle arrest induced by zearalenone in cultured DOK, Vero and Caco-2 cells: prevention by vitamin E. Toxicoloy 192:237–248. https://doi.org/10.1016/s0300-483x(03)00329-9
Agatsuma T, Takahashi A, Kabuto C, Nozoe S (1993) Revised structure and stereochemistry of hypothemycin. Chem Pharm Bull 41:373–375. https://doi.org/10.1248/cpb.41.373
Arai M, Yamanoto K, Namatame I, Tomoda H, Omura S (2003) New monordens produced by amidepsine-producing fungus Humicola sp. FO-2942. J Antibiot 6:526–533. https://doi.org/10.7164/antibiotics.56.526
Ayer WA, Lee SP, Tsuneda A, Hiratsuka Y (1980) The isolation, identification, and bioassay of the antifungal metabolites produced by Monocillium nordinii. Can J Microbiol 26:766–773. https://doi.org/10.1139/m80-133
Ayer WA, Rodriguez LP (1987) Minor metabolites of Monocillium nordinii. Phytochemistry 26:1353–1355. https://doi.org/10.1016/S0031-9422(00)81811-7
Banwell MG, Ma X, Bolte B, Zhang Y, Dlugosch M (2017) Chemical syntheses of the cochliomycins and certain related resorcylic acid lactones. Tetrahedron Lett 58:4025–4038. https://doi.org/10.1016/j.tetlet.2017.08.021
Bouaziz C, Martel C, Sharaf el dein O, Abid-Essefi S, Brenner C, Lemaire C, Bacha H (2009) Fusarial toxin-induced toxicity in cultured cells and in isolated mitochondria involves PTPC-dependent activation of the mitochondrial pathway of apoptosis. Toxicol Sci 110:363–375. https://doi.org/10.1093/toxsci/kfp117
Bravin F, Duca RC, Balaguer P, Delaforge M (2009) In vitro cytochrome P450 formation of a mono-hydroxylated metabolite of zearalenone exhibiting estrogenic activities: possible occurrence of this metabolite in vivo. Int J Mol Sci 10:1824–1837. https://doi.org/10.3390/ijms10041824
Bräse S, Encinas A, Keck J, Nising CF (2009) Chemistry and biology of mycotoxins and related fungal metabolites. Chem Rev 109:3903–3990. https://doi.org/10.1021/cr050001f
Chaikuad A, Koch P, Laufer SA, Knapp S (2008) The cysteinome of protein kinases as a target in drug development. Angew Chem Int Ed 57:4372–4385. https://doi.org/10.1002/anie.201707875
Chanmugam P, Feng L, Liou S, Jang BC, Boudreau M, Yu G, Lee JH, Kwon HJ, Beppu T, Yoshida M, Xia Y, Wilson CB, Hwang D (1995) Radicicol, a potent protein tyrosine kinase inhibitor, suppresses the expression of mitogen-induced cyclooxygenase in macrophages stimulated with lipopolysaccharide and in experimental glomerulonephritis. J Biol Chem 270:5418–54263. https://doi.org/10.1074/jbc.270.10.5418
Costa TEMM, Raghavendra NM, Penido C (2020) Natural heat shock protein 90 inhibitors in cancer and inflammation. Eur J Med Chem. https://doi.org/10.1016/j.ejmech.2020.112063
Dakas PY, Barluenga S, Totzke F, Zirrgiebel U, Winssinger N (2007) Modular synthesis of radicicol A and related resorcylic acid lactones, potent kinase inhibitors. Angew Chem Int Ed 46:6899–6902. https://doi.org/10.1002/anie.200702406
Demain AL, Sanchez S (2009) Microbial drug discovery: 80 years of progress. J Antibiot 62:5–16. https://doi.org/10.1038/ja.2008.16
Dong J, Zhu Y, Song H, Li R, He H, Liu H, Huang R, Zhou Y, Wang L, Cao Y, Zhang K (2007) Nematicidal resorcylides from the aquatic fungus Caryospora callicarpa YMF1.01026. J Chem Ecol 33:1115–1126. https://doi.org/10.1007/s10886-007-9256-7
Ellestad GA, Lovell FM, Perkinson NA, Hargreaves RT, Mcgahren WJ (1978) New zearalenone related macrolides and isocoumarins from an unidentified fungus. J Org Chem 43:2339–2343. https://doi.org/10.1021/jo00406a007
