Cacolides: Sesterterpene Butenolides from a Southern Australian Marine Sponge, Cacospongia sp.

Shamsunnahar Khushi; Laizuman Nahar; Angela Salim; Robert Capon

doi:10.3390/md16110456

Cacolides: Sesterterpene Butenolides from a Southern Australian Marine Sponge, Cacospongia sp.

Marine Drugs ◽

10.3390/md16110456 ◽

2018 ◽

Vol 16 (11) ◽

pp. 456 ◽

Cited By ~ 6

Author(s):

Shamsunnahar Khushi ◽

Laizuman Nahar ◽

Angela Salim ◽

Robert Capon

Keyword(s):

Natural Products ◽

Chemical Analysis ◽

Carboxylic Acids ◽

Marine Sponge ◽

Deep Sea ◽

Spectroscopic Analysis ◽

Chemical Diversity ◽

Commercial Fishing ◽

Southern Coast ◽

Molecular Networking

Chemical analysis of a marine sponge, Cacospongia sp. (CMB-03404), obtained during deep sea commercial fishing activities off the southern coast of Australia, yielded an unprecedented family of sesterterpene α-methyl-γ-hydroxybutenolides, cacolides A–L (1–12), together with biosynthetically related norsesterterpene carboxylic acids, cacolic acids A–C (13–15). Structures were assigned on the basis of detailed spectroscopic analysis with comparisons to known natural products and biosynthetic considerations. In addition to revealing new chemical diversity, this study provided a valuable platform for comparing and contrasting the capabilities of the traditional dereplication technologies of HPLC-DAD, HPLC-MS and NMR, with those of the emerging HPLC-MS/MS approach known as global natural products social molecular networking (GNPS), as applied to marine sponge sesterterpene tetronic acids.

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

Molecules ◽

10.3390/molecules25040853 ◽

2020 ◽

Vol 25 (4) ◽

pp. 853 ◽

Cited By ~ 2

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.

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Alkyl and Alkenyl Resorcinols From an Australian Marine Sponge, Haliclona Sp (Haplosclerida : Haliclonidae)

Australian Journal of Chemistry ◽

10.1071/ch9911393 ◽

1991 ◽

Vol 44 (10) ◽

pp. 1393 ◽

Cited By ~ 31

Author(s):

RA Barrow ◽

RJ Capon

Keyword(s):

Natural Products ◽

Marine Sponge ◽

Spectroscopic Analysis ◽

Chemical Degradation ◽

Plant Source ◽

Marine Plant ◽

Plant Sources ◽

Structure Class

Eleven alkyl and alkenyl resorcinols have been isolated from the Australian marine sponge Haliclona sp. Three of these, (3), (5) and (10), have previously been described from Australian terrestrial and marine plant sources. The remaining eight, (13)-(20), are new natural products whose structures have been secured by a combination of spectroscopic analysis and chemical degradation. This report represents the first account of this structure class being isolated from a non-plant source.

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Dilignans with a Chromanol Motif Discovered by Molecular Networking from the Stem Barks of Magnolia obovata and Their Proprotein Convertase Subtilisin/Kexin Type 9 Expression Inhibitory Activity

Biomolecules ◽

10.3390/biom11030463 ◽

2021 ◽

Vol 11 (3) ◽

pp. 463

Author(s):

Jongmin Ahn ◽

Hee-Sung Chae ◽

Pisey Pel ◽

Young-Mi Kim ◽

Young Hee Choi ◽

...

Keyword(s):

Natural Products ◽

Lipid Metabolism ◽

Inhibitory Activity ◽

Bioinformatic Analysis ◽

Chemical Diversity ◽

Molecular Networking ◽

Time Consumption ◽

Magnolia Obovata ◽

Novel Structure ◽

Small Set

Natural products have been fundamental materials in drug discovery. Traditional strategies for observing natural products with novel structure and/or biological activity are challenging due to large cost and time consumption. Implementation of the MS/MS-based molecular networking strategy with the in silico annotation tool is expected to expedite the dereplication of secondary metabolites. In this study, using this tool, two new dilignans with a 2-phenyl-3-chromanol motif, obovatolins A (1) and B (2), were discovered from the stem barks of Magnolia obovata Thunb. along with six known compounds (3–8), expanding chemical diversity of lignan skeletons in this natural source. Their structures and configurations were elucidated using spectroscopic data. All isolates were evaluated for their PCSK9 mRNA expression inhibitory activity. Obovatolins A (1) and B (2), and magnolol (3) showed potent lipid controlling activities. To identify transcriptionally controlled genes by 1 along with downregulation of PCSK9, using small set of genes (42 genes) related to lipid metabolism selected from the database, focused bioinformatic analysis was carried out. As a result, it showed the correlations between gene expression under presence of 1, which led to detailed insight of the lipid metabolism caused by 1.

