Discovery and Total Synthesis of a New Class of Minor Immunosuppressive Plant Sesterterpenoids.

Plant sesterterpenoids are an extremely rare family of natural products that generally possess novel chemical structures and diverse biological activities. Herein, we report the discovery of an unprecedented group of minor plant sesterterpenoids, gracilisoids B-E (2-5), which feature two types of highly functionalized bicyclo[3.2.

Immunosuppressive and Adipogenesis Inhibitory Sesterterpenoids with a Macrocyclic Ether System from .

Eurysoloids A () and B (), two novel diastereomeric sesterterpenoids possessing a pentacyclic 5/6/5/10/5 framework with an unusual macrocyclic ether system, were isolated from Prain. Their structures were unambiguously determined by spectroscopic, single-crystal X-ray diffraction and DP4+ analyses. A plausible biosynthetic pathway for compounds and was proposed.

Novel Polyketide-Terpenoid Hybrid Metabolites from a Potent Nematicidal Mutant Δ.

Here, we reported that detailed investigation on trace targeted metabolites from nematode-trapping fungus mutant with deletion of P450 gene led to isolation of 9 new polyketide-terpenoid hybrid derivatives, including four new glycosides of the key precursor farnesyl hydrotoluquinol () and, surprisingly, four new sesquiterpenyl epoxy-cyclohexenoids (SECs) analogues. Among them, two major target metabolites and displayed moderate nematode inhibitory ability. Moreover, the mutant lacking could form far more nematode-capturing traps within 6 h in contact with nematodes and show rapid potent nematicidal activity with killing 93.

Leucosceptroid B from glandular trichomes of Leucosceptrum canum reduces fat accumulation in Caenorhabditis elegans through suppressing unsaturated fatty acid biosynthesis.

Obesity that is highly associated with numerous metabolic diseases has become a global health issue nowdays. Plant sesterterpenoids are an important group of natural products with great potential; thus, their bioactivities deserve extensive exploration. RNA-seq analysis indicated that leucosceptroid B, a sesterterpenoid previously discovered from the glandular trichomes of Leucosceptrum canum, significantly regulated the expression of 10 genes involved in lipid metabolism in Caenorhabditis elegans.

Selected Mutations Revealed Intermediates and Key Precursors in the Biosynthesis of Polyketide-Terpenoid Hybrid Sesquiterpenyl Epoxy-cyclohexenoids.

Sesquiterpenyl epoxy-cyclohexenoids (SECs) show impressive biological activities. However, the key pathways for SECs still remain unambiguous. Unexpectedly, 11 new SECs and derivatives with diverse oxidation patterns were isolated after the deletion of gene 274.