Two New Diterpenoids from Biscogniauxia sp. and Their Activities

Abstract

Two new diterpenoids, including a seco-isopimarane type (1) and an abietane type (2), were isolated from Biscogniauxia sp. (71-10-1-1). Their structures, including absolute configurations, were elucidated by NMR spectroscopic analyses, X-ray crystallography, 13C chemical shifts calculations, and ECD calculations. This is the first report of diterpenoids from Biscogniauxia sp. Furthermore, short-term memory enhancement against Alzheimer’s disease (AD), anti-inflammatory, and cytotoxic activities of 1–2 were also evaluated. The results showed that compound 1 exhibited short-term memory enhancement activity against AD.

Secondary Metabolites of Biscogniauxia: Distribution, Chemical Diversity, Bioactivity, and Implications of the Occurrence

“…(No. 71-10-1-1) [ 19 ]. Subsequently, diterpenoids are natural compounds with a C-20 carbon skeleton that are chemically heterogeneous.…”

“…The content of mellein in Biscogniauxia is higher than that of isocoumarins; namely, 16 compounds were successfully isolated, as shown in Figure 4. One new dihydroisocoumarin (3S)-5-hydroxy-8-O-methylmellein ( 16), along with the other 3 mellein compounds 5-hydroxymethylmellein ( 17), 5-formylmellein (18), and mellein-5-carboxylic acid (19), was isolated from the n-BuOH soluble fraction of 70% EtOH extract of rice fermented with the endophytic fungus B. cylindrospora (BCRC 33717) [15]. Mellein compounds have also been isolated from B. rosacearum oak strain IRAN 4194C and are important for producer organisms and included in many biological activities, including phytotoxicity.…”

“…Three steroid compounds were also isolated from B. cylindrospora, namely 3β-hydroxystigmast-5-en-7-one (67), which was produced in rice from B. cylindrospora BCRC 33717, then extracted three times with 70% EtOH at room temperature [15] and two steroids, β-sitostenone (68) and β-sitosterol (69), in the EtOAc soluble fraction of B. cylindrospora BCRC 33717 [4] (Figure 17). [19]. Subsequently, diterpenoids are natural compounds with a C-20 carbon skeleton that are chemically heterogeneous.…”

Endophytic fungus Biscogniauxia petrensis produces antibacterial substances

“…The genus Biscogniauxia belongs to the fungal family Graphostromataceae , and its species have been found mainly as pathogens in dicotyledonous plants worldwide ( Evidente et al, 2005 ; Daranagama et al, 2018 ). Currently, numerous monomers with impressive chemical structures showing bioactivities of glycogen synthase kinase-inhibitory, acetylcholinesterase-inhibitory, anti-pathogenic fungi, anti-tumour and anti-Alzheimer’s disease (AD) activities, such as Isopyrrolonaphthoquinone, Biscogniphthalide, Eudesmanolide,Biscognienyne C, Biscognienyne D, Biscognienyne F and Dimericbiscognienyne A, have been isolated from this genus ( Wu et al, 2016 ; Nguyen et al, 2018 ; Liu et al, 2019 ; Zhao et al, 2017 , 2021a ). However, there are few reports on the antibacterial activity of the Biscogniauxia petrensis .…”