Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• cytotoxicity against L1210 murine leukemia cells and KB epidermoid carcinoma cells. Keywords: ceratinadin; cytotoxicity; marine sponge; psammaplysin; Pseudoceratina sp.; Introduction Marine sponges are widely recognized as a rich source of unique bioactive natural products. For instance, marine sponges

• , the first asymmetric total synthesis of psammaplysin A was accomplished by Smith and Morrow, and the absolute configuration of compound 1 was also confirmed through organic synthesis [7]. In our ongoing research focused on uncovering new bioactive secondary metabolites from Okinawan marine sponges, we

• a cyano group. Bromotyrosine alkaloids with cyano groups have been discovered in marine sponges and are classified into two categories. One type has a cyano group as part of a phenylacetonitrile structure [17][18][19][20][21][22][23][24], while the other type contains a cyano group as cyanoformamide

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• ; most of which are sessile and lack the ability to physically defend themselves from both predators and competitors and thus rely on chemical mechanisms for their defense [1]. Metabolites derived from marine sponges contribute more than half of all compounds identified from marine invertebrates [1][5

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• interactomes [149][150]. Conclusion Geographically, halophilic Microbulbifer bacteria are widely distributed with marine sponges (40.4%) and sediments (14.7%) being the most prolific sources for isolation (Figure 1, Table 1). Twelve groups of degradation enzymes have been expressed and characterized. A total

Synthesis of (−)-halichonic acid and (−)-halichonic acid B

• Keith P. Reber and
• Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174

• acids. Keywords: alkaloid; amino acid; aza-Prins reaction; cascade reaction; natural product; Introduction Marine sponges produce a large number of structurally diverse natural products, including many that exhibit biological activity [1][2][3]. In 2019, Tsukamoto and co-workers isolated the

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• Marine sponges have been a significant source of unique chemistry over the past 70 years, with 11,863 sponge-derived secondary metabolites currently reported in the literature [1]. This equates to ≈30% of all marine natural products identified to date, an impressive contribution. Whilst many marine

• marine sponges from AIMS were dried using a Dynamic FD12 freeze dryer and ground using a Fritsch Universal Cutting Mill Pulverisette 19, or by hand using a granite mortar and pestle. For large-scale extraction work, the ground sponge material was extracted at room temperature using an Edwards Instrument

New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• , fungi, plants, and marine sponges [1][2][3]. Azoxy natural products have occasionally been discovered by conventional isolation schemes guided by biological activities or physicochemical properties, which are not selective for the azoxy functionality. Consequently, there are only a few examples of azoxy

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• anti-inflammatory activity by the inhibition of LPS-induced TNF-α and CCL2 release in RAW 264.7 macrophages. Keywords: Acanthella cavernosa; anti-inflammatory; biosynthetic pathway; chiral separation; marine sponge; sesquiterpenoid; Introduction Marine sponges of the genus Acanthella (class

• of the cyclization mechanism and characterization of post-modification enzymes for the biosynthetic pathway of these sesquiterpenoids will provide insights into expanding the chemical space from marine sponges. Experimental General experimental procedure. The melting point was recorded using an SGW X

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

• Dmitrii A. Aksenov,
• Nikolai A. Arutiunov,
• Vladimir V. Maliuga,
• Alexander V. Aksenov and
• Michael Rubin

Beilstein J. Org. Chem. 2020, 16, 2903–2910, doi:10.3762/bjoc.16.239

• ]pyridines; nitroalkanes; polyphosphoric acid; Introduction It is hard to overstate the importance of imidazo[1,5-a]pyridines in modern organic and medicinal chemistry. Several natural alkaloids possessing this core were isolated from marine sponges, for example, cribrostatin 6 (Figure 1) [1][2][3]. The

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

• Valerian Dragutan,
• Ileana Dragutan,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

• reaction for accessing bioactive organic molecules is found in the complex synthesis of manzamine alkaloids. These efficient antitumor agents, originally isolated from several genera of marine sponges, contain a pentacyclic core with a pendant β-carboline moiety. Their total synthesis implies an elaborate

Two new aromatic polyketides from a sponge-derived Fusarium

• Mada Triandala Sibero,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Ocky K. Karna Radjasa,
• Agus Sabdono,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

• sponges in massive amounts leads to environmental disturbance since marine sponges play a key role in building coral reefs [3][4]. As a filter feeder, sponges host an enormous amount of microorganisms including algae, bacteria, actinomycetes, and fungi [5][6][7]. Many of these microorganisms produce

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• which when subjected to the reductive opening of the aziridine ring was transformed into the pyrrolidin-2-one (4R,5S)-158. Basic hydrolysis produced (3R,4S)-155. Other amino acids: Calyculins were isolated from marine sponges and they are of interest because of possible applications as protein

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• compounds of both natural and synthetic origin, containing in their structure pyrrole and imidazole rings, display a wide set of pharmacologically significant activities. The most important natural sources of such systems are marine sponges. Since the 70's of 20th century up to date more than 150

• recently from an extract of Pseudoceratina Sp. [6]. The variety of types of pharmacological activity revealed in these marine sponges’ metabolites is not inferior to the chemodiversity of their structure. Many of them are reported to have properties such as α-adrenoreceptors [7] and leukotriene B4 receptor

