Isolation of bastadin-6-O-sulfate and expedient purifications of bastadins-4, -5 and -6 from extracts of Ianthella basta

Gartshore, Christopher J.; Salib, Mariam N.; Renshaw, August A.; Molinski, Tadeusz F.

doi:10.1016/j.fitote.2017.12.003

Cited by 7 publications

(5 citation statements)

References 27 publications

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“…The species I. basta (Pallas, 1766) [ 98 ] is the most studied sponge of the family Ianthellidae, and has been sampled across a number of localities, including Guam [ 99 , 100 ], PNG [ 97 , 101 , 102 , 103 ], Indonesia [ 104 , 105 , 106 , 107 , 108 , 109 ], GBR [ 110 , 111 , 112 ], and the Exmouth Gulf, Western Australia [ 113 , 114 ]. All samples across all localities yielded a very similar chemistry, proving I. basta to be a large producer of bastadins and their precursor, the hemi-bastadins.…”

Section: Resultsmentioning

confidence: 99%

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

et al. 2021

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This study provides a review of all isolated natural products (NPs) reported for sponges within the order Verongiida (1960 to May 2020) and includes a comprehensive compilation of their geographic and physico-chemical parameters. Physico-chemical parameters were used in this study to infer pharmacokinetic properties as well as the potential pharmaceutical potential of NPs from this order of marine sponge. In addition, a network analysis for the NPs produced by the Verongiida sponges was applied to systematically explore the chemical space relationships between taxonomy, secondary metabolite and drug score variables, allowing for the identification of differences and correlations within a dataset. The use of scaffold networks as well as bipartite relationship networks provided a platform to explore chemical diversity as well as the use of chemical similarity networks to link pharmacokinetic properties with structural similarity. This study paves the way for future applications of network analysis procedures in the field of natural products for any order or family.

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Section: Resultsmentioning

confidence: 99%

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

et al. 2021

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“…This derivative features a novel aromatic substitution pattern with a meta – meta linkage between the aromatic rings and a meta – para linkage also observed in bastadins [ 90 ]. In 2018, bastadin-6- O -sulfate ester ( 217 ) was isolated from methanol extracts of the marine sponge Ianthella basta ( Figure 30 ) [ 91 ].…”

Section: Bromotyrosine Chemodiversitymentioning

confidence: 99%

“…Subsequently, for the generation of the spiroisoxazoline moiety, it has been proposed that a monooxygenase catalyzes the epoxi- Tyrosine (88) undergoes a series of enzymatic reactions: (i) a deamination catalyzed by an aminotransferase, (ii) a methylation via a methylase, a bromination through a bromoperoxidase, and (iii) a conversion of the keto group facilitated by an oximinotransferase, resulting in the formation of an oxime (89). Subsequently, for the generation of the spiroisoxazoline moiety, it has been proposed that a monooxygenase catalyzes the epoxidation of the aromatic ring ( 90) and (91), which can then cyclize to yield the isooxazolines ( 86) and (87). This process of enantiotopic epoxidation leads to an intriguing enantiodivergent desymmetrization.…”

Section: Spirocyclohexadienylisoxazolinesmentioning

confidence: 99%

Marine Bromotyrosine Derivatives in Spotlight: Bringing Discoveries and Biological Significance

Ferreira Montenegro,

Pham,

Abdoul-Latif

et al. 2024

Marine Drugs

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The Verongida order comprises several sponge families, such as Aplysinellidae, Aplysinidae, Ianthellidae, and Pseudoceratinidae, reported for producing bromotyrosine-derived compounds. First identified in 1913, bromotyrosine derivatives have since captivated interest notably for their antitumor and antimicrobial properties. To date, over 360 bromotyrosine derivatives have been reported. Our review focuses specifically on bromotyrosine derivatives newly reported from 2004 to 2023, by summarizing current knowledge about their chemical diversity and their biological activities.

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“…In this study, we have focused our attention on one of the largest fan-shaped marine demosponges Ianthella basta (Pallas, 1766) that can reach up to 2.5 m both in height and in its diameter [12] (Figure 1). Previously, ianthellids have been intensively studied due to the biosynthesis of diverse biologically active bromotyrosines [13][14][15][16] as well as their unique flat 3D network-like chitin-based skeleton [17,18]. This kind of naturally prestructured chitin has been reported as a ready-to-use renewable biomaterial for a broad variety of applications in tissue engineering [19][20][21][22][23], extreme biomimetics [24][25][26], and biomedicine [18,27,28].…”

Section: Introductionmentioning

confidence: 99%

Calcite Nanotuned Chitinous Skeletons of Giant Ianthella basta Marine Demosponge

Kertmen

Petrenko

Schimpf

et al. 2021

IJMS

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Marine sponges were among the first multicellular organisms on our planet and have survived to this day thanks to their unique mechanisms of chemical defense and the specific design of their skeletons, which have been optimized over millions of years of evolution to effectively inhabit the aquatic environment. In this work, we carried out studies to elucidate the nature and nanostructural organization of three-dimensional skeletal microfibers of the giant marine demosponge Ianthella basta, the body of which is a micro-reticular, durable structure that determines the ideal filtration function of this organism. For the first time, using the battery of analytical tools including three-dimensional micro—X-ray Fluorescence (3D-µXRF), X-ray diffraction (XRD), infra-red (FTIR), Raman and Near Edge X-ray Fine Structure (NEXAFS) spectroscopy, we have shown that biomineral calcite is responsible for nano-tuning the skeletal fibers of this sponge species. This is the first report on the presence of a calcitic mineral phase in representatives of verongiid sponges which belong to the class Demospongiae. Our experimental data suggest a possible role for structural amino polysaccharide chitin as a template for calcification. Our study suggests further experiments to elucidate both the origin of calcium carbonate inside the skeleton of this sponge and the mechanisms of biomineralization in the surface layers of chitin microfibers saturated with bromotyrosines, which have effective antimicrobial properties and are responsible for the chemical defense of this organism. The discovery of the calcified phase in the chitinous template of I. basta skeleton is expected to broaden the knowledge in biomineralization science where the calcium carbonate is regarded as a valuable material for applications in biomedicine, environmental science, and even in civil engineering.

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Isolation of bastadin-6-O-sulfate and expedient purifications of bastadins-4, -5 and -6 from extracts of Ianthella basta

Cited by 7 publications

References 27 publications

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

Marine Bromotyrosine Derivatives in Spotlight: Bringing Discoveries and Biological Significance

Calcite Nanotuned Chitinous Skeletons of Giant Ianthella basta Marine Demosponge

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