A new depsidone derivative from mangrove endophytic fungus <i>Aspergillus</i> sp. GXNU-A9

Hao, Lili; Zhou, Dexiong; Qin, Xiaoya; Zhang, Wenxiu; Yang, Ronghua; Li, Jun; Huang, Xishan

doi:10.1080/14786419.2020.1809400

Cited by 12 publications

(6 citation statements)

References 23 publications

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“…normale roots using various chromatographic methods yielded ten polyphenols ( 1 – 10 ) and four depsidone derivatives ( 11 – 14 ). The known compounds 2 – 10 and 12 – 14 were identified by analysis of mass spectral data, the NMR spectral data, specific rotations, and/or melting point data as whiskey tannin B ( 2 ) [ 19 ]; castalagin ( 3 ) [ 20 ]; 3,3′-dimethoxy ellagic acid ( 4 ) [ 21 ]; 3,3′,4-trimethoxyellagic acid ( 5 ) [ 22 ]; 3,3′,4′-trimethoxyellagic acid-4- O -β- d -glucopyranoside ( 6 ) [ 23 ]; 3,3′-dimethoxy ellagic acid-4- O -α- d -xylopyranoside ( 7 ) [ 24 ]; 1,2,4-benzenetriol ( 8 ) [ 25 ]; 1,4,6-tri- O -galloyl-glucose ( 9 ) [ 26 ]; 6- O -galloyl-glucose ( 10 ) [ 27 ]; guanxidone A ( 12 ) [ 28 ]; excelsione ( 13 ) [ 29 ]; and dioxepin-11-one ( 14 ) [ 30 ]. The structures of 1 – 1 4 are shown in Figure 1 .…”

Section: Resultsmentioning

confidence: 99%

“…Compound 11 was obtained as a white powder and had a molecular formula of C 18 H 14 O 7 based on HR-ESI-MS ( m / z 341.0669 [M − H] − , calcd 341.0661) and NMR data ( Table 2 ), requiring 12 degrees of unsaturation. MS analysis and evaluation of NMR data suggested that compound 1 1 was a tetracyclic depsidone [ 28 ]. The 1 H NMR data of 1 1 showed one singlet at δ H 6.63 (1H, s, H-8), one oxy-methylene singlet at δ H 5.25 (2H, s, H-15), and three aromatic methyl singlets at δ H 2.30 (6H, s, H-16, 17) and 2.12 (3H, s, H-18).…”

Section: Resultsmentioning

confidence: 99%

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Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale

Wang

Yang

et al. 2022

Molecules

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The roots of Melastoma malabathricum subsp. normale (D. Don) Karst. Mey have been used in traditional ethnic medicine systems in China to treat inflammation-triggered ailments, such as trauma, toothache, and fever. Therefore, the aim of this study is to screen for compounds with anti-inflammatory activity in the title plant. The extract of M. malabathricum subsp. normale roots was separated using various chromatographic methods, such as silica gel, ODS C18, MCI gel, and Sephadex LH-20 column chromatography, as well as semi-preparative HPLC. One new complex tannin, named whiskey tannin D (1), and an undescribed tetracyclic depsidone derivative, named guanxidone B (2), along with nine known polyphenols (2–10) and three known depsidone derivatives (12–14) were obtained from this plant. The structures of all compounds were elucidated by extensive NMR and CD experiments in conjunction with HR-ESI-MS data. All these compounds were isolated from this plant for the first time. Moreover, compounds 1–4, 8, and 10–14 were obtained for the first time from the genus Melastoma, and compounds 1, 2, and 11–14 have not been reported from the family Melastomataceae. This is the first report of complex tannin and depsidone derivatives from M. malabathricum subsp. normale, indicating their chemotaxonomic significance to this plant. Compounds 1–12 were investigated for their anti-inflammatory activities on the production of the nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells, and compounds 1, 11, and 12 showed anti-inflammatory activities with IC50 values of 6.46 ± 0.23 µM, 8.02 ± 0.35 µM, and 9.82 ± 0.43 µM, respectively. The structure–activity relationship showed that the catechin at glucose C-1 in ellagitannin was the key to its anti-inflammatory activity, while CH3O- at C-16 of aromatic ring A in depsidone derivatives had little effect on its anti-inflammatory activity. The study of structure–activity relationships is helpful to quickly discover new anti-inflammatory drugs. The successful isolation and structure identification of these compounds, especially complex tannin 1, not only provide materials for the screening of anti-inflammatory compounds, but also provide a basis for the study of chemical taxonomy of the genus Melastoma.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale

Wang

Yang

et al. 2022

Molecules

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“…GX4-1B, 90 a new lactone 410 from Phoma , 201 two new antimicrobial auranticins A ( 411 ) and B ( 412 ) from Pmrssia , 202 and pestalotiollides A ( 413 ) and B ( 414 ) from Pestalotiopsis . 71 An Aspergillus strain yielded tetracyclic guanxidone A ( 415 ), 203 whilst a Phomopsis strain yielded one novel pentacyclic depsidone containing an oxetane unit, phomopsidone A ( 416 ). 204 Cultivation of the fungal strain Eurotium resulted in the isolation of three new depsidone derivatives 417–419 , 205,206 whilst corynesidone C ( 420 ) was obtained from Corynespora strain.…”

Section: Secondary Metabolites From Mangrove Fungimentioning

confidence: 99%

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

et al. 2022

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“…Guanxidone A ( 157 ), a new depsidone derivative, along with three different metabolites 4‐isobenzofurancarboxylic acid ( 158 ), 7‐chloro‐6‐methoxymellein ( 159 ) and monomethylsulochrin ( 160 ) (Figure 17), were isolated from the endophytic Aspergillus sp. GXNU‐A9 hosted in the leaves of the mangrove Acanthus ilicifolius L. Interestingly, the study revealed the potent anti‐inflammatory activity of guanxidone A ( 157 ) through inhibition of the release of nitric oxide in lipopolysaccharide‐stimulated macrophage cell line RAW 264.7, with IC 50 value of 8.22 μmol l −1 (Hao et al 2020).…”

Section: Introductionmentioning

confidence: 99%

The endophytic Aspergillus strains: A bountiful source of natural products

Hagag

Abdelwahab

El-kader

et al. 2022

Journal of Applied Microbiology

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Fungi that invade plant inner tissues without inducing disease symptoms are known as fungal endophytes. They represent a promising and tremendous reservoir of natural products with valuable biological potentials for application in medicine, agriculture and industry. Among the numerous existing endophytic fungi, Aspergillus strains constitute one of the most prolific sources of secondary metabolites with diverse chemical classes and interesting biological activities. This review covers the literature of the year 2020, reporting the isolation of 202 compounds obtained from more than 10 different endophytic Aspergillus species associated with different host plants. Analysis and interpretation of the collected data revealed that chemical investigation of endophytes belonging to the genus Aspergillus may greatly contribute to the discovery of potential drug leads. The isolated metabolites were chemically various and exhibited diverse biological activities such as antibacterial, anti‐cancer, anti‐plasmodial, anti‐inflammatory, antioxidant, immunosuppressive and antifungal activities. Moreover, adoption of advanced technology in molecular biology together with modern chemical tools is anticipated to improve the discovery of new biopharmaceuticals from this valuable microbial world in the future.

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A new depsidone derivative from mangrove endophytic fungus Aspergillus sp. GXNU-A9

Cited by 12 publications

References 23 publications

Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale

Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

The endophytic Aspergillus strains: A bountiful source of natural products

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