Bio-Active Products from Mangrove Ecosystems

A special issue of Marine Drugs (ISSN 1660-3397). This special issue belongs to the section "Structural Studies on Marine Natural Products".

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 18799

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State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University, Beijing 100191, China
Interests: marine natural product chemistry; marine chemical ecology; marine bioactive compounds; biosynthesis and biotransformation
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Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
Interests: sponge; coral; symbiotic microorganisms; structure optimization; marine active lead compounds; marine traditional Chinese medicine chemistry

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Guest Editor
One Health Institute, School of Chemical Engineering and Technology, Hainan University, Haikou 570228, China
Interests: secondary metabolites of medicinal plants and mangrove microorganisms; development of drug lead compounds
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Mangrove communities represent a coastal habitat located in the intertidal zone or brackish water of tropical and subtropical coastal areas between 5°N and 5°S latitudes spanning over 118 countries. Special ecological conditions of mangroves include high salinity, nutrient limitation, tidal gradients, high temperatures, excessively high light, and muddy anaerobic or sandy soil, which lead to various morphological and physiological adaptations of inhabiting species and act as an effective selector for the metabolic pathway via the generation of unique functional metabolites with highly unique chemical scaffolds and pharmaceutical application potential. In recent decades, numerous metabolites with uncommon structures and efficacious bioactivities have been discovered in mangrove-derived microorganisms, along with mangrove plants. For this reason, mangrove ecosystems have taken the limelight as an attractive biodiversity hotspot, attracting significant attention from organic chemists and pharmacologists. Additionally, many unique and novel chemical structures with a wide range of structural classes have suggested various biosynthetic origins containing novel functional genes and corresponding enzymes with unique catalytic functions. In this Special Issue, we welcome articles describing recent studies and pertinent reviews focusing on the latest and most important developments in bioactive product discovery from mangrove ecosystems and correlating structures with chemical synthesis, biosynthesis, genomic and metabolomics approaches, biological activities, and pharmaceutical mechanisms. We are now in the process of putting together a group of top researchers whose work we would like to feature in this collection, and we would like you to participate.

Prof. Dr. Wenhan Lin
Prof. Dr. Guoqiang Li
Prof. Dr. Jing Xu
Guest Editors

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Keywords

  • mangrove ecosystems
  • bio-active products
  • signaling pathway
  • chemical synthesis and biosynthesis
  • genomic and metabolomics approaches

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Published Papers (11 papers)

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Editorial

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4 pages, 187 KiB  
Editorial
Bio-Active Products from Mangrove Ecosystems
by Wenhan Lin, Guoqiang Li and Jing Xu
Mar. Drugs 2023, 21(4), 239; https://doi.org/10.3390/md21040239 - 14 Apr 2023
Cited by 3 | Viewed by 1240
Abstract
Mangrove communities represent the coastal habitats located in intertidal zones or brackish waters of tropical and subtropical coastal areas in over 118 countries [...] Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)

