Marine Drugs

Editorial

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4 pages, 190 KiB

Open AccessEditorial

Natural Products from Marine Fungi

by Hee Jae Shin

Mar. Drugs 2020, 18(5), 230; https://doi.org/10.3390/md18050230 - 27 Apr 2020

Cited by 35 | Viewed by 5118

Abstract

Marine fungi have been studied since the first record of the species Sphaeria posidoniae (Halotthia posidoniae) on the rhizome of the sea grass Posidonia oceanica by Durieu and Montagne in 1846 [...] Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

Research

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11 pages, 1544 KiB

Open AccessArticle

Anthraquinone Derivatives from a Marine-Derived Fungus Sporendonema casei HDN16-802

by Xueping Ge, Chunxiao Sun, Yanyan Feng, Lingzhi Wang, Jixing Peng, Qian Che, Qianqun Gu, Tianjiao Zhu, Dehai Li and Guojian Zhang

Mar. Drugs 2019, 17(6), 334; https://doi.org/10.3390/md17060334 - 4 Jun 2019

Cited by 21 | Viewed by 4382

Abstract

Five new anthraquinone derivatives, auxarthrols D–H (1–5), along with two known analogues (6–7), were obtained from the culture of the marine-derived fungus Sporendonema casei. Their structures, including absolute configurations, were established on the basis [...] Read more.

Five new anthraquinone derivatives, auxarthrols D–H (1–5), along with two known analogues (6–7), were obtained from the culture of the marine-derived fungus Sporendonema casei. Their structures, including absolute configurations, were established on the basis of NMR, HRESIMS, and circular dichroism (CD) spectroscopic techniques. Among them, compound 4 represents the second isolated anthraquinone derivative with a chlorine atom, which, with compound 6, are the first reported anthraquinone derivatives with anticoagulant activity. Compounds 1 and 3 showed cytotoxic activities with IC₅₀ values from 4.5 μM to 22.9 μM, while compounds 1, 3–4, and 6–7 showed promising antibacterial activities with MIC values from 12.5 μM to 200 μM. In addition, compound 7 was discovered to display potential antitubercular activity for the first time. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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9 pages, 1438 KiB

Open AccessArticle

New Diketopiperazines from a Marine-Derived Fungus Strain Aspergillus versicolor MF180151

by Jiansen Hu, Zheng Li, Jieyu Gao, Hongtao He, Huanqin Dai, Xuekui Xia, Cuihua Liu, Lixin Zhang and Fuhang Song

Mar. Drugs 2019, 17(5), 262; https://doi.org/10.3390/md17050262 - 2 May 2019

Cited by 34 | Viewed by 4084

Abstract

Six new diketopiperazines, (±)-7,8-epoxy-brevianamide Q ((±)-1), (±)-8-hydroxy-brevianamide R ((±)-2), and (±)-8-epihydroxy-brevianamide R ((±)-3), together with four known compounds, (±)-brevianamide R ((±)-4), versicolorin B (5) and averufin (6), were isolated from a [...] Read more.

Six new diketopiperazines, (±)-7,8-epoxy-brevianamide Q ((±)-1), (±)-8-hydroxy-brevianamide R ((±)-2), and (±)-8-epihydroxy-brevianamide R ((±)-3), together with four known compounds, (±)-brevianamide R ((±)-4), versicolorin B (5) and averufin (6), were isolated from a marine-derived fungus strain Aspergillus versicolor MF180151, which was recovered from a sediment sample collected from the Bohai Sea, China. The chemical structures were established by 1D- and 2D-NMR spectra and HR-ESI-MS. 1 is the first sample of brevianamides with an epoxy moiety. Their bioactivities were evaluated against Candida albicans, Bacillus subtilis, Staphylococcus aureus, methicillin-resistant S. aureus, Pseudomonas aeruginosa, and Bacillus Calmette-Guérin. Compounds 1–4 showed no activities against the pathogens, and compounds 5 and 6 showed moderate activities against S. aureus and methicillin-resistant S. aureus. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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16 pages, 1187 KiB

