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Marine Drugs
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Marine Fungal Natural Products
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Marine Fungal Natural Products

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (31 December 2016) | Viewed by 118817

Special Issue Editor

Prof. Dr. Russell Kerr

E-Mail Website
Guest Editor
Department of Pathology and Microbiology, Atlantic Veterinary College, University of Prince Edward Island, Charlottetown, PEI C1A 4P3, Canada
Interests: natural products isolation and characterization; bioassay-guided purification of natural products / drug discovery; isolation of natural product producing bacteria and fungi; development of fermentation methods to optimize natural product production; description of microbial communities in marine invertebrates

Special Issue Information

Dear Colleagues,

Fungi from marine habitats continue to provide a prolific resource for natural product discovery. Current research in marine fungal natural product discovery focuses on topics ranging from the isolation of new fungal taxa to the isolation and characterization of new compounds. Additionally, with the growing awareness of the presence of cryptic natural products in fungal genomes, efforts are underway in numerous labs to develop new methods to induce the expression of such compounds. The goal of this Marine Drugs Special Issue is to assemble a collection of research articles outlining progress in these interrelated disciplines.

Prof. Dr. Russell Kerr
Guest Editor

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Keywords

  • marine fungi
  • natural product
  • secondary metabolite
  • biosynthesis
  • cryptic biosynthetic pathway
  • induction

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Published Papers (18 papers)

