Zanthoxylum clava-herculis is commonly called toothache tree since it was used by Native Americans as an anesthetic remedy for tooth aches, chronic rheumatism, dyspepsia, dysentery, kidney trouble, heart trouble, colds, coughs, lung ailments, and nervous debility. It is also known that swallowtail butterflies and leaf beetles use the tree as their host plant and the extract is highly toxic to fish due to it’s neurotoxicity. Many of biologically active extracts such as neohuclis, herculin (insecticidal), berberine, chelerythrine (antibacterial), N-acetylanonaine, asarinin, O-prenylpiperitol, sesamin (ichthyotoxic), O-prenylxanthoxylol, and xanthoxylin have been isolated. Benzophenathridine, a fused-ring parent structure for some of extracts, was studied for anticancer activity. Zanthoxylum clava-herculis tree bark (500 g) was suspended in 90% methanol and further suspended in chloroform. Suspended solutions were filtered and concentrated to yield 10 grams of gummy residue. The crude extract (2.5 g) was subjected to flash column chromatography from which 3 fractions were yielded. The novel product, N-(n-anisyl)ethyl-N-Methylcinnamamide was obtained from the 3rd fraction which was then further recrystallized to yield 600 mg of pure product. The final compound was identified by spectroscopic analysis (IR, Mass, NMR, and X-ray crystallography). The products are thought to have neurological effects on mammals and different biological activity tests will be performed on such in the near future.

New compound, N-(n-anisyl)ethyl-N-Methylcinnamamide extracted from Zanthoxylum clava-herculis tree bark

255th National Meeting (2018)

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