scholarly journals Natural Products Analysis  of South Pacific Marine  Sponges

2021 ◽  
Author(s):  
◽  
Taitusi Taufa
Keyword(s):  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Optical Rotation ◽  
Screening Method ◽  
Marine Sponges ◽  
Ic50 Value ◽  
Products Analysis ◽  
New Compounds ◽  
Cacospongia Mycofijiensis

<p>This thesis describes the isolation and structure elucidation of 15 new secondary metabolites from Tongan and New Zealand marine sponges. A total of 18 sponge specimens were subjected to an NMR-based screening method, of which four were analysed in detail. Examination of a two-sponge association, Stelletta crater and Desmacella dendyi from New Zealand, resulted in the isolation of two new 4-methylenesterols, craterols A (94) and B (95). To the best of the author’s knowledge, compounds 94 and 95 represent the first secondary metabolites to be reported from either species. Both 94 and 95 possess a double bond between C-5 and C-6, a feature that is unprecedented in this subgroup of marine natural products. An investigation of a Tongan sponge Zyzzya fuliginosa afforded two new pyrroloquinoline alkaloids, 6-bromodamirone B (182) and makaluvamine W (183). Makaluvamine W (183) contains an oxazole moiety, which is uncommon in this group of natural products. Both 182 and 183 lacked activity against the human promyelocytic leukemia cells (HL-60). Five new compounds were isolated from a Tongan sponge of the genus Leucetta, including two glycerol lipids (238 and 239), three glycerol ethers (244–246) and an imidazole alkaloid (243). Naamidine K (243) is a new addition to the naamidine family, while the glycerol metabolites are non-imidazole alkaloid additions to the group of compounds reported from this genus. A spectroscopic investigation into the Tongan sponge Cacospongia mycofijiensis yielded four new zampanolide analogues (282–285) and a new oxygenated sesquiterpene, isodictyodendrillin A (280). The isolation of the zampanolide analogues gives insight into the structure-activity relationship (SAR) in this family of compounds. Zampanolides B–D (282–284) displayed potent antiproliferative activity towards HL-60 cell lines in the low nanomolar range (3–5 nM), while zampanolide E (285) was significantly less potent with an IC50 value of 306 nM. In addition, the re-isolation of dactylolide (281) and zampanolide A (278) from this sponge, established a firm conclusion regarding the controversial configuration of dactylolide (281), which possesses the same absolute configuration as (–)-zampanolide A (278) and has a levorotatory optical rotation.</p>

scholarly journals Natural Products Analysis  of South Pacific Marine  Sponges

2021 ◽  
Author(s):  
◽  
Taitusi Taufa
Keyword(s):  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Optical Rotation ◽  
Screening Method ◽  
Marine Sponges ◽  
Ic50 Value ◽  
Products Analysis ◽  
New Compounds ◽  
Cacospongia Mycofijiensis

<p>This thesis describes the isolation and structure elucidation of 15 new secondary metabolites from Tongan and New Zealand marine sponges. A total of 18 sponge specimens were subjected to an NMR-based screening method, of which four were analysed in detail. Examination of a two-sponge association, Stelletta crater and Desmacella dendyi from New Zealand, resulted in the isolation of two new 4-methylenesterols, craterols A (94) and B (95). To the best of the author’s knowledge, compounds 94 and 95 represent the first secondary metabolites to be reported from either species. Both 94 and 95 possess a double bond between C-5 and C-6, a feature that is unprecedented in this subgroup of marine natural products. An investigation of a Tongan sponge Zyzzya fuliginosa afforded two new pyrroloquinoline alkaloids, 6-bromodamirone B (182) and makaluvamine W (183). Makaluvamine W (183) contains an oxazole moiety, which is uncommon in this group of natural products. Both 182 and 183 lacked activity against the human promyelocytic leukemia cells (HL-60). Five new compounds were isolated from a Tongan sponge of the genus Leucetta, including two glycerol lipids (238 and 239), three glycerol ethers (244–246) and an imidazole alkaloid (243). Naamidine K (243) is a new addition to the naamidine family, while the glycerol metabolites are non-imidazole alkaloid additions to the group of compounds reported from this genus. A spectroscopic investigation into the Tongan sponge Cacospongia mycofijiensis yielded four new zampanolide analogues (282–285) and a new oxygenated sesquiterpene, isodictyodendrillin A (280). The isolation of the zampanolide analogues gives insight into the structure-activity relationship (SAR) in this family of compounds. Zampanolides B–D (282–284) displayed potent antiproliferative activity towards HL-60 cell lines in the low nanomolar range (3–5 nM), while zampanolide E (285) was significantly less potent with an IC50 value of 306 nM. In addition, the re-isolation of dactylolide (281) and zampanolide A (278) from this sponge, established a firm conclusion regarding the controversial configuration of dactylolide (281), which possesses the same absolute configuration as (–)-zampanolide A (278) and has a levorotatory optical rotation.</p>

scholarly journals Biological and Chemical Diversity of Marine Sponge-Derived Microorganisms over the Last Two Decades from 1998 to 2017