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Structure and Absolute Configuration of Phenanthro-perylene Quinone Pigments from the Deep-Sea Crinoid Hypalocrinus naresianus

Marine Drugs ◽

10.3390/md19080445 ◽

2021 ◽

Vol 19 (8) ◽

pp. 445

Author(s):

Sahithya Phani Babu Vemulapalli ◽

Juan Carlos Fuentes-Monteverde ◽

Niels Karschin ◽

Tatsuo Oji ◽

Christian Griesinger ◽

...

Keyword(s):

Natural Products ◽

Dft Calculations ◽

Absolute Configuration ◽

13C Nmr ◽

Deep Sea ◽

Spectroscopic Analysis ◽

2D Nmr ◽

Water Soluble ◽

Spectroscopy Analysis ◽

1H And 13C Nmr

Two new water-soluble phenanthroperylene quinones, gymnochrome H (2) and monosulfated gymnochrome A (3), as well as the known compounds gymnochrome A (4) and monosulfated gymnochrome D (5) were isolated from the deep-sea crinoid Hypalocrinus naresianus, which had been collected in the deep sea of Japan. The structures of the compounds were elucidated by spectroscopic analysis including HRMS, 1D 1H and 13C NMR, and 2D NMR. The absolute configuration was determined by ECD spectroscopy, analysis of J-couplings and ROE contacts, and DFT calculations. The configuration of the axial chirality of all isolated phenanthroperylene quinones (2–5) was determined to be (P). For gymnochrome H (2) and monosulfated gymnochrome A (3), a (2′S,2″R) configuration was determined, whereas for monosulfated gymnochrome D (5) a (2′R,2″R), configuration was determined. Acetylated quinones are unusual among natural products from an echinoderm and gymnochrome H (2) together with the recently reported gymnochrome G (1) represent the first isolated acetylated phenanthroperylene quinones.

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

Marine Drugs ◽

10.3390/md17120683 ◽

2019 ◽

Vol 17 (12) ◽

pp. 683 ◽

Cited By ~ 1

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.

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The Luffarins (A-Z), Novel Terpenes From an Australian Marine Sponge, Luffariella geometrica

Australian Journal of Chemistry ◽

10.1071/ch9921705 ◽

1992 ◽

Vol 45 (10) ◽

pp. 1705 ◽

Cited By ~ 57

Author(s):

MS Butler ◽

RJ Capon

Keyword(s):

Natural Products ◽

Marine Sponge ◽

Coastal Waters ◽

Marine Natural Products ◽

Spectroscopic Analysis ◽

Marine Metabolites ◽

Chemical Correlation ◽

The Absolute ◽

Great Australian Bight ◽

Absolute Stereochemistry

A marine sponge, Luffariella geometrica Kirkpatrick, collected from the southern Australian coastal waters of the Great Australian Bight, has been found to contain 14 new bicyclic sesterterpenes, luffarin-A (14), -B (15), -C (16), -D (17), -E (18), -F (19), -G (20), -H (21), -I (22), -J (23), -K (24), -L (25), -M (26) and -N (27), a new bicyclic bisnorsesterterpene, luffarin-O (30), a new monocyclic sesterterpene, luffarin-P (32), six new acyclic sesterterpenes, luffarin-Q (35), -R (36), -S (37), -T (38), -U (39) and -V (40), two new diterpenes, luffarin-W (41) and -X (44), and two new bisnorditerpenes luffarin-Y (45) and -Z (46). These novel marine metabolites have been assigned structures, including stereochemistry, on the basis of detailed spectroscopic analysis, chemical correlation, derivatization, and biosynthetic considerations. Studies directed at the absolute stereochemistry of the luffarins have also permitted assignment of absolute stereochemistry to the known marine natural products (E)-neomanoalide (3), (Z)-neomanoalide (4) and dehydroambliol-A (47).

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