Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• efficacious in preventing macular degeneration, cataracts, and cardiovascular diseases [83]. Many microorganisms, such as bacteria, cyanobacteria, and microalgae, can also produce 7 [84]. The biosynthesis of 7 in bacteria is analogous to that in plants. The difference is that in bacteria, 7 is formed through

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• exhibit a potent ability to induce tubulin depolymerization [77], originally isolated from the cyanobacteria Nostoc sp. ATCC 53789 [78]. Notably, the cryptophycins cannot serve as substrates for P-glycoprotein and multiple drug resistance-associated proteins, making them attractive as chemotherapeutic

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

• , polycavernoside analogs such as polycavernoside C (4) were isolated from red algae [3][4]. In 2015, Navarro et al. isolated polycavernoside D (5) from a marine Okeania sp. cyanobacterium [5]. They suggested that polycavernosides were produced by marine cyanobacteria based on their high content and structural

• metabolites derived from marine Okeania sp. cyanobacteria. Results and Discussion The EtOH extract of marine Okeania sp. cyanobacterium (340 g, wet weight) collected from Akuna Beach, Okinawa, Japan, was partitioned between EtOAc and H2O. The EtOAc fraction was further partitioned into 90% aqueous MeOH and

Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs

• Binbin Gu,
• Lin-Fu Liang and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104

• bacterial lineages including actinobacteria [4][5][6][7][8][9], myxobacteria [10] and aquatic cyanobacteria [11][12], as well as in liverwort [13] and ascomycete fungi [14]. The odour qualities of 1 may be concentration dependent and range from musty at low concentrations (<1 μg L−1) to camphoraceous at

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• ; Introduction Cyanobacteria are widely accepted as a prolific source of unique bioactive metabolites [1]. Some cyanobacterial species are consumed as food, nutritional supplements, or folk medicines in many parts of the world [2][3], and have offered attractive opportunities for drug discovery. Results from the

• compound 1 is acylated at sn-3 as judged by its negative value ([α]D22.4 −5.9 (c 0.01, MeOH)). Compound 1 is the first non-glycosylated glycerolipid isolated from cyanobacteria [17][18][19][20]. Natural 3-acylated-sn-glycerols were also reported from the fungus Sclerotinia fructicola [21] and a brown alga

The stereochemical course of 2-methylisoborneol biosynthesis

• Binbin Gu,
• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82

• recognized that many soil bacteria including various genera from the actinobacteria [3][4][5][6][7] and myxobacteria [8] produce the volatile musty odour compound 2-methylisoborneol (1). The compound is also found in marine Streptomyces strains [9] and aquatic cyanobacteria that can cause drinking water

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

• cyanobacteria (Figure 3) [27]. The gene sequence eboA-E encodes five yet uncharacterized enzymes, including EboA, a putative metallo-dependent hydrolase TatD (EboB), a putative UbiA prenyltransferase (EboC), a putative 3-dehydroquinate synthase (EboD) likely catalyzing the second step in the shikimate pathway

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

• Vladimir Kubyshkin,
• Rebecca Davis and
• Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

• entry into the citric acid cycle. The dehydrogenation of proline is involved in numerous biochemical processes. For example, the dehydrogenation of proline linked to an acyl carrier protein makes a first step in the biosynthesis of some neurotoxins from cyanobacteria (ana gene cluster) [68]. The

Fabclavine diversity in Xenorhabdus bacteria

• Sebastian L. Wenski,
• Harun Cimen,
• Natalie Berghaus,
• Sebastian W. Fuchs,
• Selcuk Hazir and
• Helge B. Bode

Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84

• further structural elements, such as C-domains for the amino acid specificity [29][30]. However, an A-domain promiscuity is common in NRPS, exemplified by the biosynthesis of microcystins from cyanobacteria, RXPs or xenematide from Xenorhabdus and Photorhabdus [31][32][33]. The second strategy includes

Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis

• Takayoshi Awakawa and
• Ikuro Abe

Beilstein J. Org. Chem. 2019, 15, 1545–1551, doi:10.3762/bjoc.15.157

• AmbP1 and AmbP3 functions, elucidated through their X-ray crystal structures. The knowledge presented here will contribute to the understanding of aromatic PTase reactions and will enhance their uses as biocatalysts. Keywords: crystal structure; cyanobacteria; Friedel–Crafts reaction; hapalindole

