(Hydroxymethyl)acylfulvene:  An Illudin Derivative with Superior Antitumor Properties

• Published in: Journal of natural products (Washington, D.C.) Vol. 59; no. 9; pp. 896 - 899
• Main Authors: McMorris, Trevor C, Kelner, Michael J, Wang, Wen, Yu, Jian, Estes, Leita A, Taetle, Raymond
• Format: Journal Article
• Language: English
• Published: CINCINNATI American Chemical Society 01.09.1996; AMER SOC PHARMACOGNOSY; American Society of Pharmacognosy
• Subjects: AGENTES ANTINEOPLASTICOS; Animals; Antibiotics, Antineoplastic - pharmacology; ANTINEOPLASTIC AGENTS; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Basidiomycota - chemistry; BASIDIOMYCOTINA; BIOCHEMICAL PATHWAYS; Biological and medical sciences; BIOSINTESIS; BIOSYNTHESE; BIOSYNTHESIS; CHEMICAL COMPOSITION; CHEMICAL REACTIONS; CHEMICAL STRUCTURE; Chemistry, Medicinal; Chromatography, Thin Layer; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; Crystallography, X-Ray; CYTOTOXIC COMPOUNDS; Drug Screening Assays, Antitumor; ESPECTROMETRIA; ESTRUCTURA QUIMICA; General aspects; HL-60 Cells; Humans; Life Sciences & Biomedicine; Lung Neoplasms - drug therapy; Magnetic Resonance Spectroscopy; Medical sciences; MEDICAMENT CYTOSTATIQUE; Mice; Mice, Inbred BALB C; Neoplasm Transplantation; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; PRECURSORS; REACCIONES QUIMICAS; REACTION CHIMIQUE; Science & Technology; SESQUITERPENES; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; SESQUITERPENOIDE; SESQUITERPENOIDS; SESQUITERPENOS; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; STRUCTURE CHIMIQUE; SUBSTANCE TOXIQUE; SUSTANCIAS TOXICAS; TOXIC SUBSTANCES; VIA BIOQUIMICA DEL METABOLISMO; VOIE BIOCHIMIQUE DU METABOLISME; ANTICANCER AGENTS; Antineoplastic agent; Ketol; Aldehyde; Tricyclic compound; In vitro; Formaldehyde; Spiran; HL60 cell line; Structure activity relation; Sesquiterpenes; Established cell line; Chemical synthesis; Tumor cell
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960450y

Reaction of the fungal sesquiterpene illudin S with excess paraformaldehyde in dilute H2SO4 gives (hydroxymethyl)acylfulvene. The primary allylic hydroxyl thus formed can undergo very facile replacement by a variety of nucleophiles. (Hydroxymethyl)acylfulvene (MGI.114) was more toxic than a precursor, acylfulvene, but less toxic than the parent compound illudin S to HL 60 cells.