Types A and D Trichothecene Mycotoxins from the Fungus Myrothecium roridum

Waranya Lakornwong; Kwanjai Kanokmedhakul; Kasem Soytong; Arm Unartngam; Sarawut Tontapha; Vittaya Amornkitbamrung; Somdej Kanokmedhakul

doi:10.1055/a-0895-5753

Planta Medica, Table of Contents

Planta Med 2019; 85(09/10): 774-780
DOI: 10.1055/a-0895-5753

Natural Product Chemistry and Analytical Studies

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Types A and D Trichothecene Mycotoxins from the Fungus Myrothecium roridum

Authors

Waranya Lakornwong

¹Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
Kwanjai Kanokmedhakul

¹Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
Kasem Soytong

²Department of Plant Production Technology, Faculty of Agricultural Technology, King Mongkutʼs Institute of Technology Ladkrabang, Bangkok, Thailand
Arm Unartngam

³Bioproduct Science, Department of Science, Faculty of Liberal Arts and Science, Kasetsart University Kamphaeng Saen Campus, Nakorn Pathom, Thailand
Sarawut Tontapha

⁴Integrated Nanotechnology Research Center, Department of Physics, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
Vittaya Amornkitbamrung

⁴Integrated Nanotechnology Research Center, Department of Physics, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
Somdej Kanokmedhakul

¹Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand

Abstract

Chromatographic separation of extracts from the fungal biomass of a plant pathogenic fungus, Myrothecium roridum, yielded 8 trichothecene toxins including 6 type D trichothecenes (1–6) and 2 type A trichothecenes (7–8). 6′,12′-Epoxymyrotoxin A (1) and 7′-hydroxymytoxin B (2) were new macrocyclic trichothecenes, while the other trichothecenes were identified as myrotoxin B (3), myrotoxin D hydrate (4), 2′,3′-epoxymyrothecine A (5), miotoxin A (6), and 2 trichothecenes lacking the macrocyclic lactone system, roridin L-2 (7) and trichoverritone (8). The structures of these mycotoxins were characterized using spectroscopic methods. The absolute configurations of 1 and 2 were determined by NOESY and a comparison of their experimental and calculated ECD spectra. Most of these mycotoxins (1–4 and 6) exhibited highly potent antimalarial activity against Plasmodium falciparum. They also showed strong cytotoxicity towards KB and NCI-H187 cell lines (IC₅₀ 0.60 – 112.28 nM), as well as the Vero cell line (IC₅₀ 1.50 – 46.51 nM).

Key words

Myrothecium roridum - endophyte - trichothecenes - antimalarial activity - cytotoxicity - mycotoxin - Tuberculariaceae

Full Text

References

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