Ascandinines A–D, Indole Diterpenoids, from the Sponge-Derived Fungus <i>Aspergillus candidus</i> HDN15-152

Zhou, Guoliang; Sun, Chunxiao; Hou, Xuewen; Che, Qian; Zhang, Guojian; Gu, Qianqun; Liu, Chenguang; Zhu, Tianjiao; Li, Dehai

doi:10.1021/acs.joc.0c02575

Cited by 37 publications

(28 citation statements)

References 21 publications

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“…The fungal indoleterpenoids, ascandanines B-D (64-66) (Figure 9), were evaluated for their antiviral effects against the influenza A virus (H1N1) by the cytopathic effect (CPE) inhibition assay. However, only 65 displayed an anti-influenza A effect with IC 50 = 26 µM, which is more potent than the positive control, ribavirin (IC 50 = 31 µM) while 64 and 66 were inactive (IC 50 > 150 µM) [27].…”

Section: Antiviral Activitymentioning

confidence: 92%

“…Ascandinines A-D (63-66) (Figure 9) were also evaluated for their cytotoxicity against MGC-803 (human gastric carcinoma), HCT-116 (human colorectal), SH-SY5Y (human neuroblastoma), Hela, and HL-60 (promyelocytic leukemia) cell lines. However, only 66 was active against the HL-60 cells with an IC 50 value of 7.8 µM (the IC 50 value of a positive control, adriamycin, was 0.02 µM) [27].…”

Section: Anticancer Activitymentioning

confidence: 99%

“…The EtOAc extract of a solid rice culture of the fungus Penicillium dimorphosporum KMM 4689, isolated from soft coral samples that were collected from various points in the South China Sea, yielded seven unreported deoxyisoaustamide derivatives, namely 16α-hydroxy-17βmethoxydeoxydihydroisoaustamide (24), 16β-hydroxy-17α-methoxydeoxydihydroisoaustamide (25), 16α-hydroxy-17α-methoxydeoxydihydroisoaustamide (26), 16,17-dihydroxydeoxydih ydroisoaustamide (27), 16β,17α-dihydroxydeoxydihydroisoaustamide (28), 16α,17α-dihy droxydeoxydihydroisoaustamide (29), and 3β-hydroxydeoxyisoaustamide (30) (Figure 5). The structures of the compounds of this group are characterized by a 6/5/8/6/5 pentacyclic ring system whose indole and 1,4-diketopiperazine moieties are linked through the eight-membered hexahydroazocine ring.…”

Section: Prenylated Indolesmentioning

confidence: 99%

“…The difference between 64 and 65 is the presence of a chlorine substituent in the benzene ring of the indole moiety in 64. The relative configurations of 63-66 were determined by analysis of NOESY correlations and the absolute configurations of their stereogenic carbons were established by comparison of the calculated and experimental ECD spectra as well as by biogenetic considerations [27].…”

Section: Prenylated Indolesmentioning

confidence: 99%

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Marine-Derived Indole Alkaloids and Their Biological and Pharmacological Activities

Wibowo¹,

Ahmadi²,

Rahmawati³

et al. 2021

Marine Drugs

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Novel secondary metabolites from marine macroorganisms and marine-derived microorganisms have been intensively investigated in the last few decades. Several classes of compounds, especially indole alkaloids, have been a target for evaluating biological and pharmacological activities. As one of the most promising classes of compounds, indole alkaloids possess not only intriguing structural features but also a wide range of biological/pharmacological activities including antimicrobial, anti-inflammatory, anticancer, antidiabetic, and antiparasitic activities. This review reports the indole alkaloids isolated during the period of 2016–2021 and their relevant biological/pharmacological activities. The marine-derived indole alkaloids reported from 2016 to 2021 were collected from various scientific databases. A total of 186 indole alkaloids from various marine organisms including fungi, bacteria, sponges, bryozoans, mangroves, and algae, are described. Despite the described bioactivities, further evaluation including their mechanisms of action and biological targets is needed to determine which of these indole alkaloids are worth studying to obtain lead compounds for the development of new drugs.