• Hapalindole/ambiguine alkaloids, isolated from cyanobacteria, are composed of the total C15 prenyl moieties derived from dimethylallyl diphosphate (DMAPP) and geranyl diphosphate (GPP), and cis-indolylvinyl isonitrile 1 (Figure 2A) [15]. This natural product family includes structurally diverse compounds with

Phylogenomic analyses and distribution of terpene synthases among Streptomyces

• Lara Martín-Sánchez,
• Kumar Saurabh Singh,
• Mariana Avalos,
• Gilles P. van Wezel,
• Jeroen S. Dickschat and
• Paolina Garbeva

Beilstein J. Org. Chem. 2019, 15, 1181–1193, doi:10.3762/bjoc.15.115

• genus Streptomyces. However, if bacteria from other taxonomic groups such as myxobacteria and cyanobacteria and their geosmin synthases are included in a phylogenetic analysis, it can be seen that the geosmin synthase amino acid sequences from distantly related organisms clearly fall into distant clades

Novel unit B cryptophycin analogues as payloads for targeted therapy

• Eduard Figueras,
• Adina Borbély,
• Mohamed Ismail,
• Marcel Frese and
• Norbert Sewald

Beilstein J. Org. Chem. 2018, 14, 1281–1286, doi:10.3762/bjoc.14.109

• Cryptophycins are natural occurring cyclic depsipeptides that were first isolated from cyanobacteria Nostoc sp. ATCC 53789 in 1990 [1]. Cryptophycins target tubulin, in particular the peptide site of the vinca domain. They block microtubule formation, inhibiting their assembly and, hence, are antimitotic agents

Volatiles from three genome sequenced fungi from the genus Aspergillus

• Jeroen S. Dickschat,
• Ersin Celik and
• Nelson L. Brock

Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77

• ][30], but geosmin could not be observed as a volatile of A. fischeri. The bacterial geosmin synthase is a class I terpene synthase (TS) with two domains [31] that occurs in many actinomycetes, cyanobacteria and myxobacteria, but fungal geosmin biosynthesis must require a different enzyme, because no

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

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

• Enjuro Harunari,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

• structure and the antifungal potency, no further research has been reported for 1. There are two interesting aspects in the structure of butyrolactol A (1). First, among the polyketides, a tert-butyl group has been found exclusively in metabolites of marine cyanobacteria except for 1 [11][12][13][14

Posttranslational isoprenylation of tryptophan in bacteria

• Masahiro Okada,
• Tomotoshi Sugita and
• Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

• tricyclic skeleton that bears a newly formed pyrrolidine, similar to proline. The post-translational dimethylallylation of two tryptophan residues of a cyclic peptide, kawaguchipeptin A, from cyanobacteria has also been reported. Interestingly, the modified tryptophan residues of kawaguchipeptin A have the

• has occurred at an internal tryptophan residue of the precursor peptide. Kawaguchipeptin A Apart from the ComX pheromones, post-translational dimethylallylations of the tyrosine, threonine, serine, and tryptophan residues of cyclic peptides from cyanobacteria were reported [49][50][51]. The RiPPs

• derived from cyanobacteria, including dimethylallylated cyclic peptides, are called cyanobactins [2][37][38]. Although several cyanobactins exhibit significant biological activities, such as antibacterial and enzyme inhibitory properties, the actual biological role of prenylation in cyanobactins is still

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

• Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

• number of cyanobacteria [99][100][101][102][103]. Members of this family can feature both macrolactams and macrolactones, and both of these are introduced by ATP-grasp ligases [88]. These macrolactams are formed by the condensation between the side chains of lysine and glutamate residues, whereas the

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

• of the molecule. However, the complete natural product has not yet been synthesized [61]. The enhygrolide group of compounds comprises enhygrolide A (27) and B (28). These molecules resemble cyanobacteria-derived metabolites, known as nostoclides and cyanobacterin, which also have a γ-lactone-moiety

