Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus <italic style="font-style: italic">Talaromyces funiculosus</italic> SD-523

Yanan WANG; Xiaoming LI; Fengyi LÜ; Suiqun YANG; Linghong MENG; Bingui WANG

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Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523

Biology | Updated：2024-10-12

- Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523
- Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523
- 海洋湖沼学报(英文) 2023年41卷第3期页码：1152-1158
- Affiliations：
  
  1.CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China
  2.College of Marine Science, University of Chinese Academy of Sciences, Beijing 100049, China
  3.Laboratory of Marine Biology and Biotechnology, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao 266237, China
  4.Center for Ocean Mega-Science, Chinese Academy of Sciences, Qingdao 266071, China
- Author bio：
  
  menglh@qdio.ac.cn
  wangbg@qdio.ac.cn
- Funds：
  
  the National Natural Science Foundation of China(U2006203);the National Natural Science Foundation of Jiangsu Province(BK20201211);the Senior User Project of R/V Kexue(KEXUE2020GZ02)
- DOI：
  中图分类号：
- 收稿：2022-02-05，
  
  纸质出版：2023-05-01
- Accepted：
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Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523[J]. 海洋湖沼学报(英文), 2023,41(3):1152-1158.

WANG Yanan,LI Xiaoming,LÜ Fengyi,et al.Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523[J].Journal of Oceanology and Limnology,2023,41(03):1152-1158.
Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523[J]. 海洋湖沼学报(英文), 2023,41(3):1152-1158. DOI：

WANG Yanan,LI Xiaoming,LÜ Fengyi,et al.Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523[J].Journal of Oceanology and Limnology,2023,41(03):1152-1158. DOI：

摘要

Abstract

A new prenylated indole alkaloid 11

17-

epi

-mangrovamide A (

)

a new natural occurring product

7-dihydroxy-6-methyl-8-hydroxymethyl-xanthone (

)

two known alkaloids

mangrovamide A (

) and mangrovamide G (

)

and four known polyketide derivatives (

5‍

–

‍8

) were isolated and identified from the cold-seep sediment derived fungal strain

Talaromyces funiculosus

SD-523. Their structures were elucidated by combination of nuclear magnetic resonance (NMR)

high resolution electrospray ionization mass spectroscopy (HRESIMS)

quantum chemical electronic circular dichroism (ECD)

and DP4+ probability analysis as well as by comparison of the data with literature reports. All isolated compounds were tested for antibacteria

l activities.

关键词

Keywords

references

Benjamin C R . 1955 . Ascocarps of Aspergillus and Penicillium . Mycological Society of America , 47 ( 5 ): 669 - 687 , https://doi.org/10.2307/3755578 https://doi.org/10.2307/3755578 .

Chi L P , Li X M , Wan Y P et al . 2020 . Ophiobolin sesterterpenoids and farnesylated phthalide derivatives from the deep sea cold-seep-derived fungus Aspergillus insuetus SD-512 . Journal of Natural Products , 83 ( 12 ): 3652 - 3660 , https://doi.org/10.1021/acs.jnatprod.0c00860 https://doi.org/10.1021/acs.jnatprod.0c00860 .

Chi L P , Li X M , Wan Y P et al . 2021 . Two new phenol derivatives from the cold seep-derived fungus Aspergillus insuetus SD-512 . Chemistry & Biodiversity , 18 ( 10 ): e2100512 , https://doi.org/10.1002/cbdv.202100512 https://doi.org/10.1002/cbdv.202100512 .

Grimblat N , Zanardi M M , Sarotti A M . 2015 . Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts . The Journal of Organic Chemistry , 80 ( 24 ): 12526 - 12534 , https://doi.org/10.1021/acs.joc.5b02396 https://doi.org/10.1021/acs.joc.5b02396 .

Guo J , Ran H M , Zeng J et al . 2016 . Tafuketide, a phylogeny-guided discovery of a new polyketide from Talaromyces funiculosus Salicorn 58 . Applied Microbiology and Biotechnology , 100 ( 12 ): 5323 - 5338 , https://doi.‍org/10.1007/s00253-016-7311-4 https://doi.‍org/10.1007/s00253-016-7311-4 . https://do 10.1007/s00253-016-7311-4 http://dx.doi.org/10.1007/s00253-016-7311-4

Hu X Y , Wang C Y , Li X M et al . 2021 . Cytochalasin derivatives from the endozoic Curvularia verr uculosa CS-129, a fungus isolated from the deep-sea squat lobster Shinkaia crosnieri living in the cold seep environment . Journal of Natural Products , 84 ( 12 ): 3122 - 3130 , https://doi.org/10.1021/acs.jnatprod.1c00907 https://doi.org/10.1021/acs.jnatprod.1c00907 .

Kanse O S , Whitelaw-Weckert M , Kadam T A et al . 2015 . Phosphate solubilization by stress-tolerant soil fungus Talaromyces funiculosus SLS8 isolated from the Neem rhizosphere . Annals of Microbiology , 65 ( 1 ): 85 - 93 , https://doi.org/10.1007/s13213-014-0839-6 https://doi.org/10.1007/s13213-014-0839-6 .

