Saldedines A and B, Dibromo Proaporphine Alkaloids from a Madagascan Tunicate

Sorek, Hagit; Rudi, Amira; Goldberg, Israel; Aknin, Maurice; Kashman, Yoel

doi:10.1021/np800714k

Cited by 36 publications

(12 citation statements)

References 9 publications

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“…Two new dibromo proaporphine alkaloids, saldedines A (63) and B (64), were isolated from an unidentified tunicate of the family Didemnidae, collected at Salary Bay, ca. 100 km north of Tulear, Madagascar, in January 2007 (Sorek et al, 2009). This work was the first report of proaporphine alkaloids from a marine source (Fig.…”

Section: Isolation and Structure Determination Of Brominated Metabolitesmentioning

confidence: 65%

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Ascidian halogen-containing secondary metabolites from the family didemnidae

Djordjevic

Radulović

2019

Facta Univ Phys Chem Technol

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This review summarizes current knowledge concerning the isolation, structural elucidation, biological/pharmacological activities, and total synthesis of halogen-containing secondary metabolites isolated from ascidians of the family Didemnidae. Overall, 81 compounds are presented, displaying great structural diversity and possessing a number of significant biological/pharmacological properties. In addition to the most numerous brominated compounds, chlorinated and iodinated ones were also found. The most prolific genus in regard to the number of published papers and isolated molecules is the genus Didemnum, which was treated separately from the rest of the genera of the ascidian family. The structural complexity of the isolated metabolites prompted a number of synthetic endeavors that not only provided conclusive proof of the structure of the metabolites but also enabled the biological tests and the possible application of these metabolites.

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Section: Isolation and Structure Determination Of Brominated Metabolitesmentioning

confidence: 65%

“…Saldedines A (63) and B (64) were tested for toxicity to brine shrimps (Artemia salina) and were found to be moderately active. Compound 63 showed a greater potency with an LD 50 value of 4.4 µM, while 64 displayed an LD 50 value of 10.9 µM (Sorek et al, 2009).…”

Section: Biological Activities Of Brominated Secondary Metabolitesmentioning

confidence: 98%

Ascidian halogen-containing secondary metabolites from the family didemnidae

Djordjevic

Radulović

2019

Facta Univ Phys Chem Technol

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“…Two new dibromo proaporphine alkaloids, designated as saldedines A and B, were isolated from an unidentified Didemnidae tunicate, collected in Salary Bay, north of Tulear, Madagascar [26]. Plant proaporphine alkaloids, a major isoquinoline group, have been recognized as the biosynthetic precursors of aporphine alkaloids bearing a wide range of oxygenated substitution patterns with mainly a spiro-cyclohexadienone ring system (Figure 6).…”

Section: Resultsmentioning

confidence: 99%

“…As in many other cases, the real source of these compounds, the tunicate or guest microorganism, is unknown. The structure elucidation of the two new compounds was achieved by HRESIMS and 1D and 2D NMR spectra [26]. Finally, a qualified single crystal was obtained from CH 2 Cl 2 , enabling X-ray crystallographic analysis (Figure 6) and confirming unequivocally the structure of saldedine A. Interestingly, saldedine A crystallized as a racemic mixture in space group Pbca , wherein the two enantiomeric species are related by an inversion center.…”

Section: Resultsmentioning

confidence: 99%

Recent N-Atom Containing Compounds from Indo-Pacific Invertebrates

Kashman

Bishara

Aknin³

2010

Marine Drugs

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A large variety of unique N-atom containing compounds (alkaloids) without terrestrial counterparts, have been isolated from marine invertebrates, mainly sponges and ascidians. Many of these compounds display interesting biological activities. In this report we present studies on nitrogenous compounds, isolated by our group during the last few years, from Indo-Pacific sponges, one ascidian and one gorgonian. The major part of the review deals with metabolites from the Madagascar sponge Fascaplysinopsis sp., namely, four groups of secondary metabolites, the salarins, tulearins, taumycins and tausalarins.

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“…Compounds 5 and 6 displayed moderate antiproliferative activity against the A2780 human ovarian cancer cell line, with IC 50 values of 4.1 and 2.7 µM, respectively. 3) Two new dibromo proaporphine alkaloids, saldedines A (8) and B (9), were isolated from the DCM fraction of an unidentified Didemnidae tunicate collected at Salary Bay, Madagascar. These two compounds were reported to be the first two marine proaporphine alkaloids.…”

Section: Alkaloidsmentioning

confidence: 99%

Novel Bioactive Natural Products Isolated from Madagascar Plants and Marine Organisms (2009–2017)

Dai

Liu

Rakotondraibe

2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Madagascar's rain forests and tropical dry forests are home to numerous endemic plant species and the island is considered a biodiversity hotspot. About 80% of the Madagascan (Malagasy) population relies on traditional medicines that have been proven to contain a variety of biologically active compounds. In the search for bioactive compounds from Madagascan biodiversity, we accessed and collected most of the literature dealing with the isolation, structure elucidation, and biological activities of organic small molecules originating from Madagascan plants and marine organisms. Since we published the first review of this work in 2009 (Curr. Med. Chem., 17, 2010, Hou and Harinantenaina), the present paper covers the isolation, structures, and bioactivity of 182 new secondary metabolites isolated from Malagasy higher plants and marine organisms in the last seven years (2009-2017).

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Saldedines A and B, Dibromo Proaporphine Alkaloids from a Madagascan Tunicate

Cited by 36 publications

References 9 publications

Ascidian halogen-containing secondary metabolites from the family didemnidae

Ascidian halogen-containing secondary metabolites from the family didemnidae

Recent N-Atom Containing Compounds from Indo-Pacific Invertebrates

Novel Bioactive Natural Products Isolated from Madagascar Plants and Marine Organisms (2009–2017)

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