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• proteobacteria (e.g., Bdellovibrio bacteriovorus, Myxococcus xanthus, Ensifer adhaerens, Cupriavidus necator, Lysobacter spp.) [13][14][15][16][17], the bacteroidetes (e.g., Saprospira grandis, Tenacibaculum spp.) [18][19], and even in the cyanobacteria (e.g., Vampirovibrio chlorellavorus) [20]. Depending on

Biocatalysis for the application of CO₂ as a chemical feedstock

• Apostolos Alissandratos and
• Christopher J. Easton

Beilstein J. Org. Chem. 2015, 11, 2370–2387, doi:10.3762/bjoc.11.259

• ]. In photoautotrophic bacteria (cyanobacteria) micro-compartmentalisation of the CO2-fixing reactions increases reaction rates [35][36]. The bacterial micro-compartments, called carboxysomes, are highly elaborate proteinic structures that usually also incorporate carbonic anhydrase [36][37

• C3 carbon fixation was thought to be the only important biological process for CO2 assimilation, as a result of its prevalence in our immediate environment. It is found in photosynthetic organisms, predominantly in plants on land and algae in water, and photosynthetic prokaryotes (cyanobacteria

• to prepare tobacco plants that expressed cyanobacterial RuBisCO together with a protein that forms part of the carboxysomal structure, which led to the generation of macromolecular complexes that are observed early in the carboxysomal biogenesis in cyanobacteria. In addition, the engineered plants

Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum

• Naoya Oku,
• Miyako Matsumoto,
• Kohsuke Yonejima,
• Keijiroh Tansei and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2014, 10, 1808–1816, doi:10.3762/bjoc.10.190

• restaurants or for personal consumption. Keywords: Aphanothece sacrum; cyanobacterium; food intoxication; natural products; sacrolide A; suizenji-nori; Introduction Cyanobacteria continue to be core sources for bioactive secondary metabolites [1][2], and their significance in drug discovery has increased

• for the past two decades [3]. Some cyanobacteria form macroscopic colonies and are harvested for human consumption in many parts of the world [4]. As a part of our program to exploit untapped microbes for drug discovery, we focus on cyanobacteria that are eaten in Japan, and previously reported the

Total synthesis and biological evaluation of fluorinated cryptophycins

• Christine Weiß,
• Tobias Bogner,
• Benedikt Sammet and
• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 2060–2066, doi:10.3762/bjoc.8.231

• ; fluorinated natural product analogues; structure-activity relationship; Introduction Cryptophycins form a class of cytotoxic sixteen-membered macrocyclic depsipeptides. Cryptophycin-1 (1) was isolated for the first time in 1990 from cyanobacteria Nostoc sp. ATCC 53789 [1] (Figure 1). Moore et al. isolated

Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes

• Jan-Christoph Kehr,
• Douglas Gatte Picchi and
• Elke Dittmann

Beilstein J. Org. Chem. 2011, 7, 1622–1635, doi:10.3762/bjoc.7.191

• Jan-Christoph Kehr Douglas Gatte Picchi Elke Dittmann University of Potsdam, Institute for Biochemistry and Biology, Karl-Liebknecht-Str. 24/25, 14476 Potsdam-Golm, Germany 10.3762/bjoc.7.191 Abstract Cyanobacteria are prolific producers of natural products. Investigations into the biochemistry

• responsible for the formation of these compounds have revealed fascinating mechanisms that are not, or only rarely, found in other microorganisms. In this article, we survey the biosynthetic pathways of cyanobacteria isolated from freshwater, marine and terrestrial habitats. We especially emphasize modular

• nonribosomal peptide synthetase (NRPS) and polyketide synthase (PKS) pathways and highlight the unique enzyme mechanisms that were elucidated or can be anticipated for the individual products. We further include ribosomal natural products and UV-absorbing pigments from cyanobacteria. Mechanistic insights

2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β²-amino acids

• Markus Nahrwold,
• Arvydas Stončius,
• Anna Penner,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43

• ]. Examples are cryptophycin-1 (a highly cytotoxic depsipeptide produced by cyanobacteria Nostoc sp. GSV224 and ATCC53789) [11][12][13][14] as well as a class of lipopeptides isolated from various fungi, comprising topostatin (a topoisomerase I and II inhibitor) [15], YM-170320 (an inhibitor of ergosterol