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DOI: 10.1055/s-0043-1775448
Alterbrassacids A and B: Two Novel Fusicoccane Diterpenoids with Protective Activity Against H2O2-Induced Cardiomyocyte Injury from the Fungus Alternaria brassicicola
We acknowledge the provision of financial support by the National Natural Science Foundation of China (Nos. 82273811, 82104043, and U22A20380), the National Program for Support of Top-notch Young Professionals (No. 0106514050), the Hubei Provincial Natural Science Foundation of China (No. 2024AFA028), and the National Key Research and Development Program of China (No. 2021YFA0910500).

Abstract
Alterbrassacids A and B, two novel fusicoccane diterpenoids featuring a 5/7/6-fused ring system, along with a known structurally related compound were isolated from fungus Alternaria brassicicola. Their structures, including their absolute configurations, were determined by employing a wide range of spectroscopic analyses, DP4+ probability analyses, and ECD calculations. Preliminary studies showed that alterbrassacid A effectively protected cardiomyocyte H9C2 cells from H2O2-induced lactate dehydrogenase leakage. Furthermore, alterbrassacid A exhibited a significant protective effect on mitochondria by reducing the overproduction of reactive oxygen species and enhancing the mitochondrial membrane potential, highlighting it as a promising cardioprotectant.
Key words
Alternaria brassicicola - fusicoccane diterpenoids - isolation - structural elucidation - cardiomyocyte protective activitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775448.
- Supporting Information
Publikationsverlauf
Eingereicht: 31. Oktober 2024
Angenommen nach Revision: 27. Januar 2025
Artikel online veröffentlicht:
12. März 2025
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References and Notes
- 1 Cafaro G, Perricone C, Gerli R, Bartoloni E. Lancet 2023; 401: 21
- 2 Martin SS, Aday AW, Almarzooq ZI, Anderson CA.M, Arora P, Avery CL, Baker-Smith CM, Gibbs BB, Beaton AZ, Boehme AK, Commodore-Mensah Y, Currie ME, Elkind MS.V, Evenson KR, Generoso G, Heard DG, Hiremath S, Johansen MC, Kalani R, Kazi DS, Ko D, Liu J, Magnani JW, Michos ED, Mussolino ME, Navaneethan SD, Parikh NI, Perman SM, Poudel R, Rezk-Hanna M, Roth GA, Shah NS, St-Onge M.-P, Thacker EL, Tsao CW, Urbut SM, Van Spall HG. C, Voeks JH, Wang N.-Y, Wong ND, Wong SS, Yaffe K, Palaniappan LP. Circulation 2024; 149: e347
- 3 Colvin M.-M, Smith J.-M, Ahn Y.-S, Handarova D.-M, Martinez A.-C, Lindblad K.-A, Israni A.-K, Snyder J. Am. J. Transplant. 2024; 24: S305
- 4 Heusch G. Nat. Rev. Cardiol. 2020; 17: 773
- 5 Rai N.-K, Venugopal H, Rajesh R, Ancha P, Venkatesh S. Mol. Cell. Biochem. 2024;
- 6 Fan L.-L, Wu Y, Liu F, Wu X.-J. Heart Surg. Forum 2023; 26: E264
- 7 Ancajas C.-M.-F, Oyedele A.-S, Butt C.-M, Walker A.-S. Nat. Prod. Rep. 2024; 41: 1543
- 8 Zhang S.-T, He Y, Li F.-L, Lin S, Yang B.-Y, Mo S.-Y, Li H.-Q, Wang J.-P, Qi C.-X, Hu Z.-X, Zhang Y.-H. J. Nat. Prod. 2020; 83: 3397
