Santalane-type sesquiterpenoids and isobenzofuranones from cultures of Paraconiothyrium sporulosum YK-03

• Published in: Phytochemistry (Oxford) Vol. 211; p. 113691
• Main Authors: Zhang, Li-Hua, Gao, Wen-Ke, Li, Shi-Wei, Song, Xiao-Yan, Wu, Hong-Hua, Wang, Hai-Feng, Chen, Gang, Wang, Shao-Xia, Pei, Yue-Hu
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.07.2023; Elsevier
• Subjects: Anti-neuroinflammatory activity; Ascomycota - chemistry; Biochemistry & Molecular Biology; Isobenzofuranone; Leptosphaeriaceae; Life Sciences & Biomedicine; Marine mud-associated fungus; Molecular Structure; Paraconiothyrium sporulosum; Plant Sciences; Santalane-type sesquiterpenoid; Science & Technology; Sesquiterpenes - chemistry; Spectrum Analysis; Paraconiothyrium sporulosum; Marine mud-associated fungus; Leptosphaeriaceae; Santalane-type sesquiterpenoid; Isobenzofuranone; Anti-neuroinflammatory activity; INSECT-ASSOCIATED FUNGUS; METABOLITES; Marine mud -associated fungus; DITERPENOIDS; CLEISTANTHANE; DERIVATIVES; CASSANE
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2023.113691

Three undescribed santalane-type sesquiterpenoids (parasantalenoic acids A−C) and two undescribed epimeric isobenzofuranones (paraphthalides A and B) were isolated from cultures of the marine mud-associated fungus Paraconiothyrium sporulosum YK-03. Their structures were elucidated by analysis of the extensive spectroscopic and crystal X-ray diffraction data, combined with ECD calculations and comparison. Santalane-type sesquiterpenoids have been firstly found in the Paraconiothyrium species. Parasantalenoic acids A−C represent three rare polyhydroxylated santalane-type sesquiterpenoid carboxylic acids, and parasantalenoic acid A represents the first example of 2-chlorinated santalane-type sesquiterpenoid. A plausible biosynthetic pathway for parasantalenoic acids A−C was proposed. Additionally, the anti-neuroinflammatory activities of parasantalenoic acids A−C were investigated by evaluating their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated BV-2 microglia cells. Among them, parasantalenoic acid C showed significant anti-neuroinflammatory activity with an inhibition of 86.45 ± 2.45% at 10 μM. Three undescribed santalane-type sesquiterpenoids and two undescribed epimeric isobenzofuranones were isolated from cultures of Paraconiothyrium sporulosum YK-03, and the inhibitory effects of three undescribed santalane-type sesquiterpenoids on nitric oxide (NO) production in lipopolysaccharide-stimulated BV-2 cells were reported. [Display omitted] •Three undescribed santalanes and two undescribed isobenzofuranones were isolated.•Santalane sesquiterpenoids have been firstly found in Paraconiothyrium species.•Three rare polyhydroxylated santalane-type sesquiterpene carboxylic acids are reported.•Parasantalenoic acid A represents the first example of 2-chlorinated santalane.•The anti-neuroinflammatory activity of santalanes is firstly reported.