Semisynthesis, Structure Elucidation and Anti-Mycobacterium marinum Activity of a Series of Marine-Derived 14-Membered Resorcylic Acid Lactones with Interesting Ketal Groups
The incidence of Mycobacterium marinum infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti-M. marinum drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with...
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| Published in | Marine drugs Vol. 22; no. 10; p. 431 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Switzerland
MDPI AG
01.10.2024
MDPI |
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| Online Access | Get full text |
| ISSN | 1660-3397 1660-3397 |
| DOI | 10.3390/md22100431 |
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| Abstract | The incidence of Mycobacterium marinum infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti-M. marinum drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5′ and C-6′, exhibits a wide range of antimicrobial, antimalarial, and antifouling activities. To further explore the effect of this structural change at C-5′ and C-6′ on this compound’s activity, we synthesized a series of compounds with a structure similar to that of cochliomycin A, bearing ketal groups at C-5′ and C-6′. The R/S configuration of the diastereoisomer at C-13′ was further determined through an NOE correlation analysis of CH3 or CH2 at the derivative C-13′ position and the H-5′ and H-6′ by means of a 1D NOE experiment. Further comparative 1H NMR analysis of diastereoisomers showed the difference in the chemical shift (δ) value of the diastereoisomers. The synthetic compounds were screened for their anti-microbial activities in vitro. Compounds 15–24 and 28–35 demonstrated promising activity against M. marinum, with MIC90 values ranging from 70 to 90 μM, closely approaching the MIC90 of isoniazid. The preliminary structure–activity relationships showed that the ketal groups with aromatic rings at C-5′ and C-6′ could enhance the inhibition of M. marinum. Further study demonstrated that compounds 23, 24, 29, and 30 had significant inhibitory effects on M. marinum and addictive effects with isoniazid and rifampicin. Its effective properties make it an important clue for future drug development toward combatting M. marinum resistance. |
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| AbstractList | The incidence of Mycobacterium marinum infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti-M. marinum drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5′ and C-6′, exhibits a wide range of antimicrobial, antimalarial, and antifouling activities. To further explore the effect of this structural change at C-5′ and C-6′ on this compound’s activity, we synthesized a series of compounds with a structure similar to that of cochliomycin A, bearing ketal groups at C-5′ and C-6′. The R/S configuration of the diastereoisomer at C-13′ was further determined through an NOE correlation analysis of CH3 or CH2 at the derivative C-13′ position and the H-5′ and H-6′ by means of a 1D NOE experiment. Further comparative 1H NMR analysis of diastereoisomers showed the difference in the chemical shift (δ) value of the diastereoisomers. The synthetic compounds were screened for their anti-microbial activities in vitro. Compounds 15–24 and 28–35 demonstrated promising activity against M. marinum, with MIC90 values ranging from 70 to 90 μM, closely approaching the MIC90 of isoniazid. The preliminary structure–activity relationships showed that the ketal groups with aromatic rings at C-5′ and C-6′ could enhance the inhibition of M. marinum. Further study demonstrated that compounds 23, 24, 29, and 30 had significant inhibitory effects on M. marinum and addictive effects with isoniazid and rifampicin. Its effective properties make it an important clue for future drug development toward combatting M. marinum resistance. The incidence of Mycobacterium marinum infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti-M. marinum drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5' and C-6', exhibits a wide range of antimicrobial, antimalarial, and antifouling activities. To further explore the effect of this structural change at C-5' and C-6' on this compound's activity, we synthesized a series of compounds with a structure similar to that of cochliomycin A, bearing ketal groups at C-5' and C-6'. The R/S configuration of the diastereoisomer at C-13' was further determined through an NOE correlation analysis of CH3 or CH2 at the derivative C-13' position and the H-5' and H-6' by means of a 1D NOE experiment. Further comparative 1H NMR analysis of diastereoisomers showed the