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Research

594 KiB  
Article
Asperentin B, a New Inhibitor of the Protein Tyrosine Phosphatase 1B
by Jutta Wiese, Hülya Aldemir, Rolf Schmaljohann, Tobias A. M. Gulder and Johannes F. Imhoff
Mar. Drugs 2017, 15(6), 191; https://doi.org/10.3390/md15060191 - 21 Jun 2017
Cited by 32 | Viewed by 5076
Abstract
In the frame of studies on secondary metabolites produced by fungi from deep-sea environments we have investigated inhibitors of enzymes playing key roles in signaling cascades of biochemical pathways relevant for the treatment of diseases. Here we report on a new inhibitor of [...] Read more.
In the frame of studies on secondary metabolites produced by fungi from deep-sea environments we have investigated inhibitors of enzymes playing key roles in signaling cascades of biochemical pathways relevant for the treatment of diseases. Here we report on a new inhibitor of the human protein tyrosine phosphatase 1B (PTP1B), a target in the signaling pathway of insulin. A new asperentin analog is produced by an Aspergillus sydowii strain isolated from the sediment of the deep Mediterranean Sea. Asperentin B (1) contains an additional phenolic hydroxy function at C-6 and exhibits an IC50 value against PTP1B of 2 μM in vitro, which is six times stronger than the positive control, suramin. Interestingly, asperentin (2) did not show any inhibition of this enzymatic activity. Asperentin B (1) is discussed as possible therapeutic agents for type 2 diabetes and sleeping sickness. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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2324 KiB  
Article
Bioactive Metabolites from the Deep Subseafloor Fungus Oidiodendron griseum UBOCC-A-114129
by Marion Navarri, Camille Jégou, Arnaud Bondon, Sandrine Pottier, Stéphane Bach, Blandine Baratte, Sandrine Ruchaud, Georges Barbier, Gaëtan Burgaud and Yannick Fleury
Mar. Drugs 2017, 15(4), 111; https://doi.org/10.3390/md15040111 - 7 Apr 2017
Cited by 15 | Viewed by 4649
Abstract
Four bioactive compounds have been isolated from the fungus Oidiodendron griseum UBOCC-A-114129 cultivated from deep subsurface sediment. They were structurally characterized using a combination of LC–MS/MS and NMR analyses as fuscin and its derivatives (dihydrofuscin, dihydrosecofuscin, and secofuscin) and identified as polyketides. Albeit [...] Read more.
Four bioactive compounds have been isolated from the fungus Oidiodendron griseum UBOCC-A-114129 cultivated from deep subsurface sediment. They were structurally characterized using a combination of LC–MS/MS and NMR analyses as fuscin and its derivatives (dihydrofuscin, dihydrosecofuscin, and secofuscin) and identified as polyketides. Albeit those compounds were already obtained from terrestrial fungi, this is the first report of their production by an Oidiodendron species and by the deepest subseafloor isolate ever studied for biological activities. We report a weak antibacterial activity of dihydrosecofuscin and secofuscin mainly directed against Gram-positive bacteria (Minimum Inhibitory Concentration (MIC) equal to Minimum Bactericidal Concentration (MBC), in the range of 100 μg/mL). The activity on various protein kinases was also analyzed and revealed a significant inhibition of CDC2-like kinase-1 (CLK1) by dihysecofuscin. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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1711 KiB  
Article
Establishing the Secondary Metabolite Profile of the Marine Fungus: Tolypocladium geodes sp. MF458 and Subsequent Optimisation of Bioactive Secondary Metabolite Production
by Bethlehem Kebede, Stephen K. Wrigley, Anjali Prashar, Janina Rahlff, Markus Wolf, Jeanette Reinshagen, Philip Gribbon, Johannes F. Imhoff, Johanna Silber, Antje Labes and Bernhard Ellinger
Mar. Drugs 2017, 15(4), 84; https://doi.org/10.3390/md15040084 - 23 Mar 2017
Cited by 30 | Viewed by 6976
Abstract
As part of an international research project, the marine fungal strain collection of the Helmholtz Centre for Ocean Research (GEOMAR) research centre was analysed for secondary metabolite profiles associated with anticancer activity. Strain MF458 was identified as Tolypocladium geodes, by internal transcribed [...] Read more.
