Abstract:
Lanostane-triterpene acids obtained from the culture of the fungus Coriolellus malicola were studied by electrospray mass spectrometry in the negative ion mode using quadrupole time-of-flight and quadrupole ion trap analysers. Despite the differences observed in the mass spectra recorded with these instruments, a set of fragment ions was found to be characteristic of the family, depending on the Δ79(11) or Δ8 skeleton and the particular functional group at C-3. Copyright © 2007 John Wiley & Sons, Ltd.
Registro:
Documento: |
Artículo
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Título: | Characterisation of fungal lanostane-type triterpene acids by electrospray ionisation mass spectrometry |
Autor: | Cabrera, G.M.; Vellasco, A.P.; Levy, L.M.; Eberlin, M.N. |
Filiación: | Departamento Química Orgánica y UMYMFOR (CONICET), FCEyN, UBA, Ciudad Universitaria, Pab. II, 1428 Buenos Aires, Argentina Universidade Estadual de Campinas - UNICAMP, Instituto de Química, 13083-970 Campinas, SP, Brazil
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Palabras clave: | Antrodia malicola; Basidiomycete; Coriolellus malicola; Fungal metabolites; Mass spectrometry; Triterpene acids; triterpene derivative; article; controlled study; Coriolellus malicola; drug structure; electrospray mass spectrometry; fungus culture; high performance liquid chromatography; ion trap mass spectrometry; mycelium; negative ion electrospray; nuclear magnetic resonance spectroscopy; Polyporaceae; Acids; Fungi; Molecular Structure; Spectrometry, Mass, Electrospray Ionization; Triterpenes; Antrodia malicola; Fungi |
Año: | 2007
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Volumen: | 18
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Número: | 6
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Página de inicio: | 489
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Página de fin: | 495
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DOI: |
http://dx.doi.org/10.1002/pca.1005 |
Título revista: | Phytochemical Analysis
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Título revista abreviado: | Phytochem. Anal.
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ISSN: | 09580344
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CODEN: | PHANE
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CAS: | Acids; Triterpenes
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09580344_v18_n6_p489_Cabrera |
Referencias:
- Audier, H.E., Beugelmans, R., Das, B.C., Mass spectrometry of tetracyclic triterpenes. Part II. The lanostane group: Influence of the 9:19 cyclopropane ring (1966) Tetrahedron Lett, 36, pp. 4341-4347
- Bobeldijk, I., Boonzaaijer, G., Spies-Faber, E.J., Vaes, W.H.J., Determination of kava lactones in food supplements by liquid chromatography-atmospheric pressure chemical ionisation tandem mass spectrometry (2005) J Chromatogr A, 1087, pp. 107-114
- Burinsky, D.J., Sides, S.L., Mass spectral fragmentation reactions of angiotensin-converting enzyme (ACE) inhibitors (2004) J Am Soc Mass Spectrom, 15, pp. 1300-1314
- Cabrera, G.M., Fernández Murga, M.L., Font de Valdez, G., Seldes, A.M., Direct analysis by electrospray ionization of mixtures of phosphatidyldiacylglycerols from Lactobacillus (2000) J Mass Spectrom, 35, pp. 1452-1459
- Crockett, J., (1990) The structural determination of homoconjugated octadecadienoic acids and cardiac glycosides by using Fast Atom Bombardment, , University of Nebraska. MS Thesis
- Cuéllar, M.J., Giner, R.M., Recio, M.C., Just, M.J., Máñez, S., Ríos, J.L., Two fungal lanostane derivatives as phospholipase A2 inhlbitors (1996) J Nat Prod, 59, pp. 977-979
- Dookeran, N.N., Yalcin, T., Harrison, A.G., Fragmentation reactions of protonated α-amino acids (1996) J Mass Spectrom, 31, pp. 500-508
- Furey, A., Crewley, J., Hamilton, B., Lehane, M., James, K.J., Strategies to avoid the miss-identification of anatoxin-a using mass spectrometry in the forensic investigation of acute neurotoxic poisoning (2005) J Chromatogr A, 1082, pp. 91-97
- Gan, K.-H., Fann, Y.-F., Hsu, S.-H., Kuo, K.-W., Lin, C.-N., Mediation of the cytotoxicity of lanostanoids and steroids of Ganoderma tsugae through apoptosis and cell cycle (1998) J Nat Prod, 61, pp. 485-487
- Giner-Larza, E.M., Máñez, S., Giner-Pons, R.M., Recio, M.C., Ríos, J.-L., On the anti-inflammatory and anti-phospholipase A2 activity of extracts from lanostane-rich species (2000) J Ethnopharmacol, 73, pp. 61-69
- Griffiths, W.J., Tandem mass spectrometry in the study of fatty acids, bile acids, and steroids (2003) Mass Spectrom Rev, 22, pp. 81-152
- Griffiths, W.J., Brown, A., Reimendal, R., Yang, Y., Zhang, J., Sjövall, J., A comparison of fast atom bombardment and electrospray as methods of ionization in the study of sulphated- and sulphonated-lipids by tandem mass spectrometry (1996) Rapid Commun Mass Spectrom, 10, pp. 1169-1174
