Bioactive chemical constituents from the marine-derived fungus <italic style="font-style: italic">Cladosporium </italic>sp. DLT-5

Luting DAI; Qingyi XIE; Jiaocen GUO; Qingyun MA; Li YANG; Jingzhe YUAN; Haofu DAI; Zhifang YU; Youxing ZHAO

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Bioactive chemical constituents from the marine-derived fungus Cladosporium sp. DLT-5

Biology | Updated：2024-10-14

- Bioactive chemical constituents from the marine-derived fungus Cladosporium sp. DLT-5
- Journal of Oceanology and Limnology Vol. 42, Issue 3, Pages: 905-914(2024)
- Affiliations：
  
  1.College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China
  2.Key Laboratory of Research and Development of Natural Product from Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences & Hainan Academy of Tropical Agricultural Resource, Haikou 571101, China
- Author bio：
  
  yuzhifang@njau.edu.cn
  zhaoyouxing@itbb.org.cn
- Funds：
- DOI：
  CLC：
- Received：16 May 2023，
  
  Accepted：24 June 2023，
  
  Online First：17 July 2023，
  
  Published：01 May 2024
- Accepted：
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DAI Luting,XIE Qingyi,GUO Jiaocen,et al.Bioactive chemical constituents from the marine-derived fungus Cladosporium sp. DLT-5[J].Journal of Oceanology and Limnology,2024,42(03):905-914.
DOI：

DAI Luting,XIE Qingyi,GUO Jiaocen,et al.Bioactive chemical constituents from the marine-derived fungus Cladosporium sp. DLT-5[J].Journal of Oceanology and Limnology,2024,42(03):905-914. DOI：

摘要

Abstract

A new isochromanone

cladosporinisochromanone (

)

accompanied by 15 known compounds (

–

) were obtained from secondary metabolites produced by marine-derived fungus

Cladosporium

sp. DLT-5. NMR and HRESIMS spectra elucidation determined the planar structure of

. Subsequent electronic circular dichroism (ECD) experiment assigned the absolute configuration of

. Compounds

–

and

displayed different d

egrees of neuroprotective activities on human neuroblastoma cells SH-SY5Y. Five compounds (

–

and

) emerged resistance to protein tyrosine phosphatase 1B (PTP1B)

further kinetic analysis and molecular docking study indicated that the most potent compound

(IC

value of 10.74±0.61 μmol/L) was found as a noncompetitive inhibitor for PTP1B. Surface plasmon resonance (SPR) and molecular docking studies also demonstrated the interaction between compound

and Niemann-Pick C1 Like 1 (NPC1L1)

which has been identified as significant therapeutic target for hypercholesteremia. In addition

compounds

and

showed attractive inhibitory activity against the phytopathogenic fungi:

Colletotrichum capsici

. Therefore

library of

Cladosporium

metabolites is enriched and new active uses of known compounds are explored.

关键词

Keywords

references

Alam M B , Chowdhury N S , Sohrab M H et al . 2020 . Cerevisterol alleviates inflammation via suppression of MAPK/NF-‍κB/AP-1 and activation of the Nrf2/HO-1 signaling cascade . Biomolecules , 10 ( 2 ): 199 , https://doi.org/10.3390/biom10020199 https://doi.org/10.3390/biom10020199 .

Bensch K , Braun U , Groenewald J Z et al . 2012 . The genus Cladosporium . Studies in Mycology , 72 : 1 - 401 , https://doi.org/10.3114/sim0003 https://doi.org/10.3114/sim0003 .

Boonyaketgoson S , Trisuwan K , Bussaban B et al . 2015 . Isochromanone derivatives from the endophytic fungus Fusarium sp . PDB 51 F 5 . Tetrahedron Letters, 56 ( 36 ): 5076 - 5078 , https://doi.org/10.1016/j.tetlet.2015.07.048 https://doi.org/10.1016/j.tetlet.2015.07.048 .

Campos F R , Barison A , Daolio C et al . 2005 . Complete 1 H and 13 C NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus . Magnetic Resonance in Chemistry , 43 ( 11 ): 962 - 965 , https://doi.org/10.1002/mrc.1654 https://doi.org/10.1002/mrc.1654 .

Carroll A R , Copp B R , Davis R A et al . 2022 . Marine natural products . Natural Product Reports , 39 ( 6 ): 1122 - 1171 , https://doi.org/10.1039/d1np00076d https://doi.org/10.1039/d1np00076d .