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 853 ◽  
Author(s):  
Mei-Mei Cheng ◽  
Xu-Li Tang ◽  
Yan-Ting Sun ◽  
Dong-Yang Song ◽  
Yu-Jing Cheng ◽  
...  
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Marine Sponge ◽  
Marine Sponges ◽  
Chemical Diversity ◽  
Comprehensive Overview ◽  
Bioactive Secondary Metabolites ◽  
The Relationship ◽  
Product Chemistry

Marine sponges are well known as rich sources of biologically natural products. Growing evidence indicates that sponges harbor a wealth of microorganisms in their bodies, which are likely to be the true producers of bioactive secondary metabolites. In order to promote the study of natural product chemistry and explore the relationship between microorganisms and their sponge hosts, in this review, we give a comprehensive overview of the structures, sources, and activities of the 774 new marine natural products from sponge-derived microorganisms described over the last two decades from 1998 to 2017.

Secondary metabolites of the aspen fungus Stachybotrys cylindrospora

1993 ◽  
Vol 71 (4) ◽  
pp. 487-493 ◽  
Author(s):  
William A. Ayer ◽  
Shichang Miao
Keyword(s):  
Natural Products ◽  
Antifungal Activity ◽  
Secondary Metabolites ◽  
The Other ◽  
Spectroscopic Techniques ◽  
Blue Stain ◽  
New Compounds

The secondary metabolites produced by the fungus Stachybotrys cylindrospora, which is known to be strongly antagonistic to the blue-stain fungus Ceratocystiopsis crassivaginata, have been examined. The compounds responsible for the antifungal activity are trichodermin (5) and trichodermol (6), two previously known mycotoxins belonging to the trichothecene family. The other metabolites, stachybotrydial (1), stachybotramide (8), and 6,8-dihydroxy-3,5,7-trimethylisochroman (7), although not active against C. crassivaginata, are new natural products. The structures of the new compounds were established by spectroscopic techniques.

scholarly journals Isolation of New Secondary Metabolites from New Zealand Marine Invertebrates

2021 ◽  
Author(s):  
◽  
Joanna M Wojnar
Keyword(s):  
New Zealand ◽  
Methyl Ester ◽  
Secondary Metabolites ◽  
Chromatographic Separation ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Marine Invertebrates ◽  
Toxic Metabolites ◽  
The Family ◽  
New Compounds

<p>This study describes the isolation and structure elucidation of several known and 13 new compounds from New Zealand marine organisms. Furthermore, it describes the development of a digital mask program for the analysis of HSQC spectra of crude sponge extracts. This was used as a screening tool to identify secondary metabolite producers that warranted further analysis. As reports of metabolites from New Zealand nudibranchs are poorly represented in the literature, a study of five New Zealand nudibranch species was undertaken. These coloured and seemingly undefended nudibranchs are known to concentrate or sequester toxic metabolites from their prey, facilitating rapid isolation and structure elucidation of these metabolites. This study resulted in the isolation of a variety of metabolite classes; two new compounds, 13alpha- acetoxypukalide diol (30) and lopholide diol (31) from the nudibranch Tritonia incerta, are described. Examination of the sponge Raspailia agminata resulted in the isolation of a novel family of partially acetylated glycolipids which contain up to six glucose residues. The chromatographic separation of these compounds was a challenge due to the similarity of the congeners and their lack of a chromophore. MSguided isolation eventually led to the purification of agminosides A-E (145-149). An unidentified sponge of the order Dictyoceratida was found to contain a new isomer (186) of the known sesterterpene variabilin. As variabilin-type compounds are predominantly found from sponges of the family Irciniidae, the unidentified sponge is most likely an irciniid. In addition, the sponge contained two prenylated quinones, one of which, 189, is a new isomer of a known sponge metabolite. The sponge Darwinella oxeata contained four new nitrogenous diterpenes of the aplysulphurane (rearranged spongian) skeleton, oxeatamide A (214), isooxeatamide A (215), oxeatamide A 23-methyl ester (216) and oxeatamide B (217).</p>

scholarly journals Validation of a Spectroscopic Screening Method for Secondary Metabolites from New Zealand Extremophilic Microbes

2021 ◽  
Author(s):  
◽  
Chriselle Deborah Braganza
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Biological Activity ◽  
New Zealand ◽  
Antifungal Activity ◽  
Secondary Metabolites ◽  
Marine Bacteria ◽  
Marine Invertebrates ◽  
Screening Method ◽  
Microbial Cultures ◽  
Anoxybacillus Flavithermus

