scholarly journals Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata

Marine Drugs ◽  
2019 ◽  
Vol 17 (12) ◽  
pp. 683 ◽  
Author(s):  
Kavita Ragini ◽  
Andrew M. Piggott ◽  
Peter Karuso
Keyword(s):  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Marine Sponge ◽  
Deep Sea ◽  
Indole Alkaloids ◽  
Chemical Investigation ◽  
Enantiomerically Pure ◽  
The One ◽  
First Time

Chemical investigation of the secondary metabolites of a rare New Zealand deep-sea sponge, Lamellomorpha strongylata, resulted in the isolation of twenty-one indole alkaloids, including two new bisindoles—(Z)-coscinamide D (1), (E)-coscinamide D (2)—and four compounds isolated for the first time as natural products—lamellomorphamides A (3), B (4), C (5) and D (6). In addition, fifteen previously reported natural products were isolated, seven of which are seco analogs of hamacanthin alkaloids. The one sponge produces enantiomerically pure but opposite configurations of compounds that only differ in the number of bromines, suggesting enantiodivergent biosynthesis. In addition, four compounds were isolated as partial racemates, suggesting these compounds are biosynthesized via two independent routes.

scholarly journals Chemical Elicitors Induce Rare Bioactive Secondary Metabolites in Deep-Sea Bacteria under Laboratory Conditions

Metabolites ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 107
Author(s):  
Rafael de Felício ◽  
Patricia Ballone ◽  
Cristina Freitas Bazzano ◽  
Luiz F. G. Alves ◽  
Renata Sigrist ◽  
...  
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Deep Sea ◽  
Chemical Space ◽  
Bacterial Genome ◽  
Vast Number ◽  
Bacterial Metabolites ◽  
Laboratory Conditions ◽  
Deep Sea Bacteria

Bacterial genome sequencing has revealed a vast number of novel biosynthetic gene clusters (BGC) with potential to produce bioactive natural products. However, the biosynthesis of secondary metabolites by bacteria is often silenced under laboratory conditions, limiting the controlled expression of natural products. Here we describe an integrated methodology for the construction and screening of an elicited and pre-fractionated library of marine bacteria. In this pilot study, chemical elicitors were evaluated to mimic the natural environment and to induce the expression of cryptic BGCs in deep-sea bacteria. By integrating high-resolution untargeted metabolomics with cheminformatics analyses, it was possible to visualize, mine, identify and map the chemical and biological space of the elicited bacterial metabolites. The results show that elicited bacterial metabolites correspond to ~45% of the compounds produced under laboratory conditions. In addition, the elicited chemical space is novel (~70% of the elicited compounds) or concentrated in the chemical space of drugs. Fractionation of the crude extracts further evidenced minor compounds (~90% of the collection) and the detection of biological activity. This pilot work pinpoints strategies for constructing and evaluating chemically diverse bacterial natural product libraries towards the identification of novel bacterial metabolites in natural product-based drug discovery pipelines.

scholarly journals Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2772 ◽  
Author(s):  
You-Min Ying ◽  
Lu Huang ◽  
Ting Tian ◽  
Cui-Yu Li ◽  
Shi-Lei Wang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Natural Occurrence ◽  
Fungal Metabolites ◽  
Isolation And Identification ◽  
Late Step ◽  
Neosartorya Fischeri ◽  
The One ◽  
First Time

The One Strain Many Compounds (OSMAC) method was applied to explore the chemical diversities of secondary metabolites produced by Neosartorya fischeri NRRL 181. Four pyripyropenes 1–4, eight steroids 5–11, and four prenylated indole alkaloids 12–15, were obtained from the fungus cultured in petri dishes containing potato dextrose agar (PDA). 1,7,11-trideacetylpyripyropene A (1) and 1,11-dideacetyl pyripyropene A (2) were obtained and spectroscopically characterized (1D, 2D NMR, and HR-ESI-MS) from a natural source for the first time. It offered a sustainable source of these two compounds, which were usually used as starting materials in preparing pyripyropene derivatives. In addition, as compared with all the other naturally occurring pyripyropenes, 1 and 2 possessed unique acetylation patterns that did not follow the established late-step biosynthetic rules of pyripyropenes. The natural occurrence of 1 and 2 in the fungus implied that the timing and order of hydroxylation and acetylation in the late-step biosynthetic pathway of pyripyropenes remained to be revealed. The isolation and identification of 1–15 indicated that the OSMAC method could remarkably alter the metabolic profile and enrich the chemical diversities of fungal metabolites. Compounds 1–4 exhibited no obvious cytotoxicity against the triple-negative breast cancer cell line MDA-MB-231 as compared with taxol.

