A new benzophenanthridine alkaloid and other bioactive constituents from the stem bark of Zanthoxylum heitzii

Helle Wangensteen; Giang Thanh Thi Ho; Margey Tadesse; Christopher O Miles; Nastaran Moussavi; Bertin Mikolo; Karl Egil Malterud

doi:10.1016/j.fitote.2016.01.012

A new benzophenanthridine alkaloid and other bioactive constituents from the stem bark of Zanthoxylum heitzii

Fitoterapia. 2016 Mar:109:196-200. doi: 10.1016/j.fitote.2016.01.012. Epub 2016 Jan 21.

Authors

Helle Wangensteen¹, Giang Thanh Thi Ho², Margey Tadesse², Christopher O Miles³, Nastaran Moussavi², Bertin Mikolo⁴, Karl Egil Malterud²

Affiliations

¹ School of Pharmacy, Department of Pharmaceutical Chemistry, Section Pharmacognosy, University of Oslo, P.O. Box 1068 Blindern, 0316 Oslo, Norway. Electronic address: helle.wangensteen@farmasi.uio.no.
² School of Pharmacy, Department of Pharmaceutical Chemistry, Section Pharmacognosy, University of Oslo, P.O. Box 1068 Blindern, 0316 Oslo, Norway.
³ School of Pharmacy, Department of Pharmaceutical Chemistry, Section Pharmacognosy, University of Oslo, P.O. Box 1068 Blindern, 0316 Oslo, Norway; Norwegian Veterinary Institute, P. O. Box 750 Sentrum, 0106 Oslo, Norway.
⁴ National Polytechnic High School, Marien Ngouabi University, BP 69 Brazzaville, People's Republic of Congo.

PMID: 26802607
DOI: 10.1016/j.fitote.2016.01.012

Abstract

Heitziquinone (7), a new benzophenanthridine alkaloid, together with five known compounds; isoarnottianamide (5), rhoifoline B (6), isobauerenol (8), 6-hydroxypellitorine (9) and sylvamide (10), were isolated as minor compounds from the hexane extract of stem bark from Zanthoxylum heitzii. Four previously reported compounds (1-4) were found, as well. Compounds 5 and 7 were both found to exist as 4:1 mixtures of two atropisomers. The structures were elucidated by 1D and 2D NMR spectroscopy and by mass spectrometry. Compounds 5-10 were identified for the first time in this species, and they are all rare natural compounds. Pellitorine (4), one of the main compounds from the hexane bark extract, was found to be responsible for the brine shrimp larvae toxicity (LC50 37 μM, 8 μg/ml) of the crude extract (LC50 24 μg/ml). Low cytotoxicity against a macrophage cell line was observed.

Keywords: Alkaloids; Amides; Artemia salina; Cytotoxicity; Zanthoxylum heitzii.

MeSH terms

Animals
Artemia / drug effects
Benzophenanthridines / chemistry*
Benzophenanthridines / isolation & purification
Fatty Acids, Unsaturated / chemistry
Fatty Acids, Unsaturated / isolation & purification
Mice
Molecular Structure
Plant Bark / chemistry*
Plant Extracts / chemistry
Plant Stems / chemistry
Polyunsaturated Alkamides / chemistry
Polyunsaturated Alkamides / isolation & purification
RAW 264.7 Cells
Toxicity Tests
Zanthoxylum / chemistry*

Substances

Benzophenanthridines
Fatty Acids, Unsaturated
Plant Extracts
Polyunsaturated Alkamides
pellitorine