An acylated phloroglucinol with antimicrobial properties from Helichrysum caespititium

• Published in: Phytochemistry (Oxford) Vol. 53; no. 1; pp. 93 - 96
• Main Authors: Mathekga, ADM, Meyer, JJM, Horn, MM, Drewes, SE
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 01.01.2000
• Subjects: 2-methyl-4-[2',4',6'-trihydroxy-3'-(2-methylpropanoyl)phenyl]but-2-enyl acetate; Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Asteraceae - chemistry; Biochemistry & Molecular Biology; Biological and medical sciences; Chemical control; Colony Count, Microbial; Control; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; General pharmacology; Helichrysum caespititium; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Phloroglucinol - analogs & derivatives; Phloroglucinol - chemistry; Phloroglucinol - isolation & purification; Phytopathology. Animal pests. Plant and forest protection; Plant Sciences; Science & Technology; Structure-Activity Relationship; antimicrobial; phloroglucinol; Helichrysum caespititium; Asteraceae; CONSTITUENTS; Bioassay; Plant pathogen; Molecular structure; Pesticides; Phloroglucinol; Compositae; Biological activity; Antimicrobial agent; Fungicide; Fungi; Dicotyledones; Angiospermae; Plant origin; Bacteria; Isolation; Spermatophyta; Antibacterial agent; Thallophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(99)00424-0

A new acylated form of a phloroglucinol with significant antimicrobial properties was isolated by bioactivity guided fractionation from Helichrysum caespititium (Asteraceae). The structure elucidation, and conformation of the new phloroglucinol, 2-methyl-4-[2',4',6'-trihydroxy-3'-(2-methylpropanoyl) phenyl]but-2-enyl acetate, was established by high field NMR spectroscopic and MS data. The compound inhibited growth of Bacillus cereus, B. pumilus, B. subtilis and Micrococcus kristinae at the very low concentration of 0.5 mu g/ml and Staphylococcus aureus at 5.0 mu g/ml. Six fungi tested were similarly inhibited at low MICs, Aspergillus flavus and A. niger (1.0 mu g/ml), Cladosporium cladosporioides (5 mu g/ml), C. cucumerinum and C. sphaerospermum (0.5 mu g/ml) and Phytophthora capsici at 1.0 mu g/ml. (C) 2000 Elsevier Science Ltd. All rights reserved.