Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2014 Apr 22;19(4):5088-108.
doi: 10.3390/molecules19045088.

Natural dibenzo-α-pyrones and their bioactivities

Ziling Mao  1 , Weibo Sun  1 , Linyun Fu  1 , Haiyu Luo  1 , Daowan Lai  1 , Ligang Zhou  2
Affiliations
Review

Natural dibenzo-α-pyrones and their bioactivities

Ziling Mao et al. Molecules. .

Abstract

Natural dibenzo-α-pyrones are an important group of metabolites derived from fungi, mycobionts, plants and animal feces. They exhibit a variety of biological activities such as toxicity on human and animals, phytotoxicity as well as cytotoxic, antioxidant, antiallergic, antimicrobial, antinematodal, and acetylcholinesterase inhibitory properties. Dibenzo-α-pyrones are biosynthesized via the polyketide pathway in microorganisms or metabolized from plant-derived ellagitannins and ellagic acid by intestinal bacteria. At least 53 dibenzo-α-pyrones have been reported in the past few decades. This mini-review aims to briefly summarize the occurrence, biosynthesis, biotransformation, as well as their biological activities and functions. Some considerations related to synthesis, production and applications of dibenzo-α-pyrones are also discussed.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The basic skeleton of dibenzo-α-pyrones.
Figure 2
Figure 2
Structures of dibenzo-α-pyrones isolated from fungi.
Figure 2
Figure 2
Structures of dibenzo-α-pyrones isolated from fungi.
Figure 3
Figure 3
Dibenzo-α-pyrones produced by transformation of intestinal bacteria.
Figure 4
Figure 4
Structures of the dibenzo-α-pyrones from plants.
Figure 5
Figure 5
The structure of murayalactone (53).
Scheme 1
Scheme 1
Proposed transformation from ellagic acid to urolithins by intestinal bacteria [6,7,63].
Scheme 2
Scheme 2
Biosynthetic pathways of graphislactones in the cultured lichen mycobionts [3].
Scheme 3
Scheme 3
Hypothetical biosynthetic pathways of alternariol (10) and its derivatives (11, 14) in an endophytic fungus from Datura stramonium [25].
See this image and copyright information in PMC

References

    1. Lou J., Fu L., Peng Y., Zhou L. Metabolites from Alternaria fungi and their bioactivities. Molecules. 2013;18:5891–5935. doi: 10.3390/molecules18055891. - DOI - PMC - PubMed
    1. Tanahashi T., Kuroishi M., Kuwahara A., Nagakura N., Hamada N. Four phenolics from the cultured lichen mycobiont of Graphis scripta var. pulverulenta. Chem. Pharm. Bull. 1997;45:1183–1185. doi: 10.1248/cpb.45.1183. - DOI
    1. Tanahashi T., Takenaka Y., Nagakura N., Hamada N. 6H-Dibenzo[b,d]pyran-6-one derivatives from the cultured lichen mycobionts of Graphis spp. and their biosynthetic origin. Phytochemistry. 2003;62:71–75. doi: 10.1016/S0031-9422(02)00402-8. - DOI - PubMed
    1. Shirataki Y., Toda S. Antioxidative effects of dibenzo-α-pyrones in fruits of Trapa natans on lipid peroxidation. Nat. Med. 2001;55:247–250.
    1. Liang D., Luo H., Liu Y.-F., Hao Z.-Y., Wang Y., Zhang C.-L., Zhang Q.-J., Chen R.-Y., Yu D.-Q. Lysilactones A-C, three 6H-dibenzo[b,d]pyran-6-one glycosides from Lysimachia clethroides, total synthesis of lysilactone A. Tetrahedron. 2013;69:2093–2097. doi: 10.1016/j.tet.2013.01.029. - DOI

Publication types

MeSH terms