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      Structure modification, antialgal, antiplasmodial, and toxic evaluations of a series of new marine-derived 14-membered resorcylic acid lactone derivatives


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          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 327 and 3071 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 ( 171) 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 (EC 50 = 6.67 and 8.55 μmol/L), respectively, which were similar in efficacy to those of the positive control SeaNine 211 (EC 50 = 2.90 and 9.74 μmol/L). More importantly, 38, 39, and 6971 showed potent antiplasmodial activities against Plasmodium falciparum with IC 50 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.

          Supplementary Information

          The online version contains supplementary material available at 10.1007/s42995-021-00103-0.

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          Most cited references41

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          Human malaria parasites in continuous culture

          Plasmodium falciparum can now be maintained in continuous culture in human erythrocytes incubated at 38 degrees C in RPMI 1640 medium with human serum under an atmosphere with 7 percent carbon dioxide and low oxygen (1 or 5 percent). The original parasite material, derived from an infected Aotus trivirgatus monkey, was diluted more than 100 million times by the addition of human erythrocytes at 3- or 4-day intervals. The parasites continued to reproduce in their normal asexual cycle of approximately 48 hours but were no longer highly synchronous. The have remained infective to Aotus.
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            Malaria biology and disease pathogenesis: insights for new treatments.

            Plasmodium falciparum malaria, an infectious disease caused by a parasitic protozoan, claims the lives of nearly a million children each year in Africa alone and is a top public health concern. Evidence is accumulating that resistance to artemisinin derivatives, the frontline therapy for the asexual blood stage of the infection, is developing in southeast Asia. Renewed initiatives to eliminate malaria will benefit from an expanded repertoire of antimalarials, including new drugs that kill circulating P. falciparum gametocytes, thereby preventing transmission. Our current understanding of the biology of asexual blood-stage parasites and gametocytes and the ability to culture them in vitro lends optimism that high-throughput screenings of large chemical libraries will produce a new generation of antimalarial drugs. There is also a need for new therapies to reduce the high mortality of severe malaria. An understanding of the pathophysiology of severe disease may identify rational targets for drugs that improve survival.
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              Synchronization of Plasmodium falciparum erythrocytic stages in culture.

              Synchronous development of the erythrocytic stages of a human malaria parasite, Plasmodium falciparum, in culture was accomplished by suspending cultured parasites in 5% D-sorbitol and subsequent reintroduction into culture. Immediately after sorbitol treatment, cultures consisted mainly of single and multiple ring-form infections. At the same time, varying degrees of lysis of erythrocytes infected with the more mature stages of the parasite was evident. Approximately 95% of the parasites were in the ring stage of development at 48 and 96 hr after sorbitol treatment-likewise, a high percentage of trophozoite and schizont stages was observed at 24, 72, and 120 hr. D-Mannitol produced similar, selective, lytic effects.

                Author and article information

                Mar Life Sci Technol
                Mar Life Sci Technol
                Marine Life Science & Technology
                Springer Singapore (Singapore )
                28 June 2021
                28 June 2021
                February 2022
                : 4
                : 1
                : 88-97
                [1 ]GRID grid.4422.0, ISNI 0000 0001 2152 3263, Key Laboratory of Marine Drugs, the Ministry of Education of China, School of Medicine and Pharmacy, , Ocean University of China, ; Qingdao, 266003 China
                [2 ]GRID grid.484590.4, ISNI 0000 0004 5998 3072, Laboratory for Marine Drugs and Bioproducts, , Qingdao National Laboratory for Marine Science and Technology, ; Qingdao, 266237 China
                [3 ]GRID grid.464256.7, ISNI 0000 0000 9749 5118, State Key Laboratory for Marine Corrosion and Protection, , Luoyang Ship Material Research Institute (LSMRI), ; Qingdao, 266237 China
                [4 ]GRID grid.501516.6, ISNI 0000 0004 0601 8631, Center of Cellular and Molecular Biology of Diseases, , Instituto de Investigaciones Científcas y Servicios de Alta Tecnología, City of Knowledge, ; Clayton, Apartado 0816-02852 Panama
                [5 ]GRID grid.426114.4, ISNI 0000 0000 9974 7390, Syngenta Jealott’s Hill International Research Centre, ; Bracknell, Berkshire, RG42 6EY UK
                © The Author(s) 2021

                Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

                : 10 December 2020
                : 1 April 2021
                Research Paper
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                © Ocean University of China 2022

                marine natural product,14-membered resorcylic acid lactone,zeaenol,semisynthesis,antialgal activity,antiplasmodial activity


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