El-Sharkawy SH, Abul-Hajj YJ (1988) Microbial transformation of zearalenone, 2. Reduction, hydroxylation, and methylation products. J Org Chem 53:515–519. https://doi.org/10.1021/jo00238a008
El-Elimat T, Figueroa M, Raja HA, Graf TN, Swanson SM, Falkinham JO, Wani MC, Pearce CJ, Oberlies NH (2015) Biosynthetically distinct cytotoxic polyketides from Setophoma terrestris. Eur J Org Chem 2015:109–121. https://doi.org/10.1002/ejoc.201402984
Gao J, Radwan MM, León F, Dale OR, Husni AS, Wu Y, Lupien S, Wang X, Manly SP, Hill RA, Dugan FM, Cutler HG, Cutler SJ (2013) Neocosmospora sp.-derived resorcyclic acid lactones with in vitro binding affinity for human opioid and cannabinoid receptors. J Nat Prod 76:824–828. https://doi.org/10.1021/np300653d
Harčárová M, Čonková E, Proškovcová M, Felis M (2020) In vivo assessment of zearalenone toxicity. Folia Vet 64:60–65. https://doi.org/10.2478/fv-2020-0018
Heberlig GW, Wirz M, Wang M, Boddy CN (2014) Resorcylic acid lactone biosynthesis relies on a stereotolerant macrocyclizing thioesterase. Org Lett 16:5858–5861. https://doi.org/10.1021/ol502747t
Hellwig V, Bartschmid AM, Mu¨ller H, Greif G, Kleymann G, Zitzmann W, Tichy HV, Stadler M (2003) Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata. J Nat Prod 66:829–837. https://doi.org/10.1021/np020556v
Hoffmeister D, Keller NP (2007) Natural products of filamentous fungi: enzymes, genes, and their regulation. Nat Prod Rep 24:393–416. https://doi.org/10.1039/b603084j
Hoshino Y, Ivanova VB, Yazawa K, Ando A, Mikami Y (2002) Queenslandon, a new antifungal compound produced by Chrysosporium queenslandicum: production, isolation, and structure elucidation. J Antibiot 55:516–519. https://doi.org/10.7164/antibiotics.55.516
Isaacs JS, Xu W, Neckers L (2003) Heat shock protein 90 as a molecular target for cancer therapeutics. Cancer Cell 3:213–217. https://doi.org/10.1016/s1535-6108(03)00029-1
Isaka M, Suyarnsestakorn C, Tanticharoen M (2002) Aigialomycins A-E, new resorcylic macrolides from the marine mangrove fungus Aigialus parvus. J Org Chem 67:1561–1566. https://doi.org/10.1021/jo010930g
Isaka M, Chinthanom P, Veeranondha S, Supothina S, Luangsa-ard JJ (2008) Novel cyclopropyl diketones and 14-membered macrolides from the soil fungus Hamigera avellanea BCC 17816. Tetrahedron 64:11028–11033. https://doi.org/10.1016/j.tet.2008.09.077
Isaka M, Yangchum A, Intamas S, Kocharin K, Gareth Jones EB, Kongsaeree P, Prabpai S (2009) Aigialomycins and related polyketide metabolites from the mangrove fungus Aigialus parvus BCC 5311. Tetrahedron 65:4396–4403. https://doi.org/10.1016/j.tet.2009.03.050
Isaka M, Chinthanom P, Kongthong S, Supothina S, Ittiworapong P (2010) Hamigeromycins C-G, 14-membered macrolides from the fungus Hamigera avellanea BCC 17816. Tetrahedron 66:955–961. https://doi.org/10.1016/j.tet.2009.11.101
Jana N, Nanda S (2018) Resorcylic acid lactones (RALs) and their structural congeners: recent advances in their biosynthesis, chemical synthesis and biology. New J Chem 42:17803–17873. https://doi.org/10.1039/C8NJ02534G
Kim JW, Shim SH (2019) The fungus Colletotrichum as a source for bioactive secondary metabolites. Arch Pharm Res 42:735–753. https://doi.org/10.1007/s12272-019-01142-z
Kim JE, Son HK, Lee YW (2018) Biosynthetic mechanism and regulation of zearalenone on fusarium graminearum. JSM Mycotoxins 68:1–6. https://doi.org/10.2520/myco.68-1-2
Lai D, Mao Z, Xu D, Zhang X, Wang A, Xie R, Zhou L, Liu Y (2016) Hyalodendriellins A–F, new 14-membered resorcylic acid lactones from the endophytic fungus Hyalodendriella sp. Ponipodef12. RSC Adv 6:108989–109000. https://doi.org/10.1039/C6RA24009G