Research

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20 pages, 2994 KiB  
Article
Secondary Metabolites with Antifungal Activities from Mangrove Derived Fungus Monascus purpureus WMD2424
by Ming-Der Wu, Jih-Jung Chen and Ming-Jen Cheng
Mar. Drugs 2023, 21(4), 200; https://doi.org/10.3390/md21040200 - 24 Mar 2023
Cited by 3 | Viewed by 1759
Abstract
The mold Monascus, also called red yeast rice, anka, or koji, has been used as the natural food coloring agent and food additives for more than 1000 years in Asian countries. It has also been used in Chinese herbology and traditional Chinese [...] Read more.
The mold Monascus, also called red yeast rice, anka, or koji, has been used as the natural food coloring agent and food additives for more than 1000 years in Asian countries. It has also been used in Chinese herbology and traditional Chinese medicine due to its easing digestion and antiseptic effects. However, under different culture conditions, the ingredients in Monascus-fermented products may be changed. Therefore, an in-depth understanding of the ingredients, as well as the bioactivities of Monascus-derived natural products, is important. Here, through the thorough investigation into the chemical constituents of M. purpureus wmd2424, five previously undescribed compounds, monascuspurins A–E (15), were isolated from the EtOAc extract of mangrove-derived fungus Monascus purpureus wmd2424 cultured in RGY medium. All the constituents were confirmed via HRESIMS and 1D- and 2D-NMR spectroscopy. Their antifungal activity was also evaluated. Our results showed that four constituents (compounds 35) possessed mild antifungal activity against Aspergillus niger, Penicillium italicum, Candida albicans, and Saccharomyces cerevisiae. It is worth mentioning that the chemical composition of the type strain Monascus purpureus wmd2424 has never been studied. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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11 pages, 2105 KiB  
Article
New Chlorinated Metabolites and Antiproliferative Polyketone from the Mangrove Sediments-Derived Fungus Mollisia sp. SCSIO41409
by Jian Cai, Xueni Wang, Xia Gan, Qian Zhou, Xiaowei Luo, Bin Yang, Yonghong Liu, Disna Ratnasekera and Xuefeng Zhou
Mar. Drugs 2023, 21(1), 32; https://doi.org/10.3390/md21010032 - 30 Dec 2022
Cited by 9 | Viewed by 2115
Abstract
Two new chlorinated metabolites, 8-chlorine-5-hydroxy-2,3-dimethyl-7-methoxychromone (1) and 3,4-dichloro-1H-pyrrole-2,5-dione (3), and eight known compounds (2 and 49) were isolated from the mangrove sediments-derived fungus Mollisia sp. SCSIO41409. Their structures were elucidated by physicochemical properties [...] Read more.
Two new chlorinated metabolites, 8-chlorine-5-hydroxy-2,3-dimethyl-7-methoxychromone (1) and 3,4-dichloro-1H-pyrrole-2,5-dione (3), and eight known compounds (2 and 49) were isolated from the mangrove sediments-derived fungus Mollisia sp. SCSIO41409. Their structures were elucidated by physicochemical properties and extensive spectroscopic analysis. The absolute configuration of stemphone C (4) was established for the first time by the X-ray crystallographic analysis. Compounds 3 and 4 showed different intensity of antimicrobial activities against several pathogenic fungi and bacteria, and antiproliferative activities against two human prostate cancer cell lines (IC50 values 2.77 to 9.60 μM). Further, stemphone C (4) showed a reducing PC-3 cell colony formation, inducing apoptosis and blocking the cell cycle at S-phase in a dose-dependent manner; thus, it could be considered as a potential antiproliferative agent and a promising anti-prostate cancer lead compound. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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16 pages, 4684 KiB  
Article
Epigenetic Manipulation Induced Production of Immunosuppressive Chromones and Cytochalasins from the Mangrove Endophytic Fungus Phomopsis asparagi DHS-48
by Ting Feng, Chengwen Wei, Xiaolin Deng, Dandan Chen, Zhenchang Wen and Jing Xu
Mar. Drugs 2022, 20(10), 616; https://doi.org/10.3390/md20100616 - 29 Sep 2022
Cited by 6 | Viewed by 2059
Abstract
A mangrove endophytic fungus Phomopsis asparagi DHS-48 was found to be particularly productive with regard to the accumulation of substantial new compounds in our previous study. In order to explore its potential to produce more unobserved secondary metabolites, epigenetic manipulation was used on [...] Read more.
