Biodiversity Literature Repository
Published January 31, 2022 | Version v1
Journal article Restricted

Metabolites isolated from the human intestinal fungus Penicillium oxalicum SL2 and their agonistic effects on PXR and FXR

Creators

  • 1. , Zhi-Lin Luan & , Cheng-Peng Sun & , Bao-Jing Zhang & , Ling-Ling Jin & , & , Hou-Li Zhang & , Zhen-Long Yu & , Chao Wang & * , Xiao-Chi Ma & ** & Dalian Key Laboratory of Metabolic Target Characterization and Traditional Chinese Medicine Intervention, College of Pharmacy, College of Integrative Medicine, The National & Local Joint Engineering Research Center for Drug Development of Neurodegenerative Disease, Dalian Medical University, Dalian, 116044, People's Republic of China & , Zhi-Lin Luan & , Cheng-Peng Sun & , Bao-Jing Zhang

Description

Zhao, Wen-Yu, Luan, Zhi-Lin, Sun, Cheng-Peng, Zhang, Bao-Jing, Jin, Ling-Ling, Deng, Sa, Zhang, Hou-Li, Yu, Zhen-Long, Wang, Chao, Ma, Xiao-Chi (2022): Metabolites isolated from the human intestinal fungus Penicillium oxalicum SL2 and their agonistic effects on PXR and FXR. Phytochemistry (112974) 193: 1-11, DOI: 10.1016/j.phytochem.2021.112974, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112974

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:DD3DFFB09012FFB9FFFDFFCBFF8BCB57

Cites
Publication: 10.3389/fimmu.2014.00427 (DOI)
Publication: 10.1038/s41467-020-16431-1 (DOI)
Publication: 10.3390/md11083068 (DOI)
Publication: 10.1021/acs.orglett.8b01272 (DOI)
Publication: 10.1021/jf062032x (DOI)
Publication: 10.1152/physrev.00018.2018 (DOI)
Publication: 10.1021/np0497954 (DOI)
Publication: 10.1016/j.phytol.2008.07.008 (DOI)
Publication: 10.1186/1758-2946-4-17 (DOI)
Publication: 10.3389/fmicb.2012.00421 (DOI)
Publication: 10.1038/nature18848 (DOI)
Publication: 10.1021/acs.jnatprod.0c00393 (DOI)
Publication: 10.1021/ol7029867 (DOI)
Publication: 10.1186/s41182-017-0072-7 (DOI)
Publication: 10.3389/fimmu.2017.00788 (DOI)
Publication: 10.1021/np200037z (DOI)
Publication: 10.1016/j.bmc.2007.06.012 (DOI)
Publication: 10.1016/j.ejmech.2019.111652 (DOI)
Publication: 10.1056/NEJMra1600266 (DOI)
Publication: 10.1016/j.tetasy.2004.01.032 (DOI)
Publication: 10.1186/s40168-017-0373-4 (DOI)
Publication: 10.3389/fmicb.2011.00153 (DOI)
Publication: 10.1016/j.ijbiomac.2019.12.057 (DOI)
Publication: 10.1016/j.bioorg.2020.103637 (DOI)
Publication: 10.1021/acs.jafc.8b05628 (DOI)
Publication: 10.1021/acs.orglett.7b02738 (DOI)
Publication: 10.1016/j.cclet.2018.02.006 (DOI)
Publication: 10.1016/j.ijbiomac.2020.05.100 (DOI)
Publication: 10.1016/j.ijbiomac.2021.04.187 (DOI)
Has part
Dataset: http://table.plazi.org/id/FDD266569013FFB8FCCFFF5DFA11CB94 (URL)
Figure: 10.5281/zenodo.8194399 (DOI)
Figure: 10.5281/zenodo.8194401 (DOI)
Figure: 10.5281/zenodo.8194403 (DOI)
Figure: 10.5281/zenodo.8194405 (DOI)
Dataset: http://table.plazi.org/id/FDD266569016FFBDFF99FF5DFD62CB94 (URL)
Dataset: http://table.plazi.org/id/FDD266569016FFBDFCCFFF5DFA49CB94 (URL)
Dataset: http://table.plazi.org/id/FDD266569016FFBDFF99FCEFFD62C807 (URL)
Dataset: http://table.plazi.org/id/FDD266569016FFBDFCCFFA35FAA0CD7F (URL)
Figure: 10.5281/zenodo.8194407 (DOI)
Figure: 10.5281/zenodo.8194409 (DOI)
Figure: 10.5281/zenodo.8194411 (DOI)
Figure: 10.5281/zenodo.8194413 (DOI)