As part of an international research project, the marine fungal strain collection of the Helmholtz Centre for Ocean Research (GEOMAR) research centre was analysed for secondary metabolite profiles associated with anticancer activity. Strain MF458 was identified as Tolypocladium geodes, by internal transcribed spacer region (ITS) sequence similarity and its natural product production profile. By using five different media in two conditions and two time points, we were able to identify eight natural products produced by MF458. As well as cyclosporin A (1), efrapeptin D (2), pyridoxatin (3), terricolin A (4), malettinins B and E (5 and 6), and tolypocladenols A1/A2 (8), we identified a new secondary metabolite which we termed tolypocladenol C (7). All compounds were analysed for their anticancer potential using a selection of the NCI60 cancer cell line panel, with malettinins B and E (5 and 6) being the most promising candidates. In order to obtain sufficient quantities of these compounds to start preclinical development, their production was transferred from a static flask culture to a stirred tank reactor, and fermentation medium development resulted in a nearly eight-fold increase in compound production. The strain MF458 is therefore a producer of a number of interesting and new secondary metabolites and their production levels can be readily improved to achieve higher yields. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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3016 KiB  
Article
Zosteropenillines: Polyketides from the Marine-Derived Fungus Penicillium thomii
by Shamil Sh. Afiyatullov, Elena V. Leshchenko, Dmitrii V. Berdyshev, Maria P. Sobolevskaya, Alexandr S. Antonov, Vladimir A. Denisenko, Roman S. Popov, Mikhail V. Pivkin, Anatoly A. Udovenko, Evgeny A. Pislyagin, Gunhild Von Amsberg and Sergey A. Dyshlovoy
Mar. Drugs 2017, 15(2), 46; https://doi.org/10.3390/md15020046 - 17 Feb 2017
Cited by 14 | Viewed by 6318
Abstract
Twelve new polyketides, zosteropenillines A–L (1–12), together with known polyketide pallidopenilline A (13), were isolated from the ethylacetate extract of the fungus Penicillium thomii associated with the seagrass Zostera marina. Their structures were established based on spectroscopic methods. The absolute configuration of zosteropenilline [...] Read more.
Twelve new polyketides, zosteropenillines A–L (1–12), together with known polyketide pallidopenilline A (13), were isolated from the ethylacetate extract of the fungus Penicillium thomii associated with the seagrass Zostera marina. Their structures were established based on spectroscopic methods. The absolute configuration of zosteropenilline A (1) as 4R, 5S, 8S, 9R, 10R, and 13S was determined by a combination of the modified Mosher’s method, X‐ray analysis, and NOESY data. Absolute configurations of zosteropenillines B–D (2–4) were determined by timedependent density functional theory (TD‐DFT) calculations of ECD spectra. The effect of compounds 1–3, 7, 8, 10, and 11 on the viability of human drug‐resistant prostate cancer cells PC3 as well as on autophagy in these cancer cells and inhibitory effects of compounds 1, 2, and 8–10 on NO production in LPS‐induced RAW 264.7 murine macrophages were examined. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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2403 KiB  
Article
Induction of Diverse Bioactive Secondary Metabolites from the Mangrove Endophytic Fungus Trichoderma sp. (Strain 307) by Co-Cultivation with Acinetobacter johnsonii (Strain B2)
by Liuhong Zhang, Shah Iram Niaz, Dilfaraz Khan, Zhen Wang, Yonghong Zhu, Haiyun Zhou, Yongcheng Lin, Jing Li and Lan Liu
Mar. Drugs 2017, 15(2), 35; https://doi.org/10.3390/md15020035 - 10 Feb 2017
Cited by 52 | Viewed by 7263
Abstract
Two new sesquiterpenes, microsphaeropsisin B (1) and C (2), and two new de-O-methyllasiodiplodins, (3R, 7R)-7-hydroxy-de-O-methyllasiodiplodin (4) and (3R)-5-oxo-de-O-methyllasiodiplodin (5), together with one new [...] Read more.
Two new sesquiterpenes, microsphaeropsisin B (1) and C (2), and two new de-O-methyllasiodiplodins, (3R, 7R)-7-hydroxy-de-O-methyllasiodiplodin (4) and (3R)-5-oxo-de-O-methyllasiodiplodin (5), together with one new natural product (6) and twelve known compounds (3, 7–17), were isolated from the co-cultivation of mangrove endophytic fungus Trichoderma sp. 307 and aquatic pathogenic bacterium Acinetobacter johnsonii B2. Their structures, including absolute configurations, were elucidated by extensive analysis of spectroscopic data, electronic circular dichroism, Mo2(AcO)4-induced circular dichroism, and comparison with reported data. All of the isolated compounds were tested for their α-glucosidase inhibitory activity and cytotoxicity. New compounds 4 and 5 exhibited potent α-glucosidase inhibitory activity with IC50 values of 25.8 and 54.6 µM, respectively, which were more potent than the positive control (acarbose, IC50 = 703.8 µM). The good results of the tested bioactivity allowed us to explore α-glucosidase inhibitors in lasiodiplodins. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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1184 KiB  
