Insights into Ergochromes of the Plant Pathogen Claviceps purpurea

Abstract

Claviceps purpurea is an ergot fungus known for its neurotropic alkaloids, which have been identified as the main cause of ergotism, a livestock and human disease triggered by ergot consumption. Tetrahydroxanthone dimers, the so-called ergopigments, presumably also contribute to this toxic effect. Overexpression of the cluster-specific transcription factor responsible for the formation of these pigments in C. purpurea led to the isolation of three new metabolites (8−10). The new pigments were characterized utilizing HRMS, NMR techniques, and CD spectroscopy and shown to be xanthone dimers. Secalonic acid A and its 2,4′-and 4,4′-linked isomers were also isolated, and their absolute configuration was investigated. The contribution of secalonic acid A, its isomers, and new metabolites to the toxicity of C. purpurea was investigated in HepG2 and CCF-STTG1 cells. Along with cytotoxic properties, secalonic acid A was found to inhibit topoisomerase I and II activity.

Secalonic Acid and Benzoic Acid Analogues Exhibiting Cyto toxicity against Cancer Cells Isolated from <i>Claviceps yanagawaensis</i>

“…Compound 2 is similar to 1 and estimated to have the same 5S, 6R, 10aR, 5'S, 6'R, and 10a'S configuration based on NMR and CD spectra. Secalonic acid analogues with a lactone ring have been reported, including ergoflavin, ergochrysin A, and ergochrysin B, and secalonic acid analogues with a lactone ring and hydroxy group attached at the 8-position, as in 2, were isolated from Claviceps by Lünne et al [17]. Lactone cyclization of ergoflavin, ergochrysin A, and ergochrysin B is predicted to proceed via the addition of H 2 O to the 8-8a olefin and condensation of the hydroxy group at the 8-position with the carboxymethyl group at the 10a-position (Figure S19) [25] [26].…”

Mycotherapy: Potential of Fungal Bioactives for the Treatment of Mental Health Disorders and Morbidities of Chronic Pain

“…Such effects, however, are deemed low risk, uncommon and mostly associated with recreational use [ 107 ]. Additionally, secalonic acid A and its isomers are also found in Claviceps purpurea which has anti-cancer activity via topoisomerase I and II inhibition [ 108 ].…”

ERGOT Claviceps purpurea (Fries) Tulasne ALKALOID DIVERSITY AND VIRULENCE: EVOLUTION, GENETIC DIVERSIFICATION, AND METABOLIC ENGINEERING (review)

“…Таким образом, на сорвеменном этапе исследований C. purpureaэто, с одной стороны, важнейший продуцент большого количества биологически активных соединений (алкалоидов) и уникальная модель системы паразит-хозяин (218)(219)(220)(221), с другой -патоген, наносящий значительный экономический ущерб производителям зерна, кормовой и животноводческой отрасли по всему миру (222,223). В то время как медицинские и биотехнологические исследования сосредоточены на положительных эффектах алкалоидов (224) и других вторичных метаболитов спорыньи и особенностях их получения (224)(225)(226)(227)(228), в растениеводстве, животноводстве и пищевой промышленности опасность эргоалкалоидов остается острой и вызывающей беспокойство общемировой проблемой (229)(230)(231)(232).…”