scholarly journals Brominated Bisindole Alkaloids from the Celtic Sea Sponge Spongosorites calcicola

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3890 ◽  
Author(s):  
Laurence K. Jennings ◽  
Neyaz M. D. Khan ◽  
Navdeep Kaur ◽  
Daniel Rodrigues ◽  
Christine Morrow ◽  
...  
Keyword(s):  
Natural Products ◽  
Cytotoxic Activity ◽  
Bioactive Compounds ◽  
Indole Alkaloids ◽  
Marine Species ◽  
Chemical Study ◽  
Central Core ◽  
Chemical Investigation ◽  
Chemical Profiles ◽  
New Metabolites

As part of an ongoing program to identify new bioactive compounds from Irish marine bioresources, we selected the subtidal sponge Spongosorites calcicola for chemical study, as fractions of this species displayed interesting cytotoxic bioactivities and chemical profiles. The first chemical investigation of this marine species led to the discovery of two new bisindole alkaloids of the topsentin family, together with six other known indole alkaloids. Missing the usual central core featured by the representatives of these marine natural products, the new metabolites may represent key biosynthetic intermediates for other known bisindoles. These compounds were found to exhibit weak cytotoxic activity against HeLa tumour cells, suggesting a specificity towards previously screened carcinoma and leukaemia cells.

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.

scholarly journals Bioluminescence of the Largest Luminous Vertebrate, the Kitefin Shark, Dalatias licha: First Insights and Comparative Aspects

2021 ◽  
Vol 8 ◽  
Author(s):  
Jérôme Mallefet ◽  
Darren W. Stevens ◽  
Laurent Duchatelet
Keyword(s):  
Experimental Study ◽  
New Zealand ◽  
Deep Sea ◽  
Hormonal Control ◽  
Shark Species ◽  
Control Analysis ◽  
Light Organs ◽  
First Time ◽  
Insight Into

Bioluminescence has often been seen as a spectacular yet uncommon event at sea but considering the vastness of the deep sea and the occurrence of luminous organisms in this zone, it is now more and more obvious that producing light at depth must play an important role structuring the biggest ecosystem on our planet. Three species of deepwater sharks (Dalatias licha, Etmopterus lucifer, and Etmopterus granulosus) were collected from the Chatham Rise, off New Zealand, and for the first time, we documented their luminescence. Comparison of glowing shark pictures, combined with histological description of light organs and hormonal control analysis, highlight the evolutive conservation of the bioluminescence process within Dalatiidae and Etmopteridae. A special emphasis is placed on the luminescence of D. licha, the largest known luminous vertebrate. This first experimental study of three luminous shark species from New Zealand provides an insight into the diversity of shark bioluminescence and highlights the need for more research to help understand these unusual deep-sea inhabitants: the glowing sharks.

scholarly journals Total Synthesis of Phorbazole B

Molecules ◽  
2020 ◽  
Vol 25 (20) ◽  
pp. 4848
Author(s):  
Yngve Guttormsen ◽  
Magnus E. Fairhurst ◽  
Sunil K. Pandey ◽  
Johan Isaksson ◽  
Bengt Erik Haug ◽  
...  
Keyword(s):  
Natural Products ◽  
High Resolution ◽  
Secondary Metabolites ◽  
Total Synthesis ◽  
Cancer Cells ◽  
Marine Sponge ◽  
Inhibitory Activity ◽  
Late Stage ◽  
Nmr Techniques

Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was developed. The synthesis relied on the use of an oxazole precursor, which was protected with an iodine in the reactive 4-position, followed by complete chlorination of all pyrrole positions. Attempts to prepare phorbazole A and C, which contain a 3,4-dichlorinated pyrrole, were unsuccessful as the desired chlorination pattern on the pyrrole could not be obtained. The identities of the dichlorinated intermediates and products were determined using NMR techniques including NOESY/ROESY, 1,1-ADEQUATE and high-resolution CLIP-HSQMBC.

Natural Products from Deep-Sea-Derived Fungi ̶ A New Source of Novel Bioactive Compounds?