Leslie Gunatilaka AA (2006) Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J Nat Prod 69:509–526. https://doi.org/10.1021/np058128n
Li L, Zhang X, Tan X, Sun B, Wu B, Yu M, Zhang T, Zhang Y, Ding G (2019) Rhinoclactones A-E, resorcylic acid analogs from desert plant endophytic fungus Rhinocladiella similis. Molecules 24:1405. https://doi.org/10.3390/molecules24071405
Li XQ, Xu K, Liu XM, Zhang P (2020) A systematic review on secondary metabolites of Paecilomyces species: chemical diversity and biological activity. Planta Med 86:805–821. https://doi.org/10.1055/a-1196-1906
Liu L, Liu R, Basnet BB, Bao L, Han J, Ren J, Zeng Z, Zhuang W, Liu H (2017) A new seco-pimarane diterpene and four new β-resorcylic acid lactones from a fungicolous Hypomyces subiculosus. RSC Adv 7:51986–51992. https://doi.org/10.1039/C7RA11365J
Liu QA, Shao CL, Gu YC, Blum M, Gan LS, Wang KL, Chen M, Wang CY (2014) Antifouling and fungicidal resorcylic acid lactones from the sea Anemone-derived fungus Cochliobolus lunatus. J Agric Food Chem 62:3183–3191. https://doi.org/10.1021/jf500248z
Lone KP (1997) Natural sex steroids and their xenobiotic analogs in animal production: growth, carcass quality, pharmacokinetics, metabolism, mode of action, residues, methods, and epidemiology. CRC Crit Rev Food Sci Nutr 37:93–209. https://doi.org/10.1080/10408399709527771
Luongo D, De Luna R, Russo R, Severino L (2008) Effects of four Fusarium toxins (fumonisin B1, α-zearalenol, nivalenol and deoxynivalenol) on porcine whole-blood cellular proliferation. Toxicon 52:156–162. https://doi.org/10.1016/j.toxicon.2008.04.162
Malekinejad H, Schoevers EJ, Daemen IJ, Zijlstra C, Colenbrander B, Fink-Gremmels J, Roelen BA (2007) Exposure of oocytes to the Fusarium toxins zearalenone and deoxynivalenol causes aneuploidy and abnormal embryo development in pigs. Biol Reprod 77:840–847. https://doi.org/10.1095/biolreprod.107.062711
McLellan CA, Turbyville TJ, Kithsiri Wijeratne EM, Kerschen A, Vierling E, Queitsch C, Whitesell L, Leslie Gunatilaka AA (2007) A rhizosphere fungus enhances arabidopsis thermotolerance through production of an HSP90 inhibitor. Plant Physiol 145:174–182. https://doi.org/10.1104/pp.107.101808
Mejia EJ, Loveridge ST, Stepan G, Tsai A, Jones GS, Barnes T, White KN, Drašković M, Tenney K, Tsiang M, Geleziunas R, Cihlar T, Pagratis N, Tian Y, Yu H, Crews P (2014) Study of marine natural products including resorcyclic acid lactones from Humicola fuscoatra that reactivate latent HIV-1 expression in an in vitro model of central memory CD4 + T cells. J Nat Prod 77:618–624. https://doi.org/10.1021/np400889x
Mirrington RN, Ritchie E, Shoppee CW, Taylor WC, Sternhell S (1964) The constitution of radicicol. Tetrahedron Lett 7:365–370. https://doi.org/10.1016/0040-4039(64)80029-0
Moulin E, Zoete V, Barluenga S, Karplus M, Winssinger N (2005) Design, synthesis, and biological evaluation of HSP90 inhibitors based on conformational analysis of radicicol and its analogues. J Am Chem Soc 127:6999–7004. https://doi.org/10.1021/ja043101w
Nozawa K, Nakajima S (1979) Isolation of radicicol from Penicillium luteoaurantium and meleagrin, a new metabolite, from Penicillium meleagrinum. J Nat Prod 4:374–377. https://doi.org/10.1021/np50004a004
Paranagama PA, Kithsiri Wijeratne EM, Leslie Gunatilaka AA (2007) Uncovering biosynthetic potential of plant-associated fungi: effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii. J Nat Prod 70:1939–1945. https://doi.org/10.1021/np070504b