A mangrove endophytic fungus Phomopsis asparagi DHS-48 was found to be particularly productive with regard to the accumulation of substantial new compounds in our previous study. In order to explore its potential to produce more unobserved secondary metabolites, epigenetic manipulation was used on this fungus to activate cryptic or silent genes by using the histone deacetylase (HDAC) inhibitor sodium butyrate and the DNA methyltransferase (DNMT) inhibitor 5-azacytidine (5-Aza). Based on colony growth, dry biomass, HPLC, and 1H NMR analyses, the fungal chemical diversity profile was significantly changed compared with the control. Two new compounds, named phaseolorin J (1) and phomoparagin D (5), along with three known chromones (24) and six known cytochalasins (611), were isolated from the culture treated with sodium butyrate. Their structures, including their absolute configurations, were elucidated using a combination of detailed HRESIMS, NMR, and ECD and 13C NMR calculations. The immunosuppressive and cytotoxic activities of all isolated compounds were evaluated. Compounds 1 and 8 moderately inhibited the proliferation of ConA (concanavalin A)-induced T and LPS (lipopolysaccharide)-induced B murine spleen lymphocytes. Compound 5 exhibited significant in vitro cytotoxicity against the tested human cancer cell lines Hela and HepG2, which was comparative to the positive control adriamycin and fluorouracil. Our finding demonstrated that epigenetic manipulation should be an efficient strategy for the induction of new metabolites from mangrove endophytic fungi. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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14 pages, 3171 KiB  
Article
Immunosuppressive Cytochalasins from the Mangrove Endophytic Fungus Phomopsis asparagi DHS-48
by Zhao Feng, Xuexia Zhang, Jingwan Wu, Chengwen Wei, Ting Feng, Dongdong Zhou, Zhenchang Wen and Jing Xu
Mar. Drugs 2022, 20(8), 526; https://doi.org/10.3390/md20080526 - 18 Aug 2022
Cited by 8 | Viewed by 1851
Abstract
Three new cytochalasins, phomoparagins A-C (13), along with five known analogs (48), were isolated from Phomopsis asparagi DHS-48, a mangrove-derived endophytic fungus. Their structures, including their absolute configurations, were elucidated using a combination of detailed [...] Read more.
Three new cytochalasins, phomoparagins A-C (13), along with five known analogs (48), were isolated from Phomopsis asparagi DHS-48, a mangrove-derived endophytic fungus. Their structures, including their absolute configurations, were elucidated using a combination of detailed HRESIMS, NMR, and ECD techniques. Notably, 1 possessed an unprecedented 5/6/5/8/5-fused pentacyclic skeleton. These compounds were tested for their inhibitory activity against concanavalin A (ConA)/lipopolysaccharide (LPS)-induced spleen lymphocyte proliferation and calcineurin (CN) enzyme. Several metabolites (2 and 46) exhibited fascinating inhibitory activities with a relatively low toxicity. Furthermore, 2 was demonstrated to inhibit ConA-stimulated activation of NFAT1 dephosphorylation and block NFAT1 translocation in vitro, subsequently inhibiting the transcription of interleukin-2 (IL-2). Our results provide evidence that 2 may, at least partially, suppress the activation of spleen lymphocytes via the CN/NFAT signaling pathway, highlighting that it could serve as an effective immunosuppressant that is noncytotoxic and natural. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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11 pages, 2869 KiB  
Article
Integrating Activity-Guided Strategy and Fingerprint Analysis to Target Potent Cytotoxic Brefeldin A from a Fungal Library of the Medicinal Mangrove Acanthus ilicifolius
by Cui-Fang Wang, Jie Ma, Qian-Qian Jing, Xi-Zhen Cao, Lu Chen, Rong Chao, Ji-Yong Zheng, Chang-Lun Shao, Xiao-Xi He and Mei-Yan Wei
Mar. Drugs 2022, 20(7), 432; https://doi.org/10.3390/md20070432 - 29 Jun 2022
Cited by 7 | Viewed by 1926
Abstract
Mangrove-associated fungi are rich sources of novel and bioactive compounds. A total of 102 fungal strains were isolated from the medicinal mangrove Acanthus ilicifolius collected from the South China Sea. Eighty-four independent culturable isolates were identified using a combination of morphological characteristics and [...] Read more.
Mangrove-associated fungi are rich sources of novel and bioactive compounds. A total of 102 fungal strains were isolated from the medicinal mangrove Acanthus ilicifolius collected from the South China Sea. Eighty-four independent culturable isolates were identified using a combination of morphological characteristics and internal transcribed spacer (ITS) sequence analyses, of which thirty-seven strains were selected for phylogenetic analysis. The identified fungi belonged to 22 genera within seven taxonomic orders of one phyla, of which four genera Verticillium, Neocosmospora, Valsa, and Pyrenochaeta were first isolated from mangroves. The cytotoxic activity of organic extracts from 55 identified fungi was evaluated against human lung cancer cell lines (A-549), human cervical carcinoma cell lines (HeLa), human hepatoma cells (HepG2), and human acute lymphoblastic leukemia cell lines (Jurkat). The crude extracts of 31 fungi (56.4%) displayed strong cytotoxicity at the concentration of 50 μg/mL. Furthermore, the fungus Penicillium sp. (HS-N-27) still showed strong cytotoxic activity at the concentration of 25 µg/mL. Integrating cytotoxic activity-guided strategy and fingerprint analysis, a well-known natural Golgi-disruptor and Arf-GEFs inhibitor, brefeldin A, was isolated from the target active strain HS-N-27. It displayed potential activity against A549, HeLa and HepG2 cell lines with the IC50 values of 101.2, 171.9 and 239.1 nM, respectively. Therefore, combining activity-guided strategy with fingerprint analysis as a discovery tool will be implemented as a systematic strategy for quick discovery of active compounds. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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13 pages, 1228 KiB  
Communication
Sesquiterpenoids from the Mangrove-Derived Aspergillus ustus 094102
by Pengyan Gui, Jie Fan, Tonghan Zhu, Peng Fu, Kui Hong and Weiming Zhu
Mar. Drugs 2022, 20(7), 408; https://doi.org/10.3390/md20070408 - 22 Jun 2022
Cited by 6 | Viewed by 1626
Abstract
Four new drimane sesquiterpenoids (14) and three known ones (57) were isolated from the fermentation broth of the mangrove-derived Aspergillus ustus 094102. Compound 5 was further resolved as four purified compounds 5a5d. [...] Read more.
Four new drimane sesquiterpenoids (14) and three known ones (57) were isolated from the fermentation broth of the mangrove-derived Aspergillus ustus 094102. Compound 5 was further resolved as four purified compounds 5a5d. By means of extensive spectroscopic and ECD analysis as well as the chemical transformation, their structures were identified as (2R,3R,5S,9R,10S)-2,3,9,11-tetrahydroxydrim-7-en-6-one (ustusol F, 1), (2R,3R,5R,9S,10R)-2,3,11-trihydroxydrim-7-en-6-one (9-deoxyustusol F, 2), (3S,5R,9R,10R)-3,11,12-trihydroxydrim-7-en-6-one (ustusol G, 3), (5S,6R,9S,10S, 11R,2′E,4′E)-(11-dideoxy-11-hydroxystrobilactone A-6-yl)-5-carboxypenta-2,4-dienoate (ustusolate H, 4), ((5S,6R,9S,10S)-strobilactone A-6-yl) (2E,4E)-6,7-dihydroxyocta-2,4-dienoate (ustusolate I, 5), (2′E,4′E;6′,7′-erythro)-ustusolate I (5a) and (2′E,4′E;ent-6′,7′-erythro)-ustusolate I (5b), (2′E,4′E,6′R,7′R)-ustusolate I (5c) and (2′E,4′E,6′S,7′S)-ustusolate I (5d), (5S,6R,9S,10S,2′E,4′E)-(strobilactone A-6-yl)-5-carboxypenta-2,4-dienoate (ustusolate J, 6), and (2S,5S,9R,10S)-2,9,11-trihydroxydrim-7-en-6-one (ustusol B, 7), respectively. Compound 5 showed antiproliferation against the human tumor cells CAL-62 and MG-63 with the IC50 values of 16.3 and 10.1 µM, respectively. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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13 pages, 2296 KiB  
Article
Talaromarins A–F: Six New Isocoumarins from Mangrove-Derived Fungus Talaromyces flavus TGGP35
by Jin Cai, Xiao-Chen Zhu, Wei-Nv Zeng, Bin Wang, You-Ping Luo, Jing Liu, Min-Jing Chen, Gao-Yu Li, Guo-Lei Huang, Guang-Ying Chen, Jing Xu and Cai-Juan Zheng
Mar. Drugs 2022, 20(6), 361; https://doi.org/10.3390/md20060361 - 27 May 2022
Cited by 7 | Viewed by 2162
Abstract
Six new isocoumarin derivative talaromarins A-F (16), along with 17 known analogues (723), were isolated from the mangrove-derived fungus Talaromyces flavus (Eurotiales: Trichocomaceae) TGGP35. Their structures were identified by detailed IR, UV, 1D/2D NMR and [...] Read more.
Six new isocoumarin derivative talaromarins A-F (16), along with 17 known analogues (723), were isolated from the mangrove-derived fungus Talaromyces flavus (Eurotiales: Trichocomaceae) TGGP35. Their structures were identified by detailed IR, UV, 1D/2D NMR and HR-ESI-MS spectra. The absolute configurations of new compounds were determined by the modified Mosher’s method and a comparison of their CD spectra with dihydroisocoumarins described in the literature. The antioxidant, antibacterial, anti-phytopathogenic and inhibitory activity against α-glucosidase of all the isolated compounds were tested. Compounds 611, 1719 and 2122 showed similar or better antioxidant activity than the IC50 values ranging from 0.009 to 0.27 mM, compared with the positive control trolox (IC50 = 0.29 mM). Compounds 10, 18, 21 and 23 exhibited strong inhibitory activities against α-glucosidase with IC50 values ranging from 0.10 to 0.62 mM, while the positive control acarbose had an IC50 value of 0.5 mM. All compounds showed no antibacterial or anti-phytopathogenic activity at the concentrations of 50 μg/mL and 1 mg/mL, respectively. These results indicated that isocoumarins will be useful to developing antioxidants and as diabetes control agents. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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Review