- 9 Cheng L, Zheng X, Li Q, Wei M.-S, Chen C.-M, Zhu H.-C, Zeng C.-L, Hao X.-C, Zhang Y.-H. Nat. Prod. Res. 2022; 36: 3603
- 10 Luo Z.-W, Yin F.-C, Wang X.-B, Kong L.-Y. Chin. J. Nat. Med. 2024; 22: 195
- 11 Gu X.-X, Sun W.-G, Hu Z.-X. Chin. J. Nat. Med. 2024; 22: 577
- 12 Newman D.-J, Cragg G.-M. J. Nat. Prod. 2020; 83: 770
- 13 Ohkanda J. Chem. Lett. 2021; 50: 57
- 14 Helf M.-J, Buntin K, Klančar A, Rust M, Petersen F, Pistorius D, Weber E, Wong J, Krastel P. Nat. Prod. Rep. 2024; 50: 57
- 15 Chen B.-L, Wu Q.-W, Xu D.-D, Zhang X.-J, Ding Y.-H, Bao S.-Q, Zhang X.-M, Wang L, Chen Y. Angew. Chem. Int. Ed. 2022; 61: e202117476
- 16 Ohkanda J, Kusumoto A, Punzalan L, Masuda R, Wang C.-Y, Parvatkar P, Akase D, Aida M, Uesugi M, Higuchi Y, Kato N. Chem. Eur. J. 2018; 24: 16066
- 17 Tang Y, Xue Y.-B, Du G, Wang J.-P, Liu J.-J, Sun B, Li X.-N, Yao G.-M, Luo Z.-W, Zhang Y.-H. Angew. Chem. Int. Ed. 2016; 55: 4069
- 18 Hu Z.-X, Sun W.-G, Li F.-L, Guan J.-K, Lu Y.-Y, Liu J.-J, Tang Y, Du G, Xue Y.-B, Luo Z.-W, Wang J.-P, Zhu H.-C, Zhang Y.-H. Org. Lett. 2018; 20: 5198
- 19 Li F.-L, Lin S, Zhang S.-T, Pan L.-F, Chai C.-W, Su J.-C, Yang B.-Y, Liu J.-J, Wang J.-P, Hu Z.-X, Zhang Y.-H. J. Nat. Prod. 2020; 83: 1931
- 20 Jang J.-P, Jang M, Hwang G.-J, Kim M.-H, Ahn J.-S, Ko S.-K, Jang J.-H. Bioorg. Med. Chem. Lett. 2022; 57: 128504
- 21 Jiang Y.-L, Renata H. Nat. Chem. 2024; 16: 1531
- 22 Khatun A, Hazra K, Mahato B, Koley R, Ghorai R, Adhikary A, Debnath B, Das S. Eur. J. Med. Chem. 2024; 11: 100158
- 23 D’Ambola M, Fiengo L, Chini M.-G, Cotugno R, Bader A, Bifulco G, Braca A, De Tommasi N, De Tommasi F, Piaz F.-D. J. Nat. Prod. 2019; 82: 539
- 24 Geng B.-C, Chen X, Chi J.-Y, Li F.-L, Yim W.-Y, Wang K, Li C.-H, Xie M.-H, Zhu P, Fan Z.-F, Shi J.-W, Hu Z.-X, Zhang Y.-H, Dong N.-G. Theranostics 2023; 13: 3781
- 25 Lear M.-J, Hirai K, Ogawa K, Yamashita S, Hirama M. J. Antibiot. 2019; 72: 350
- 26 Kitamura T, Shiroshita S, Takahashi D, Toshima K. Chem. Eur. J. 2020; 26: 14351
- 27 Liu M.-T, He Y, Shen L, Anbari WH. A, Li H.-Q, Wang J.-P, Qi C.-X, Hu Z.-X, Zhang Y.-H. Eur. J. Org. Chem. 2019; 2928
- 28 Gao W.-X, Chai C.-C, He Y, Li F.-L, Hao X.-C, Cao F, Gu L.-H, Liu J.-J, Hu Z.-X, Zhang Y.-H. Org. Lett. 2019; 21: 8469
- 29 Tazawa A, Ye Y, Ozaki T, Liu C.-W, Ogasawara Y, Dairi T, Higuchi Y, Kato N, Gomi K, Minami A, Oikawa H. Org. Lett. 2018; 20: 6178
- 30 Zhang H, Zhang R.-H, Liao X.-M, Yang D, Wang Y.-C, Zhao Y.-L, Xu G.-B, Liu C.-H, Li Y.-J, Liao S.-G, Zhou M. J. Med. Chem. 2021; 64: 9166
- 31 Yang A.-L, Guo L.-F, Zhang Y.-F, Qiao C.-J, Wang Y.-J, Li J.-Y, Wang M, Xing J.-L, Li F, Ji L.-L, Guo H.-T, Zhang R. Biochim. Biophys. Acta, Gen. Subj. 2023; 1867: 130413
- 32 Yu Y, Su F.-F, Xu C. Biomed. Pharmacother. 2024; 174: 116489
- 33 Jang S, Javadov S. Arch. Biochem. Biophys. 2017; 630: 1
- 34 Gong Y.-C, Lin J, Ma Z.-T, Yu M, Wang M.-H, Lai D.-W, Fu G.-S. Life Sci. 2021; 278: 119511