Qin F, Li Y, Lin R, Zhang X, Mao Z, Ling J, Yang Y, Zhuang X, Du S, Cheng X, Xie B (2019) Antibacterial radicicol analogues from Pochonia chlamydosporia and their biosynthetic gene cluster. J Agric Food Chem 67:7266–7273. https://doi.org/10.1021/acs.jafc.9b01977
Rawlins P, Mander T, Sadeghi R, Hill S, Gammon G, Foxwell B, Wrigley S, Moore M (1999) Inhibition of endotoxin-induced TNF-α production in macrophages by 5Z-7-oxo-zeaennol and other fungal resorcylic acid lactones. Int J Immunopharmacol 21:799–814. https://doi.org/10.1016/s0192-0561(99)00047-8
Ruddick JA, Scott PM, Harwig J (1976) Teratological evaluation of zearalenone administered orally to the rat. Bull Environ Contam Toxicol 15:678–681. https://doi.org/10.1007/bf01685617
Saetang P, Rukachaisirikul V, Phongpaichit S, Sakayaroj J, Shi X, Chen J, Shen X (2016) β-Resorcylic macrolide and octahydronaphthalene derivatives from a seagrass-derived fungus from Fusarium sp. PSU-ES123. Tetrahedron 72:6421–6427. https://doi.org/10.1016/j.tet.2016.08.048
Schirmer A, Kennedy J, Murli S, Reid R, Santi DV (2006) Targeted covalent inactivation of protein kinases by resorcylic acid lactone polyketides. Proc Natl Acad Sci USA 103:4234–4239. https://doi.org/10.1073/pnas.0600445103
Sharma SV, Agatsuma T, Nakano H (1998) Targeting of the protein chaperone, HSP90, by the transformation suppressing agent, radicicol. Oncogene 16:2639–2645. https://doi.org/10.1038/sj.onc.1201790
Shen W, Mao H, Huang Q, Dong J (2015) Benzenediol lactones: a class of fungal metabolites with diverse structural features and biological activities. Eur J Med Chem 97:747–777. https://doi.org/10.1016/j.ejmech.2014.11.067
Shinonaga H, Kawamura Y, Ikeda A, Aoki M, Sakai N, Fujimoto N, Kawashima A (2009a) Pochonins K-P: new radicicol analogues from Pochonia chlamydosporia var. chlamydosporia and their WNT-5A expression inhibitory activities. Tetrahedron 65:3446–3453. https://doi.org/10.1016/j.tet.2009.02.027
Shinonaga H, Kawamura Y, Ikeda A, Aoki M, Sakai N, Fujimoto N, Kawashima A (2009b) The search for a hair-growth stimulant: new radicicol analogues as WNT-5A expression inhibitors from Pochonia chlamydosporia var. chlamydosporia. Tetrahedron Lett 50:108–110. https://doi.org/10.1016/j.tetlet.2008.10.099
Shao CL, Wu HX, Wang CY, Liu QA, Xu Y, Wei MY, Qian PY, Gu YC, Zheng CJ, She ZG, Lin YC (2011) Potent antifouling resorcylic acid lactones from the Gorgonian-derived fungus Cochliobolus lunatus. J Nat Prod 74:629–633. https://doi.org/10.1021/np100641b
Song JH, Shim A, Kim YJ, Ahn JH, Kwon BE, Pham TT, Lee J, Chang SY, Ko HJ (2018) Antiviral and anti-inflammatory activities of pochonin D, a heat shock protein 90 inhibitor, against Rhinovirus infection. Biomol Ther 26:576–583. https://doi.org/10.4062%2Fbiomolther.2017.233
Stadler M, Tichy HV, Katsiou E, Hellwig V (2003) Chemotaxonomy of pochonia and other conidial fungi with verticillium-like anamorphs. Mycol Prog 2:95–122. https://doi.org/10.1007/s11557-006-0048-1
Sugawara F, Kim KW, Kobayashi K, Uzawa J, Yoshida S, Murofushi N, Takahashi N, Strobel GA (1992) Zearalenone derivatives produced by the fungus Drechslera portulacae. Phytochemistry 31:1987–1990. https://doi.org/10.1016/0031-9422(92)80346-G
Talontsi FM, Facey P, Kongue Tatong MD, Tofazzal Islam M, Frauendorf H, Draeger S, Tiedemann AV, Laatsch H (2012) Zoosporicidal metabolites from an endophytic fungus Cryptosporiopsis sp. of Zanthoxylum leprieurii. Phytochemisty 83:87–94. https://doi.org/10.1016/j.phytochem.2012.06.006
