This review covers the isolation, structural determination, biological activities and biomimetic synthesis of all natural dimeric sesquiterpenoids, along with a detailed discussion of the biogenesis of these metabolites. Syntheses leading to the revision of structures have also been included, and 368 references are cited.

Biotransformation of huperzine A (hupA) by a fungal endophyte, Ceriporia lacerate HS-ZJUT-C13A, afforded compounds 1-5 and three tremulane sesquiterpenoids, 6-8. Huptremules A-D (1-4) feature unusual sesquiterpenoid-alkaloid hybrid structures that integrate the characteristics of fungal metabolites (tremulane sesquiterpenoids) and the exogenous substrate (hupA). These results support the use of fungal endophytes as biocatalysts for the biotransformation of natural products, particularly those originating from the host plant.

A highly reducing polyketide synthase gene cluster from the Magnaporthe oryzae genome was previously identified to produce phytotoxic compounds including pyriculol. A homologous gene cluster was found in Neurospora crassa through bioinformatics analysis. Heterologous expression of this cluster led to the production of salicylic aldehyde sordarial and related intermediates. A series of combinatorial gene expression experiments established the set of genes required to produce sordarial, and the likely biosynthetic pathway.

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Two new bergamotane sesquiterpene lactones, named expansolides C and D (1 and 2), together with two known compounds expansolides A and B (3 and 4), were isolated from the plant pathogenic fungus Penicillium expansum ACCC37275. The structures of the new compounds were established by detailed analyses of the spectroscopic data, especially 1D-, 2D-NMR, and HR-ESI-MS. In an in vitro bioassay, the epimeric mixture of expansolides C and D (1 and 2) (in a ratio of 2:1 at the temprature of the bioassay) exhibited more potent α-glucosidase inhibitory activity (IC =0.50 ± 0.02 mm) as compared with the positive control acarbose (IC = 1.90 ± 0.05 mm). To the best of our knowledge, it was the first report on the α-glucosidase inhibitory activity of bergamotane sesquiterpenes.