Published February 28, 2019
| Version v1
Journal article
Restricted
Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L.
Authors/Creators
- 1. ∗∗ & ∗ & UMR 152 Pharma Dev, Université de Toulouse, IRD, UPS, France
Description
Barakat, Fatima, Vansteelandt, Marieke, Triastuti, Asih, Jargeat, Patricia, Jacquemin, Denis, Graton, Jérôme, Mejia, Kember, Cabanillas, Billy, Vendier, Laure, Stigliani, Jean-Luc, Haddad, Mohamed, Fabre, Nicolas (2019): Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L. Phytochemistry 158: 142-148, DOI: 10.1016/j.phytochem.2018.11.007, URL: http://dx.doi.org/10.1016/j.phytochem.2018.11.007
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:8024FF86BD72FFE049236344FF8D0011
References
- Barone, G., Gomez-Paloma, L., Duca, D., Silvestri, A., Riccio, R., Bifulco, G., 2002. Structure validation of natural products by quantum-mechanical GIAO calculations of 13C NMR chemical shifts. Chem. Eur. J. 8, 3233-3239. https://doi.org/10.1002/ 1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0. https://doi.org/.
- Becke, Axel D., 1993. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652. https://doi.org/10.1063/1.464913.
- Chen, Y., Guo, H., Du, Z., Liu, X.-Z., Che, Y., Ye, X., 2009. Ecology-based screen identifies new metabolites from a cordyceps-colonizing fungus as cancer cell proliferation inhibitors and apoptosis inducers: gliocladicillins as antitumor agents. Cell Prolif 42, 838-847. https://doi.org/10.1111/j.1365 2184.2009.00636.x.
- Cooper, J.K., Li, K., Aube, J., Coppage, D.A., Konopelski, J.P., 2018. Application of the DP4 probability method to flexible cyclic peptides with multiple independent stereocenters: the true structure of cyclocinamide A. Org. Lett. 20, 4314-4317. https:// doi.org/DOI:10.1021/acs.orglett.8b01756.
- Curtis, P.J., Greatbanks, D., Hesp, B., Cameron, A.F., Freer, A.A., 1977. Sirodesmins A, B, C, and G, antiviral epipolythiopiperazine-2,5-diones of fungal origin: X-Ray analysis of sirodesmin A diacetate. J. Chem. Soc. Perkin Trans. 1, 180-189. https://doi.org/ 10.1039/p19770000180.
- Elliott, C.E., Gardiner, D.M., Thomas, G., Cozijnsen, A., Van DeWouw, A., Howlett, B.J., 2007. Production of the toxin sirodesmin PL by Leptosphaeria Maculans during infection of Brassica Napus. Mol. Plant Pathol. 8, 791-802. https://doi.org/DOI:10. 1111/J.1364-3703.2007.00433.X.
- Ferreira, M.C., Vieira, M.L.A., Zani, C.L., Alves, T.M.A., Junior, P.A.S., Murta, S.M.F., Romanha, A.J., Gil, L.H.V.G., Carvalho, A.G.O., Zilli, I.E., Vital, M.J.S., Rosa, C.A., Rosa, L.H., 2015. Molecular phylogeny, diversity, symbiosis and discover of bioactive compounds of endophytic fungi associated with the medicinal Amazonian plant Carapa Guianensis Aublet (Meliaceae). Biochem. Syst. Ecol. 59, 36-44. https://doi. org/10.1016/j.bse.2014.12.017.
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J., 2016. Gaussian 16, Revision A.03. Gaussian, Inc., Wallingford, CT.
- Fujimoto, H., Sumino, M., Okuyama, E., Ishibashi, M., 2004. Immunomodulatory constituents from an ascomycete, Chaetomium Seminudum. J. Nat. Prod. 67, 98-102. https://doi.org/10.1021/np0302201.
- Gardner, D.E., 1997. Botryosphaeria mamane sp. nov. associated with witches'-brooms on the endemic forest tree sophora chrysophylla in Hawaii. Mycologia 89, 298-303. https://doi.org/10.2307/3761086.
- Gunatilaka, A.A.L., 2006. Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J. Nat. Prod. 69, 509-526. https://doi.org/10.1021/np058128n.
