Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Anoumedem, Elodie Gisèle M.; Mountessou, Bel Youssouf G.; Kouam, Siméon F.; Narmani, Abolfazl; Surup, Frank

doi:10.3390/antibiotics9110753

Cited by 15 publications

(24 citation statements)

References 29 publications

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“…was the first discovered member of the so-called 3-decalinoyltetramic acid family from fungi [ 20 ]. This was followed by other compounds, including altersetin [ 21 ], ophiosetin [ 22 ], simplicone B [ 23 ], and oxaleimide A [ 24 ]. Fungal tetramic acids are commonly synthesized from hybrid polyketide synthases (PKS) and non-ribosomal peptide synthetases (NRPS) [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372

et al. 2021

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Submerged mycelial cultures of the ascomycete Colpoma quercinum CCTU A372 were found to produce five previously undescribed tetramic acids, for which we propose the trivial names colposetins A–C (1–3) and colpomenoic acids A and B (4 and 5), along with the known compounds penicillide (6) and monodictyphenone (7). The planar structures of 1–5 were determined by high-resolution electrospray ionization mass spectrometry (HR-ESIMS) and extensive 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. Their absolute configurations were determined by the combination of electronic circular dischroism (ECD) analysis, J-based configurational analysis, and a rotating-frame Overhauser effect spectroscopy (ROESY) experiment. Colposetin B displayed weak antimicrobial activity against Bacillus subtilis and Mucor hiemalis (MIC 67 µg/mL).

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Section: Resultsmentioning

confidence: 99%

Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372

et al. 2021

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“…and Diels) Chatrou in the Cameroon region. Compounds 29-30 showed weak cytotoxic activities against the KB3.1 cell line, with IC 50 values of 1.25 µg/mL and 2.29 µg/mL, respectively, but had no antimicrobial activity against the tested bacteria (Staphylococcus aureus DSM 346 and Bacillus subtilis DSM 10) [46]. 5R-hydroxyrecifeiolide 31 (Figure 4), 5S-hydroxyrecifeiolide 32 (Figure 4), and ent-cladospolide F-H 33-35 (Figure 4) were also isolated from the endophytic fungal strain Cladosporium cladosporioides MA-299, which was obtained from the leaves of the mangrove plant Bruguiera gymnorrhiza from Hainan Island, China.…”

Section: Other Polyketidesmentioning

confidence: 99%

Endophytic Fungi: An Effective Alternative Source of Plant-Derived Bioactive Compounds for Pharmacological Studies

Wen

Okyere

Wang

et al. 2022

JoF

110

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Plant-associated fungi (endophytic fungi) are a biodiversity-rich group of microorganisms that are normally found asymptomatically within plant tissues or in the intercellular spaces. Endophytic fungi promote the growth of host plants by directly producing secondary metabolites, which enhances the plant’s resistance to biotic and abiotic stresses. Additionally, they are capable of biosynthesizing medically important “phytochemicals” that were initially thought to be produced only by the host plant. In this review, we summarized some compounds from endophyte fungi with novel structures and diverse biological activities published between 2011 and 2021, with a focus on the origin of endophytic fungi, the structural and biological activity of the compounds they produce, and special attention paid to the exploration of pharmacological activities and mechanisms of action of certain compounds. This review revealed that endophytic fungi had high potential to be harnessed as an alternative source of secondary metabolites for pharmacological studies.

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“…More recently, simplicilones A and B, a pair of compounds that closely resemble 23 , were isolated from the endophytic fungus Simplicillium subtropicum SPC3 ( Cordycipitaceae ) found in the fresh bark of the African medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou [ 74 ]. While 24 and 25 were found to be antibiotic, 23 did not show any antibiotic activity.…”

Section: Diverse Structures and Biological Activities Of Tetramic Aci...mentioning

confidence: 99%

Recent advances in the chemo-biological characterization of decalin natural products and unraveling of the workings of Diels–Alderases

Watanabe

Sato

Osada

2022

Fungal Biol Biotechnol

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The Diels–Alder (DA) reaction refers to a [4 + 2] cycloaddition reaction that falls under the category of pericyclic reactions. It is a reaction that allows regio- and stereo-selective construction of two carbon–carbon bonds simultaneously in a concerted manner to generate a six-membered ring structure through a six-electron cyclic transition state. The DA reaction is one of the most widely applied reactions in organic synthesis, yet its role in biological systems has been debated intensely over the last four decades. A survey of secondary metabolites produced by microorganisms suggests strongly that many of the compounds possess features that are likely formed through DA reactions, and most of them are considered to be catalyzed by enzymes that are commonly referred to as Diels–Alderases (DAases). In recent years, especially over the past 10 years or so, we have seen an accumulation of a substantial body of work that substantiates the argument that DAases indeed exist and play a critical role in the biosynthesis of complex metabolites. This review will cover the DAases involved in the biosynthesis of decalin moieties, which are found in many of the medicinally important natural products, especially those produced by fungi. In particular, we will focus on a subset of secondary metabolites referred to as pyrrolidine-2-one-bearing decalin compounds and discuss the decalin ring stereochemistry and the biological activities of those compounds. We will also look into the genes and enzymes that drive the biosynthetic construction of those complex natural products, and highlight the recent progress made on the structural and mechanistic understanding of DAases, especially regarding how those enzymes exert stereochemical control over the [4 + 2] cycloaddition reactions they catalyze.

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Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Cited by 15 publications

References 29 publications

Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372

Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372

Endophytic Fungi: An Effective Alternative Source of Plant-Derived Bioactive Compounds for Pharmacological Studies

Recent advances in the chemo-biological characterization of decalin natural products and unraveling of the workings of Diels–Alderases

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