difference in the chemical shift (δ) value of the diastereoisomers. The synthetic compounds were screened for their anti-microbial activities in vitro. Compounds 15-24 and 28-35 demonstrated promising activity against M. marinum, with MIC90 values ranging from 70 to 90 μM, closely approaching the MIC90 of isoniazid. The preliminary structure-activity relationships showed that the ketal groups with aromatic rings at C-5' and C-6' could enhance the inhibition of M. marinum. Further study demonstrated that compounds 23, 24, 29, and 30 had significant inhibitory effects on M. marinum and addictive effects with isoniazid and rifampicin. Its effective properties make it an important clue for future drug development toward combatting M. marinum resistance.The incidence of Mycobacterium marinum infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti-M. marinum drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5' and C-6', exhibits a wide range of antimicrobial, antimalarial, and antifouling activities. To further explore the effect of this structural change at C-5' and C-6' on this compound's activity, we synthesized a series of compounds with a structure similar to that of cochliomycin A, bearing ketal groups at C-5' and C-6'. The R/S configuration of the diastereoisomer at C-13' was further determined through an NOE correlation analysis of CH3 or CH2 at the derivative C-13' position and the H-5' and H-6' by means of a 1D NOE experiment. Further comparative 1H NMR analysis of diastereoisomers showed the difference in the chemical shift (δ) value of the diastereoisomers. The synthetic compounds were screened for their anti-microbial activities in vitro. Compounds 15-24 and 28-35 demonstrated promising activity against M. marinum, with MIC90 values ranging from 70 to 90 μM, closely approaching the MIC90 of isoniazid. The preliminary structure-activity relationships showed that the ketal groups with aromatic rings at C-5' and C-6' could enhance the inhibition of M. marinum. Further study demonstrated that compounds 23, 24, 29, and 30 had significant inhibitory effects on M. marinum and addictive effects with isoniazid and rifampicin. Its effective properties make it an important clue for future drug development toward combatting M. marinum resistance. The incidence of infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti- drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5' and C-6', exhibits a wide range of antimicrobial, antimalarial, and antifouling activities. To further explore the effect of this structural change at C-5' and C-6' on this compound's activity, we synthesized a series of compounds with a structure similar to that of cochliomycin A, bearing ketal groups at C-5' and C-6'. The / configuration of the diastereoisomer at C-13' was further determined through an NOE correlation analysis of CH or CH at the derivative C-13' position and the H-5' and H-6' by means of a 1D NOE experiment. Further comparative H NMR analysis of diastereoisomers showed the difference in the chemical shift ( ) value of the diastereoisomers. The synthetic compounds were screened for their anti-microbial activities in vitro. Compounds - and - demonstrated promising activity against , with MIC values ranging from 70 to 90 μM, closely approaching the MIC of isoniazid. The preliminary structure-activity relationships showed that the ketal groups with aromatic rings at C-5' and C-6' could enhance the inhibition of . Further study demonstrated that compounds , , , and had significant inhibitory effects on and addictive effects with isoniazid and rifampicin. Its effective properties make it an important clue for future drug development toward combatting resistance. The incidence of Mycobacterium marinum infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti- M. marinum drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5′ and C-6′, exhibits a wide range of antimicrobial, antimalarial, and antifouling activities. To further explore the effect of this structural change at C-5′ and C-6′ on this compound’s activity, we synthesized a series of compounds with a structure similar to that of cochliomycin A, bearing ketal groups at C-5′ and C-6′. The R / S configuration of the diastereoisomer at C-13′ was further determined through an NOE correlation analysis of CH 3 or CH 2 at the derivative C-13′ position and the H-5′ and H-6′ by means of a 1D NOE experiment. Further comparative 1 H NMR analysis of diastereoisomers showed the difference in the chemical shift ( δ ) value of the diastereoisomers. The synthetic compounds were screened for their anti-microbial activities in vitro. Compounds 15 – 