Cheng A L , Uetani N , Simoncic P D et al . 2002 . Attenuation of leptin action and regulation of obesity by protein tyrosine phosphatase 1 B. Developmental Cell , 2 ( 4 ): 497 - 503 , https://doi.org/10.1016/S1534-5807(02)00149-1 https://doi.org/10.1016/S1534-5807(02)00149-1 .

Cox R H , Morris P , Cutler H G et al . 1983 . Proton and carbon-13 nuclear magnetic resonance studies of the conformation of cytochalasin H derivatives and plant growth regulating effects of cytochalasins . Journal of Agricultural and Food Chemistry , 31 ( 2 ): 405 - 408 , https://doi.org/10.1021/jf00116a055 https://doi.org/10.1021/jf00116a055 .

Dai L T , Yang L , Kong F D et al . 2021 . Cytotoxic indole-diterpenoids from the marine-derived fungus Penicillium sp. KFD28 . Marine Drugs , 19 ( 11 ): 613 , https://doi.org/10.3390/md19110613 https://doi.org/10.3390/md19110613 .

Dettrakul S , Kittakoop P , Isaka M et al . 2003 . Antimycobacterial pimarane diterpenes from the fungus Diaporthe sp . Bioorganic & Medicinal Chemistry Letters , 13 ( 7 ): 1253 - 1255 , https://doi.org/10.1016/S0960-894X(03)00111-2 https://doi.org/10.1016/S0960-894X(03)00111-2 .

Fan Y Q , Jiang C J , Li P H et al . 2023 . A new chloro-azaphilone derivative with pro-angiogenesis activity from the hadal trench-derived fungus Chaetomium globosum YP-106 . Journal of Oceanology and Limnology , 41 ( 3 ): 1145 - 1151 , https://doi.org/10.1007/s00343-022-2017-1 https://doi.org/10.1007/s00343-022-2017-1 .

Goldsmith M , Abramovitz L , Peer D . 2014 . Precision nanomedicine in neurodegenerative diseases . ACS Nano , 8 ( 3 ): 1958 - 1965 , https://doi.org/10.1021/nn501292z https://doi.org/10.1021/nn501292z .

Gu B B , Zhang Y Y , Ding L J et al . 2015 . Preparative separation of sulfur-containing diketopiperazines f rom marine fungus Cladosporium sp. using high-speed counter-current chromatography in stepwise elution mode . Marine Drugs , 13 ( 1 ): 354 - 365 , https://doi.org/10.3390/md13010354 https://doi.org/10.3390/md13010354 .

Hosotani N , Kumagai K , Nakagawa H et al . 2005 . Antimycins A10 - A16 , seven new antimycin antibiotics produced by Streptomyces spp. SPA-10191 and SPA-8893. The Journal of Antibiotics , 58 ( 7 ): 460 - 467 , https://doi.org/10.1038/ja.2005.61 https://doi.org/10.1038/ja.2005.61 .

Hu M Q , Yang F , Huang Y W et al . 2021 . Structural insights into the mechanism of human NPC 1 L 1 -mediated cholesterol uptake. Science Advances , 7 ( 29 ): eabg 3188 , https://doi.org/10.1126/sciadv.abg3188 https://doi.org/10.1126/sciadv.abg3188 .

Jung H A , Islam M N , Lee C M et al . 2013 . Kinetics and molecular docking studies of an anti-diabetic complication inhibitor fucosterol from edible brown algae Eisenia bicyclis and Ecklonia stolonifera . Chemico-Biological Interactions , 206 ( 1 ): 55 - 62 , https://doi.org/10.1016/j.cbi.2013.08.013 https://doi.org/10.1016/j.cbi.2013.08.013 .

Kim J W , Choi H G , Song J H et al . 2019 . Bioactive secondary metabolites from an endophytic fungus Phoma sp. PF2 derived from Artemisia princeps Pamp . The Journal of Antibiotics , 72 ( 3 ): 174 - 177 , https://doi.org/10.1038/s41429-018-0131-2 https://doi.org/10.1038/s41429-018-0131-2 .

Kobayashi S , Senoo F , Kihara M et al . 1971 . Studies on the syntheses of benzoheterocyclic compounds. VI. Diphenide and its methoxyl derivatives . Chemical and Pharmaceutical Bulletin , 19 ( 6 ): 1262 - 1267 , https://doi.org/10.1248/cpb.19.1262 https://doi.org/10.1248/cpb.19.1262 .

Kong F D , Fan P , Zhou L M et al . 2019 . Penerpenes A-D, four indole terpenoids with potent protein tyrosine phosphatase inhibitory activity from the marine-derived fungus Penicillium sp. KFD28 . Organic Letters , 21 ( 12 ): 4864 - 4867 , https://doi.org/10.1021/acs.orglett.9b01751 https://doi.org/10.1021/acs.orglett.9b01751 .