<p>The existing protocol for the screening of natural products from marine invertebrates and macroalgae has been demonstrated successfully at VUW on multiple occasions. This study describes the evaluation of an adapted version of the protocol to screen liquid microbial cultures. The adapted protocol was carried out using an NMR-guided approach and was used to screen 10 New Zealand extremophilic microbes. Investigation of the bacteria Anoxybacillus flavithermus led to the isolation of the known compound 1-acetyl-β-carboline (25), which was briefly evaluated for its biological activity. A detailed investigation on the marine bacteria Shewanella sp. resulted in the isolation of indole-3-carboxaldehyde (93) and 14 known 2,5-diketopiperazines (36, 38, 41–44, 53, 54, 94–99). Three of the isolated 2,5-DKPs were tested against Saccharomyces cerevisiae to evaluate their antifungal activity, the results of which are also described. Overall, the use of the adapted screening method proved successful to guide the isolation of secondary metabolites from microbial cultures.</p>

scholarly journals Phytochemistry and Antioxidant Activities of the Methanolic Leaf Extract of Clerodendrum splendens (Lamiaceae)

2018 ◽  
pp. 12-20
Author(s):  
Nganso Ditchou Yves Oscar ◽  
Amang A Ngoung GA ◽  
Soh Desire ◽  
Simo Nemg Fredy Brice ◽  
Nyasse Barthelemy
Keyword(s):  
Antioxidant Activity ◽  
Natural Products ◽  
Secondary Metabolites ◽  
Vitamin C ◽  
Leaf Extract ◽  
Antioxidant Activities ◽  
Maximum Activity ◽  
Hepatic Lipids ◽  
Ic50 Value ◽  
Ic50 Values

This paper aimed at studying the antioxidant efficacy of the methanolic leaf extract of Clerodendrum splendens, a plant of the Lamiaceae family. Phytochemical tests carried out on extracts of Clerodendrum splendens leaves have been able to detect the presence of secondary metabolites such as Flavonoids, Tannins, Saponins and Terpenoids. The results of the antioxidant activity have shown that CSF2, CSF3 fractions and CSB, CSG fractions similarly inhibited hepatic lipids but significantly less than vitamin C. Compared to all fractions, the CSB fraction shows the best inhibitor on the peroxidation of hepatic lipids because at 150 μg/mL, there is a maximum activity (2.5 μg/mL of protein). However, it is found that CSF3, CSF2 and CSG have higher IC50 values than vitamin C (5.613±0.117) while CSEB, CSB and CSC fractions showed lower IC50 values than vitamin C, which is used as the reference reducing compound. The lower the IC50 value compared to vitamin C, the greater the antioxidant capacity of the plant extract. The results of this study suggest that Clerodendrum splendens represents an untapped source of compounds with potential antioxidant activity that could be explored in the development of new therapeutic natural products.

scholarly journals New Halogenated Secondary Metabolites from Red Algae of the South Pacific

2021 ◽  
Author(s):  
◽  
Victoria Woolner
Keyword(s):  
New Zealand ◽  
Secondary Metabolites ◽  
Structure Elucidation ◽  
Detailed Examination ◽  
Red Alga ◽  
Marine Natural Product ◽  
Extensive Investigation ◽  
Ic50 Value ◽  
Mass Spectrometric Evidence ◽  
Related Compounds

<p>An NMR- and MS-directed study led to the isolation and structure elucidation of several halogenated secondary metabolites from a New Zealand and a Tongan red alga. An extensive investigation was carried out on the New Zealand red alga Rhodophyllis membranacea following mass spectrometric evidence for an unusual tetrahalogenated indole with the exceptionally rare inclusion of bromine, chlorine and iodine within a fraction of a semi-purified extract. Due to the difficulty associated with the structure elucidation of proton deficient molecules, a strategic isolation and structure elucidation of several polyhalogenated indoles was employed in order to unequivocally assign the halogen positions on the indolic core. This resulted in the isolation and characterisation of 11 new tetrahalogenated indoles (123–133), four of which contain bromine, chlorine and iodine (124 and 129–131) and represent the first isolation of such compounds. Additionally, four new pentahalogenated indoles (134–137) and an uncharacterised tribromotrichloroindole were isolated. The synthetically known compound 4-chloroisatin (138) was isolated as a new marine natural product, while 4-chloro-3-hydroxyl-3-(2-oxopropyl)-2-oxindole (139) was established to be an artefact of isolation. Several compounds were found to exhibit antifungal properties against Saccharomyces cerevisiae.  A detailed examination of the Tongan alga Callophycus serratus led to the isolation of six new meroditerpenoids: callophycol C (227), iodocallophycols E (228) and F (229), iodocallophycoic acid B (230), deiodocallophycoic B (231) and callophycoic acid I (232). The relative configurations in compounds 228–231 are proposed to differ from closely related compounds in the literature. Iodocallophycol E (228) exhibited moderate cytotoxicity against the HL-60 cell line with an IC50 value of 6.0 μM.</p>

scholarly journals POTENCIAL BIOTECNOLÓGICO DE LAS ESPONJAS EN LA PRODUCCIÓN DE NUEVOS FÁRMACOS: PERSPECTIVAS Y LIMITACIONES

