New lanostanoids from the fungus Ganoderma concinna.
Three new compounds, 5 alpha-lanosta-7,9(11),24-triene-3beta-hydroxy-26-al (1), 5 alpha-lanosta-7,9(11),24-triene-15 alpha-26-dihydroxy-3-one (2), and 8 alpha,9 alpha-epoxy-4,4,14 alpha-trimethyl-3,7,11,15,20-pentaoxo-5 alpha-pregnane (3), were isolated from Ganoderma concinna along with 12 known compounds. The structures of compounds 1 and 2 were determined on the basis of MS and NMR studies. The structure of 3 was determined by MS, NMR, and single-crystal X-ray diffraction. Compounds 1, 2, and 3 induce apoptosis in human promyelocytic leukemia HL-60 cells, as indicated by examining the morphological features of cells and detection of DNA fragmentation by gel electrophoresis.
González
Antonio G
AG
Instituto Universitario de Bio-Orgánica "Antonio González", Instituto de Productos Naturales y Agrobiología.-CSIC, Avenida Astrofísico F. Sánchez 3, 38206 La Laguna, Tenerife, Spain.
León
Francisco
F
Rivera
Augusto
A
Padrón
Juan I
JI
González-Plata
Javier
J
Zuluaga
Juan C
JC
Quintana
José
J
Estévez
Francisco
F
Bermejo
Jaime
J
D017209:Apoptosis / Q000187:drug effects; D006690:Bisbenzimidazole; D002855:Chromatography, Thin Layer; D003105:Colombia; D018360:Crystallography, X-Ray; D053938:DNA Fragmentation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007810:Lanosterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007951:Leukemia, Myeloid; D013058:Mass Spectrometry; D008856:Microscopy, Fluorescence; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010784:Photomicrography; D011124:Polyporaceae / Q000737:chemistry*; D011278:Pregnanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013172:Spores, Fungal; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
C456057:5-lanosta-7,9(11),24-triene-15,26-dihydroxy-3-one; C456056:5-lanosta-7,9(11),24-triene-3-hydroxy-26-al; C456058:8,9-epoxy-4,4,14-trimethyl-3,7,11,15,20-pentaoxo-5-pregnane; D011278:Pregnanes; D014315:Triterpenes; D007810:Lanosterol; D006690:Bisbenzimidazole