References

  • Arrieta, M.C., Stiemsma, L.T., Amenyogbe, N., Brown, E.M., Finlay, B., 2014. The intestinal microbiome in early life: health and disease. Front. Immunol. 5, 427. https://doi.org/10.3389/fimmu.2014.00427.
  • Bernardes, E.T., Pettersen, V.K., Gutierrez, M.W., Laforest-Lapointe, I., Jendzjowsky, N. G., Cavin, J.B., Vicentini, F.A., Keenan, C.M., Ramay, H.R., Samara, J., Macnaughton, W.K., Wilson, R.J.A., Kelly, M.M., Mccoy, K.D., Sharkey, K.A., Arrieta, M.C., 2020. Intestinal fungi are causally implicated in microbiome assembly and immune development in mice. Nat. Commun. 11, 2577. https://doi.org/ 10.1038/s41467-020-16431-1.
  • Briggs, L.H., Cambie, R.C., 1958. Constituents of Phebalium nudum I. Bark. Tetrahedron 2, 256-270. https://doi.org/10.3390/md11083068.
  • Chen, Y., Jiang, N., Wei, Y.J., Li, X., Ge, H.M., Jiao, R.H., Tan, R.X., 2018. Citrofulvicin, an antiosteoporotic polyketide from Penicillium velutinum. Org. Lett. 20, 3741-3744. https://doi.org/10.1021/acs.orglett.8b01272.
  • Chidananda, C., Sattur, A.P., 2007. Sclerotiorin, a novel inhibitor of lipoxygenase from Penicillium frequentans. J. Agric. Food Chem. 55, 2879-2883. https://doi.org/ 10.1021/jf062032x.
  • Cryan, J.F., O' riordan, K.J., Cowan, C.S.M., Sandhu, K.V., Bastiaanssen, T.F.S., Boehme, M., Codagnone, M.G., Cussotto, S., Fulling, C., Golubeva, A.V., Guzzetta, K. E., Jaggar, M., Long-Smith, C.M., Lyte, J.M., Martin, J.A., Molinero-Perez, A., Moloney, G., Morelli, E., Morillas, E., O' connor, R., Cruz-Pereira, J.S., Peterson, V.L., Rea, K., Ritz, N.L., Sherwin, E., Spichak, S., Teichman, E.M., Van De Wouw, M., Ventura-Silva, A.P., Wallace-Fitzsimons, S.E., Hyland, N., Clarke, G., Dinan, T.G., 2019. The microbiota-gut-brain axis. Physiol. Rev. 99, 1877-2013. https://doi.org/ 10.1152/physrev.00018.2018.
  • Dalsgaard, P.W., Blunt, J.W., Munro, M.H., Larsen, T.O., Christophersen, C., 2004. Psychrophilin B and C: cyclic nitropeptides from the psychrotolerant fungus Penicillium rivulum. J. Nat. Prod. 67, 1950-1952. https://doi.org/10.1021/ np0497954.
  • Diliberto, J.J., Srinivas, P., Overstreet, D., Usha, G., Burka, L.T., Birnbaum, L.S., 1990. Metabolism of citral, an alpha,beta-unsaturated aldehyde, in male F344 rats. Drug Metab. Dispos. 18, 866-875.
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalman, G.V., Barone, G., 2016. Gaussian 16. Gaussian, Inc., Wallingford CT.
  • Gallardo, G.L., Pena t, N.I., Cabrera, G.M., 2008. Neric acid derivatives produced by the honey bee fungal entomopathogen Ascosphaera apis. Phytochem. Lett. 1, 155-158. https://doi.org/10.1016/j.phytol.2008.07.008.
  • Guo, Y.Z., Wei, Q., Gao, J., Liu, B.Y., Zhang, T., Hua, H.M., Hu, Y.C., 2019. Metabolites of the psychrophilic fungus Pseudogymnoascus pannorum. Nat. Prod. Res. Dev. 31, 446-449.
  • Hanwell, M.D., Curtis, D.E., Lonie, D.C., Vandermeersch, T., Zurek, E., Hutchison, G.R., 2012. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J. Cheminf. 4, 17. https://doi.org/10.1186/1758-2946-4-17.
  • Hatoum, R., Labrie, S., Fliss, I., 2012. Antimicrobial and probiotic properties of yeasts: from fundamental to novel applications. Front. Microbiol. 3, 421. https://doi.org/ 10.3389/fmicb.2012.00421.
