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Review
. 2023 Apr 19:4:1088966.
doi: 10.3389/ffunb.2023.1088966. eCollection 2023.

Tridepsides as potential bioactives: a review on their chemistry and the global distribution of their lichenic and non-lichenic natural sources

Hooman Norouzi  1 , Mohammad Sohrabi  2 , Masoud Yousefi  3 , Joel Boustie  4
Affiliations
Review

Tridepsides as potential bioactives: a review on their chemistry and the global distribution of their lichenic and non-lichenic natural sources

Hooman Norouzi et al. Front Fungal Biol. .

Abstract

Tridepsides, as fully oxidized polyketides, have been known to exist in lichens for more than a century. Recent studies have showed that these possible defensive lichenochemicals possess various biological activities. Also, a candidate biosynthetic gene cluster was recently reported for gyrophoric acid (GA), an important tridepside. The present study focused on biosynthesis, natural sources, biological activities, and bioanalytical methods of tridepside molecules. Our survey shows that, so far, lichenic tridepsides have been reported from 37 families, 111 genera, and 526 species of lichen. Because many of their species contain tridepsides, the families Parmeliaceae, Lobariaceae, and Peltigeraceae can be considered critical lichenic sources of tridepsides. Furthermore, several species of Hypotrachyna in Parmeliaceae family showed lichenic tridepsides, suggesting that this genus is a viable source of tridepsides. This research also explored tridepsides from non-lichenic sources, such as non-lichenized fungi, lichenicolous fungi, endophytes, parasites, and liverworts, which offer substantial potential as biotechnological sources to produce tridepsides, which are produced in small amounts in lichen thalli. Two lichenic tridepsides have also been detected in non-lichenic sources: GA and tenuiorin (TE). Additionally, no significant correlation was found between tridepside biosynthesis and geographical distribution patterns for several potentially tridepside-producing lichens. We further showed that GA is the most studied tridepside with various reported biological activities, including anticancer, wound healing, photoprotection, anti-aging, antioxidant, cardiovascular effect, DNA interaction, anti-diabetes, anti-Alzheimer's, anti-bacterial, and antifungal. Last but not least, this study provides an overview of some bioanalytical methods used to analyze tridepsides over the past few years.

Keywords: biome-based distribution; global distribution; gyrophoric acid; lichenic tridepsides; lichenochemicals; non-lichenic tridepsides.

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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
Deduced biosynthetic pathway of some of the common lichenic tridepsides. SAT, starter acetyltransferase; KS, ketosynthase; AT, acyltransferase; PT, product template domain; ACP1, acyl carrier protein 1, ACP2: acyl carrier protein 2; TE, thioesterase).
Figure 2
Figure 2
Chemical structure of common lichenic tridepsides and their derivatives.
Figure 3
Figure 3
Lichen species frequency; (A) Family-based frequency of tridepside-producing lichen species reported in this study; (B) Frequency of tridepside-producing lichen species based on their detected tridepside; total number of tridepside-producing lichen species that we could find in the literature was 526; (Tridepsides’ abbreviations → GA: Gyrophoric acid/MGA: Methylgyrophoric acid/TE: Tenuiorin/5-O-MHA: 5-O-methylhiascic acid/HA: Hiascic acid/4-O-MGA: 4-O-methylgyrophoric acid/UA: Umbilicaric acid/4,5-O-MHA: 4,5-di-O-methylhiascic acid/OA: Ovoic acid/3M-2,4-O-MGA: 3-methoxy-2,4-di-O-methylgyrophoric acid/2,4-O-MGA: 2,4-di-O-methylgyrophoric acid/2-O-ATE: 2-O-acetyltenuiorin/LA: Lasallic acid/CA: Crustinic acid/MHA: Methylhiascic acid/DA: Deliseic acid/2,4,5-O-MGA: 2,4,5-tri-O-methylhiascic acid/2-O-MGA: 2-O-methylgyrophoric acid/2”-O-MGA: 2”-O-methylgyrophoric acid/TA: Trivaric acid/Dep C: depsidellin C/Dep B: depsidellin B/Dep A: depsidellin A/2”-O-MTE: 2”-O-methyltenuiorin/2’-O-MTE: 2’-O-methyltenuiorin/2’, 2”-O-MTE: 2’,2”-di-O-methyltenuiorin/3-HUA: 3-hydroxyumbilicaric acid/3MUA; 3-methoxyumbilicaric acid/2”-O-MHA: 2’’-O-methylhiascic acid/4-O-MHA: 4-O-methylhiascic acid/2’-O-MHA: 2’-O-Methylhiascic acid/2-O-MHA: 2-O-methylhiascic acid/3-HGA: 3-hydroxygyrophoric acid/2, 2’-O-MGA: 2,2’-di-O-methylgyrophoric acid/4,2”-O-MGA: 4,2”-di-O-methylgyrophoric acid).
Figure 4
Figure 4
Heatplot of tridepside-producing lichen families. The plot shows the presence of different tridepsides in various lichen families (tridepsides’ abbreviations correspond to those of Figure 3 caption).
Figure 5
Figure 5
Global distribution of tridepside-containing lichen species based on the occurrence data from ALA, GBIF, BioCollecions, iNaturalists, and BISON databases.
Figure 6
Figure 6
Biome-based occurrence of tridepside-containing lichen species; each bar represents the percentage of geographical occurrence of one lichen species in different biomes defined by Olson et al. (2001); Updated scientiitalic>fic names from Mycobank are shown here as updated name (= synonymy): Melanelixia fuliginosa (=Melanelia fuliginosa); Melanelixia subaurifera (=Melanelia subaurifera); Parmotrema tinctorum (=Parmelia tinctorum).
Figure 7
Figure 7
Chemical structures of reported non-lichenic tridepsides.
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