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

• from a marine Okeania sp. cyanobacterium. The relative configuration was elucidated primarily by analyzing the two dimensional nuclear magnetism resonance (2D NMR) data. The absolute configuration was clarified by comparing the electronic circular dichroism (ECD) data of 1 with those of known analogs

• 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

• , 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

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

• , Japan 10.3762/bjoc.19.13 Abstract A new antibacterial 3-monoacyl-sn-glycerol, nostochopcerol (1), was isolated from a cultured algal mass of the edible cyanobacterium Nostochopsis lobatus MAC0804NAN. The structure of compound 1 was established by the analysis of NMR and MS data while its chirality was

• established by comparison of optical rotation values with synthetically prepared authentics. Compound 1 inhibited the growth of Bacillus subtilis and Staphylococcus aureus at MIC of 50 μg/mL and 100 μg/mL, respectively. Keywords: antibacterial; cyanobacterium; edible; monoacylglycerol; Nostochopsis lobatus

First total synthesis of hoshinoamide A

• Haipin Zhou,
• Zihan Rui,
• Yiming Yang,
• Shengtao Xu,
• Yutian Shao and
• Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

• 210009, China Taizhou Medical Hi-Tech Development Public Services Platform, Taizhou 225300, China 10.3762/bjoc.17.201 Abstract Hoshinoamides A, B and C, linear lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata, with potent antiplasmodial activity against chloroquine

• , hoshinoamides A, B [11] and C [12], from a microbial metabolite of marine cyanobacterium Caldora penicillata (Figure 1). Hoshinoamides A and B showed potent activities against chloroquine-sensitive Plasmodium falciparum 3D7 with IC50 values of 0.52 and 1.0 μM, respectively. Hoshinoamide C inhibited the growth

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

• biosyntheses, two research groups independently sequenced the genome of a cyanobacterium, Fischerella ambigua UTEX 1903, and performed a biosynthetic study [18][19]. Among the identified biosynthetic enzymes, the major contributors of the structural diversity are two prenyltransferases (AmbP1 and AmbP3) [18

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

• Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

• ], Helicobacter pylori [41], Pseudomonas aeruginosa [42], Campylobacter jejuni [43], Treponema pallidum [44], the cyanobacterium Synechocystis spp. [45], Mesorhizobium loti [46] and Mycoplasma pneumoniae [47]. Furthermore, partial PINs for Bacillus subtilis [48] and Streptococcus pneumoniae [49] have been

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

• , Japan 10.3762/bjoc.10.190 Abstract Macroscopic gelatinous colonies of freshwater cyanobacterium Aphanothece sacrum, a luxury ingredient for Japanese cuisine, were found to contain a new oxylipin-derived macrolide, sacrolide A (1), as an antimicrobial component. The configuration of two chiral centers

• 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

• isolation of an unusual ω-1 fatty acid (9Z,12Z)-9,12,15-hexadecatrienoic acid from a freshwater periphytic cyanobacterium Nostoc verrucosum [4]. Aphanothece sacrum is also an edible cyanobacterium, which is an endemic species in the Aso water system in the Kyushu District, Japan. It inhabits oligotrophic

Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin

• Rajendra S. Rohokale and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2014, 10, 667–671, doi:10.3762/bjoc.10.59

• acid; Introduction Microginin 1 (Figure 1), isolated from the cyanobacterium Microcystis aeruginosa, is a linear pentapeptide consisting of L-Tyr-L-N-Me-Tyr-L-Val-L-Ala and (2S,3R)-α-hydroxy-β-aminodecanoic acid ((2S,3R)-AHDA, 2a) [1]. Microginin is used as a hypertensive agent based on its biological

Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog

• Werner Telle,
• Gerhard Kelter,
• Heinz-Herbert Fiebig,
• Peter G. Jones and
• Thomas Lindel

Beilstein J. Org. Chem. 2014, 10, 316–322, doi:10.3762/bjoc.10.29

• Analytical Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany 10.3762/bjoc.10.29 Abstract The marine natural product malevamide D from the cyanobacterium Symploca hydnoides was synthesized for the first time. The final peptide coupling linked the dolaisoleuine and dolaproine subunits. The

• depsipeptide malevamide D (1, Figure 1) belongs to the dolastatin class of marine natural products and has been isolated from the cyanobacterium Symploca hydnoides by Scheuer and co-workers in 2002 (7.5 mg, 0.014% of the dry weight) [1]. Malevamide D (1) was reported to exhibit in vitro cytotoxicity in the

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

• the cyanobacterium Microcystis aeruginosa [17][18][19]. Microcystins are produced by different genera of freshwater cyanobacteria and inhibit eukaryotic protein phosphatases of types 1 and 2A. A signature of this heptapeptide family is the unusual β-amino acid Adda (3-amino-9-methoxy-2,6,8-trimethyl

• necessary to finally yield anatoxin-a and homoanatoxin-a [38]. NRPS and PKS pathways in marine cyanobacteria Barbamide Several NRPS/PKS assembly lines were identified and partially characterized for the marine cyanobacterium Lyngbya majuscula [39]. These filamentous tropical cyanobacteria are important

• second biosynthetic pathway identified in a strain of the tropical marine cyanobacterium Lyngbya majuscula was assigned to jamaicamides 8. Jamaicamides are neurotoxins and show sodium-channel-blocking activity. The lipopeptide is highly functionalized and contains a bromo-alkynyl, a chlorovinylidene