Open AccessArticle

Phenalenones from a Marine-Derived Fungus Penicillium sp.

by Sung Chul Park, Elin Julianti, Sungjin Ahn, Donghwa Kim, Sang Kook Lee, Minsoo Noh, Dong-Chan Oh, Ki-Bong Oh and Jongheon Shin

Mar. Drugs 2019, 17(3), 176; https://doi.org/10.3390/md17030176 - 18 Mar 2019

Cited by 16 | Viewed by 4565

Abstract

Six new phenalenone derivatives (1–6), along with five known compounds (7–11) of the herqueinone class, were isolated from a marine-derived fungus Penicillium sp. The absolute configurations of these compounds were assigned based on chemical modifications [...] Read more.

Six new phenalenone derivatives (1–6), along with five known compounds (7–11) of the herqueinone class, were isolated from a marine-derived fungus Penicillium sp. The absolute configurations of these compounds were assigned based on chemical modifications and their specific rotations. 4-Hydroxysclerodin (6) and an acetone adduct of a triketone (7) exhibited moderate anti-angiogenetic and anti-inflammatory activities, respectively, while ent-peniciherqueinone (1) and isoherqueinone (9) exhibited moderate abilities to induce adipogenesis without cytotoxicity. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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12 pages, 1761 KiB

Open AccessArticle

New Bis-Alkenoic Acid Derivatives from a Marine-Derived Fungus Fusarium solani H915

by Shun-Zhi Liu, Xia Yan, Xi-Xiang Tang, Jin-Guo Lin and Ying-Kun Qiu

Mar. Drugs 2018, 16(12), 483; https://doi.org/10.3390/md16120483 - 3 Dec 2018

Cited by 22 | Viewed by 4254

Abstract

Fusarium solani H915 is a fungus derived from mangrove sediments. From its ethyl acetate extract, a new alkenoic acid, fusaridioic acid A (1), three new bis-alkenoic acid esters, namely, fusariumester A₁ (2), A₂ (3) [...] Read more.

Fusarium solani H915 is a fungus derived from mangrove sediments. From its ethyl acetate extract, a new alkenoic acid, fusaridioic acid A (1), three new bis-alkenoic acid esters, namely, fusariumester A₁ (2), A₂ (3) and B (4), together with three known compounds (5–7), were isolated. The structures of the new compounds were comprehensively characterized by high resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). Additionally, the antifungal activities against tea pathogenic fungi Pestalotiopsis theae and Colletotrichum gloeosporioides were studied. The new compound, 4, containing a β-lactone ring, exhibited moderate inhibitory activity against P. theae, with an MIC of 50 μg/disc. Hymeglusin (6), a typical β-lactone antibiotic and a terpenoid alkaloid, equisetin (7), exhibited potent inhibitory activities against both fungal species. The isolated compounds were evaluated for their effects on zebrafish embryo development. Equisetin clearly imparted toxic effect on zebrafish even at low concentrations. However, none of the alkenoic acid derivatives exhibited significant toxicity to zebrafish eggs, embryos, or larvae. Thus, the β-lactone containing alkenoic acid derivatives from F. solani H915 are low in toxicity and are potent antifungal agents against tea pathogenic fungi. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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13 pages, 1775 KiB

Open AccessArticle

Meroterpenoids and Isocoumarinoids from a Myrothecium Fungus Associated with Apocynum venetum

by Yanchao Xu, Cong Wang, Haishan Liu, Guoliang Zhu, Peng Fu, Liping Wang and Weiming Zhu

Mar. Drugs 2018, 16(10), 363; https://doi.org/10.3390/md16100363 - 1 Oct 2018

Cited by 24 | Viewed by 4222

Abstract

Four new meroterpenoids 1–4 and four new isocoumarinoids 5–8, along with five known isocoumarinoids (9–13), were isolated from the fungus Myrothecium sp. OUCMDZ-2784 associated with the salt-resistant medicinal plant, Apocynum venetum (Apocynaceae). Their structures [...] Read more.