- Jacquemin, D., Adamo, C., 2015. Computational molecular electronic spectroscopy with TD-DFT. In: Ferre, N., Filatov, M., Huix-Rotllant, M. (Eds.), Density-functional Methods for Excited States. Top. Curr. Chem. Springer, Cham, pp. 347-375.
- Jiang, C.-S., Guo, Y.-W., 2011. Epipolythiodioxopiperazines from fungi: chemistry and bioactivities. Mini Rev. Med. Chem. 11, 728-745.
- Kajula, M., Ward, J.M., Turpeinen, A., Tejesvi, M.V., Hokkanen, J., Tolonen, A., Hakkanen, H., Picart, P., Ihalainen, J., Sahl, H.-G., Pirttila, A.M., Mattila, S., 2016. Bridged epipolythiodiketopiperazines from Penicillium raciborskii, an endophytic fungus of Rhododendron tomentosum Harmaja. J. Nat. Prod. 79, 685-690. https://doi. org/10.1021/np500822k.
- Liu, Y., Mandi, A., Li, X.-M., Meng, L.-H., Kurtan, T., Wang, B.-G., 2015. Peniciadametizine A, a dithiodiketopiperazine with a unique spiro[furan-2,7'- pyrazino[1,2-b][1,2]oxazine] skeleton, and a related analogue, peniciadametizine B, from the marine sponge-derived fungus Penicillium adametzioides. Mar. Drugs 13, 3640-3652. https://doi.org/10.3390/md13063640.
- Mahlo, S.M., McGaw, L.J., Eloff, J.N., 2013. Antifungal activity and cytotoxicity of isolated compounds from leaves of Breonadia salicina. J. Ethnopharmacol. 148, 909-913. https://doi.org/10.1016/j.jep.2013.05.041.
- Meng, L.-H., Li, X.-M., Lv, C.-T., Huang, C.-G., Wang, B.-G., 2014. Brocazines A-F, cytotoxic bisthiodiketopiperazine derivatives from Penicillium brocae MA-231, an endophytic fungus derived from the marine mangrove plant Avicennia marina. J. Nat. Prod. 77, 1921-1927. https://doi.org/10.1021/np500382k.
- Meng, L.-H., Wang, C.-Y., Mandi, A., Li, X.-M., Hu, X.-Y., Kassack, M.U., Kurtan, T., Wang, B.-G., 2016. Three diketopiperazine alkaloids with spirocyclic skeletons and one bisthiodiketopiperazine derivative from the mangrove-derived endophytic fungus Penicillium brocae MA-231. Org. Lett. 18, 5304-5307. https://doi.org/10.1021/acs. orglett.6b02620.
- Mullbacher, A., Waring, P., Tiwari-Palni, U., Eichner, R.D., 1986. Structural relationship of epipolythiodioxopiperazines and their immunomodulating activity. Mol. Immunol. 23, 231-235. https://doi.org/10.1016/0161-5890(86)90047-7.
- Nagarajan, R., Huckstep, L.L., Lively, D.H., DeLong, D.C., Marsh, M.M., Neuss, N., 1968. Aranotin and related metabolites from Arachniotus aureus. I. Determination of structure. J. Am. Chem. Soc. 90, 2980-2982. https://doi.org/10.1021/ja01013a055.
- Niu, S., Liu, D., Shao, Z., Proksch, P., Lin, W., 2017. Eutypellazines N- S, new thiodiketopiperazines from a deep sea sediment derived fungus Eutypella sp. with anti-VRE activities. Tetrahedron Lett. 58, 3695-3699. https://doi.org/10.1016/j.tetlet.2017. 08.015.
- Novaes, L.F.T., Sarotti, A.M., Pilli, R.A., 2015. Total synthesis and tentative structural elucidation of cryptomoscatone E3: interplay of experimental and computational studies. J. Org. Chem. 80, 12027-12037. https://doi.org/DOI:10.1021/acs.joc. 5b01956.
- Pedras, M.S.C., Abrams, S.R., Seguin-Swartz, G., Quail, J.W., Jia, Z., 1989. Phomalirazine, a novel toxin from the phytopathogenic fungus Phoma Lingam. J. Am. Chem. Soc. 1, 1904-1905. https://doi.org/10.1021/ja00187a068. https://doi.org/.
