Three New Indole Diketopiperazine Alkaloids from <i>Aspergillus ochraceus</i>

Wen, Hang; Liu, Xiaorui; Zhang, Qing; Deng, Yanfang; Zang, Yi; Wang, Jianping; Liu, Junjun; Zhou, Qun; Hu, Linzhen; Zhu, Hucheng; Chen, Chunmei; Zhang, Yonghui

doi:10.1002/cbdv.201700550

Cited by 31 publications

(18 citation statements)

References 33 publications

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“…Additionally, the configuration of the C‐8/C‐9 double bond and C‐12 were shown to be ( R ) and ( S ), respectively . Clearly, the isopentenylation of the benzene ring or indole ring and the oxidoreduction and sulfuration of diketopiperazine ring resulted in diversities of the structures . Research on the preliminarily cytotoxic activities of compounds and fractions showed that the cytotoxic effects of Fr.…”

Section: Discussionmentioning

confidence: 99%

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

Xia

Chen

Wang

et al. 2020

Chemistry & Biodiversity

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Three new indole diketopiperazine alkaloids, 11-methylneoechinulin E and variecolorin M, and (+)-variecolorin G, along with 12 known analogs, were isolated from a soft coral-associated epiphytic fungus Aspergillus sp. EGF 15-0-3. The structures of the new compounds were unambiguously established by extensive spectroscopic analyses including HR-ESI-MS, 1D and 2D NMR spectroscopy and optical rotation measurements. The absolute configurations of (+)-and (À )-variecolorin G were determined by experimental and quantum-chemical ECD investigations and single-crystal X-ray diffraction analysis. Variecolorin G is a pair of enantiomeric mixtures with a ratio of 1 : 2. Moreover, (+)-neoechinulin A is firstly reported as a natural product. The cytotoxic activities of all the isolated compounds against NCI-H1975 gefitinib resistance (NCI-H1975/GR) cell lines were preliminarily evaluated by MTT method.

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Section: Discussionmentioning

confidence: 99%

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

Xia

Chen

Wang

et al. 2020

Chemistry & Biodiversity

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“…4 Herein, we report the isolation of a new congener, Amoenamide B ( 1 ), along with Asperochramide A ( 2 ), which was isolated from Aspergillus ochraceus (cgmcc 3.6281), recently. 5…”

Section: Introductionmentioning

confidence: 99%

Isolation of a new indoxyl alkaloid, Amoenamide B, from Aspergillus amoenus NRRL 35600: Biosynthetic implications and correction of the structure of Speramide B

Kai

Kato

Sherman

et al. 2018

Tetrahedron Letters

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A new prenylated indoxyl alkaloid, Amoenamide B (1), was isolated from Aspergillus amoenus NRRL 35600 along with Asperochramide A (2). Although many prenylated oxyindole alkaloids, containing bicyclo[2.2.2]diazaoctane cores, have been isolated from the fungus of the genera Aspergillus and Penicillium to date, 1 is the fourth compound with the indoxyl unit containing the cores. During the structure elucidation of 1, we found that the planar structure matched to that of Speramide A (3), isolated from A. ochraceus KM007, but the reported structure of 3 was incorrect and turned out to be that of Taichunamide H (4), recently isolated from A. versicolor HDN11–84.

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“…The EtOAc layer (7.0 mg) was concentrated in vacuo and then identified as 2-(2-hydroxyethyl) phenol. 1.5 Biological Assays 1.5.1 Anti-inflammatory Activity Anti-inflammatory activity of the new compounds was evaluated using the ELISA with indomethacin and dexamethasone serving as the positive controls [23] . RAW 264.7 cells were cultured in DMEM (HyClone, Logan, USA) supplemented with 10% heat inactivated fetal bovine serum (FBS) (HyClone) at 37°C in a humidified atmosphere with 5% CO 2 .…”

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confidence: 99%

Polysubstituted Phenyl Glucosides Produced by the Fungus Metarrhizium anisopliae

et al. 2020

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Metarhizosides A-G (1-7), seven new polysubstituted phenyl glucosides, were isolated from the extracts of solid rice medium of a marine-derived fungus Metarrhizium anisopliae. Compounds 1-7 all contain a polysubstituted phenyl group and the sugar unit is identified as 4′-O-methyl-β-D-glucopyranose. Their structures were elucidated by NMR spectroscopy and chemical method. These compounds were evaluated for anti-inflammatory activity by using LPSstimulated murine macrophage RAW 264.7 cells and the cytotoxicities against four human cancer cell lines.

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Three New Indole Diketopiperazine Alkaloids from Aspergillus ochraceus

Cited by 31 publications

References 33 publications

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

New Indole Diketopiperazine Alkaloids from Soft Coral‐Associated Epiphytic Fungus Aspergillus sp. EGF 15‐0‐3

Isolation of a new indoxyl alkaloid, Amoenamide B, from Aspergillus amoenus NRRL 35600: Biosynthetic implications and correction of the structure of Speramide B

Polysubstituted Phenyl Glucosides Produced by the Fungus Metarrhizium anisopliae

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