Li X J , Gao J M , Chen H et al . 2012 . Toxins from a symbiotic fungus, Leptographium qinlingensis associated with Dendroctonus armandi and their in vitro toxicities to Pinus armandi seedlings . European Journal of Plant Pathology , 134 ( 2 ): 239 - 247 , https://doi.org/10.1007/s10658-012-9981-9 https://doi.org/10.1007/s10658-012-9981-9 .

Liu J K , Xie M , Li X Z et al . 2018 . Main allelochemicals from the rhizosphere soil of Saussurea Lappa (Decne.) Sch. Bip. and their effects on plants' antioxidase systems . Molecules , 23 ( 10 ): 2506 , https://doi.org/10.3390/molecules23102506 https://doi.org/10.3390/molecules23102506 .

Long H L , Qiu X H , Cao L et al . 2021 . Discovery of the signal pathways and major bioactive compounds responsible for the anti-hypoxia effect of Chinese cordyceps . Journal of Ethnopharmacology , 277 : 114215 , https://doi.org/10.1016/j.jep.2021.114215 https://doi.org/10.1016/j.jep.2021.114215 .

Peng J X , Lin T , Wang W et al . 2013 . Antiviral alkaloids produced by the mangrove-derived fungus Cladosporium sp. PJX-41 . Journal of Natural Products , 76 ( 6 ): 1133 - 1140 , https://doi.org/10.1021/np400200k https://doi.org/10.1021/np400200k .

Pongcharoen W , Rukachaisirikul V , Phongpaichit S et al . 2006 . Pimarane diterpene and cytochalasin derivatives from the endophytic fungus Eutypella scoparia PSU-D44 . Journal of Natural Products , 69 ( 5 ): 856 - 858 , https://doi.org/10.1021/np0600649 https://doi.org/10.1021/np0600649 .

Rischer M , Lee S R , Eom H J et al . 2019 . Spirocyclic cladosporicin A and cladosporiumins I and J from a Hydractinia -associated Cladosporium sphaerospermum SW67 . Organic Chemistry Frontiers , 6 ( 8 ): 1084 - 1093 , https://doi.org/10.1039/c8qo01104d https://doi.org/10.1039/c8qo01104d .

Ruffels J , Griffin M , Dickenson J M . 2004 . Activation of ERK 1 / 2 , JNK and PKB by hydrogen peroxide in human SH-SY5Y neuroblastoma cells: role of ERK 1 / 2 inH2O2-induced cell death. European Journal of Pharmacology , 483 ( 2-3 ): 163 - 173 , https://doi.org/10.1016/j.ejphar.2003.10.032 https://doi.org/10.1016/j.ejphar.2003.10.032 .

Sun L , Li D L , Tao M H et al . 2012 . Scopararanes C-G: new oxygenated pimarane diterpenes from the marine sediment-derived fungus Eutypella scoparia FS26 . Marine Drugs , 10 ( 12 ): 539 - 550 , https://doi.org/10.3390/md10030539 https://doi.org/10.3390/md10030539 .

Tayone W C , Kanamaru S , Honma M et al . 2011 . Absolute stereochemistry of novel isochromanone derivatives from Leptosphaeria sp. KTC 727 . Bioscience, Biotechnology, and Biochemistry , 75 ( 12 ): 2390 - 2393 , https://doi.org/10.1271/bbb.110621 https://doi.org/10.1271/bbb.110621 .

Wang X N , Radwan M M , Taráwneh A H et al . 2013 . Antifungal activity against plant pathogens of metabolites from the endophytic fungus Cladosporium cladosporioides . Journal of Agricultural and Food Chemistry , 61 ( 19 ): 4551 - 4555 , https://doi.org/10.1021/jf400212y https://doi.org/10.1021/jf400212y .

Wu W , Dai H Q , Bao L et al . 2011 . Isolation and structural elucidation of proline-containing cyclopentapeptides from an endolichenic Xylaria sp . Journal of Natural Products , 74 ( 5 ): 1303 - 1308 , https://doi.org/10.1021/np100909y https://doi.org/10.1021/np100909y .

Xiong H Y , Fei D Q , Zhou J S et al . 2009 . Steroids and other constituents from the mushroom Armillaria lueo - virens . Chemistry of Natural Compounds , 45 ( 5 ): 759 - 761 , https://doi.org/10.1007/s10600-009-9456-1 https://doi.org/10.1007/s10600-009-9456-1 .

