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1-(6-Methylsalicyloyl)glycerol from stony coral-derived Micromonospora sp.

Abstract

A new natural product, 1-(6-methylsalicyloyl)glycerol (1) was isolated from the culture extract of the stony coral-derived Micromonospora sp. C029. The structure of 1 was determined by extensive analysis of 1D and 2D NMR spectroscopic data. The absolute configuration was determined to be S by comparison of specific rotation with synthetic (R)- and (S)-1. Compound 1 showed weak antimicrobial activity against Kocuria rizhophila. Structurally related benzoyl glycerol is not reported from actinomycetes, suggesting that isolation of actinomycetes from little studied environments should be important for the discovery of novel natural products.

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References

  1. Bérdy J. Thoughts and facts about antibiotics: Where we are now and where we are heading. J Antibiot. 2012;65:385–95.

    Article  Google Scholar 

  2. Maldonado LA, Fenical W, Jensen PR, Kauffman CA, Mincer TJ, Ward AC, et al. Salinispora arenicola gen. nov., sp. nov. and Salinispora tropica sp. nov., obligate marine actinomycetes belonging to the family Micromonosporaceae. Int J Syst Evol Microbiol. 2005;55:1759–66.

    Article  CAS  Google Scholar 

  3. Mincer TJ, Fenical W, Jensen PR. Culture-dependent and culture-independent diversity within the obligate marine actinomycete genus Salinispora. Appl Environ Microbiol. 2005;71:7019–28.

    Article  CAS  Google Scholar 

  4. Fenical W, Jensen PR. Developing a new resource for drug discovery: Marine actinomycete bacteria. Nat Chem Biol. 2006;2:666–73.

    Article  CAS  Google Scholar 

  5. Jensen PR, Moore BS, Fenical W. The marine actinomycete genus Salinispora: A model organism for secondary metabolite discovery. Nat Prod Rep. 2015;32:738–51.

    Article  CAS  Google Scholar 

  6. Buangrab K, Sutthacheep M, Yeemin T, Harunari E, Igarashi Y, Sripreechasak P, et al. Streptomyces corallincola and Kineosporia corallincola sp. nov., two new coral-derived marine actinobacteria. Int J Syst Evol Microbiol. 2022;72. https://doi.org/10.1099/ijsem.0.005249.

  7. Nonaka GI, Nishioka I. Tannins and related compounds. X. rhubarb (2): isolation and structures of a glycerol gallate, gallic acid glucoside gallates, galloylglucoses and isolindleyin. Chem Pharm Bull. 1983;31:1652–8.

    Article  CAS  Google Scholar 

  8. Saijo R, Nonaka G, Nishioka I. Gallic acid esters of bergenin and norbergenin from Mallotus japonicus. Phytochemistry 1990;29:267–70.

    Article  CAS  Google Scholar 

  9. Fico G, Braca A, Tomè F, Morelli I. Phenolic derivatives from Nigella damascena seeds. Pharm Biol. 2000;38:371–3.

    Article  CAS  Google Scholar 

  10. Latté KP, Kaloga M, Schäfer A, Kolodziej H. An ellagitannin, n-butyl gallate, two aryltetralin lignans, and an unprecedented diterpene ester from Pelargonium reniforme. Phytochemistry 2008;69:820–6.

    Article  Google Scholar 

  11. Yan HJ, Gao SS, Li CS, Li XM, Wang BG. Chemical constituents of a marine-derived endophytic fungus Penicillium commune G2M. Molecules 2010;15:3270–5.

    Article  CAS  Google Scholar 

  12. Gao SS, Li XM, Du FY, Li CS, Proksch P, Wang BG. Secondary metabolites from a marine-derived endophytic fungus Penicillium chrysogenum QEN-24S. Mar Drugs. 2011;9:59–70.

    Article  CAS  Google Scholar 

  13. Talontsi FM, Facey P, Tatong MDK, Tofazzal Islam M, Frauendorf H, Draeger S, et al. Zoosporicidal metabolites from an endophytic fungus Cryptosporiopsis sp. of Zanthoxylum leprieurii. Phytochemistry 2012;83:87–94.

    Article  CAS  Google Scholar 

  14. Sharma AR, Harunari E, Oku N, Matsuura N, Trianto A, Igarashi Y. Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus. Beilstein J Org Chem. 2020;16:297–304.

    Article  CAS  Google Scholar 

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Acknowledgements

P388 cells were obtained from JCRB Cell Bank under accession code JCRB0017 (Lot. 06252002).

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Correspondence to Yasuhiro Igarashi.

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Harunari, E., Doyo, H., Phongsopitanun, W. et al. 1-(6-Methylsalicyloyl)glycerol from stony coral-derived Micromonospora sp.. J Antibiot 76, 83–87 (2023). https://doi.org/10.1038/s41429-022-00578-8

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