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3. Callistrilones A and B, Triketone-Phloroglucinol-Monoterpene Hybrids with a New Skeleton from Callistemon rigidus.

Author

Cao JQ, Huang XJ, Li YT, Wang Y, Wang L, Jiang RW, and Ye WC

Subjects
Anti-Bacterial Agents chemistry, Anti-Bacterial Agents pharmacology, Circular Dichroism, Enterococcus faecium drug effects, Gram-Positive Bacteria drug effects, Microbial Sensitivity Tests, Molecular Structure, Monoterpenes chemistry, Monoterpenes pharmacology, Myrtaceae chemistry, Nuclear Magnetic Resonance, Biomolecular, Plant Leaves chemistry, Staphylococcus aureus drug effects, Anti-Bacterial Agents isolation & purification, Monoterpenes isolation & purification, Phloroglucinol analogs & derivatives, Phloroglucinol chemistry, Phloroglucinol isolation & purification, Phloroglucinol pharmacology
Abstract

The first triketone-phloroglucinol-monoterpene hybrids, callistrilones A and B (1 and 2), along with a postulated biosynthetic intermediate (3) were isolated from the leaves of Callistemon rigidus. Compounds 1 and 2 featured a new carbon skeleton with an unprecedented [1]benzofuro[2,3-a]xanthene or [1]benzofuro[3,2-b]xanthene pentacyclic ring system composed of three kinds of building blocks. Their structures and absolute configurations were elucidated by spectroscopic analysis, X-ray diffraction, and electronic circular dichroism (ECD) calculations. A plausible biogenetic pathway for the new compounds is also proposed. Compound 1 exhibited moderate antibacterial activity against Gram-positive bacteria including multiresistant strains.

Published
2016
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