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Review
. 2021 Dec 22:12:766440.
doi: 10.3389/fmicb.2021.766440. eCollection 2021.

Duclauxin Derivatives From Fungi and Their Biological Activities

Hamza Shahid  1 , Teng Cai  1 , Yuyang Wang  1 , Caiqing Zheng  1 , Yuting Yang  1 , Ziling Mao  1 , Ping Ding  2 , Tijiang Shan  1
Affiliations
Review

Duclauxin Derivatives From Fungi and Their Biological Activities

Hamza Shahid et al. Front Microbiol. .

Abstract

Duclauxin is a heptacyclic oligophenalenone dimer consisting of an isocoumarin and a dihydroisocoumarin unit. These two tricyclic moieties are joined by a cyclopentane ring to form a unique hinge or castanets-like structure. Duclauxin is effective against numerous tumor cell lines because it prevents adenosine triphosphate (ATP) synthesis by inhibiting mitochondrial respiration. There are about 36 reported natural duclauxin analogs mainly produced by 9 Penicillium and Talaromyces species (T. duclauxii, T. aculeatus, T. stipitatus, T. bacillisporus, T. verruculosus, T. macrosporus, P. herquei, P. manginii, and Talaromyces sp.). These metabolites exhibit remarkable biological activities, including antitumor, enzyme inhibition, and antimicrobial, showing tremendous potential in agricultural and medical applications. This review highlights the chemical structures and biological activities of fungal duclauxins, together with biosynthesis, absolute configuration, and mode of action for important duclauxins. Furthermore, phylogenetic analysis and correct names of Penicillium and Talaromyces species producing duclauxins are presented in this review.

Keywords: biological activities; biosynthesis; duclauxin derivatives; fungi; secondary metabolites.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
Structural representation of duclauxin (1).
FIGURE 2
FIGURE 2
Phylogenetic tree of Penicillium and Talaromyces species regarding duclauxins, based on the rDNA-ITS sequence obtained from the NCBI database. The tree was constructed with the maximum likelihood method in MEGA 7.0 using default parameters, and bootstrap values were calculated after 1,000 replications. The previous or invalid species name is presented with red color between the parenthesis.
FIGURE 3
FIGURE 3
Structural representation of heptacyclic duclauxin derivatives.
FIGURE 4
FIGURE 4
Structural representation of octal- and nona-cyclic duclauxin derivatives.
FIGURE 5
FIGURE 5
Structural representation of N-containing duclauxin derivatives.
FIGURE 6
FIGURE 6
Structural representation of asymmetrical duclauxin derivatives.
FIGURE 7
FIGURE 7
Distribution of biological activities of duclauxin derivatives.
FIGURE 8
FIGURE 8
Acetylcholinesterase (AChE) is an enzyme that catalyzes acetylcholine into choline and acetate, resulting in the termination of synaptic transmission, responsible for Alzheimer’s disease. AChE is an enzymatic target for the treatment of Alzheimer’s disease. It has been shown in Figure 7 that the compound named talaromycesone A (16) inhibited the enzyme AChE from breaking down acetylcholine into choline and acetate.
FIGURE 9
FIGURE 9
Proposed biosynthetic pathway of duclauxin (1) and its derivatives.
See this image and copyright information in PMC

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