Yang L , Kong D X , Xiao N et al . 2022 . Antidiabetic lanostane triterpenoids from the fruiting bodies of Ganoderma weberianum . Bioorganic Chemistry , 127 : 106025 , https://doi.org/10.1016/j.bioorg.2022.106025 https://doi.org/10.1016/j.bioorg.2022.106025 .

Zhang B , Wu J T , Zheng C J et al . 2021a . Bioactive cyclohexene derivatives from a mangrove-derived fungus Cladosporium sp. JJM22 . Fitoterapia , 149 : 104823 , https://doi.org/10.1016/j.fitote.2020.104823 https://doi.org/10.1016/j.fitote.2020.104823 .

Zhang F Z , Li X M , Yang S Q et al . 2019 . Thiocladospolides A-D, 12-membered macrolides from the mangrove-derived endophytic fungus Cladosporium cladosporioides MA-299 and structure revision of pandangolide 3 . Journal of Natural Products , 82 ( 6 ): 1535 - 1541 , https://doi.org/10.1021/acs.jnatprod.8b01091 https://doi.org/10.1021/acs.jnatprod.8b01091 .

Zhang F , Zhou L M , Kong F D et al . 2020 . Altertoxins with quorum sensing inhibitory activities from the marine-derived fungus Cladosporium sp. KFD33 . Marine Drugs , 18 ( 1 ): 67 , https://doi.org/10.20944/preprints201912.0398.v1 https://doi.org/10.20944/preprints201912.0398.v1 .

Zhang R S , Liu W J , Zeng J et al . 2022a . Niemann-Pick C1-Like 1 inhibitors for reducing cholesterol absorption . European Journal of Medicinal Chemistry , 230 : 114111 , https://doi.org/10.1016/j.ejmech.2022.114111 https://doi.org/10.1016/j.ejmech.2022.114111 .

Zhang R S , Liu W J , Zeng J et al . 2022b . Recent advances in the screening methods of NPC 1 L 1 inhibitors. Biomedicine & Pharmacotherapy , 155 : 113732 , https://doi.org/10.1016/j.biopha.2022.113732 https://doi.org/10.1016/j.biopha.2022.113732 .

Zhang R S , Song Z M , Wang X T et al . 2021b . One-step modification to identify dual-inhibitors targeting both pancreatic triglyceride lipase and Niemann-Pick C1-like 1 . European Journal of Medicinal Chemistry , 216 : 113358 , https://doi.org/10.1016/j.ejmech.2021.113358 https://doi.org/10.1016/j.ejmech.2021.113358 .

Zhang Z Z , He X Q , Wu G W et al . 2018 . Aniline-tetramic acids from the deep-sea-derived fungus Cladosporium sphaerospermum L 3 P 3 cultured with the HDAC inhibitor SAHA. Journal of Natural Products , 81 ( 7 ): 1651 - 1657 , https://doi.org/10.1021/acs.jnatprod.8b00289 https://doi.org/10.1021/acs.jnatprod.8b00289 .

Zhao B T , Nguyen D H , Le D D et al . 2018 . Protein tyrosine phosphatase 1B inhibitors from natural sources . Archives of Pharmacal Research , 41 ( 2 ): 130 - 161 , https://doi.org/10.1007/s12272-017-0997-8 https://doi.org/10.1007/s12272-017-0997-8 .

Zhou L M , Kong F D , Fan P et al . 2019 . Indole-diterpenoids with protein tyrosine phosphatase inhibitory activities from the marine-derived fungus Penicillium sp. KFD28 . Journal of Natural Products , 82 ( 9 ): 2638 - 2644 , https://doi.org/10.1021/acs.jnatprod.9b00620 https://doi.org/10.1021/acs.jnatprod.9b00620 .

Zhou X F , Sun J F , Ma W L et al . 2014 . Bioactivities of six sterols isolated from marine invertebrates . Pharmaceutical Biology , 52 ( 2 ): 187 - 190 , https://doi.org/10.3109/13880209.2013.821664 https://doi.org/10.3109/13880209.2013.821664 .

Zhu M L , Gao H Q , Wu C M et al . 2015 . Lipid-lowering polyketides from a soft coral-derived fungus Cladosporium sp. TZP29 . Bioorganic & Medicinal Chemistry Letters , 25 ( 17 ): 3606 - 3609 , https://doi.org/10.1016/j.bmcl.2015.06.072 https://doi.org/10.1016/j.bmcl.2015.06.072 .

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Bioactive chemical constituents from the marine-derived fungus Cladosporium sp. DLT-5

DOI：

摘要

Abstract

关键词

Keywords

references