Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Abstract

Cadinane-type sesquiterpenes have a wide spectrum of biological activity, but their use as wood preservatives and the structure-activity relationships of their derivatives have not yet been reported. A total of 13 compounds were synthesized from T-cadinol, T-muurolol, and a-cadinol and their chemical structures were confirmed by IR, MS, and 1 H and 13 C NMR. The antifungal properties of 16 compounds against three wood-decay fungi were evaluated in vitro. a-Cadinol showed strong antifungal activity against Lenzites betulina, Trametes versicolor, and Laetiporus sulphureus (total mean IC 50 0.10 mM). Among the derivatives synthesized, 3b-ethoxy-T-muurolol (0.24 mM), 4jH-cadinan-10b-ol (0.25 mM), 4jH-muurolan-10b-ol (0.29 mM), and 4jH-cadinan-10a-ol (0.25 mM) showed good antifungal activity against all fungi tested. Correlation was observed between the antifungal activity of the compounds tested and log P. Furthermore, the presence of an unsaturated double bond and oxygen-containing functional groups in the compounds plays a key role in their antifungal activity. The stereo configuration of cadinane-type sesquiterpenes also influences their antifungal activity. Understanding how the structure of natural compounds relates to their antifungal function is important and may facilitate their application as novel wood preservatives.

Antitermitic and antifungal activities of eugenol and its congeners from the flower buds of Syzgium aromaticum (clove)

“…The genera Trametes, Lenzites, and Laetiporus, belong to basidiomycete class, are recognized worldwide as major wood decay fungi (Wu et al, 2005). According to the survey of previous years, tremendous economic and resource losses were caused by fungi and termites in wood biodegradation.…”

Sub-lethal concentrations of Colombian Austroeupatorium inulifolium (H.B.K.) essential oil and its effect on fungal growth and the production of enzymes

“…Also the antifungal activity of cadinene sesquiterpenes against Sclerotium rolfsii ITCC 5313, Rizhoctonia solani ITCC 1742, F. oxysporum ITCC 5365, Macrophomina phaseolina ITCC 5143, has been reported in previous studies (Kundu et al, 2013). In a study conducted by Wu et al (2005), a potential relationship between the chemical structure and the experimentally determined antifungal activity of the cadinenetype sesquiterpene compounds has been demostrated.…”

Functional Characterization of TvCyt2, a Member of the p450 Monooxygenases From Trichoderma virens Relevant During the Association With Plants and Mycoparasitism

“…Several studies have demonstrated the properties of sesquiterpenes; their oxygenated forms have a wide spectrum of biological activities, participating as inducers of plant defense mechanisms as well as important antimicrobial properties. This activity has been related with the presence of one or both an unsaturated double bond or oxygen-containing functional group (Kramer and Abraham 2012;Petrelli et al 2016;Wu et al 2005). In plant-microbe associations, sesquiterpenes are crucial for the establishment of the interaction, an example is when Laccaria bicolor interacts with Populus or Arabidopsis plants (Ditengou et al 2015), highlighting the relevance of secondary metabolites in biological interactions.…”