  • Honda, K., Littman, D.R., 2016. The microbiota in adaptive immune homeostasis and disease. Nature 535, 75-84. https://doi.org/10.1038/nature18848.
  • Hua, X.L., Bian, X.Q., Wu, X., Li, J.Y., Hua, H.M., Pei, Y.H., Han, A.H., Bai, J., 2014. Penioxalamine A, a novel prenylated spiro-oxindole alkaloid from Penicillium oxalicum TW01-1. Tetrahedron Lett. 55, 3864-3867. https://doi.org/10.1021/acs. jnatprod.0c00393.
  • Iida, M., Ooi, T., Kito, K., Yoshida, S., Kanoh, K., Shizuri, Y., Kusumi, T., 2008. Three new polyketide-terpenoid hybrids from Penicillium sp. Org. Lett. 10, 845-848. https:// doi.org/10.1021/ol7029867.
  • Jiang, W.X., Chen, E.D., Gong, T., Zhu, P., 2017. Studies on the secondary metabolites of Penicillium sp. HLS-216 isolated from the marine sponge Gelliodes carnosa. J. Pharm. Res. 36, 67-71. https://doi.org/10.1186/s41182-017-0072-7.
  • Laforest-Lapointe, I., Arrieta, M.C., 2017. Patterns of early-life gut microbial colonization during human immune development: an ecological perspective. Front. Immunol. 8, 788. https://doi.org/10.3389/fimmu.2017.00788.
  • Li, C.S., An, C.Y., Li, X.M., Gao, S.S., Cui, C.M., Sun, H.F., Wang, B.G., 2011. Triazole and dihydroimidazole alkaloids from the marine sediment-derived fungus Penicillium paneum SD-44. J. Nat. Prod. 74, 1331-1334. https://doi.org/10.1021/np200037z.
  • Li, C.S., Li, X.M., Gao, S.S., Lu, Y.H., Wang, B.G., 2013. Cytotoxic anthranilic acid derivatives from deep sea sediment-derived fungus Penicillium paneum SD-44. Mar. Drugs 11, 3068-3076. https://doi.org/10.3390/md11083068.
  • Li, W., Shao, Y.T., Yin, T.P., Yan, H., Shen, B.C., Li, Y.Y., Xie, H.D., Sun, Z.W., Ma, Y.L., 2020. Penisarins A and B, sesquiterpene coumarins isolated from an endophytic Penicillium sp. J. Nat. Prod. 83, 3471-3475. https://doi.org/10.1021/acs. jnatprod.0c00393.
  • Liu, J., Wu, G., Cui, G., Wang, W.X., Zhao, M., Wang, C., Zhang, Z., Peng, S., 2007. A new class of anti-thrombosis hexahydropyrazino-[1',2':1,6]pyrido-[3,4-b]-indole-1,4- dions: design, synthesis, logK determination, and QSAR analysis. Bioorg. Med. Chem. 15, 5672-5693. https://doi.org/10.1016/j.bmc.2007.06.012.
  • Luan, Z.L., Huo, X.K., Dong, P.P., Tian, X.G., Sun, C.P., Lv, X., Feng, L., Ning, J., Wang, C., Zhang, B.J., Ma, X.C., 2019. Highly potent non-steroidal FXR agonists protostane-type triterpenoids: structure-activity relationship and mechanism. Eur. J. Med. Chem. 182, 111652. https://doi.org/10.1016/j.ejmech.2019.111652.
  • Luan, Z.L., Qiao, F., Zhao, W.Y., Ming, W.H., Yu, Z.L., Liu, J., Dai, S.Y., Jiang, S.H., Lian, C.J., Sun, C.P., Zhang, B.J., Zheng, J., Ma, S.C., Ma, X.C., 2021. Discovery of new iridoids as farnesoid X receptor agonists from Morinda officinalis : agonistic potentials and molecular stimulation. Chin. J. Chem. 39, 1288-1296. https://doi. org/10.1021/acs.jnatprod.0c00393.
  • Lynch, S.V., Pedersen, O., 2016. The human intestinal microbiome in health and disease. N. Engl. J. Med. 375, 2369-2379. https://doi.org/10.1056/NEJMra1600266.
  • Nanda, S., Scott, A.I., 2004. Asymmetric synthesis of (E)- and (Z)-3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid. Tetrahedron: Asymmetry 15, 963-970. https:// doi.org/10.1016/j.tetasy.2004.01.032.