2011 ◽  
Vol 26 (2) ◽  
pp. 31
Author(s):  
R. N. Águila-Ramírez ◽  
C. J. Hernández-Guerrero ◽  
B. González-Acosta
Keyword(s):  
Clinical Trials ◽  
Natural Products ◽  
Pharmacological Activity ◽  
Natural Environment ◽  
Marine Sponges ◽  
Biotechnological Production ◽  
Antiviral Compounds ◽  
Genetic Modifications ◽  
New Compounds

La búsqueda de productos naturales con actividad farmacológica a partir de esponjas marinas tiene un gran potencial debido a las interesantes actividades que algunos compuestos presentan en ensayos clínicos, principalmente en la búsqueda de compuestos anticancerígenos y antivirales. Sin embargo, también existen diversas problemáticas que pueden frenar el desarrollo de un nuevo compuesto. Por lo que en esta revisión se pretende dar un panorama general de las perspectivas y limitantes que se presentan en la búsqueda de nuevos compuestos a partir de esponjas en el medio natural, en el establecimiento de cultivos de esponjas, de primorfos y células madre como una alternativa o el aislamiento de bacterias asociadas a ellas que produzcan dichos metabolitos con la finalidad de realizar modificaciones genéticas que permitan una producción biotecnológica. Biotechnical potential of sponges in new pharmaceutics production: perspectives and limits The search for natural products with pharmacological activity of marine sponges has great potential due to the interesting activities that some compounds have in clinical trials, mainly in the search of anticancer and antiviral compounds. However, there are various problems that may limit the development of a new compound. In this review we intended to give an overview of the perspectives and limitations that occur in the search of new compounds from sponges of the natural environment, in the establishment of culture of sponges, primorph and steam cells as an alternative, or isolated bacteria from sponges which are the metabolites producers to development genetic modifications for a biotechnological production.

scholarly journals Penigrisacids A–D, Four New Sesquiterpenes from the Deep-Sea-Derived Penicillium griseofulvum

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 507 ◽  
Author(s):  
Cui-Ping Xing ◽  
Chun-Lan Xie ◽  
Jin-Mei Xia ◽  
Qing-Mei Liu ◽  
Wei-Xiang Lin ◽  
...  
Keyword(s):  
Tumor Cells ◽  
Deep Sea ◽  
Optical Rotation ◽  
Electronic Circular Dichroism ◽  
Planar Structures ◽  
Extensive Analysis ◽  
Ic50 Value ◽  
Penicillium Griseofulvum ◽  
The Absolute ◽  
New Compounds

Four new (penigrisacids A–D, 1–4) and one known (5) carotane sesquiterpenoids were isolated from the deep-sea-derived fungus Penicillium griseofulvum, along with four known compounds (6–9). The planar structures and relative configurations of the new compounds were determined by extensive analysis of the NMR and HRESIMS data. The absolute configurations were established by comparison of the experimental and calculated ECD (electronic circular dichroism) spectra or OR (optical rotation) value. Compound 9 exhibited potent anti-food allergic activity with IC50 value of 28.7 μM, while 4 showed weak cytotoxicity against ECA-109 tumor cells (IC50 = 28.7 μM).

scholarly journals A Review of the Secondary Metabolites From the Marine Sponges of the Genus Aaptos

2020 ◽  
Vol 15 (9) ◽  
pp. 1934578X2095143
Author(s):  
Qianqian He ◽  
Shuang Miao ◽  
Na Ni ◽  
Yuqing Man ◽  
Kaikai Gong
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Chemical Ecology ◽  
Marine Natural Products ◽  
Organic Molecules ◽  
Biological Activities ◽  
Marine Sponges ◽  
Marine Natural Product ◽  
Natural Product Research

Marine sponges, which belong to the phylum Porifera (Metazoa), are considered the single best source of marine natural products. Among them, members of the genus Aaptos are attractive targets for marine natural product research owing to their abundant biogenetic ability to produce aaptamine derivatives. Apart from aaptamine alkaloids, there are also reports of other compounds from Aaptos sponges. This work reviews the secondary metabolites isolated from Aaptos species from 1982 to 2020, with 46 citations referring to 62 compounds (47 for aaptamines and 15 for others). The emphasis is placed on the structure of the organic molecules, relevant biological activities, chemical ecology aspects, and biosynthesis studies, which are described in the classifications of aaptamines and other compounds in the order of the published year.

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