Isolation and structure determination of a new analog of polycavernosides from marine Okeania sp. cyanobacterium

• Kairi Umeda,
• Naoaki Kurisawa,
• Ghulam Jeelani,
• Tomoyoshi Nozaki,
• Kiyotake Suenaga and
• Arihiro Iwasaki

Beilstein J. Org. Chem. 2024, 20, 645–652, doi:10.3762/bjoc.20.57

• . Polycavernoside E (1) exhibited moderate antitrypanosomal activity against Trypanosoma brucei rhodesiense. Furthermore, the isolation of polycavernoside E (1) from marine cyanobacteria provides additional evidence that marine cyanobacteria, and not red algae, are responsible for the biosynthesis of

• polycavernosides. Keywords: macrolide glycoside; marine cyanobacterium; marine natural products; polycavernosides; terminal alkyne; Introduction In 1991, an outbreak of food poisoning caused by a species of red algae known as ‘Polycavernosa tsudai’ occurred in Guam, which resulted in killing of three people. Two

• novel macrolide glycosides, polycavernosides A (2) and B (3), were reported as the causative compounds for the illness [1]. After that, the second fatal food poisoning incidents occurred in the Philippines caused by the ingestion of polycavernoside A (2)-contaminated red algae [2]. Subsequently

Introduction of a human- and keyboard-friendly N-glycan nomenclature

• Friedrich Altmann,
• Johannes Helm,
• Martin Pabst and
• Johannes Stadlmann

Beilstein J. Org. Chem. 2024, 20, 607–620, doi:10.3762/bjoc.20.53

• to the proglycan systems (Figure 11) the extremely diverse and unusual structures found in invertebrates or algae demand IUPAC code or graphical representations [44][53][54][55]. Moss N‐glycans are included here to demonstrate the ability of the proglycan system to annotate nonsugar substituents

Functional characterisation of twelve terpene synthases from actinobacteria

• Anuj K. Chhalodia,
• Houchao Xu,
• Georges B. Tabekoueng,
• Binbin Gu,
• Kizerbo A. Taizoumbe,
• Lukas Lauterbach and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100

• viridis [14][15][16]. Only few terpene synthases have been characterised from other organisms, including enzymes from insects [17], octocorals [18][19], red algae [20][21], and amobae [22][23]. Despite these previous efforts, for many known terpenes still no terpene synthases catalysing their formation

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• visible and near IR regions [11][12][13][14]. Similarly, simple quinoxaline-based heterocycles have shown their potential as photosensitizers to induce toxicity in a single cell green algae such as Chlamydomonas reinhardtii [15] and also displayed efficacy against Mycobacterium tuberculosis and other

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

• :1). Additional transformation of compound 230 following an A–AB–ABC synthetic strategy resulted in the desired complex tricyclic skeleton opening the door for the total synthesis of 12-epi-JBIR-23/24 (Scheme 61). The sulfated β-glycoside peyssonnoside A was isolated only recently from the red algae

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• EboA-E have not been investigated yet in detail. The wide spread occurrence of the ebo gene cluster region within genomes of bacterial symbionts associated, e.g., with marine algae, such as Maribacter sp. MS6 [29][30][31], sparked our interest. To provide more insights into the structural basis of UbiA

Structural basis for endoperoxide-forming oxygenases

• Takahiro Mori and
• Ikuro Abe

Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71

• ]. Artemisinin, the antimalarial agent isolated from the plant Artemisia annua [8][13][14], and ergosterol peroxides with anticancer and antiviral activities, identified in many fungi, algae, lichens, and plants, also belong to this group [15][16][17]. Due to the significant biological activities of the

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• hydrocarbons (PAHs) [5][6]. Among all of the compounds in this class, 1,2- and 1,4-naphthoquinones stand out, as they are present in plants, fungi, lichens, bacteria, algae, viruses, insects, and higher organisms and perform several biochemical functions, such as defense, transference of electrons in various

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• (1–3)-Xyl hexamer, an analogue of xylans found in algae cell-walls [206]. TMSOTf promoted the glycosylation of the Bz-protected disaccharide acceptor with the Bz-protected tetrasaccharide trichloroacetimidate donor. Although not yet reported, the authors suggested that this method can be extended to

A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry

• Marine Vallet,
• Filip Kaftan,
• Veit Grabe,
• Fatemeh Ghaderiardakani,
• Simona Fenizia,
• Aleš Svatoš,
• Georg Pohnert and
• Thomas Wichard

Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91

• distributions of metabolites and identifying specific symbiotic bacteria. Keywords: algae; AP-SMALDI; ectoine; holobiont; high-resolution mass spectrometry; mass spectrometry imaging; marine bacteria; Ulva; Introduction In intertidal zones with high temporal and spatial ecosystem variations, bacteria and

• macroalgae establish close mutualistic relationships, in which both gain reciprocal benefits forming an ecological unit (holobiont) [1][2][3]. Chemical exchange and physical proximity are the basis of this algae–bacterial mutualism [4], but little is known about the spatial distribution of the bacteria on

• the algal host and the locally released and exchanged compounds within the algal chemosphere [3]. Bacterial biofilms on macroalgae can be crucial for developing algae and their interactions with other marine organisms. The exchange of resources in this spatially limited region is of high interest for

Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

• Anuj Kumar Chhalodia and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

• preferred gas-phase reaction. The ecology of marine bacteria in their interaction with algae is particularly interesting in which the bacteria can promote the algal growth, but can also kill their host [10][11]. For both processes, the phytohormone indole-3-acetic acid is used as a messenger molecule [10

• release sulfur volatiles [13][14] that are especially important headspace constituents from marine bacteria of the Roseobacter group [15][16][17]. In these organisms, sulfur volatiles are to a large extent generated from algal (DMSP), a metabolite that is produced in massive amounts by algae [18], thus

• giving another example for the complex interactions between marine bacteria and algae. Known DMSP degradation pathways include its hydrolysis to dimethyl sulfide (DMS) and 3-hydroxypropanoic acid (15) by the enzyme DddD [19], or the lysis to DMS and acrylic acid (16) for which various enzymes including

Identification of volatiles from six marine Celeribacter strains

• Anuj Kumar Chhalodia,
• Jan Rinkel,
• Dorota Konvalinkova,
• Jörn Petersen and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

• and various types of marine algae, e.g., the first described organisms Roseobacter litoralis DSM 6996T and R. denitrificans DSM 7001T were obtained from seaweed [7], while Dinoroseobacter shibae DSM 16493T and Marinovum algicola DSM 10251T are both isolates from the dinoflagellate Prorocentrum lima [8

• required for a significant antibiotic activity [34]. The biosynthesis of tropone [35] and of the algicidal sulfur-containing roseobacticides [36] are most likely connected to the TDA pathway. Interestingly, in the interaction with marine algae P. inhibens can change its lifestyle from a symbiotic

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• of supplemented pure NRP compounds, e.g., surfactin and bacillaene. The impact of antibiotics on algae-associated bacterial communities was investigated by Geng et al. in 2016, who revealed a dose-depended influence of pure tropodithietic acid on the microbiome structure of Nannochloropsis salina [63

Computational tools for drawing, building and displaying carbohydrates: a visual guide

• Kanhaya Lal,
• Rafael Bermeo and
• Serge Perez

Beilstein J. Org. Chem. 2020, 16, 2448–2468, doi:10.3762/bjoc.16.199

• represented in eleven shapes and ten colours. There is the hope that it will cope better with the rapidly growing information on the structure and functions of glycans and polysaccharides from microbes, plants and algae. The rendering of glycan drawing and symbol representations motivated the development of

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

Current understanding and biotechnological application of the bacterial diterpene synthase CotB2

• Ronja Driller,
• Daniel Garbe,
• Norbert Mehlmer,
• Monika Fuchs,
• Keren Raz,
• Dan Thomas Major,
• Thomas Brück and
• Bernhard Loll

Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228

• family was widened by molecules isolated from other marine organisms, like sponges, sea whips and the brown algae of this genus Dictyota [70]. Two modifications would transform 3,7,18-dolabellatriene (12, Scheme 3) into a potent cytotoxic molecule with activity towards murine leukemia cells or human non

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• -position (C2) of the acetate unit (Figure 3B) [13]. In contrast, methylation at the carbons derived from the carbonyl carbon of the acetate (C1) is quite unusual in fatty acids and polyketides. This unusual methylation pattern is reported for the polyketides of eukaryotic algae dinoflagellates. Some of the

New sesquiterpenoids from the South China Sea soft corals Clavularia viridis and Lemnalia flava