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24 pages, 665 KiB  
Review
Antimicrobial Secondary Metabolites from the Mangrove Plants of Asia and the Pacific
by Mazdida Sulaiman, Veeranoot Nissapatorn, Mohammed Rahmatullah, Alok K. Paul, Mogana Rajagopal, Nor Azizun Rusdi, Jaya Seelan Sathya Seelan, Monica Suleiman, Zainul Amiruddin Zakaria and Christophe Wiart
Mar. Drugs 2022, 20(10), 643; https://doi.org/10.3390/md20100643 - 15 Oct 2022
Cited by 6 | Viewed by 3764
Abstract
Microbes such as the White Spot Syndrome Virus account for severe losses in the shrimp farming industry globally. This review examines the literature on the mangrove plants of Asia and the Pacific with antibacterial, antifungal, or antiviral activities. All of the available data [...] Read more.
Microbes such as the White Spot Syndrome Virus account for severe losses in the shrimp farming industry globally. This review examines the literature on the mangrove plants of Asia and the Pacific with antibacterial, antifungal, or antiviral activities. All of the available data published on this subject were collected from Google Scholar, PubMed, Science Direct, Web of Science, ChemSpider, PubChem, and a library search from 1968 to 2022. Out of about 286 plant species, 119 exhibited antimicrobial effects, and a total of 114 antimicrobial natural products have been identified including 12 with MIC values below 1 µg/mL. Most of these plants are medicinal. The mangrove plants of Asia and the Pacific yield secondary metabolites with the potential to mitigate infectious diseases in shrimp aquaculture. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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35 pages, 14826 KiB  
Review
Unusual Secondary Metabolites from the Mangrove Ecosystems: Structures, Bioactivities, Chemical, and Bio-Syntheses
by Meng-Jun Wu, Baofu Xu and Yue-Wei Guo
Mar. Drugs 2022, 20(8), 535; https://doi.org/10.3390/md20080535 - 20 Aug 2022
Cited by 10 | Viewed by 3422
Abstract
Mangrove ecosystems are widely distributed in the intertidal zone of tropical and subtropical estuaries or coasts, containing abundant biological communities, for example, mangrove plants and diverse groups of microorganisms, featuring various bioactive secondary metabolites. We surveyed the literature from 2010 to 2022, resulting [...] Read more.
Mangrove ecosystems are widely distributed in the intertidal zone of tropical and subtropical estuaries or coasts, containing abundant biological communities, for example, mangrove plants and diverse groups of microorganisms, featuring various bioactive secondary metabolites. We surveyed the literature from 2010 to 2022, resulting in a collection of 134 secondary metabolites, and classified them into two major families in terms of the biological sources and 15 subfamilies according to the chemical structures. To highlight the structural diversity and bioactivities of the mangrove ecosystem-associated secondary metabolites, we presented the chemical structures, bioactivities, biosynthesis, and chemical syntheses. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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21 pages, 6315 KiB  
Review
Progress in Isoindolone Alkaloid Derivatives from Marine Microorganism: Pharmacology, Preparation, and Mechanism
by Sijin Hang, Hui Chen, Wenhui Wu, Shiyi Wang, Yiwen Fang, Ruilong Sheng, Qidong Tu and Ruihua Guo
Mar. Drugs 2022, 20(6), 405; https://doi.org/10.3390/md20060405 - 20 Jun 2022
Cited by 9 | Viewed by 2596
Abstract
Compound 1 (SMTP-7, also FGFC1), an isoindolone alkaloid from marine fungi Starchbotrys longispora FG216 and fungi Stachybotrys microspora IFO 30018, possessed diverse bioactivities such as thrombolysis, anti-inflammatory and anti-oxidative properties, and so on. It may be widely used for the treatment of various [...] Read more.
Compound 1 (SMTP-7, also FGFC1), an isoindolone alkaloid from marine fungi Starchbotrys longispora FG216 and fungi Stachybotrys microspora IFO 30018, possessed diverse bioactivities such as thrombolysis, anti-inflammatory and anti-oxidative properties, and so on. It may be widely used for the treatment of various diseases, including cerebral infarction, stroke, ischemia/reperfusion damage, acute kidney injury, etc. Especially in cerebral infarction, compound 1 could reduce hemorrhagic transformation along with thrombolytic therapy, as the traditional therapies are accompanied with bleeding risks. In the latest studies, compound 1 selectively inhibited the growth of NSCLC cells with EGFR mutation, thus demonstrating its excellent anti-cancer activity. Herein, we summarized pharmacological activities, preparation of staplabin congeners—especially compound 1—and the mechanism of compound 1, with potential therapeutic applications. Full article
(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)
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