1. Nematicidal Cyclic Lipodepsipeptides and a Xanthocillin Derivative from a Phaeosphariaceous Fungus Parasitizing Eggs of the Plant Parasitic Nematode Heterodera filipjevi
- Author
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Rémy Bertrand Teponno, Marc Stadler, Abdelfattah A. Dababat, Steffen Bernecker, Soleiman E. Helaly, Samad Ashrafi, and Wolfgang Maier
- Subjects
Magnetic Resonance Spectroscopy ,Nematoda ,Stereochemistry ,Eggs ,Pharmaceutical Science ,Antineoplastic Agents ,Fungus ,01 natural sciences ,Analytical Chemistry ,Anti-Infective Agents ,Ascomycota ,Ophiosphaerella ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,Pharmacology ,Heterodera filipjevi ,Molecular Structure ,biology ,010405 organic chemistry ,Host (biology) ,Chemistry ,Antinematodal Agents ,Organic Chemistry ,Absolute configuration ,Nuclear magnetic resonance spectroscopy ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Nematode ,Complementary and alternative medicine ,Fermentation ,Molecular Medicine ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
The new cyclic lipodepsipeptide ophiotine (1), two new arthrichitin derivatives named arthrichitins B (4) and C (5), a new xanthocillin-like alkaloid, xanthomide Z (2), and the previously described arthrichitin (3) were isolated from the liquid culture broth of a nematode-associated fungus with affinities to the genus Ophiosphaerella. The structural elucidation and determination of the absolute configuration of the new molecules were accomplished using a combination of spectroscopic and chemical techniques, including 1D and 2D NMR, HRMS, and Marfey's analysis. Opiotine (1) displayed moderate nematicidal activity against the host nematode ( Heterodera filipjevi), while xanthomide Z (2) exhibited very weak activity. Arthrichitin C (5) showed very weak cytotoxic effects on several cancer cell lines, with IC50 values in the range of 24-33 μM. Xanthomide Z is among few xanthocillin derivatives that comprise formamide functions instead of the cyano functions that are usually observed in this class of fungal alkaloids.
- Published
- 2018
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