Tanaka Y, Shiomi K, Kamei K, Sugoh-Hagino M, Enomoto Y, Fang F, Yamaguchi Y, Masuma R, Zhang CG, Zhang XW, Omura S (1998) Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites. J Antibiot 51:153–160. https://doi.org/10.7164/antibiotics.51.153
Thomas R (2001) A biosynthetic classification of fungal and streptomycete fused-ring aromatic polyketides. ChemBioChem 2(20010903):612–627. https://doi.org/10.1002/1439-7633(20010903)2:9%3C612::AID-CBIC612%3E3.0.CO;2-Z
Turbyville TJ, Wijeratne EMK, Liu MX, Burns AM, Seliga CJ, Leuvano LA, David CL, Faeth SH, Whitesell L, Gunatilaka AAL (2006) Search for Hsp90 inhibitors with potent anticancer activity: isolation and SAR studied of radicicol and monocillin I from two plant-associated fungi of the sonoran desert. J Nat Prod 69:178–184. https://doi.org/10.1021%2Fnp058095b
Wang KL, Zhang G, Sun J, Xu Y, Han Z, Liu LL, Shao CL, Liu QA, Wang CY, Qian PY (2016) Cochliomycin A inhibits the larval settlement of Amphibalanus amphitrite by activating the NO/cGMP pathway. Biofouling 32:35–44. https://doi.org/10.1080/08927014.2015.1121245
Wang R, Han Z, Liu B, Zhou B, Wang N, Jiang Q, Qiao Y, Song C, Chai J, Chang J (2018) Identification of natural compound radicicol as potent FTO inhibitor. Mol Pharmaceutics 15:4092–4098. https://doi.org/10.1021/acs.molpharmaceut.8b00522
Wang S, Xu Y, Maine EA, Kithsiri Wijeratne EM, Espinosa-Artiles P, Leslie Gunatilaka AA, Molnár I (2008) Functional characterization of the biosynthesis of radicicol, an Hsp90 inhibitor resorcylic acid lactone from Chatomium chiversii. Chem Biol 15:1328–1338. https://doi.org/10.1016/j.chembiol.2008.10.006
Wang X, Wang C, Duan L, Zhang L, Liu H, Xu YM, Liu Q, Mao T, Zhang W, Chen M, Lin M, Gunatilaka AAL, Xu Y, Molnar I (2019) Rational reprogramming of O-methylation regioselectivity for combinatorial biosynthetic tailoring of benzenediol lactone scaffolds. J Am Chem Soc 141:4355–4364. https://doi.org/10.1021/jacs.8b12967
Wee JL, Sundermann K, Licari P, Galazzo J (2006) Cytotoxic hypothemycin analogues from Hypomyces subiculosus. J Nat Prod 69:1456–1459. https://doi.org/10.1021/np060258o
Wicklow DT, Jordan AM, Gloer JB (2009) Antifungal metabolites (monorden, monocillins I, II, III) from Colletotrichum graminicola, a systemic vascular pathogen of maize. Mycol Res 113:1433–1442. https://doi.org/10.1016/j.mycres.2009.10.001
Wijeratne EMK, Paranagama PA, Gunatilaka AAL (2006) Five new isocoumarins from sonoran desert plant-associated fungal strains Parapaeosphaeria quadriseptata and Chaetomium chiversii. Tetrahedron 62:8439–8446. https://doi.org/10.1016/j.tet.2006.06.089
Winssinger N, Barluenga S (2007) Chemistry and biology of resorcylic acid lactones. Chem Commun 43:22–36. https://doi.org/10.1039/b610344h
Xu J, Chen A, Go ML, Nacro K, Liu B, Chai CLL (2011) Exploring aigialomycin D and its analogues as protein kinase inhibitors for cancer targets. ACS Med Chem Lett 2:662–666. https://doi.org/10.1021/ml200067t
Xu L, He Z, Xue J, Chen X, Wei X (2010) β-Resorcylic acid lactones from a Paecilomyces fungus. J Nat Prod 73:885–889. https://doi.org/10.1021/np900853n
Xu L, Xue J, Zou Y, He S, Wei X (2012) Three new β-resorcyclic acid lactones from Paecilomyces sp. SC0924. Chin J Chem 30:1273–1277. https://doi.org/10.1002/cjoc.201200406
