Structure modification, antialgal, antiplasmodial, and toxic evaluations of a series of new marine-derived 14-membered resorcylic acid lactone derivatives
Tóm tắt
Marine natural products play critical roles in the chemical defense of many marine organisms and are essential, reputable sources of successful drug leads. Sixty-seven 14-membered resorcylic acid lactone derivatives 3–27 and 30–71 of the natural product zeaenol (1) isolated from the marine-derived fungus Cochliobolus lunatus were semisynthesized by chlorination, acylation, esterification, and acetalization in one to three steps. The structures of these new derivatives were established by HRESIMS and NMR techniques. All the compounds (1–71) were evaluated for their antialgal and antiplasmodial activities. Among them, 14 compounds displayed antifouling activities against adhesion of the fouling diatoms. In particular, 9 and 34 exhibited strong and selective inhibitory effects against the diatoms Navicula laevissima and Navicula exigua (EC50 = 6.67 and 8.55 μmol/L), respectively, which were similar in efficacy to those of the positive control SeaNine 211 (EC50 = 2.90 and 9.74 μmol/L). More importantly, 38, 39, and 69–71 showed potent antiplasmodial activities against Plasmodium falciparum with IC50 values ranging from 3.54 to 9.72 μmol/L. Very interestingly, the five antiplasmodial derivatives displayed non-toxicity in the cytotoxicity assays and the zebrafish embryos model, thus, representing potential promising antiplasmodial drug agents. The preliminary structure–activity relationships indicated that biphenyl substituent at C-2, acetonide at positions C-5′ and C-6′, and tri- or tetra-substituted of acyl groups increased the antiplasmodial activity. Therefore, combining evaluation of chemical ecology with pharmacological models will be implemented as a systematic strategy, not only for environmentally friendly antifoulants but also for structurally novel drugs.
Tài liệu tham khảo
Bhadury P, Mohammad BT, Wright PC (2006) The current status of natural products from marine fungi and their potential as anti-infective agents. J Ind Microbiol Biotechnol 33:325–337
Bodor N, Sloan KB, Kaminski JJ, Shih C, Pogany S (1983) A convenient synthesis of (acyloxy) alkyl α-ethers of phenols. J Org Chem 48:5280–5284
Chakraborty J, Ghosh A, Nanda S (2020) Asymmetric total syntheses of naturally occurring α, β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction. Org Biomol Chem 18:2331–2345
Conrad MD, Rosenthal PJ (2019) Antiplasmodial drug resistance in Africa: the calm before the storm? Lancet Infect Dis 19:e338–e351
Corbett Y, Herrera L, Gonzalez J, Cubilla L, Capson T, Coley PD, Kursar TA, Romero LI, Ortega-Barria E (2004) A novel DNA-based microfluorimetric method to evaluate antiplasmodial drug activity. Am J Trop Med Hyg 70:119–124
Doda SR, Raghavendar A, Haridasyam SB, Putta CS, Kanakadurgarao B, Kadari S (2019) Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol. Heterocycl Commun 25:78–84
Ferguson NM (2018) Challenges and opportunities in controlling mosquito-borne infections. Nature 559:490–497
Hachani MA, Dhib A, Fathalli A, Ziadi B, Turki S, Aleya L (2018) Harmful epiphytic dinoflagellate assemblages on macrophytes in the Gulf of Tunis. Harmful Algae 77:29–42
Hou XM, Wang CY, Gerwick WH, Shao CL (2019) Marine natural products as potential anti-tubercular agents. Eur J Med Chem 165:273–292
Isaka M, Suyarnsestakorn C, Tanticharoen M, Kongsaeree P, Thebtaranonth Y (2002) Aigialomycins A-E, new resorcylic macrolides from the marine mangrove fungus Aigialus parvus. J Org Chem 67:1561–1566
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
Kadaria S, Yerrabellya H, Yerrabellya JR, Gogulaa T, Gouda Y, Thalaria G, Doda SR (2018) Stereoselective total synthesis of paecilomycin E and F and its two congeners cochliomycin C and 6-epi-cochliomycin C. Synth Commun 48:1867–1875
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
Lambros C, Vanderberg J (1979) Synchronization of Plasmodium falciparum erythrocytic stages in culture. J Parasitol 65:418–420
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