2018 ◽  
Vol 25 (2) ◽  
pp. 186-207 ◽  
Author(s):  
Georgios Daletos ◽  
Weaam Ebrahim ◽  
Elena Ancheeva ◽  
Mona El-Neketi ◽  
Weiguo Song ◽  
...  
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Secondary Metabolites ◽  
Bioactive Compounds ◽  
Deep Sea ◽  
Underlying Assumption ◽  
Pharmacologically Active ◽  
Promising Source ◽  
New Metabolites

Background: Over the last two decades, deep-sea-derived fungi are considered to be a new source of pharmacologically active secondary metabolites for drug discovery mainly based on the underlying assumption that the uniqueness of the deep sea will give rise to equally unprecedented natural products. Indeed, up to now over 200 new metabolites have been identified from deep-sea fungi, which is in support of the statement made above. Results: This review summarizes the new and/or bioactive compounds reported from deepsea- derived fungi in the last six years (2010 – October 2016) and critically evaluates whether the data published so far really support the notion that these fungi are a promising source of new bioactive chemical entities.

Pigments of Fungi. LIX. Synthesis of (1S,3S)- and (1R,3R)-Austrocortilutein and (1S,3S)-Austrocortirubin from Citramalic Acid

2000 ◽  
Vol 53 (4) ◽  
pp. 245 ◽  
Author(s):  
Melvyn Gill ◽  
Michael F. Harte ◽  
Abilio Ten
Keyword(s):  
Natural Products ◽  
Diels Alder ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Naturally Occurring ◽  
First Time

The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein (1) is synthesized for the first time in enantiomerically pure form by Diels–Alder cycloaddition between the functionalized butadiene derivative (8) and the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the latter being derived from (R)-citramalic acid (3). The natural products (1S,3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepared for the first time by using the same strategy.

scholarly journals Bioactive Nitrogenous Secondary Metabolites from the Marine Sponge Genus Haliclona

Marine Drugs ◽  
2019 ◽  
Vol 17 (12) ◽  
pp. 682 ◽  
Author(s):  
Jiaying Zhu ◽  
Yang Liu ◽  
Zijun Liu ◽  
Hao Wang ◽  
Huawei Zhang
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Secondary Metabolites ◽  
Marine Sponge ◽  
Literature Search ◽  
Extensive Literature ◽  
Symbiotic Microorganisms ◽  
Bioactive Properties ◽  
Potential Applications ◽  
Extensive Literature Search

Marine sponge genus Haliclona, one of the most prolific sources of natural products, contains over 600 species but only a small part of them had been classified and chemically investigated. On the basis of extensive literature search, this review firstly summarizes 112 nitrogenous secondary metabolites from classified and unclassified Haliclona sponges as well as from their symbiotic microorganisms. Most of these substances have only been found in Haliclona sponges, and display diverse bioactive properties with potential applications in new drug discovery.

scholarly journals Isolation and Structure Elucidation of New Secondary Metabolites from New Zealand Marine Red Algae

2021 ◽  
Author(s):  
◽  
Wendy Lynne Popplewell
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Red Algae ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Product Analysis ◽  
Algal Extracts

<p>The natural product analysis of New Zealand red algae has been neglected in recent years, and there is obvious scope for the chemical re-evaluation of New Zealand marine red algae. This study describes the isolation and structure elucidation of 12 new and eight known compounds from four different genera of red algae. To aid in this process, 34 red algae were screened in order to generate a digital HSQC spectra mask, a screening tool developed by the VUW Marine Natural Products group to identify extracts of interest for further analysis. All 34 algal extracts were screened using the HSQC mask and four extracts were identified as interesting and analysed in detail. Examination of extracts of the red algae Plocamium costatum and Ballia callitricha lead to the isolation of three known metabolites. Eleven new oxylipins, labillarides A to K, are reported from the alga Phacelocarpus labillardieri. Labillarides A to H are polyunsaturated alpha-pyrone macrocycles, all of which show similarities to the previously reported compounds isolated from southern Australian collections of the algae. Labillarides E to H are of particular interest as they represent the two diastereomeric pairs associated with variation at the C-3 and C-8 chiral centres. Labillarides I and J are related enol macrocycles while labillaride K is a furan-3-one oxylipin, all of which have biogenic significance to the macrocyclic alpha-pyrones. Labillarides A, B and I exhibit moderate cytotoxicity while labillaride C shows moderate antibacterial activity. A new nitrogenous bromophenol, colensolide A, was isolated from the alga Osmundaria colensoi along with five known bromophenols. The presence of nitrogen-containing sidechains in bromophenols is unusual but not unprecedented. The bicyclic nitrogenous moiety observed in colensolide A is proposed to be of histidine origin. Several of the known bromophenols exhibit antibacterial activity and one shows moderate cytotoxicity.</p>

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