Article
Indolediketopiperazine Alkaloids from Eurotium cristatum EN-220, an Endophytic Fungus Isolated from the Marine Alga Sargassum thunbergii
by Feng-Yu Du, Xin Li, Xiao-Ming Li, Li-Wei Zhu and Bin-Gui Wang
Mar. Drugs 2017, 15(2), 24; https://doi.org/10.3390/md15020024 - 25 Jan 2017
Cited by 65 | Viewed by 7475
Abstract
Four new indolediketopiperazine derivatives (1–4), along with nine known congeners (5–13), were isolated and identified from the culture extract of Eurotium cristatum EN-220, an endophytic fungus obtained from the marine alga Sargassum thunbergii. The [...] Read more.
Four new indolediketopiperazine derivatives (1–4), along with nine known congeners (5–13), were isolated and identified from the culture extract of Eurotium cristatum EN-220, an endophytic fungus obtained from the marine alga Sargassum thunbergii. The structures of thesecompounds were elucidated on the basis of extensive spectroscopic analysis and the absolute configurations of compounds 1–4 were established by NOESY experiments and by chiral HPLC analyses of their acid hydrolysates. The absolute configuration of C-8 (a quaternary carbon substituted with a hydroxyl group) in 5 of preechinulin class was firstly determined by electronic circular dichroism (ECD) calculations. All these compounds were evaluatedfor brine shrimp (Artemia salina) lethality and nematicidal activity as well as antioxidativeand antimicrobial potency. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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1563 KiB  
Communication
Asymmetric Total Synthesis of Ieodomycin B
by Shuangjie Lin, Jianting Zhang, Zhibin Zhang, Tianxiang Xu, Shuangping Huang and Xiaoji Wang
Mar. Drugs 2017, 15(1), 17; https://doi.org/10.3390/md15010017 - 18 Jan 2017
Cited by 11 | Viewed by 5708
Abstract
Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 [...] Read more.
Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection–lactonization one-pot reaction. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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1195 KiB  
Article
Pyran Rings Containing Polyketides from Penicillium raistrickii
by Li-Ying Ma, De-Sheng Liu, De-Guo Li, Yu-Ling Huang, Hui-Hui Kang, Chun-Hua Wang and Wei-Zhong Liu
Mar. Drugs 2017, 15(1), 2; https://doi.org/10.3390/md15010002 - 23 Dec 2016
Cited by 17 | Viewed by 7245
Abstract
Five new pyran rings containing polyketides, penicipyrans A–E (1–5), together with the known pestapyrone A (6), were isolated from the saline soil-derived Penicillium raistrickii. Their structures were determined by interpretation of NMR and HRESIMS data. The [...] Read more.
Five new pyran rings containing polyketides, penicipyrans A–E (1–5), together with the known pestapyrone A (6), were isolated from the saline soil-derived Penicillium raistrickii. Their structures were determined by interpretation of NMR and HRESIMS data. The absolute configurations of compounds 4 and 5 were established by the modified Mosher’s method and single-crystal X-ray diffraction analysis, respectively. These compounds possessed high structural diversity including two α-pyrones (1, 2), three isocoumarins (3, 4, 6), and one dihydropyran derivative (5). Among them, Compound 5 exhibited cytotoxicity against HL-60 and K562 cell lines with IC50 values of 4.4 and 8.5 μM, respectively. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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2349 KiB  
Article
Cytoglobosins H and I, New Antiproliferative Cytochalasans from Deep-Sea-Derived Fungus Chaetomium globosum
by Zhihan Zhang, Xitian Min, Junjun Huang, Yue Zhong, Yuehua Wu, Xiaoxia Li, Yinyue Deng, Zide Jiang, Zongze Shao, Lianhui Zhang and Fei He
Mar. Drugs 2016, 14(12), 233; https://doi.org/10.3390/md14120233 - 20 Dec 2016
Cited by 27 | Viewed by 6100
Abstract
Cytoglobosins H (1) and I (2), together with seven known cytochalasan alkaloids (3–9), were isolated from the deep-sea-derived fungus Chaetomium globosum. The structures of new compounds 1 and 2 were elucidated by extensive 1D [...] Read more.
