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9 pages, 6194 KB

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Antimicrobial Meroterpenoids and Erythritol Derivatives Isolated from the Marine-Algal-Derived Endophytic Fungus Penicillium chrysogenum XNM-12

by Kuo Xu, Xu-Lun Wei, Lin Xue, Zhong-Feng Zhang and Peng Zhang

Mar. Drugs 2020, 18(11), 578; https://doi.org/10.3390/md18110578 - 20 Nov 2020

Cited by 28 | Viewed by 3695

Abstract

One new meroterpenoid-type alkaloid, oxalicine C (1), and two new erythritol derivatives, penicierythritols A (6) and B (7), together with four known meroterpenoids (2–5), were isolated from the marine algal-derived endophytic fungus Penicillium chrysogenum XNM-12. Their planar structures were determined by means of spectroscopic analyses, including UV, 1D and 2D NMR, and HRESIMS spectra. Their stereochemical configurations were established by comparing the experimental and calculated electronic circular dichroism (ECD) spectra for compound 1, as well as by comparison of the optical rotations with literature data for compounds 6 and 7. Notably, oxalicine C (1) represents the first example of an oxalicine alkaloid with a cleaved α-pyrone ring, whereas penicierythritols A (6) and B (7) are the first reported from the Penicillium species. The antimicrobial activities of compounds 1–7 were evaluated. Compounds 1 and 6 exhibited moderate antibacterial effects against the plant pathogen Ralstonia solanacearum with minimum inhibitory concentration (MIC) values of 8 and 4 μg/mL, respectively. Compound 6 also possesses moderate antifungal properties against the plant pathogen Alternaria alternata with a MIC value of 8 μg/mL. Full article

(This article belongs to the Special Issue Marine Natural Products in Crop Protection)

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8 pages, 939 KB

Open AccessArticle

Benzophenone Derivatives from an Algal-Endophytic Isolate of Penicillium chrysogenum and Their Cytotoxicity

by Dong-Lin Zhao, Xiao-Long Yuan, Yong-Mei Du, Zhong-Feng Zhang and Peng Zhang

Molecules 2018, 23(12), 3378; https://doi.org/10.3390/molecules23123378 - 19 Dec 2018

Cited by 26 | Viewed by 4157

Abstract

Chromatographic separation of a marine algal-derived endophytic fungus Penicillium chrysogenum AD-1540, which was isolated from the inner tissue of the marine red alga Grateloupia turuturu, yielded two new benzophenone derivatives, chryxanthones A and B (compounds 1 and 2, respectively). Their structures were undoubtedly determined by comprehensive analysis of spectroscopic data (1D/2D NMR and HRESIMS). The relative and absolute configurations were assigned by analysis of the coupling constants and time-dependent density functional theory (TDDFT) calculations of their electronic circular dichroism (ECD) spectra, respectively. Both compounds possessed an unusual dihydropyran ring (ring D) fused to an aromatic ring, rather than the commonly occurring prenyl moiety, and a plausible biosynthetic pathway was postulated. The cytotoxicities of compounds 1 and 2 were evaluated against six human cell lines, and both of the compounds demonstrated weak to moderate cytotoxicities with IC₅₀ values ranging from 20.4 to 46.4 μM. These new compounds further demonstrate the potential of marine-derived fungi as an untapped source of pharmaceutical components with unique properties that could be developed as drug candidates. Full article

(This article belongs to the Section Natural Products Chemistry)

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7 pages, 942 KB

Open AccessArticle

Prenylated Diphenyl Ethers from the Marine Algal-Derived Endophytic Fungus Aspergillus tennesseensis

by Zhao-Xia Li, Xiu-Fang Wang, Guang-Wei Ren, Xiao-Long Yuan, Ning Deng, Gui-Xia Ji, Wei Li and Peng Zhang

Molecules 2018, 23(9), 2368; https://doi.org/10.3390/molecules23092368 - 17 Sep 2018