Four new meroterpenoids 1–4 and four new isocoumarinoids 5–8, along with five known isocoumarinoids (9–13), were isolated from the fungus Myrothecium sp. OUCMDZ-2784 associated with the salt-resistant medicinal plant, Apocynum venetum (Apocynaceae). Their structures were elucidated by means of spectroscopic analysis, X-ray crystallography, ECD spectra and quantum chemical calculations. Compounds 1–5, 7, 9 and 10 showed weak α-glucosidase inhibition with the IC₅₀ values of 0.50, 0.66, 0.058, 0.20, 0.32, 0.036, 0.026 and 0.37 mM, respectively. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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9 pages, 2502 KiB

Open AccessArticle

Two Novel Aspochalasins from the Gut Fungus Aspergillus sp. Z4

by Xinyang Li, Wanjing Ding, Pinmei Wang and Jinzhong Xu

Mar. Drugs 2018, 16(10), 343; https://doi.org/10.3390/md16100343 - 20 Sep 2018

Cited by 12 | Viewed by 3760

Abstract

Two novel aspochalasins, tricochalasin A (1) and aspochalasin A2 (2), along with three known compounds (3–5) have been isolated from the different culture broth of Aspergillus sp., which was found in the gut of a [...] Read more.

Two novel aspochalasins, tricochalasin A (1) and aspochalasin A2 (2), along with three known compounds (3–5) have been isolated from the different culture broth of Aspergillus sp., which was found in the gut of a marine isopod Ligia oceanica. Compound 1 contains a rare 5/6/6 tricyclic ring fused with the aspochalasin skeleton. The structures were determined on the basis of electrospray ionisation mass spectroscopy (ESIMS), nuclear magnetic resonance (NMR) spectral data, and the absolute configurations were further confirmed by modified Mosher’s method. Cytotoxicity against the prostate cancer PC3 cell line were assayed by the MTT method. Compound 3 showed strong activity while the remaining compounds showed weak activity. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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12 pages, 1808 KiB

Open AccessArticle

Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508

by Jian-Lin Xu, Hong-Xin Liu, Yu-Chan Chen, Hai-Bo Tan, Heng Guo, Li-Qiong Xu, Sai-Ni Li, Zi-Lei Huang, Hao-Hua Li, Xiao-Xia Gao and Wei-Min Zhang

Mar. Drugs 2018, 16(9), 329; https://doi.org/10.3390/md16090329 - 11 Sep 2018

Cited by 26 | Viewed by 4238

Abstract

Five new benzophenone derivatives named tenellones D–H (1–5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), [...] Read more.

Five new benzophenone derivatives named tenellones D–H (1–5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), were isolated from the deep marine sediment-derived fungus Phomopsis lithocarpus FS508. All of the structures for these new compounds were fully characterized and established on the basis of extensive spectroscopic interpretation and X-ray crystallographic analysis. Compound 5 exhibited cytotoxic activity against HepG-2 and A549 cell lines with IC₅₀ values of 16.0 and 17.6 μM, respectively. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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13 pages, 1364 KiB

Open AccessArticle

Perylenequione Derivatives with Anticancer Activities Isolated from the Marine Sponge-Derived Fungus, Alternaria sp. SCSIO41014

by Xiaoyan Pang, Xiuping Lin, Pei Wang, Xuefeng Zhou, Bin Yang, Junfeng Wang and Yonghong Liu

Mar. Drugs 2018, 16(8), 280; https://doi.org/10.3390/md16080280 - 14 Aug 2018

Cited by 45 | Viewed by 4973

Abstract

Seven new secondary metabolites classified as two perylenequinone derivatives (1 and 2), an altenusin derivative (3), two phthalide racemates (4 and 5), and two phenol derivatives (6 and 7), along with twenty-one known compounds ( [...] Read more.