Cytoglobosins H (1) and I (2), together with seven known cytochalasan alkaloids (3–9), were isolated from the deep-sea-derived fungus Chaetomium globosum. The structures of new compounds 1 and 2 were elucidated by extensive 1D and 2D NMR and mass spectroscopic data. All the compounds were evaluated for their antiproliferative activities against MDA-MB-231 human breast cancer cells, LNCaP human prostate cancer cells, and B16F10 mouse melanoma cells. Compound 6 showed significant antiproliferative activity against LNCaP and B16F10 cell lines with IC50 values of 0.62 and 2.78 μM, respectively. Further testing confirmed that compound 6 inhibited the growth of LNCaP cells by inducing apoptosis. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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466 KiB  
Article
First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge
by Rajiv Dahiya, Sunil Singh, Ajay Sharma, Suresh V. Chennupati and Sandeep Maharaj
Mar. Drugs 2016, 14(12), 228; https://doi.org/10.3390/md14120228 - 15 Dec 2016
Cited by 30 | Viewed by 7203
Abstract
A natural heptacyclopeptide, stylissamide G (7), previously isolated from the Bahamian marine sponge Stylissa caribica from the Caribbean Sea, was synthesized via coupling of the tetrapeptide l-phenylalanyl-l-prolyl-l-phenylalanyl-l-proline methyl ester with the tripeptide Boc-l [...] Read more.
A natural heptacyclopeptide, stylissamide G (7), previously isolated from the Bahamian marine sponge Stylissa caribica from the Caribbean Sea, was synthesized via coupling of the tetrapeptide l-phenylalanyl-l-prolyl-l-phenylalanyl-l-proline methyl ester with the tripeptide Boc-l-leucyl-l-isoleucyl-l-proline, followed by cyclization of the linear heptapeptide fragment. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FT-IR, 1H NMR, 13C NMR and mass spectrometry. Results of pharmacological activity studies indicated that the newly synthesized cycloheptapeptide displayed good anthelmintic potential against Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea at 2 mg/mL and in addition, potent antifungal activity against pathogenic Candida albicans and dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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1018 KiB  
Article
Two New Diphenylketones and a New Xanthone from Talaromyces islandicus EN-501, an Endophytic Fungus Derived from the Marine Red Alga Laurencia okamurai
by Hong-Lei Li, Xiao-Ming Li, Hui Liu, Ling-Hong Meng and Bin-Gui Wang
Mar. Drugs 2016, 14(12), 223; https://doi.org/10.3390/md14120223 - 7 Dec 2016
Cited by 33 | Viewed by 6356
Abstract
Two new diphenylketones (1 and 2), a new xanthone (3), and a known xanthone analogue (4) were isolated and identified from Talaromyces islandicus EN-501, an endophytic fungus obtained from the fresh collected marine red alga Laurencia okamurai [...] Read more.
Two new diphenylketones (1 and 2), a new xanthone (3), and a known xanthone analogue (4) were isolated and identified from Talaromyces islandicus EN-501, an endophytic fungus obtained from the fresh collected marine red alga Laurencia okamurai. Their structures were elucidated on the basis of NMR spectroscopic and X-ray crystallographic analysis. The joint isolation of benzophenones and xanthones from the same fungal strain supports the biogenesis of xanthones via a benzophenone intermediate. It is worth mentioning that xanthones 3 and 4 have a methyl group at C-6 and C-2, respectively, which is uncommon compared with typical xanthones usually having a methyl group at C-8. Compounds 1–4 exhibited potent antioxidative activities against DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonate) radicals with IC50 values ranging from 0.58 to 6.92 μg/mL, which are stronger than that of the positive controls BHT (butylated hydroxytoluene) and ascorbic acid. Compounds 1, 3, and 4 also showed inhibitory activities against several pathogenic bacteria. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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550 KiB  
Article
Polyketides with Immunosuppressive Activities from Mangrove Endophytic Fungus Penicillium sp. ZJ-SY2
by Hongju Liu, Senhua Chen, Weiyang Liu, Yayue Liu, Xishan Huang and Zhigang She
Mar. Drugs 2016, 14(12), 217; https://doi.org/10.3390/md14120217 - 25 Nov 2016
Cited by 64 | Viewed by 6916
Abstract