Cited by 38 | Viewed by 3846

Abstract

Considerable attention has been paid to marine derived endophytic fungi, owing to their capacity to produce novel secondary metabolites with potent bioactivities. In this study, two new compounds with a prenylated diphenyl ether structure—diorcinol L (1) and (R)-diorcinol B (2)—were isolated from the marine algal-derived endophytic fungus Aspergillus tennesseensis, along with seven known compounds: (S)-diorcinol B (3), 9-acetyldiorcinol B (4), diorcinol C (5), diorcinol D (6), diorcinol E (7), diorcinol J (8), and a dihydrobenzofuran derivative 9. Their structures were elucidated by extensive NMR spectroscopy studies. Compound 2 represents the first example of an R-configuration in the prenylated moiety. All these isolated compounds were examined for antimicrobial and cytotoxic activities. Compounds 1–9 exhibited antimicrobial activities against some human- and plant-pathogenic microbes with MIC values ranging from 2 to 64 μg/mL. Moreover, compound 9 displayed considerable inhibitory activity against the THP-1 cell line in vitro, with an IC₅₀ value of 7.0 μg/mL. Full article

(This article belongs to the Section Natural Products Chemistry)

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9 pages, 3754 KB

Open AccessArticle

Two New Diketomorpholine Derivatives and a New Highly Conjugated Ergostane-Type Steroid from the Marine Algal-Derived Endophytic Fungus Aspergillus alabamensis EN-547

by Sui-Qun Yang, Xiao-Ming Li, Xin Li, Lu-Ping Chi and Bin-Gui Wang

Mar. Drugs 2018, 16(4), 114; https://doi.org/10.3390/md16040114 - 31 Mar 2018

Cited by 24 | Viewed by 5362

Abstract

Chemical investigation of the marine algal-derived endophytic fungus Aspergillus alabamensis EN-547 resulted in the isolation of 4-epi-seco-shornephine A methyl ester (1) and 4-epi-seco-shornephine A carboxylic acid (2), two new secondary metabolites having a rare diketomorpholine motif, and 28-acetoxy-12β,15α,25-trihydroxyergosta-4,6,8(14),22-tetraen-3-one (3), a new highly conjugated ergostane-type steroid, together with four known metabolites (4–7). Their chemical structures were elucidated by detailed analysis of their NMR spectra, ECDs, HRESIMS, optical rotation, and X-ray crystallographic data, and by comparison with literature data as well. The antimicrobial activities of compounds 1–7 were evaluated. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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12 pages, 225 KB

Open AccessArticle

Secondary Metabolites from a Marine-Derived Endophytic Fungus Penicillium chrysogenum QEN-24S

by Shu-Shan Gao, Xiao-Ming Li, Feng-Yu Du, Chun-Shun Li, Peter Proksch and Bin-Gui Wang

Mar. Drugs 2011, 9(1), 59-70; https://doi.org/10.3390/md9010059 - 27 Dec 2010

Cited by 97 | Viewed by 16498

Abstract

Penicillium chrysogenum QEN-24S, an endophytic fungus isolated from an unidentified marine red algal species of the genus Laurencia, displayed inhibitory activity against the growth of pathogen Alternaria brassicae in dual culture test. Chemical investigation of this fungal strain resulted in the isolation of four new (1–3 and 5) and one known (4) secondary metabolites. Their structures were identified as two polyketide derivatives penicitides A and B (1 and 2), two glycerol derivatives 2-(2,4-dihydroxy-6-methylbenzoyl)-glycerol (3) and 1-(2,4-dihydroxy-6-methylbenzoyl)-glycerol (4), and one monoterpene derivative penicimonoterpene (5). Penicitides A and B (1 and 2) feature a unique 10-hydroxy- or 7,10-dihydroxy-5,7-dimethylundecyl moiety substituting at C-5 of the α-tetrahydropyrone ring, which is not reported previously among natural products. Compound 5 displayed potent activity against the pathogen A. brassicae, while compound 1 exhibited moderate cytotoxic activity against the human hepatocellular liver carcinoma cell line. Full article

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