- Pedras, M.S.C., Biesenthal, C.J., 2001. Isolation, structure determination, and phytotoxicity of unusual dioxopiperazines form the phytopathogenic fungus Phoma Lingam. Phytochemistry 58, 905-909.
- Pongcharoen, W., Rukachaisirikul, V., Phongpaichit, S., Sakayaroj, J., 2007. A new dihydrobenzofuran derivative from the endophytic fungus Botryosphaeria Mamane PSU- M76. Chem. Pharm. Bull. 55, 1404-1405. https://doi.org/10.1248/cpb.55.1404.
- Schreckenbach, G., Ziegler, T., 1995. Calculation of NMR shielding tensors using gauge-including atomic orbitals and modern density functional theory. J. Phys. Chem. 99, 606-611. https://doi.org/DOI:10.1021/j100002a024.
- Seephonkai, P., Kongsaeree, P., Prabpai, S., Isaka, M., Thebtaranonth, Y., 2006. Transformation of an irregularly bridged epidithiodiketopiperazine to trichodermamide A. Org. Lett. 8, 3073-3075. https://doi.org/10.1021/ol061046l.
- Seya, H., Nozawa, K., Nakajima, S., Kawai, K.-I., Udagawa, S.-I., 1986. Studies on fungal products. Part 8. Isolation and structure of emestrin, a novel antifungal macrocyclic epidithiodioxopiperazine from Emericella striata. X-ray molecular structure of emestrin. J. Chem. Soc. Perkin Trans. 1, 109-116.
- Shahid-ul-Islam, Rather, L.J., Mohammad, F., 2016. Phytochemistry, biological activities and potential of annatto in natural colorant production for industrial applications. J. Adv. Res. 7, 499-514. https://doi.org/10.1016/j.jare.2015.11.002.
- Smith, G.S., Goodman, J.M., 2010. Assigning stereochemistry to single diastereoisomers: the DP4 probability. J. Am. Chem. Soc. 132, 12946-12959. https://doi.org/10.1021/ ja105035r.
- TINKER, software tools for molecular design, copyright © 1990-2018, Washington University in Saint Louis (WU), The University of Texas at Austin (UT Austin), and Sorbonne University (Sorbonne); https://dasher.wustl.edu/tinker/.
- Tomasi, J., Benedetta, M., Roberto, C., 2005. Quantum mechanical continuum solvation models. Chem. Rev. 105, 2999-3094. https://doi.org/10.1021/cr9904009.
- Vigushin, D.M., Mirsaidi, N., Brooke, G., Sun, C., Pace, P., Inman, L., Moody, C.J., Coombes, R.C., 2004. Gliotoxin is a dual inhibitor of farnesyltransferase and geranylgeranyltransferase I with antitumor activity against breast cancer in vivo. Med. Oncol. 21, 21-30. https://doi.org/10.1385/MO:21:1:21.
- Wang, X., Li, Y., Zhang, X., Lai, I.D., Zhou, L., 2017. Structural diversity and biological activities of the cyclodipeptides from fungi. Molecules 22, 1-86. https://doi.org/10. 3390/molecules22122026.
- Welch, T.R., Williams, R.M., 2014. Epidithiodioxopiperazines. Occurrence, synthesis and biogenesis. Nat. Prod. Rep. 31, 1376-1404. https://doi.org/10.1039/C3NP70097F.
- Zhang, H.W., Song, Y.C., Tan, R.X., 2006. Biology and chemistry of endophytes. Nat. Prod. Rep. 23, 753-771. https://doi.org/10.1039/b609472b.
- Zheng, C.-J., Kim, C.-J., Bae, K.S., Kim, Y.-H., Kim, W.-G., 2006. Bionectins A- C, epidithiodioxopiperazines with anti-MRSA activity, from Bionectra byssicola F120. J. Nat. Prod. 69, 1816-1819. https://doi.org/10.1021/np060348t.
- Zhu, M., Zhang, X., Feng, H., Dai, J., Li, J., Che, Q., Gu, Q., Zhu, T., Li, D., 2017. Penicisulfuranols A-F, alkaloids from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. J. Nat. Prod. 80, 71-75. https://doi.org/10.1021/acs. jnatprod.6b00483.