  • Nash, A.K., Auchtung, T.A., Wong, M.C., Smith, D.P., Gesell, J.R., Ross, M.C., Stewart, C. J., Metcalf, G.A., Muzny, D.M., Gibbs, R.A., Ajami, N.J., Petrosino, J.F., 2017. The gut mycobiome of the Human Microbiome Project healthy cohort. Microbiome 5, 153. https://doi.org/10.1186/s40168-017-0373-4.
  • Parfrey, L.W., Walters, W.A., Knight, R., 2011. Microbial eukaryotes in the human microbiome: ecology, evolution, and future directions. Front. Microbiol. 2, 153. https://doi.org/10.3389/fmicb.2011.00153.
  • Sun, C.P., Yan, J.K., Yi, J., Zhang, X.Y., Yu, Z.L., Huo, X.K., Liang, J.H., Ning, J., Feng, L., Wang, C., Zhang, B.J., Tian, X.G., Zhang, L., Ma, X., 2020a. The study of inhibitory effect of natural flavonoids toward beta-glucuronidase and interaction of flavonoids with beta-glucuronidase. Int. J. Biol. Macromol. 143, 349-358. https://doi.org/ 10.1016/j.ijbiomac.2019.12.057.
  • Sun, C.P., Zhang, J., Zhao, W.Y., Yi, J., Yan, J.K., Wang, Y.L., Morisseau, C., Liu, Z.B., Hammock, B.D., Ma, X.C., 2020b. Protostane-type triterpenoids as natural soluble epoxide hydrolase inhibitors: inhibition potentials and molecular dynamics. Bioorg. Chem. 96, 103637. https://doi.org/10.1016/j.bioorg.2020.103637.
  • Tang, J.L., Zhou, Z.Y., Yang, T., Yao, C., Wu, L.W., Li, G.Y., 2019. Azaphilone alkaloids with anti-inflammatory activity from fungus Penicillium sclerotiorum cib-411. J. Agric. Food Chem. 67, 2175-2182. https://doi.org/10.1021/acs.jafc.8b05628.
  • Wang, C., Huo, X.K., Luan, Z.L., Cao, F., Tian, X.G., Zhao, X.Y., Sun, C.P., Feng, L., Ning, J., Zhang, B.J., Ma, X.C., 2017. Alismanin A, a triterpenoid with a C34 skeleton from Alisma orientale as a natural agonist of human pregnane X receptor. Org. Lett. 19, 5645-5648. https://doi.org/10.1021/acs.orglett.7b02738.
  • Wang, P.L., Li, D.Y., Xie, L.R., Hua, H.M., Li, Z.L., 2014. Isolation and identification of the secondary metabolites from the marine-derived fungus Penicillium oxalicum. J. Shenyang Pharm. Univ. 31, 252-255.
  • Wang, W.W., Zhang, X.T., Zhao, Y., Liu, X.L., Zhang, Z.H., Wang, M.A., 2018. Divergent synthesis of four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid, esters and evaluation for the antifungal activity. Chin. Chem. Lett. 29, 1872-1874. https://doi. org/10.1016/j.cclet.2018.02.006.
  • Yuan, X.N., Chen, G., Bai, J., Hua, H.M., Xu, W.F., Pei, Y.H., 2014. Isolation and identification of the secondary metabolites from Penicillium oxalicum HSY-P-17. J. Shenyang Pharm. Univ. 31, 360-362.
  • Yun, W.J., Zhang, X.Y., Liu, T.T., Liang, J.H., Sun, C.P., Yan, J.K., Huo, X.K., Tian, X.G., Zhang, B.J., Huang, H.L., Ma, X.C., 2020. The inhibition effect of uncarialin A on voltage-dependent L-type calcium channel subunit alpha-1C: inhibition potential and molecular stimulation. Int. J. Biol. Macromol. 159, 1022-1030. https://doi.org/ 10.1016/j.ijbiomac.2020.05.100.
  • Zhao, W.Y., Zhang, X.Y., Zhou, M.R., Tian, X.G., Lv, X., Zhang, H.L., Deng, S., Zhang, B. J., Sun, C.P., Ma, X.C., 2021. Natural soluble epoxide hydrolase inhibitors from Alisma orientale and their potential mechanism with soluble epoxide hydrolase. Int. J. Biol. Macromol. 183, 811-817. https://doi.org/10.1016/j.ijbiomac.2021.04.187.