Abstract
New bioactive 13-epi-neoverrucosane diterpenoid, 5β-acetoxy-13-epi-neoverrucosanic acid (1) along with three known secondary metabolites, 13-epi-neoverrucosan-5β-ol (2), chelodane (3) and (E)-β-farnesene (4) were isolated from the MeOH extract of east Malaysia’s liverwort Pleurozia subinflata. The chemical structure of new compound was elucidated by the analyses of its spectroscopic data (FTIR, NMR and HR-ESI-MS). These epi-neoverrucosane-type compounds seem to be notable chemosystematic markers for P. subinflata in Borneo. Compound 3 was widespread in marine sponges however this is the first record for 3 to be found in liverwort. These metabolites were tested for their antifungal potentials against selected fungi from the marine environment. Compound 1 exhibited effective antifungal activity against Lagenidium thermophilum.Graphic
Highlights
Liverworts are the largest group of pioneering land plants which arose during the adaptation of plants from marine to terrestrial environment [1]
The latest epi-neoverrucosane analog was reported in 2013 [14]. We report yet another new epi-neoverrucosane diterpenoid, 5β-acetoxy-13-epi-neoverrucosanic acid (1) was isolated, along with three known secondary metabolites, 13-epi-neoverrucosan-5β-ol (2), chelodane (3) and (E)-βfarnesene (4) from east Malaysia’s liverwort Pleurozia subinflata (Fig. 1)
Compound 1 was isolated as colorless oil and analyzed for the molecular formula C 22H34O4 by HR-ESI-MS [M − H]− ion at m/z 361.2391
Summary
Liverworts are the largest group of pioneering land plants which arose during the adaptation of plants from marine to terrestrial environment [1]. They produced terpenoids and/ or aromatic compounds as their major lipophilic constituents [2,3,4,5]. Many types of sesquiterpenoids from liverworts are the enantiomer to those metabolites from higher plants [6] While, diterpenoids such as clerodanes, dolabellanes, fusicoccanes, kauranes, labdanes, pimaranes and others were found in numerous liverworts [6]. First verrucosane diterpenoid was isolated from Mylia verrucosa [10] Later, some analogs such as neoverrucosane-, homoverrucosane-, epi-neoverrucosane- and epi-homoverrucosane-type were reported [11,12,13]. Our research examined the antifungal effects of the four isolated compounds against selected fungi separated marine organisms
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