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Section: Antiviral Activitymentioning

confidence: 92%

Section: Anticancer Activitymentioning

confidence: 99%

Section: Prenylated Indolesmentioning

confidence: 99%

Section: Prenylated Indolesmentioning

confidence: 99%

See 2 more Smart Citations

Marine-Derived Indole Alkaloids and Their Biological and Pharmacological Activities

Wibowo¹,

Ahmadi²,

Rahmawati³

et al. 2021

Marine Drugs

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show abstract

“…Marine-derived fungi are valuable resources for the exploration of structurally novel and bioactive compounds and drug leads [8][9][10][11]. In particular, chemical studies of marine sponge-derived fungi have afforded a variety of bioactive secondary metabolites [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Cyclopeptide Derivatives from the Sponge-Derived Fungus Acremonium persicinum F10

2021

Marine Drugs

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Cyclopeptides usually play a pivotal role, either in the viability or virulence of fungi. Two types of cyclopeptides, six new hydroxamate siderophore cyclohexapeptides (1–6), including acremonpeptides E and F, and their complexes with aluminum and ferric ions; one new cyclic pentapeptolide, aselacin D (9); together with a known compound, aselacin C (10), were isolated and characterized from the sponge-derived fungus Acremonium persicinum F10. In addition, two new siderophore analogues chelating gallium ions (Ga3+), Ga (Ⅲ)-acremonpeptide E (7) and Ga (Ⅲ)-acremonpeptide F (8), using isolated acremonpeptides E and F, were prepared. The planar structures of 1–10 were elucidated by HRESIMS and (1D and 2D) NMR. The absolute configurations of amino acids were determined by means of the advanced Marfey’s method and X-ray single-crystal diffraction analysis. X-ray fluorescence (XRF) spectrometer was performed to disclose the elements of compound 1, indicating the existence of aluminum (Al). Al (Ⅲ)-acremonpeptides E (1), Ga (Ⅲ)-acremonpeptides E (5), Al (Ⅲ)-acremonpeptide F (7), and Ga (Ⅲ)-acremonpeptide F (8) displayed high in vitro anti-fungal activities, which are comparable to amphotericin B, against Aspergillus fumigatus and Aspergillus niger.

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Discovery, Total Synthesis, and Anti‐Inflammatory Evaluation of Naturally Occurring Naphthopyrone‐Macrolide Hybrids as Potent NLRP3 Inflammasome Inhibitors

Sun,

Jiang,

et al. 2024

Angewandte Chemie

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Numerous clinical disorders have been linked to the etiology of dysregulated NLRP3 (NACHT, LRR, and PYD domain‐containing protein 3) inflammasome activation. Despite its potential as a pharmacological target, modulation of NLRP3 activity remains challenging. Only a sparse number of compounds have been reported that can modulate NLRP3 and none of them have been developed into a commercially available drug. In this research, we identified three potent NLRP3 inflammasome inhibitors, gymnoasins A−C (1−3), with unprecedented pentacyclic scaffolds, from an Antarctic fungus Pseudogymnoascus sp. HDN17‐895, which represent the first naturally occurring naphthopyrone‐macrolide hybrids. Additionally, biomimetic synthesis of gymnoasin A (1) was also achieved validating the chemical structure and affording ample amounts of material for exhaustive bioactivity assessments. Biological assays indicated that 1 could significantly inhibited in vitro NLRP3 inflammasome activation and in vivo pro‐inflammatory cytokine IL‐1β release, representing a valuable new lead compound for the development of novel therapeutics with the potential to inhibit the NLRP3 inflammasome.

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Ascandinines A–D, Indole Diterpenoids, from the Sponge-Derived Fungus Aspergillus candidus HDN15-152

Cited by 37 publications

References 21 publications

Marine-Derived Indole Alkaloids and Their Biological and Pharmacological Activities

Marine-Derived Indole Alkaloids and Their Biological and Pharmacological Activities

Cyclopeptide Derivatives from the Sponge-Derived Fungus Acremonium persicinum F10

Discovery, Total Synthesis, and Anti‐Inflammatory Evaluation of Naturally Occurring Naphthopyrone‐Macrolide Hybrids as Potent NLRP3 Inflammasome Inhibitors

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