Seven new secondary metabolites classified as two perylenequinone derivatives (1 and 2), an altenusin derivative (3), two phthalide racemates (4 and 5), and two phenol derivatives (6 and 7), along with twenty-one known compounds (8–28) were isolated from cultures of the sponge-derived fungus, Alternaria sp. SCSIO41014. The structures and absolute configurations of these new compounds (1–7) were determined by spectroscopic analysis, X-ray single crystal diffraction, chiral-phase HPLC separation, and comparison of ECD spectra to calculations. Altertoxin VII (1) is the first example possessing a novel 4,8-dihydroxy-substituted perylenequinone derivative, while the phenolic hydroxy groups have commonly always substituted at C-4 and C-9. Compound 1 exhibited cytotoxic activities against human erythroleukemia (K562), human gastric carcinoma cells (SGC-7901), and hepatocellular carcinoma cells (BEL-7402) with IC₅₀ values of 26.58 ± 0.80, 8.75 ± 0.13, and 13.11 ± 0.95 μg/mL, respectively. Compound 11 showed selectively cytotoxic activity against K562, with an IC₅₀ value of 19.67 ± 0.19 μg/mL. Compound 25 displayed moderate inhibitory activity against Staphylococcus aureus with an MIC value of 31.25 μg/mL. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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10 pages, 2232 KiB

Open AccessArticle

Sorbicillasins A–B and Scirpyrone K from a Deep-Sea-Derived Fungus, Phialocephala sp. FL30r

by Zhenzhen Zhang, Xueqian He, Qian Che, Guojian Zhang, Tianjiao Zhu, Qianqun Gu and Dehai Li

Mar. Drugs 2018, 16(7), 245; https://doi.org/10.3390/md16070245 - 23 Jul 2018

Cited by 15 | Viewed by 4638

Abstract

Two new nitrogen-containing sorbicillinoids named sorbicillasins A and B (1 and 2) and a new 3,4,6-trisubstituted α-pyrone derivative, scirpyrone K (3), together with two known biosynthetically related polyketides (4–5), were isolated from the deep-sea-derived [...] Read more.

Two new nitrogen-containing sorbicillinoids named sorbicillasins A and B (1 and 2) and a new 3,4,6-trisubstituted α-pyrone derivative, scirpyrone K (3), together with two known biosynthetically related polyketides (4–5), were isolated from the deep-sea-derived fungus Phialocephala sp. FL30r by using the OSMAC (one strain-many compounds) method. The structures of 1–3, including absolute configurations, were deduced based on MS, NMR, and time-dependent density functional theory (TD-DFT) calculations of specific ECD (electronic circular dichroism) spectra. Compounds 1 and 2 possessed a novel hexahydropyrimido[2,1-a] isoindole moiety, and compound 3 exhibited weak radical scavenging activity against DPPH (2,2-diphenyl-1-picrylhydrazyl) with an IC₅₀ value of 27.9 μM. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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Review

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36 pages, 16637 KiB

Open AccessReview

Novel Natural Products from Extremophilic Fungi

by Xuan Zhang, Shou-Jie Li, Jin-Jie Li, Zi-Zhen Liang and Chang-Qi Zhao

Mar. Drugs 2018, 16(6), 194; https://doi.org/10.3390/md16060194 - 4 Jun 2018

Cited by 56 | Viewed by 7762

Abstract

Extremophilic fungi have been found to develop unique defences to survive extremes of pressure, temperature, salinity, desiccation, and pH, leading to the biosynthesis of novel natural products with diverse biological activities. The present review focuses on new extremophilic fungal natural products published from [...] Read more.

Extremophilic fungi have been found to develop unique defences to survive extremes of pressure, temperature, salinity, desiccation, and pH, leading to the biosynthesis of novel natural products with diverse biological activities. The present review focuses on new extremophilic fungal natural products published from 2005 to 2017, highlighting the chemical structures and their biological potential. Full article

(This article belongs to the Special Issue Natural Products from Marine Fungi)

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