Didymellanosine, a new decahydrofluorene analogue, and ascolactone C from <i>Didymella</i> sp. IEA-3B.1, an endophyte of <i>Terminalia catappa</i>

Ariantari, Ni Putu; Ancheeva, Elena; Frank, Mary Margaret; Stuhldreier, Fabian; Meier, Dieter; Gröner, Yvonne; Reimche, Irene; Teusch, Nicole; Wesselborg, Sebastian; Müller, Werner; Kalscheuer, Rainer; Liu, Zhen; Proksch, Peter

doi:10.1039/c9ra10685e

Cited by 12 publications

(7 citation statements)

References 52 publications

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“…However, these could be cofacial based on biogenetic considerations, as all previously described fungal metabolites with a cyclopenta[b]fluorene (6/5/6/5) ring system have CH 3 -20 and CH 3 -22 oriented on the same face, including embellicine A ( 1 ). 16 − 18 The relative configuration of H-1′ was assigned based on its cross-peak with H-16 and H-9′. The restricted rotation of the benzene ring inside the 13-membered macrocycle was further supported by the NOESY correlation of H-15 with H-8′, while H 3 -25 and H-14 correlated with H-6′.…”

Section: Resultsmentioning

confidence: 94%

“…Phomapyrrolidones A–C were reported concurrently and found to exhibit weak antitubercular activity . Recently, ascomylactams A–C and didymellanosine were characterized and reported to exhibit cytotoxic and antimicrobial activities. Didymellanosine is the first 13-membered macrocyclic alkaloid with a cyclopenta[b]fluorene ring system conjugated with adenosine .…”

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confidence: 99%

“…Recently, ascomylactams A–C and didymellanosine were characterized and reported to exhibit cytotoxic and antimicrobial activities. Didymellanosine is the first 13-membered macrocyclic alkaloid with a cyclopenta[b]fluorene ring system conjugated with adenosine . A structurally related group of compounds, hirsutellones, − pyrrocidines, − and pyrrospirones, , have a decahydrofluorene skeleton and gained considerable attention , for their unique core and pharmacological activities as antimicrobial and cytotoxic leads.…”

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confidence: 99%

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Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.

et al. 2023

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Macrocyclic alkaloids with a cyclopenta[b]fluorene ring system are a relatively young structural class of fungal metabolites, with the first members reported in 2013. Bioassay-guided fractionation of a Sarocladium sp. (fungal strain MSX6737) led to a series of both known and new members of this structural class (1−5), including the known embellicine A (1), three new embellicine analogues (2, 4, and 5), and a semisynthetic acetylated analogue (3). The structures were identified by examining both high-resolution electrospray ionization mass spectrometry data and one-dimensional and twodimensional NMR spectra. The relative configurations of these molecules were established via 1 H− 1 H coupling constants and nuclear Overhauser effect spectroscopy, while comparisons of the experimental electronic circular dichroism (ECD) spectra with the time-dependent density functional theory ECD calculations were utilized to assign their absolute configurations, which were in good agreement with the literature. These alkaloids (1−5) showed cytotoxic activity against a human breast cancer cell line (MDA-MB-231) that ranged from 0.4 to 4.8 μM. Compounds 1 and 5 were also cytotoxic against human ovarian (OVCAR3) and melanoma (MDA-MB-435) cancer cell lines.

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Section: Resultsmentioning

confidence: 94%

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confidence: 99%

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confidence: 99%

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Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.

et al. 2023

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“…One of the new peaks in pUARA-N15.1 was also OA. The other new peak (compound B1 ) was determined to be 3,6,8-trihydroxy-3-methyl-3,4-dihydroisocoumarin by HR-ESI–MS and NMR (Ariantari et al 2020 ; Kameda et al 1973 ) (Fig. S24 - S26 ).…”

Section: Resultsmentioning

confidence: 99%

Activation of secondary metabolite gene clusters in Chaetomium olivaceum via the deletion of a histone deacetylase

Zhao,

Cao,

Wang

et al. 2024

Appl Microbiol Biotechnol

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Histone acetylation modifications in filamentous fungi play a crucial role in epigenetic gene regulation and are closely linked to the transcription of secondary metabolite (SM) biosynthetic gene clusters (BGCs). Histone deacetylases (HDACs) play a pivotal role in determining the extent of histone acetylation modifications and act as triggers for the expression activity of target BGCs. The genus Chaetomium is widely recognized as a rich source of novel and bioactive SMs. Deletion of a class I HDAC gene of Chaetomium olivaceum SD-80A, g7489, induces a substantial pleiotropic effect on the expression of SM BGCs. The C. olivaceum SD-80A ∆g7489 strain exhibited significant changes in morphology, sporulation ability, and secondary metabolic profile, resulting in the emergence of new compound peaks. Notably, three polyketides (A1–A3) and one asterriquinone (A4) were isolated from this mutant strain. Furthermore, our study explored the BGCs of A1–A4, confirming the function of two polyketide synthases (PKSs). Collectively, our findings highlight the promising potential of molecular epigenetic approaches for the elucidation of novel active compounds and their biosynthetic elements in Chaetomium species. This finding holds great significance for the exploration and utilization of Chaetomium resources. Key points • Deletion of a class I histone deacetylase activated secondary metabolite gene clusters. • Three polyketides and one asterriquinone were isolated from HDAC deleted strain. • Two different PKSs were reported in C. olivaceum SD-80A.

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“…Cyclopenta[ b ]fluorene-type compounds are a subgroup of fungal polyketide/nonribosomal peptide hybrid products, which belong to the decahydrofluorene class, structurally characterized by a 13-membered ether ring fused with a cyclopenta[ b ]fluorene (6/5/6/5) ring system, a 1,4-substituted benzene ring, and a γ-lactam (or succinimide). Embellicines A and B, 1 phomapyrrolidones A–C, 2 ascomylactams A–C, 3 didymellanosines, 4 embellicines C–E 5 and ascomylactams D and E 6 have shown significant cytotoxic activities. These compounds have also attracted attention from many biological and chemical scholars to study their activity mechanism, biosynthesis and chemical synthesis owing to the novel structure and significant activity of the decahydrofluorene class.…”

Section: Introductionmentioning

confidence: 99%

Didymorenloids A and B, two polycyclic cyclopenta[b]fluorene-type alkaloids with anti-hepatoma activity from the mangrove endophytic fungus Didymella sp. CYSK-4

Chen,

Yang,

Zhu

et al. 2024

Org. Chem. Front.

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Didymellanosine, a new decahydrofluorene analogue, and ascolactone C from Didymella sp. IEA-3B.1, an endophyte of Terminalia catappa

Abstract: An unusual decahydrofluorene-class alkaloid from Didymella sp. exhibited NFκB inhibitory and antimicrobial activities.

Cited by 12 publications

References 52 publications

Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.

Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus Sarocladium sp.

Activation of secondary metabolite gene clusters in Chaetomium olivaceum via the deletion of a histone deacetylase

Didymorenloids A and B, two polycyclic cyclopenta[b]fluorene-type alkaloids with anti-hepatoma activity from the mangrove endophytic fungus Didymella sp. CYSK-4

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