Sesquiterpene Glycosides from Cosmospora joca

Abstract

Five novel sesquiterpene glycosides, namely, cosmosporasides A-E (1-5), were isolated from the ethyl acetate extract of the fermented broth of Cosmospora joca. The structures of 1-5 were elucidated on the basis of spectroscopic data analyses, monosaccharide composition analyses, and monosaccharide chirality analyses. The relative configuration of the sesquiterpene moiety of 3-5 was determined by J-based configuration analyses and supported by NOESY assignments. The inhibitory effects of 1-5 on the nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW264.7 cells were evaluated; all except 3 inhibited NO production at 100 μM. 4 was the most potent, with an average maximum inhibition and a median inhibitory concentration value of 71.70 ± 1.23% and 65.98 ± 0.53 μM, respectively.

Antifungal Long-Chain Alkenyl Sulphates Isolated from Culture Broths of the Fungus Chaetopsina sp.

“…Although no molecules have been so far isolated from Chaetopsina sp., examples of several antifungal agents isolated from Cosmospora sp. or others anamorphs of this genus belonging to Fusarium species exist, such as the cosmosporasides [5] or the parnafungins [6]. In this report, we describe the fermentation, isolation, purification, and structural elucidation of three longchain alkenyl sulphates (▶ Fig.…”

Biosynthesis of Cosmosporasides Reveals the Assembly Line for Fungal Hybrid Terpenoid Saccharides

“…Regarding the terpene hybrid compounds, apart from the abovementioned TKs and TPs, a third important and growing family is terpenoid saccharides (TSs), some of which exhibit significant biomedical and agricultural activities [4] . In comparison with TKs and TPs, the TS family compounds have more variable hybrid combination modes; these are mainly classified into four types, examples of which are shown in Figure 1 and Figure S2: 1) cyclic terpenoid–cyclic saccharide (cT‐cS), an unmodified monosaccharide linked with a polycyclic terpenoid backbone; [4c,d] 2) linear terpenoid–cyclic saccharide (lT‐cS), a monosaccharide attached to a linear simple terpenoid derivative backbone; [4f,g] 3) cyclic terpenoid–linear saccharide polyol (cT‐lSP), a monocyclic or dicyclic terpenoid scaffold linked with a saccharide polyol moiety; [4a,h] and 4) linear terpenoid–linear saccharide polyol (lT‐lSP), a linear terpenoid moiety linked with a saccharide polyol, [4b,e] which is the rarest combination of TS natural products.…”

Description and analysis of glycosidic residues in the largest open natural products database

“…Examples of NP with circular and linear sugar moieties. (a) 6-C-Glucopyranosylpilloin (COCONUT ID CNP0256263), a flavonoid structure with a cyclic sugar moiety (in blue) attached [24]; (b) Moriniafungin F (CNP0174070), a sordarin derivate where the sugar cycle (in blue) forms a spiro ring system with the adjacent cycle (spiro atom marked in red)[25]; (c) Cosmosporaside A (CNP0357595), a sesquiterpene glycoside with a linear sugar moiety (in blue)[26]; (d) Lavaudioside B (CNP0083726), an iridoid glycoside having both a linear (in blue) and a circular (in red) glycosidic moiety [27]. …”