Nine polyketides, including two new benzophenone derivatives, peniphenone (1) and methyl peniphenone (2), along with seven known xanthones (3–9) were obtained from mangrove endophytic fungus Penicillium sp. ZJ-SY2 isolated from the leaves of Sonneratia [...] Read more.
Nine polyketides, including two new benzophenone derivatives, peniphenone (1) and methyl peniphenone (2), along with seven known xanthones (3–9) were obtained from mangrove endophytic fungus Penicillium sp. ZJ-SY2 isolated from the leaves of Sonneratia apetala. Their structures were elucidated on the basis of MS, 1D, and 2D NMR data. Compounds 1, 3, 5, and 7 showed potent immunosuppressive activity with IC50 values ranging from 5.9 to 9.3 μg/mL. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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2253 KiB  
Article
Phomopsichin A–D; Four New Chromone Derivatives from Mangrove Endophytic Fungus Phomopsis sp. 33#
by Meixiang Huang, Jing Li, Lan Liu, Sheng Yin, Jun Wang and Yongcheng Lin
Mar. Drugs 2016, 14(11), 215; https://doi.org/10.3390/md14110215 - 22 Nov 2016
Cited by 30 | Viewed by 6853
Abstract
Four new chromone derivatives, phomopsichins A–D (1–4), along with a known compound, phomoxanthone A (5), were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp. 33#. Their structures were elucidated based on comprehensive spectroscopic analysis [...] Read more.
Four new chromone derivatives, phomopsichins A–D (1–4), along with a known compound, phomoxanthone A (5), were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp. 33#. Their structures were elucidated based on comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction or theoretical calculations of electronic circular dichroism (ECD). They feature a tricyclic framework, in which a dihydropyran ring is fused with the chromone ring. Compounds 1–5 showed weak inhibitory activities on acetylcholinesterase as well as α-glucosidase, weak radical scavenging effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as OH, and weak antimicrobial activities. Compounds 1–4 showed no cytotoxic activity against MDA-MB-435 breast cancer cells. Their other bioactivities are worthy of further study, considering their unique molecular structures. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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959 KiB  
Article
Marine Fungi as Producers of Benzocoumarins, a New Class of Inhibitors of Glycogen-Synthase-Kinase 3β
by Jutta Wiese, Johannes F. Imhoff, Tobias A. M. Gulder, Antje Labes and Rolf Schmaljohann
Mar. Drugs 2016, 14(11), 200; https://doi.org/10.3390/md14110200 - 28 Oct 2016
Cited by 21 | Viewed by 7474
Abstract
The glycogen-synthase-kinase 3 (GSK-3) is an important target in drug discovery. This enzyme is involved in the signaling pathways of type 2 diabetes, neurological disorders, cancer, and other diseases. Therefore, inhibitors of GSK-3 are promising drug candidates for the treatment of a broad [...] Read more.
The glycogen-synthase-kinase 3 (GSK-3) is an important target in drug discovery. This enzyme is involved in the signaling pathways of type 2 diabetes, neurological disorders, cancer, and other diseases. Therefore, inhibitors of GSK-3 are promising drug candidates for the treatment of a broad range of diseases. Here we report pannorin (1), alternariol (2), and alternariol-9-methylether (3) to be promising inhibitors of the isoform GSK-3β showing sub-μM IC50 values. The in vitro inhibition is in the range of the known highly active GSK-3β inhibitor TDZD-8. Compounds 1–3 have a highly oxygenated benzocoumarin core structure in common, which suggests that this may be a new structural feature for efficient GSK-3β inhibition. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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1781 KiB  
Article
Dihydroisocoumarins from the Mangrove-Derived Fungus Penicillium citrinum
by Guo-Lei Huang, Xue-Ming Zhou, Meng Bai, Yu-Xin Liu, Yan-Lei Zhao, You-Ping Luo, Yan-Yan Niu, Cai-Juan Zheng and Guang-Ying Chen
Mar. Drugs 2016, 14(10), 177; https://doi.org/10.3390/md14100177 - 10 Oct 2016
Cited by 48 | Viewed by 6330
Abstract
Three new dihydroisocoumarin penicimarins G–I (1–3), together with one known dihydroisocoumarin (4) and three known meroterpenoids (5–7), were obtained from a fungus Penicillium citrinum isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected [...] Read more.