Kimura Y , Kozawa M , Baba K et al . 1983 . New constitutents of roots of Polygonum cuspidatum . Planta Medica , 48 ( 7 ): 164 - 168 , https://doi.org/10.1055/s-2007-969914 https://doi.org/10.1055/s-2007-969914 .

Lee S R , Schalk F , Schwitalla J W et al . 2020 . Polyhalogenation of isoflavonoids by the termite-associated Actinomadura sp. RB 99 . Journal of Natural Products , 83 ( 10 ): 3102 - 3110 , https://doi.‍org/10.1021/acs.jnatprod.0c00676 https://doi.‍org/10.1021/acs.jnatprod.0c00676 . https://do 10.1021/acs.jnatprod.0c00676 http://dx.doi.org/10.1021/acs.jnatprod.0c00676

Li X F , Jeong J H , Lee K T et al . 2003 . γ -Pyrone derivatives, kojic acid methyl ethers from a marine-derived fungus Altenaria sp . Archives of Pharmacal Research , 26 ( 7 ): 532 - 534 , https://doi.org/10.1007/BF02976876 https://doi.org/10.1007/BF02976876 .

Lü F Y , Li X M , Chi L P et al . 2020 . A new acyclic peroxide from Aspergillus nidulans SD-531, a fungus obtained from deep-sea sediment of cold spring in the South China Sea . Journal of Oceanology and Limnology , 38 ( 4 ): 1225 - 1232 , https://doi.‍org/10.1007/s00343-020-0052-3 https://doi.‍org/10.1007/s00343-020-0052-3 . https://do 10.1007/s00343-020-0052-3 http://dx.doi.org/10.1007/s00343-020-0052-3

Mukhtar I , Quan X H , Chou T S et al . 2019 . First report of Talaromyces funiculosus causing fruit core rot of peach ( Prunus persica ) in China . Plant Disease , 103 ( 8 ): 2124 - 2125 , https://doi.org/10.1094/PDIS-11-18-2050-PDN https://doi.org/10.1094/PDIS-11-18-2050-PDN .

Padhi S , Masi M , Cimmino A et al . 2019 . Funiculosone, a substituted dihydroxanthene-1,9-dione with two of its analogues produced by an endolichenic fungus Talaromyces funiculosus and their antimicrobial activity . Phytochemistry , 157 : 175 - 183 , https://doi.org/10.1016/j.phytochem.2018.10.031 https://doi.org/10.1016/j.phytochem.2018.10.031 .

Pierce C G , Uppuluri P , Tristan A R et al . 2008 . A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing . Nature Protocols , 3 ( 9 ): 1494 - 1500 , https://doi.org/10.1038/nprot.2008.141 https://doi.org/10.1038/nprot.2008.141 .

Pockrandt D , Ludwig L , Fan A L et al . 2012 . New insights into the biosynthesis of prenylated xanthones: XptB from Aspergillus nidulans catalyses an O -prenylation of xanthones . ChemBioChem , 13 ( 18 ): 2764 - 2771 , https://doi.org/10.1002/cbic.201200545 https://doi.org/10.1002/cbic.201200545 .

Sparapano L , Evidente A . 1995 . Biological activity of cyclopaldic acid, a major toxin of Seiridium cupressi , its six derivatives, and iso -cyclopaldic acid . Natural Toxins , 3 ( 3 ): 156 - 165 , https://doi.org/10.1002/nt.2620030307 https://doi.org/10.1002/nt.2620030307 .

Tarcz S , Xie X L , Li S M . 2014 . Substrate and catalytic promiscuity of secondary metabolite enzymes: O -prenylation of hydroxyxanthones with different prenyl donors by a bisindolyl benzoquinone C - and N -prenyltransferase . RSC Advances , 4 ( 35 ): 17986 - 17992 , https://doi.org/10.1039/C4RA00337C https://doi.org/10.1039/C4RA00337C .

Wang S , Li X M , Teuscher F et al . 2006 . Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum , an endophytic fungus derived from the marine red alga Polysiphonia urceolata . Journal of Natural Products , 69 ( 11 ): 1622 - 1625 , https://doi.org/10.1021/np060248n https://doi.org/10.1021/np060248n .

Williams R M , Kwast E , Coffman H et al . 1989 . Remarkable, enantio-divergent biogenesis of brevianamide A and B . Journal of the American Chemical Society , 111 ( 8 ): 3064 - 3065 , https://doi.org/10.1021/ja00190a050 https://doi.org/10.1021/ja00190a050 .

Yang B , Dong J D , Lin X P et al . 2014 . New prenylated indole alkaloids from fungus Penicillium sp. derived of mangrove soil sample . Tetrahedron , 70 ( 25 ): 3859 - 3863 , https://doi.org/10.1016/j.tet.2014.04.043 https://doi.org/10.1016/j.tet.2014.04.043 .

Yang B , Tao H M , Lin X P et al . 2018 . Prenylated indole alkaloi ds and chromone derivatives from the fungus Penicillium sp. SCSIO041218 . Tetrahedron , 74 ( 1 ): 77 - 82 , https://doi.org/10.1016/j.tet.2017.11.038 https://doi.org/10.1016/j.tet.2017.11.038 .

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Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523

Discovery of prenylated indole alkaloid and natural xanthone from cold-seep sediment derived fungus Talaromyces funiculosus SD-523

DOI：

摘要

Abstract

关键词

Keywords

references