Abstract:Cladosporine A (1), a new indole diterpenoid alkaloid, was isolated from the extract of a fungal strain Cladosporium sp. JNU17DTH12-9-01. Its structure was elucidated by extensive spectroscopic analysis, and the absolute configurations were determined by electronic circular dichroism (ECD) experiments. This is the first report of the presence of indole diterpenoid alkaloid in the genus Cladosporium. The antimicrobial activities against Staphylococcus aureus 209P, Escherichia coli ATCC0111, Aspergillus niger R3… Show more
“…Cladosporium is one of the largest genera of dematiaceous hyphomycetes. The Cladosporium genus has been of interest in recent years because of its ability to produce a variety of bioactive secondary metabolites. − We isolated a series of aspulvinone analogues, including eight new compounds named aspulvins A–H ( 1 – 8 ), from rice cultures of Cladosporium sp. 7951.…”
Eight new aspulvinone analogues, aspulvins A–H
(
1
–
8
) and aspulvinones D, M, O, and R
(
9
–
12
), were isolated from cultures of the endophytic
fungus
Cladosporium
sp. 7951. Detailed spectroscopic analyses were
conducted to determine the structures of the new compounds. All isolates displayed
different degrees of inhibitory activity against the severe acute respiratory syndrome
coronavirus 2 main protease (SARS-CoV-2 M
pro
) at 10 μM. Notably,
compounds
9
,
10
, and
12
showed potential
SARS-CoV-2 M
pro
inhibition with IC
50
values of 10.3 ± 0.6,
9.4 ± 0.6, and 7.7 ± 0.6 μM, respectively. For all compounds except
3
and
4
, the anti-inflammatory activity occurred by
inhibiting the release of lactate dehydrogenase (LDH) with IC
50
values
ranging from 0.7 to 7.4 μM. Compound
10
showed the most potent
anti-inflammatory activity by inhibiting Casp-1 cleavage, IL-1β maturation, NLRP3
inflammasome activation, and pyroptosis. The findings reveal that the aspulvinone
analogues
9
,
10
, and
12
could be promising
candidates for coronavirus disease 2019 (COVID-19) treatment as they inhibit SARS-CoV-2
infection and reduce inflammatory reactions caused by SARS-CoV-2.
“…Cladosporium is one of the largest genera of dematiaceous hyphomycetes. The Cladosporium genus has been of interest in recent years because of its ability to produce a variety of bioactive secondary metabolites. − We isolated a series of aspulvinone analogues, including eight new compounds named aspulvins A–H ( 1 – 8 ), from rice cultures of Cladosporium sp. 7951.…”
Eight new aspulvinone analogues, aspulvins A–H
(
1
–
8
) and aspulvinones D, M, O, and R
(
9
–
12
), were isolated from cultures of the endophytic
fungus
Cladosporium
sp. 7951. Detailed spectroscopic analyses were
conducted to determine the structures of the new compounds. All isolates displayed
different degrees of inhibitory activity against the severe acute respiratory syndrome
coronavirus 2 main protease (SARS-CoV-2 M
pro
) at 10 μM. Notably,
compounds
9
,
10
, and
12
showed potential
SARS-CoV-2 M
pro
inhibition with IC
50
values of 10.3 ± 0.6,
9.4 ± 0.6, and 7.7 ± 0.6 μM, respectively. For all compounds except
3
and
4
, the anti-inflammatory activity occurred by
inhibiting the release of lactate dehydrogenase (LDH) with IC
50
values
ranging from 0.7 to 7.4 μM. Compound
10
showed the most potent
anti-inflammatory activity by inhibiting Casp-1 cleavage, IL-1β maturation, NLRP3
inflammasome activation, and pyroptosis. The findings reveal that the aspulvinone
analogues
9
,
10
, and
12
could be promising
candidates for coronavirus disease 2019 (COVID-19) treatment as they inhibit SARS-CoV-2
infection and reduce inflammatory reactions caused by SARS-CoV-2.
“…Its antimicrobial activity was evaluated against S. aureus and E. coli. Strong antibacterial activity was reported against S. aureus with an MIC value of 4 μg/ml ( Han et al, 2021 ).…”
Section: Resultsmentioning
confidence: 99%
“…Han et al isolated cladosporine A ( 60 ) and tested it for antifungal activity against A. nige r and C. albicans. Potent antifungal activity was observed against C. albicans with an MIC value of 16 μg/ml ( Han et al, 2021 ).…”
Antimicrobial resistance has been posing an alarming threat to the treatment of infectious diseases over the years. Ineffectiveness of the currently available synthetic and semisynthetic antibiotics has led the researchers to discover new molecules with potent antimicrobial activities. To overcome the emerging antimicrobial resistance, new antimicrobial compounds from natural sources might be appropriate. Secondary metabolites from natural sources could be prospective candidates in the development of new antimicrobial agents with high efficacy and less side effects. Among the natural secondary metabolites, diterpenoids are of crucial importance because of their broad spectrum of antimicrobial activity, which has put it in the center of research interest in recent years. The present work is aimed at reviewing recent literature regarding different classes of natural diterpenes and diterpenoids with significant antibacterial, antifungal, antiviral, and antiprotozoal activities along with their reported structure–activity relationships. This review has been carried out with a focus on relevant literature published in the last 5 years following the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) guidelines. A total of 229 diterpenoids from various sources like plants, marine species, and fungi are summarized in this systematic review, including their chemical structures, classification, and significant antimicrobial activities together with their reported mechanism of action and structure–activity relationships. The outcomes herein would provide researchers with new insights to find new credible leads and to work on their synthetic and semisynthetic derivatives to develop new antimicrobial agents.
“…JNU17DTH12-9-01, which was the first report of the existence of IDT in Cladosporium spp. The MIC(minimum inhibitory concentration) of this compound to Staphylococcus aureus 209P and Candida albicans FIM 709 was 4 μg/mL and 16 μg/mL, respectively [ 37 ]. Fig.…”
Indole diterpenoids (IDTs) are an essential class of structurally diverse fungal secondary metabolites, that generally appear to be restricted to a limited number of fungi, such as Penicillium, Aspergillus, Claviceps, and Epichloe species, etc. These compounds share a typical core structure consisting of a cyclic diterpene skeleton of geranylgeranyl diphosphate (GGPP) and an indole ring moiety derived from indole-3-glycerol phosphate (IGP). 3-geranylgeranylindole (3-GGI) is the common precursor of all IDTs. On this basis, it is modified by cyclization, oxidation, and prenylation to generate a large class of compounds with complex structures. These compounds exhibit antibacterial, anti-insect, and ion channel inhibitory activities. We summarized 204 compounds of IDTs discovered from various fungi over the past 50 years, these compounds were reclassified, and their biological activities were summarized. This review will help to understand the structural diversity of IDTs and provide help for their physiological activities.
Graphical Abstract
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