Antifungal activity of Liriodenine from Michelia formosana heartwood against wood-rotting fungi

Abstract

Wood-rotting fungi lead to great economic losses of lignocellulosic materials. The influence of extractives on the decay resistance of Michelia formosana wood and the antifungal activities of heartwood extract and its constituent against wood-rotting fungi were evaluated. Results revealed that extractives had a strong influence on the decay resistance of M. formosana heartwood. The unextracted heartwood block was resistant to fungi, while the extracted heartwood block was not. Antifungal activities of ethanolic extract from heartwood were assessed; results revealed that the ethanolic extract possessed good antifungal activity against wood-rotting fungi. The ethanolic extract was further separated into four fractions including n-hexane-soluble fraction, ethyl acetate-soluble fraction, n-butanol-soluble fraction, and water-soluble fraction. Among these fractions, the n-hexane-soluble fraction exhibited the best antifungal ability. An alkaloid, liriodenine, was isolated from the active n-hexane-soluble fraction. IC 50 values of liriodenine against the white-rot fungi Lenzites betulina and Trametes versicolor were 0.76 and 3.50 lg/mL, respectively. IC 50 values of liriodenine against the brown-rot fungi Laetiporus sulphureus, Gloeophyllum trabeum, and Fomitopsis pinicola were all lower than 2.0 lg/mL. Results indicated that liriodenine exhibited a broad spectrum of antifungal activity and great potential to develop as an environmentally benign fungicide for the preservation of lignocellulosic materials.

Anti-Infective and Anti-Cancer Properties of the Annona Species: Their Ethnomedicinal Uses, Alkaloid Diversity, and Pharmacological Activities

“…Glaucine 68 isolated from the aerial component of Glaucium oxylobum showed moderate skin anti-fungal activities against Microsporum canis, Microsporum gypseum, and Trichophyton mentagrophytes [93]. Antifungal activities of the non-Annona isolated alkaloids were evaluated against non-pathogenic fungi including liriodenine 11 from the wood of Michelia formosa which indicated a low activity against several wood decaying fungi both white and brown rot-fungi, Lenzites betulina, Trametes versicolor, Laetiporus sulphureus, Gloeophyllum trabeum, and Fomitopsis pinicola [94]. Similar alkaloids were also previously evaluated against pathogenic bacteria, including liriodenine from the roots of Zanthoxylum nitidum which showed a good antimicrobial activity against MRSA with MIC value of 93.8 µg/mL [95].…”

Transcriptomic Responses of Phanerochaete chrysosporium to Oak Acetonic Extracts: Focus on a New Glutathione Transferase

“…Moreover, some highly reactive wood compounds (known as extractives) are released primarily during wood degradation processes. Some studies have reported the toxicity and antifungal activity of these molecules (4)(5)(6)(7). This suggests that during wood degradation, fungal cells are under oxidative stress.…”

The Constituents of Michelia compressa var. formosana and Their Bioactivities

“…formosana is an evergreen tree mainly distributed in Taiwan, Japan, and Ryukyu Islands [1]. In the previous literature, its heartwood exhibited high resistance against rots due to the presence of liriodenine [6]. The chemical investigations of leaves [5,7], barks [8], root barks [2], root wood [4], heartwood [9,10], stems [11], and pericarps [12] have been reported, but the anti-inflammatory and cytotoxic properties of constituents from heartwood are not known.…”

“…In addition, the extract of Michelia champaca leaves has also exhibited an anti-inflammatory activity in pro-inflammatory conditions [ 3 ]. Moreover, the aporphine alkaloid and sesquiterpene lactone constituents of this genus have caused a great interest due to their diverse structures and significant biological activities [ 2 , 3 , 4 , 5 , 6 ].…”