• metabolites of marine sponges with interesting biological properties has received considerable attention from both chemists and pharmacologists. In the middle of 2000s, the authors of the studies [17][18][19] proposed a facile one-pot two-step procedure for the synthesis of diversely substituted 2

Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

• Qun Göthel,
• Thanchanok Sirirak and
• Matthias Köck

Beilstein J. Org. Chem. 2015, 11, 2334–2342, doi:10.3762/bjoc.11.254

• products; NMR spectroscopy; Introduction Bromotyrosine-derived alkaloids are unique brominated metabolites which were isolated mainly from marine sponges of the order Verongida. For more than 50 years, bromotyrosine alkaloids raised the interests of synthetic and natural products chemists due to their

The marine sponge Agelas citrina as a source of the new pyrrole–imidazole alkaloids citrinamines A–D and N-methylagelongine

• Christine Cychon,
• Ellen Lichte and
• Matthias Köck

Beilstein J. Org. Chem. 2015, 11, 2029–2037, doi:10.3762/bjoc.11.220

• ) which consist of a pyridinium ring and an ester linkage instead of the aminoimidazole moiety and the common amide bond in PIAs. Keywords: Agelas citrina; marine sponges; mauritiamine; NMR; pyrrole–imidazole alkaloids; Introduction The family of pyrrole-imidazole alkaloids (PIAs) represents a

• fascinating example of a large variety of secondary metabolites produced exclusively by marine sponges. To date, more than 150 PIAs have been isolated mainly from various species of the families Agelasidae, Axinellidae, Dyctionellidae, and Hymeniacidonidae and some of them show promising biological activities

• of compound 5 was identified to be the N-methyl derivative of agelongine (12). Debromoagelongine (daminin (21) [16]) is the third compound in the agelongine family. All agelongine analogues were isolated from marine sponges. The citrinamines A–D (1–4) were further evaluated for antimicrobial and

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

• Louis P. Sandjo,
• Victor Kuete and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

• on pyridoacridine-related metabolites as one biologically interesting group of alkaloids identified from marine sources. They are produced by marine sponges, ascidians and tunicates, and they are structurally comprised of four to eight fused rings including heterocycles. Acridine, acridone

• phosphatase B (PtpB) [31] and serine protease [32]. The focus of this review is on pyridoacridine-related metabolites as one of the many interesting groups of alkaloids produced from marine sources. They are generally produced by marine sponges, ascidians [33] and tunicates [34] and they are structurally

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

• Ana Čikoš,
• Irena Ćaleta,
• Dinko Žiher,
• Mark B. Vine,
• Ivaylo J. Elenkov,
• Marko Dukši,
• Dubravka Gembarovski,
• Marina Ilijaš,
• Snježana Dragojević,
• Ivica Malnar and
• Sulejman Alihodžić

Beilstein J. Org. Chem. 2015, 11, 1447–1457, doi:10.3762/bjoc.11.157

• ]. A previously mentioned example of a protein phosphatase inhibitor okadaic acid is a toxin associated with diarrheic shellfish poisoning [28]. Another example are structurally complex tubulin polymerization-inhibiting macrolides such as spongistatins, a family of compounds isolated from marine

• sponges, which display extraordinary antitumor activity [29]. At the same time, the spiroketal-containing integramycin acts as an HIV-1 protease inhibitor [27]. The studies of Hayashi et al. have shown that the integrity of the spiroketal subunit is essential for the inhibition of telomerase by

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

• peroxides isolated from marine sponges exhibiting fungicidal and antitumor activities [329][330] is an interesting example of the synthesis of complex structures. The polyunsaturated compound (E)-methyl 6-methyleneundec-2-en-10-ynoate (235) was subjected to ozonolysis to obtain methoxyhydroperoxide, (E

New tridecapeptides of the theonellapeptolide family from the Indonesian sponge Theonella swinhoei

• Annamaria Sinisi,
• Barbara Calcinai,
• Carlo Cerrano,
• Henny A. Dien,
• Angela Zampella,
• Claudio D’Amore,
• Barbara Renga,
• Stefano Fiorucci and
• Orazio Taglialatela-Scafati

Beilstein J. Org. Chem. 2013, 9, 1643–1651, doi:10.3762/bjoc.9.188

• hepatic carcinoma cell line. Keywords: antiproliferative activity; cyclic peptides; marine metabolites; theonellapeptolides; 2D NMR; Introduction Three decades of extensive chemical investigation [1] have clearly evidenced that marine sponges of the genus Theonella (Lithistida, Theonellidae) are

Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy

• Daisuke Shigeoka,
• Takuma Kamon and
• Takehiko Yoshimitsu

Beilstein J. Org. Chem. 2013, 9, 860–865, doi:10.3762/bjoc.9.99

• isolated from marine sponges Agelas dendromorpha and Cymbastela sp., is one such substance, which has drawn considerable attention due to its potential applicability in the development of anticancer agents [1][2][3][4][5]. The intriguing biological activity of 1 has stimulated interest in developing