Citation: Qi Tan, Run-Zhu Fan, Wencong Yang, Ge Zou, Tao Chen, Jianying Wu, Bo Wang, Sheng Yin, Zhigang She. (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01[J]. Chinese Chemical Letters, ;2024, 35(9): 109390. doi: 10.1016/j.cclet.2023.109390 shu

(+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01

Qi Tan ^a ,
Run-Zhu Fan ^b ,
Wencong Yang ^a ,
Ge Zou ^a ,
Tao Chen ^a ,
Jianying Wu ^a ,
Bo Wang ^a ,
Sheng Yin ^{b, *,} ,
Zhigang She ^{a, *,}

a.
School of Chemistry, Sun Yat-sen University, Guangzhou 510006, China
b.
School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

yinsh2@mail.sysu.edu.cn

cesshzhg@mail.sysu.edu.cn

Received Date: 21 October 2023
Revised Date: 4 December 2023
Accepted Date: 6 December 2023
Available Online: 14 December 2023

Figures(6)

(±)-Mycosphatide A (1a/1b), a pair of highly oxidized enantiomeric polyketides featuring a unique 5/5/6/5-fused tetracyclic ring system, were isolated from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Their structures were established by extensive spectroscopic analyses, single crystal X-ray diffraction, and experimental electronic circular dichroism (ECD) spectra comparison. The plausible biosynthetic pathway of 1 was proposed, which involved the generation of a key spiro[4.5]decane scaffold. Compounds (+)-1a and (−)-1b exhibited significant lipid-lowering activity in 3T3-L1 adipocytes model, with EC₅₀ values of 7.85 ± 1.56 and 8.87 ± 0.80 µmol/L, respectively.
- Mangrove endophytic fungus,
- Mycosphaerella sp.,
- Polyketide,
- Highly oxidized,
- Lipid-lowering activity
1. [1]
  G.A. Bray, G. Frühbeck, D.H. Ryan, et al., Lancet 387 (2016) 1947–1956. doi: 10.1016/S0140-6736(16)00271-3
2. [2]
  S.A. Polyzos, J. Kountouras, C.S. Mantzoros, Metabolism 92 (2019) 82–97. doi: 10.1016/j.metabol.2018.11.014
3. [3]
  T.D. Müller, M. Blüher, M.H. Tschöp, et al., Nat. Rev. Drug. Discov. 21 (2022) 201–223. doi: 10.1038/s41573-021-00337-8
4. [4]
  K.D. Hall, S. Kahan, Med. Clin. North. Am. 102 (2018) 183–197. doi: 10.1016/j.mcna.2017.08.012
5. [5]
  Y.J. Tak, S.Y. Lee, Curr. Obes. Rep. 10 (2021) 14–30. doi: 10.1007/s13679-020-00422-w
6. [6]
  C.M. Perdomo, R.V. Cohen, P. Sumithran, et al., Lancet 401 (2023) 1116–1130. doi: 10.1016/S0140-6736(22)02403-5
7. [7]
  D.J. Newman, G.M. Gragg, J. Nat. Prod. 83 (2020) 770–803. doi: 10.1021/acs.jnatprod.9b01285
8. [8]
  A.G. Atanasov, S.B. Zotchev, V.M. Dirsch, et al., Nat. Rev. Drug. Discov. 20 (2021) 200–216. doi: 10.1038/s41573-020-00114-z
9. [9]
  S. Chen, R. Cai, Z. Liu, et al., Nat. Prod. Rep. 39 (2022) 560–595. doi: 10.1039/D1NP00041A
10. [10]
  M. Zhang, J.M. Liu, J.L. Zhao, et al., Chin. Chem. Lett. 27 (2016) 957–960. doi: 10.1016/j.cclet.2016.02.008
11. [11]
  R. Cai, H. Jiang, Z. Xiao, et al., Org. Lett. 21 (2019) 9633–9636. doi: 10.1021/acs.orglett.9b03796
12. [12]
  X. Huang, H. Huang, H. Li, et al., Org. Lett. 15 (2013) 721–723. doi: 10.1021/ol303549c
13. [13]
  W. Yang, T. Chen, Y. Chen, et al., J. Org. Chem. 87 (2022) 16807–16819. doi: 10.1021/acs.joc.2c02501
14. [14]
  L.H. Meng, X.M. Li, Y. Liu, et al., Chin. Chem. Lett. 26 (2015) 610–612. doi: 10.1016/j.cclet.2015.01.024
15. [15]
  H. Zhou, Y. Li, Y. Tang, Nat. Prod. Rep. 27 (2010) 839–868. doi: 10.1039/b911518h
16. [16]
  D.T. Wagner, D.C. Stevens, M.R. Mehaffey, et al., Chem. Commun. 52 (2016) 8822–8825. doi: 10.1039/C6CC04418B
17. [17]
