Chemical transformations on botryane skeleton. Effect on the cytotoxic activity.
Eighteen compounds with a botryane skeleton have been obtained through chemical transformations of various toxins from the fungus Botrytis cinerea. During the course of these transformations, the C-10 carbon of the botryane skeleton was found to exhibit an interesting high regioselectivity to oxidizing and reducing agents. In addition, the cytotoxicity of 27 botryane derivatives was determined in vitro against Hs578T, MDA-MB-231, HT-1080, U87-MG, IMR-90, and HUVEC cell lines. The results of this study confirm that the cytotoxicity of botrydial (1) and its derivatives is related to the presence of a 1,5-dialdehyde functionality.
Reino
José L
JL
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apartado 40, 11510 Puerto Real, Cádiz, Spain.
Durán-Patrón
Rosa
R
Segura
Inmaculada
I
Hernández-Galán
Rosario
R
Riese
Hans H
HH
Collado
Isidro G
IG
D000447:Aldehydes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D020171:Botrytis / Q000737:chemistry*; D001943:Breast Neoplasms; D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002849:Chromatography, Gas; D004354:Drug Screening Assays, Antitumor; D005260:Female; D005354:Fibrosarcoma; D006801:Humans; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects; D014471:Umbilical Veins / Q000166:cytology
D000447:Aldehydes; D000972:Antineoplastic Agents, Phytogenic; D001643:Bridged Bicyclo Compounds; D009183:Mycotoxins; D012717:Sesquiterpenes; C432873:botrydial