Xu LX, Wu P, Wei HH, Xue JH, Hu XP, Wei XY (2013) Paecilomycins J-M, four new β-resorcylic acid lactones from Paecilomyces sp. SC0924. Tetrahedron Lett 54:2648–2650. https://doi.org/10.1016/j.tetlet.2013.03.036
Xu LX, Xue JH, Wu P, You XY, Wei XY (2014) Absolute configurations of four resorcylic acid lactones, Paecilomycins J-M, by CD/TDDFT calculations. Chirality 26:44–50. https://doi.org/10.1002/chir.22264
Xu L, Wu P, Xue J, Molnar I, Wei X (2017) Antifungal and cytotoxic β–resorcylic acid lactones from a Paecilomyces species. J Nat Prod 80:2215–2223. https://doi.org/10.1021/acs.jnatprod.7b00066
Xu WF, Xue XJ, Qi YX, Wu NN, Wang CY, Shao CL (2019) Cochliomycin G, a 14-membered resorcylic acid lactone from a marine-derived fungus Cochliobolus lunatus. Nat Prod Res Ahead of print. https://doi.org/10.1080/14786419.2019.1633646
Yang SX, Gao JM, Zhang Q, Laatsch H (2011) Toxic polyketides produced by Fusarium sp., an endophytic fungus isolated from Melia azedarach. Bioorg Med Chem Lett 21:1887–1889. https://doi.org/10.1016/j.bmcl.2010.12.043
Yang X, Khong TT, Chen L, Choi HD, Kang JS, Son BW (2008) 8’-Hydroxyzearalanone and 2’-hydroxyzearalanol: resorcyclic acid lactone derivatives from the marine-derived fungus Penicillium sp. Chem Pharm Bull 56:1355–1356. https://doi.org/10.1248/cpb.56.1355
Yuan S, Gopal JV, Ren S, Chen L, Liu L, Gao Z (2020) Anticancer fungal natural products: Mechanisms of action and biosynthesis. Eur J Med Chem 202:112502. https://doi.org/10.1016/j.ejmech.2020.112502
Zhang W, Shao CL, Chen M, Liu QA, Wang CY (2014) Brominated resorcylic acid lactones from the marine-derived fungus Cochliobolus lunatus induced by histone deacetylase inhibitors. Tetrahedron Lett 55:4888–4891. https://doi.org/10.1016/j.tetlet.2014.06.096
Zhao A, Lee SH, Mojena M, Jenkins RG, Patrick DR, Huber HE, Goetz MA, Hensens OD, Zink DL, Vilella D, Dombrowski AW, Lingham RB, Huang L (1999) Resorcylic acid lactones: naturally occurring potent and selective inhibitors of MEK. J Antibiot 52:1086–1094. https://doi.org/10.7164/antibiotics.52.1086
Zhao Y, Huang ZJ, Rahman M, Luo Q, Thorlacius H (2013) Radicicol, an Hsp90 inhibitor, inhibits intestinal inflammation and leakage in abdominal sepsis. J Surg Res 182:312–318. https://doi.org/10.1016/j/jss.2012.10.038
Zhong L, Xu L, Meng X, Peng Y, Chen Y, Sui P, Wang M, Zhou L (2011) Botrallin from the endophytic fungus Hyalodendriella sp. Ponipodef12 and its antimicrobial activity. Afr J Biotechnol 10:18174–18178. https://doi.org/10.5897/AJB11.1801
Zhou J, Gao Y, Chang JL, Yu HY, Chen J, Zhou M, Meng XG, Ruan HL (2020) Resorcylic acid lactones from an Ilyonectria sp. J Nat Prod 83:1505–1514. https://doi.org/10.1021/acs.jnatprod.9b01167
Zourgui L, Golli EE, Bouaziz C, Bacha H, Hassen W (2008) Cactus (Opuntia ficus-indica) cladodes prevent oxidative damage induced by the mycotoxin zearalenone in Balb/C mice. Food Chem Toxicol 46:1817–1824. https://doi.org/10.1016/j.fct.2008.01.023
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We appreciate Inhye Lee, undergrad student from College of Pharmacy, Duksung Women’s University for her efforts in collecting and searching literatures for this paper. This work was supported by Duksung Women’ University research in 2020.
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Bang, S., Shim, S.H. Beta resorcylic acid lactones (RALs) from fungi: chemistry, biology, and biosynthesis. Arch. Pharm. Res. 43, 1093–1113 (2020). https://doi.org/10.1007/s12272-020-01275-6
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DOI: https://doi.org/10.1007/s12272-020-01275-6