- Hasan, C.M., Shahnaz, S., Muhammad, I., Gray, A.I., Waterman, P.G., Chemistry in the annonaceae, XXIII. 24-methylene-lanosta-7,9(11)-dien-3b-ol from Artrabotrys odorotissimus stem bark (1987) J Nat Prod, 50, pp. 762-763
- Hsu, F.-H., Turk, J., Studies on phosphatidylserine by tandem quadrupole and multiple stage quadrupole ion-trap mass spectrometry with electrospray ionization: Structural characterization and the fragmentation processes (2005) J Am Soc Mass Spectrom, 16, pp. 1510-1522
- Josephs, J.L., Sanders, M., Creation and comparison of MS/MS spectral libraries using quadrupole ion trap and triple-quadrupole mass spectrometers (2004) Rapid Comnmn Mass Spectrom, 18, pp. 743-759
- Kaminaga, T., Yasukawa, K., Kanno, H., Tai, T., Nunoura, Y., Takido, M., Inhibitory effects of lanostane-type triterpene acids, the components of Poria cocos, on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin (1996) Oncology, 53, pp. 382-385
- Keller, A.C., Maillard, M.P., Hostettmann, K., Antimicrobial steroids from the fungus (1996) Fomitopsis pinicolo, Phytochemistry, 41, pp. 1041-1046
- Kemanl Wangun, H.V., Berg, A., Hertel, W., Nkengfack, A.E., Hertweck, C., Anti-inflammatory and anti-hyaluronate lyase activities of lanostanoids from Piptoporus betulinus (2004) J Antibiot, 57, pp. 755-758
- Langouet, S., Paehler, A., Welti, D.H., Kerriguy, N., Guillouzo, A., Turesky, R.J., Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine in rat and human hepatocytes (2002) Carcinogenesis, 23, pp. 115-122
- Limb, J.-K., Kim, Y.H., Han, S.-Y., Jhon, G.-J., Isolation and characterization of monoacetyldiglycerides from bovine udder (1999) J Lipid Res, 40, pp. 2169-2176
- Lin, T., Asam, M.R., Glish, G.L., The dissociation of dimethylpyrroles: Evidence for reaction from isomeric parent ions (1996) J Am Soc Mass Spectrom, 7, pp. 930-937
- Miao, X.-S., Metcalfe, C.D., Hao, C., March, R.E., Electrospray ionization mass spectrometry of ginsenosides (2002) J Mass Spectrom, 37, pp. 495-506
- O'Hair, R.A.J., Broughton, P.S., Styles, M.L., Frink, B.T., Hadad, C.M., The Fragmentation pathways of protonated glycine: A computational study (2000) J Am Soc Mass Spectrom, 11, pp. 687-696
- Rösecke, J., König, W.A., Steroids from the fungus Fomitopsis pinicolo (1999) Phytochemistry, 52, pp. 1621-1627
- Sturm, S., Stuppner, H., Analysis of cucurbitacins in medicinal plants by high-pressure liquid chromatography-mass spectrometry (2000) Phytochem Anal, 11, pp. 121-127
- Tai, T., Akahori, A., Shingu, T., A lanostane triterpenoid from Poria cocos (1992) Phytochemistry, 31, pp. 2548-2549
- Tai, T., Shingu, T., Kikuchi, T., Tezuka, Y., Akahori, A., Isolation of lanostane-type triterpene acids having an acetoxyl group from sclerotia of Poria cocos (1995) Phytochemistry, 40, pp. 225-231
- Tai, T., Shingu, T., Kikuchi, T., Tezuka, Y., Akahori, A., Triterpenes from the surface layer of Poria cocos (1995) Phytochemistry, 39, pp. 1165-1169
- Ukiya, M., Aklhisa, T., Tokuda, H., Hirano, M., Oshikubo, M., Nobukuni, Y., Kimura, Y., Nishino, H., Inhibition of tumor-promoting effects by poricoic acids G and H and other lanostane-type triterpenes and cytotoxic activity of porlcoic acids A and G from Poria cocos (2002) J Nat Prod, 65, pp. 462-465
- Yasukawa, K., Kaminaga, T., Kitanaka, S., Tai, T., Nunoura, Y., Natori, S., Tanido, M., 3β-p-Hydroxybenzoyldehydrotumulosic acid from Poria cocos, and its anti-inflammatory effect (1998) Phytochemistry, 48, pp. 1357-1360
- Zaretskii, Z.V.I., Larka, E.A., Herbert, C.G., Beynon, J.H., Djerassi, C., Dan, P., Kustanovich, Z., Translational energy release and stereochemistry of steroids (1983) Int J Mass Spectrom Ion Plays, 47, pp. 137-140
- Zaretskii, Z.V.I., Kustanovich, Z., Kingston, E.E., Beynon, J.H., Djerassi, C., Tökes, L., Translational energy release and stereochemistry of steroids (1986) Org Mass Spectrom, 21, pp. 125-130
Citas:
---------- APA ----------
Cabrera, G.M., Vellasco, A.P., Levy, L.M. & Eberlin, M.N.
(2007)
. Characterisation of fungal lanostane-type triterpene acids by electrospray ionisation mass spectrometry. Phytochemical Analysis, 18(6), 489-495.
http://dx.doi.org/10.1002/pca.1005---------- CHICAGO ----------
Cabrera, G.M., Vellasco, A.P., Levy, L.M., Eberlin, M.N.
"Characterisation of fungal lanostane-type triterpene acids by electrospray ionisation mass spectrometry"
. Phytochemical Analysis 18, no. 6
(2007) : 489-495.
http://dx.doi.org/10.1002/pca.1005---------- MLA ----------
Cabrera, G.M., Vellasco, A.P., Levy, L.M., Eberlin, M.N.
"Characterisation of fungal lanostane-type triterpene acids by electrospray ionisation mass spectrometry"
. Phytochemical Analysis, vol. 18, no. 6, 2007, pp. 489-495.
http://dx.doi.org/10.1002/pca.1005---------- VANCOUVER ----------
Cabrera, G.M., Vellasco, A.P., Levy, L.M., Eberlin, M.N. Characterisation of fungal lanostane-type triterpene acids by electrospray ionisation mass spectrometry. Phytochem. Anal. 2007;18(6):489-495.
http://dx.doi.org/10.1002/pca.1005