  H.H. Yeh, S.L. Chang, Y.M. Chiang, et al., Org. Lett. 15 (2013) 756–759. doi: 10.1021/ol303328t
18. [18]
  E. Abdelraheem, B. Thair, R.F. Varela, et al., ChemBioChem 23 (2022) e202200212. doi: 10.1002/cbic.202200212
1. [1]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
2. [2]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
3. [3]
  Huaran Zhang , Yuting Huang , Yingjie Tang , Dekun Kong , Yi Zou . Genome mining of multi-substituted alkylresorcinols from a hybrid highly reducing- and type Ⅲ- polyketide pathway. Chinese Chemical Letters, 2024, 35(7): 108968-. doi: 10.1016/j.cclet.2023.108968
4. [4]
  Xu Zhang , Jiang Li , Kai-Zhou Lu , Ya-Nan Yang , Jian-Shuang Jiang , Xiang Yuan , Zi-Ming Feng , Fei Ye , Pei-Cheng Zhang . Neosophoflavonoids A–C, A class of highly oxidized hybrid flavonoids from Sophora flavescens with antidiabetic effects. Chinese Chemical Letters, 2024, 35(10): 109456-. doi: 10.1016/j.cclet.2023.109456
5. [5]
  Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
6. [6]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
7. [7]
  Shuige Zhao , Pengcheng Yan , Peipei Liu , Haishan Liu , Ning Li , Peng Fu , Weiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950
8. [8]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
9. [9]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
10. [10]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
11. [11]
  Gu Gong , Mengzhu Li , Ning Sun , Ting Zhi , Yuhao He , Junan Pan , Yuntao Cai , Longlu Wang . Versatile oxidized variants derived from TMDs by various oxidation strategies and their applications. Chinese Chemical Letters, 2024, 35(6): 108705-. doi: 10.1016/j.cclet.2023.108705
12. [12]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
13. [13]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
14. [14]
  Xiaoman Dang , Zhiying Wu , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Highly robust supramolecular polymer networks crosslinked by metallacycles. Chinese Chemical Letters, 2024, 35(12): 110208-. doi: 10.1016/j.cclet.2024.110208
15. [15]
  Nianqiang Jiang , Yiqiang Ou , Yanpeng Zhu , Dingyong Zhong , Jiaobing Wang . Assembly of fullerenes using a highly preorganized janusarene. Chinese Chemical Letters, 2025, 36(4): 110004-. doi: 10.1016/j.cclet.2024.110004
16. [16]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
17. [17]
  Minying Wu , Xueliang Fan , Wenbiao Zhang , Bin Chen , Tong Ye , Qian Zhang , Yuanyuan Fang , Yajun Wang , Yi Tang . Highly dispersed Ru nanospecies on N-doped carbon/MXene composite for highly efficient alkaline hydrogen evolution. Chinese Chemical Letters, 2024, 35(4): 109258-. doi: 10.1016/j.cclet.2023.109258
18. [18]
  Ling Tang , Yan Wan , Yangming Lin . Lowering the kinetic barrier via enhancing electrophilicity of surface oxygen to boost acidic oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100345-100345. doi: 10.1016/j.cjsc.2024.100345
19. [19]
  Zhi Wang , Lingpeng Yan , Yelin Hao , Jingxia Zheng , Yongzhen Yang , Xuguang Liu . Highly efficient and photothermally stable CDs@ZIF-8 for laser illumination. Chinese Chemical Letters, 2024, 35(10): 109430-. doi: 10.1016/j.cclet.2023.109430
20. [20]
  Dian-Xue Ma , Yu-Wu Zhong . Achieving highly-efficient room-temperature phosphorescence with a nylon matrix. Chinese Journal of Structural Chemistry, 2024, 43(9): 100391-100391. doi: 10.1016/j.cjsc.2024.100391

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沈阳化工大学材料科学与工程学院沈阳 110142