Mallampudi NA, Srinivas B, Reddy JG, Mohapatra DK (2019) Total synthesis and structural revision of monocillin VII. Org Lett 21:5952–5956
Miller LH, Ackerman HC, Su X, Wellems TE (2013) Malaria biology and disease pathogenesis: insights for new treatments. Nat Med 19:156–167
Mohapatra DK, Reddy DS, Mallampudi NA, Gaddam J, Polepalli S, Jain N, Yadav JS (2014) The protecting-group directed diastereoselective Nozaki–Hiyama–Kishi (NHK) reaction: total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues. Org Biomol Chem 12:9683–9695
Molino PJ, Wetherbee R (2008) The biology of biofouling diatoms and their role in the development of microbial slimes. Biofouling 24:365–379
Molinski TF, Dalisay DS, Lievens SL (2009) Drug development from marine natural products. Nat Rev Drug Discov 8:69–85
Ohba K, Nakata M (2018) Convergent total synthesis of paecilomycin B and 6′-epi-paecilomycin B by a Barbier-type reaction using 2,4,6-triisopropylphenyllithium. J Org Chem 83:7019–7032
Ortlepp S, Pedpradap S, Dobretsov S, Proksch P (2008) Antifouling activity of sponge-derived polybrominated diphenyl ethers and synthetic analogues. Biofouling 24:201–208
Paul VJ, Arthur KE, Ritson-Williams R, Ross C, Sharp K (2007) Chemical defenses: from compounds to communities. Biol Bull 213:226–251
Pierce CG, Uppuluri P, Teistan AR, Wormley JFL, Mowat E, Ramage G, Lopez-ribot JL (2008) A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing. Nat Protoc 3:1494–1500
Reddy AS, Bhavani G, Jonnala S, Bantu R, Reddy BVS (2019) A concise and stereoselective total synthesis of paecilomycin E. Nat Prod Commun 14:131–133
Richards FM, Alderton WK, Kimber GM, Liu Z, Strang I, Redfern WS, Valentin JP, Winter MJ, Hutchinson TH (2008) Validation of the use of zebrafish larvae in visual safety assessment. J Pharmacol Toxicol Methods 58:50–58
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
Shen W, Mao H, Huang Q, Dong JY (2015) Benzenediol lactones: a class of fungal metabolites with diverse structural features and biological activity. Eur J Med Chem 97:747–777
Shinde P, Banerjee P, Mandhare A (2019) Marine natural products as source of new drugs: a patent review (2015–2018). Expert Opin Ther Pat 29:283–309
Simmons TL, Andrianasolo E, McPhail K (2005) Marine natural products as anticancer drugs. Mol Cancer Ther 4:333–342
Stoessl A, Stothers JB (1983) Tetrahydroaltersolanol B, a hexahydroanthronol from Alternaria solani. Can J Chem 61:378–382
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
Thiraporn A, Rukachaisirikul V, Iawsipo R, Somwang T, Tadpetch K (2017) Total synthesis and cytotoxic activity of 5′-hydroxyzearalenone and 5′β-hydroxyzearalenone. Eur J Org Chem 2017:7133–7147
Trager W, Jensen JB (1976) Human malaria parasites in continuous culture. Science 193:673–675
Wang SF, Liu KC, Wang XM, He QX, Chen XQ (2011) Toxic effects of celastrol on embryonic development of zebrafish (Danio rerio). Drug Chem Toxicol 34:61–65
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
WHO (2020) World malaria report 2019. https://www.who.int/malaria/publications/world-malaria-report-2019/en/. https://www.who.int/publications/i/item/9789241565721
Xu LX, He ZX, Xue JH, Chen XP, Wei XY (2010) β-Resorcylic acid lactones from a Paecilomyces fungus. J Nat Prod 73:885–889
Xu J, Jiang CH, Zhang ZL, Ma WQ, Guo YW (2014) Recent progress regarding the bioactivity, biosynthesis and synthesis of naturally occurring resorcinolic macrolides. Acta Pharmacol Sin 35:316–330
Xu WF, Xue XJ, Qi YX, Wu NN, Wang CY, Shao CL (2021) Cochliomycin G, a 14-membered resorcylic acid lactone from a marine-derived fungus Cochliobolus lunatus. Nat Prod Res 35:490–493
Yang ZQ, Geng X, Solit D, Pratilas CA, Rosen N, Danishefsky SJ (2004) New efficient synthesis of resorcinylic macrolides via ynolides: establishment of cycloproparadicicol as synthetically feasible preclinical anticancer agent based on Hsp90 as the target. J Am Chem Soc 126:7881–7889
Zhang XQ, Spadafora C, Pineda LM, Ng MG, Sun JH, Wang W, Wang CY, Gu YC, Shao CL (2017) Discovery, semisynthesis, antiparasitic and cytotoxic evaluation of 14-membered resorcylic acid lactones and their derivatives. Sci Rep 7:11822