Three new dihydroisocoumarin penicimarins G–I (1–3), together with one known dihydroisocoumarin (4) and three known meroterpenoids (5–7), were obtained from a fungus Penicillium citrinum isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of spectroscopic data. The absolute configuration of 1 was determined by the X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of 2 and 3 were determined by comparison of their circular dichroism (CD) spectra with the literature. All compounds were evaluated for their antibacterial activities and cytotoxic activities. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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1664 KiB  
Article
Additional New Cytotoxic Triquinane-Type Sesquiterpenoids Chondrosterins K–M from the Marine Fungus Chondrostereum sp.
by Lei Huang, Wen-Jian Lan, Rong Deng, Gong-Kan Feng, Qing-Yan Xu, Zhi-Yu Hu, Xiao-Feng Zhu and Hou-Jin Li
Mar. Drugs 2016, 14(9), 157; https://doi.org/10.3390/md14090157 - 26 Aug 2016
Cited by 20 | Viewed by 6284
Abstract
By the method of 1H NMR prescreening and tracing the diagnostic proton signals of the methyl groups, three additional new triquinane-type sesquiterpenoids—chondrosterins K–M (1–3) and the known sesquiterpenoid anhydroarthrosporone (4)—were isolated from the marine fungus Chondrostereum [...] Read more.
By the method of 1H NMR prescreening and tracing the diagnostic proton signals of the methyl groups, three additional new triquinane-type sesquiterpenoids—chondrosterins K–M (1–3) and the known sesquiterpenoid anhydroarthrosporone (4)—were isolated from the marine fungus Chondrostereum sp. Their structures were elucidated on the basis of MS, 1D, and 2D NMR data. Chondrosterin K is a rare hirsutane sesquiterpenoid, in which a methyl group was migrated from C-2 to C-6 and has a double bond between C-2 and C-3. Compounds 1–3 showed significant cytotoxicities against various cancer cell lines in vitro. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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973 KiB  
Article
An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
by Chengqian Pan, Yutong Shi, Bibi Nazia Auckloo, Xuegang Chen, Chen-Tung Arthur Chen, Xinyi Tao and Bin Wu
Mar. Drugs 2016, 14(8), 156; https://doi.org/10.3390/md14080156 - 18 Aug 2016
Cited by 20 | Viewed by 6086
Abstract
A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. [...] Read more.
A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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Article
New Polyketides and New Benzoic Acid Derivatives from the Marine Sponge-Associated Fungus Neosartorya quadricincta KUFA 0081
by Chadaporn Prompanya, Tida Dethoup, Luís Gales, Michael Lee, José A. C. Pereira, Artur M. S. Silva, Madalena M. M. Pinto and Anake Kijjoa
Mar. Drugs 2016, 14(7), 134; https://doi.org/10.3390/md14070134 - 16 Jul 2016
Cited by 26 | Viewed by 7614
Abstract
Two new pentaketides, including a new benzofuran-1-one derivative (1) and a new isochromen-1-one (5), and seven new benzoic acid derivatives, including two new benzopyran derivatives (2a, b), a new benzoxepine derivative (3), two new [...] Read more.
Two new pentaketides, including a new benzofuran-1-one derivative (1) and a new isochromen-1-one (5), and seven new benzoic acid derivatives, including two new benzopyran derivatives (2a, b), a new benzoxepine derivative (3), two new chromen-4-one derivatives (4b, 7) and two new benzofuran derivatives (6a, b), were isolated, together with the previously reported 2,3-dihydro-6-hydroxy-2,2-dimethyl-4H-1-benzopyran-4-one (4a), from the culture of the marine sponge-associated fungus Neosartorya quadricincta KUFA 0081. The structures of the new compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compounds 1, 2a, 4b, 5, 6a and 7, the absolute configurations of their stereogenic carbons were determined by an X-ray crystallographic analysis. None of the isolated compounds were active in the tests for antibacterial activity against Gram-positive and Gram-negative bacteria, as well as multidrug-resistant isolates from the environment (MIC > 256 μg/mL), antifungal activity against yeast (Candida albicans ATTC 10231), filamentous fungus (Aspergillus fumigatus ATTC 46645) and dermatophyte (Trichophyton rubrum FF5) (MIC > 512 µg/mL) and in vitro growth inhibitory activity against the MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A375-C5 (melanoma) cell lines (GI50 > 150 µM) by the protein binding dye SRB method. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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