24 and 28 – 35 demonstrated promising activity against M. marinum , with MIC 90 values ranging from 70 to 90 μM, closely approaching the MIC 90 of isoniazid. The preliminary structure–activity relationships showed that the ketal groups with aromatic rings at C-5′ and C-6′ could enhance the inhibition of M. marinum . Further study demonstrated that compounds 23 , 24 , 29 , and 30 had significant inhibitory effects on M. marinum and addictive effects with isoniazid and rifampicin. Its effective properties make it an important clue for future drug development toward combatting M. marinum resistance. The incidence of Mycobacterium marinum infection is on the rise; however, the existing drug treatment cycle is lengthy and often requires multi-drug combination. Therefore, there is a need to develop new and effective anti-M. marinum drugs. Cochliomycin A, a 14-membered resorcylic acid lactone with an acetonide group at C-5′ and C-6′, exhibits a wide range of antimicrobial, antimalarial, and antifouling activities. To further explore the effect of this structural change at C-5′ and C-6′ on this compound’s activity, we synthesized a series of compounds with a structure similar to that of cochliomycin A, bearing ketal groups at C-5′ and C-6′. The R /S configuration of the diastereoisomer at C-13′ was further determined through an NOE correlation analysis of CH[sub.3] or CH[sub.2] at the derivative C-13′ position and the H-5′ and H-6′ by means of a 1D NOE experiment. Further comparative [sup.1] H NMR analysis of diastereoisomers showed the difference in the chemical shift (δ ) value of the diastereoisomers. The synthetic compounds were screened for their anti-microbial activities in vitro. Compounds 15 –24 and 28 –35 demonstrated promising activity against M. marinum , with MIC[sub.90] values ranging from 70 to 90 μM, closely approaching the MIC[sub.90] of isoniazid. The preliminary structure–activity relationships showed that the ketal groups with aromatic rings at C-5′ and C-6′ could enhance the inhibition of M. marinum . Further study demonstrated that compounds 23 , 24 , 29 , and 30 had significant inhibitory effects on M. marinum and addictive effects with isoniazid and rifampicin. Its effective properties make it an important clue for future drug development toward combatting M. marinum resistance. |
| Audience | Academic |
| Author | Cheng, Ya-Jie Yin, Jun-Na Wei, Mei-Yan Wu, Yan-Wei Zhang, Qun Wang, Cui-Fang Shao, Chang-Lun Zhang, Xiu-Li Gu, Yu-Cheng |
| AuthorAffiliation | 1 Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China; yinjunna@163.com (J.-N.Y.); wangcuifang0115@163.com (C.-F.W.); xiulizhang@ouc.edu.cn (X.-L.Z.); yajiecheng1212@163.com (Y.-J.C.); wuyanwei1214@163.com (Y.-W.W.); zhangqunnn@163.com (Q.Z.); shaochanglun@163.com (C.-L.S.) 2 Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China 3 Syngenta Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK |
| AuthorAffiliation_xml | – name: 2 Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China – name: 1 Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China; yinjunna@163.com (J.-N.Y.); wangcuifang0115@163.com (C.-F.W.); xiulizhang@ouc.edu.cn (X.-L.Z.); yajiecheng1212@163.com (Y.-J.C.); wuyanwei1214@163.com (Y.-W.W.); zhangqunnn@163.com (Q.Z.); shaochanglun@163.com (C.-L.S.) – name: 3 Syngenta Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK |
| Author_xml | – sequence: 1 givenname: Jun-Na surname: Yin fullname: Yin, Jun-Na – sequence: 2 givenname: Cui-Fang surname: Wang fullname: Wang, Cui-Fang – sequence: 3 givenname: Xiu-Li surname: Zhang fullname: Zhang, Xiu-Li – sequence: 4 givenname: Ya-Jie surname: Cheng fullname: Cheng, Ya-Jie – sequence: 5 givenname: Yan-Wei surname: Wu fullname: Wu, Yan-Wei – sequence: 6 givenname: Qun surname: Zhang fullname: Zhang, Qun – sequence: 7 givenname: Chang-Lun orcidid: 0000-0001-7230-188X surname: Shao fullname: Shao, Chang-Lun – sequence: 8 givenname: Mei-Yan surname: Wei fullname: Wei, Mei-Yan – sequence: 9 givenname: Yu-Cheng orcidid: 0000-0002-6400-6167 surname: Gu fullname: Gu, Yu-Cheng |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/39452839$$D View this record in MEDLINE/PubMed |
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| Keywords | diastereoisomers ketal groups Mycobacterium marinum 14-membered resorcylic acid lactones anti-Mycobacterium marinum |
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| Title | Semisynthesis, Structure Elucidation and Anti-Mycobacterium marinum Activity of a Series of Marine-Derived 14-Membered Resorcylic Acid Lactones with Interesting Ketal Groups |
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