• Qihao Wu,
• Yuan Gao,
• Meng-Meng Zhang,
• Li Sheng,
• Jia Li,
• Xu-Wen Li,
• Hong Wang and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2019, 15, 695–702, doi:10.3762/bjoc.15.64

• . viridis and L. flava. In fact, to our knowledge, naturally occurring laurane- (1–4) and cuparane-derived (5) sesquiterpenoids, are extremely rare in soft corals. Previously, such sesquiterpenoids have only been isolated from the red algae of the genus Laurencia [14][16][17][21] and some sea hares that

• prey–predator relationship, the common symbiotic organisms in the algae and the soft corals might be the source of these metabolites. In fact, many investigations have proved that [23] numerous natural products are actually produced by microbes and/or microbial interactions with the “host from whence

Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds

• Melissa M. Cadelis and
• Brent R. Copp

Beilstein J. Org. Chem. 2018, 14, 2229–2235, doi:10.3762/bjoc.14.197

• terpenoid natural products containing the 1,4-dialdehyde moiety have been isolated from sources such as fungi, algae, sponges and molluscs [1]. Many of these natural products exhibit biological activity, ranging from anti-inflammatory to antimicrobial and antifeedant activities [1]. The prototypical

• from a diet-derived (Caulerpa algae) precursor and is predominantly present in the predator-deterring mucous secretion of the mollusc [7]. Two structurally-related masked dialdehydes, 5 (from Caulerpa ashmeadii) [8] and onchidal (6) [9][10] (from the defensive secretion of the mollusc Onchidella

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• the need to include sanitary procedures in the processing of bile acids. Alternative sources of sterols can be found in eukaryotic microorganisms like yeast and algae [41]. However, technological and scientific knowledge on these metabolic pathways are still in an early stage, and will not be included

Herpetopanone, a diterpene from Herpetosiphon aurantiacus discovered by isotope labeling

• Xinli Pan,
• Nicole Domin,
• Sebastian Schieferdecker,
• Hirokazu Kage,
• Martin Roth and
• Markus Nett

Beilstein J. Org. Chem. 2017, 13, 2458–2465, doi:10.3762/bjoc.13.242

• , whereas a plant-derived sesquiterpene with this feature was already reported in 1965. Oplopanone (2, Figure 3) was originally isolated from Oplopanax japonicus [18][19], but can also be found in a number of other plants as well as red algae [20][21]. Comparison of the chemical shifts in 1 with published

18-Hydroxydolabella-3,7-diene synthase – a diterpene synthase from Chitinophaga pinensis

• Jeroen S. Dickschat,
• Jan Rinkel,
• Patrick Rabe,
• Arman Beyraghdar Kashkooli and
• Harro J. Bouwmeester

Beilstein J. Org. Chem. 2017, 13, 1770–1780, doi:10.3762/bjoc.13.171

• been included in this study. It is difficult to judge what the correct structure for the compounds isolated from the brown algae and from A. odorata is, but the NMR data and isotopic labelling experiments presented here clearly point to the structure of 3 for the material obtained by us from the

Aqueous semisynthesis of C-glycoside glycamines from agarose

• Juliana C. Cunico Dallagnol,
• Alexandre Orsato,
• Diogo R. B. Ducatti,
• Miguel D. Noseda,
• Maria Eugênia R. Duarte and
• Alan G. Gonçalves

Beilstein J. Org. Chem. 2017, 13, 1222–1229, doi:10.3762/bjoc.13.121

• -group-free; reductive amination; Findings Agarose (1) is the term utilized to describe a type of galactose-containing polysaccharides biosynthesized by certain species of algae belonging to the division Rhodophyta (red seaweeds). It is a linear biopolymer constituted of the disaccharide repeating unit

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• to about 1,500. Interestingly, about 60% of them were obtained ligated to carbohydrates, which range from monosaccharides to 10 residue-long oligosaccharides. Lectins occur in plants, animals, algae, bacteria, fungi and yeasts, and viruses. Their involvement in key biologically-important recognition

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

• Katarina Kemper,
• Max Hirte,
• Markus Reinbold,
• Monika Fuchs and
• Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

• isoprenoid precursors are synthesized via the mevalonate pathway (MVA) starting from acetyl-CoA [26]. Alternatively, in the majority of eubacteria, cyanobacteria, green algae and in the plastids of plants isoprenoid biosynthesis originates from glyceraldehyde-3-phosphate (G3P) and pyruvate [26][27