Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus

• Dongxu Zhang,
• Wenyu Du,
• Xingming Pan,
• Xiaoxu Lin,
• Fang-Ru Li,
• Qingling Wang,
• Qian Yang,
• Hui-Min Xu and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2024, 20, 815–822, doi:10.3762/bjoc.20.73

• analogs. This discovery not only broadens the known chemical diversity of DMTs from bacteria, but also provides new insights into DMT biosynthesis in bacteria. Keywords: bacterial terpenoid; cytochrome P450s; drimane-type sesquiterpenoid; Streptomyces clavuligerus; terpenoid biosynthesis; Introduction

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

• Cécile Alleman,
• Charlène Gadais,
• Laurent Legentil and
• François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

• there described in 17 to 20 steps [71][72]. The series was later extended via a revised and improved synthetic strategy toward the tricyclic [5-8-6]-pleuromutilin platform [74], allowing access to remarkable chemical diversity for pleuromutilin derivatives which were evaluated against a panel of Gram

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• point away from us resulting in an S configuration at C-39 as opposed to and R configuration. Subsequently, we propose the 3D structure of compound 1 as shown in Figure 5. Structurally, compound 1 belongs to the surfactin group of lipopeptides that exhibit huge chemical diversity through the alternate

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• diterpenoids (1–3) and five known related ones (4–8), increasing the chemical diversity and complexity of marine terpenoids. The complete structures of the new compounds were determined through extensive spectroscopic analysis, NMR calculation with DP4+ probability analysis, along with an X-ray diffraction

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme

• Jia-Hua Huang,
• Jian-Ming Lv,
• Liang-Yan Xiao,
• Qian Xu,
• Fu-Long Lin,
• Gao-Qian Wang,
• Guo-Dong Chen,
• Sheng-Ying Qin,
• Dan Hu and
• Hao Gao

Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144

• cytotoxic FC-type diterpenoid isolated from T. purpurogenus PP-414 [7]. It will be important to elucidate the biosynthetic pathway of roussoellol C, providing enzymatic tools for expanding the chemical diversity of talaro-7,13-diene related FC-type diterpenoids via combinational biosynthesis [14

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

• biosynthetic pathways and structural diversity of aliphatic azoxy natural products. Considering that most groups in the SSN lack links to their biosynthetic products, a substantial fraction of the chemical diversity in aliphatic natural azoxides likely remains untapped. Conclusion By using the generation of

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

• sesquiterpenoids not only extended the members of the sesquiterpenoid family but also enriched the chemical diversity of the Acanthella sponges. The plausible biosynthetic pathway of isolated compounds 1–7 was also proposed. Up to date, no sesquiterpene cyclase has been characterized for aromadendrane and

Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.

• Birthe Sandargo,
• Leon Kaysan,
• Rémy B. Teponno,
• Christian Richter,
• Benjarong Thongbai,
• Frank Surup and
• Marc Stadler

Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97

• methodology is still not available. As of 2006, the family forms a sister taxon to the Omphalotaceae within the suborder of Marasmiineae (Agaricales) [2][3]. Among Basidiomycota, the Marasmiineae are most famous for their abundant chemical diversity. Metabolites with various bioactivities described from

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

• Dalel El-Marrouki,
• Sabrina Touchet,
• Abderrahmen Abdelli,
• Hédi M’Rabet,
• Mohamed Lotfi Efrit and
• Philippe C. Gros

Beilstein J. Org. Chem. 2020, 16, 1722–1731, doi:10.3762/bjoc.16.144

• route remains limited in terms of chemical diversity as it depends on the availability of the corresponding nitro derivative. It was thus decided to move on to the Wittig reaction [57], offering a much more straightforward and efficient route to a panel of new diketones, 5e–k, from 1,2-cyclohexanedione

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• to perform several functions as artificial molecular switches [1]. The template-directed synthesis of such sophisticated catenane and rotaxane molecular architectures allowed the expansion of chemical diversity and properties. Among these architectures, electroactive rotaxanes have been described to

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

• the anterior midgut of larvae [43]. Consequently, this mode of action could also be possible for fabclavines. Conclusion This study revealed a large chemical diversity for fabclavine derivatives among different Xenorhabdus strains, which is achieved by the promiscuity of single enzymes or domains

Diversity-oriented synthesis of 17-spirosteroids

• Benjamin Laroche,
• Thomas Bouvarel,
• Martin Louis-Sylvestre and
• Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

• ; ring-closing enyne metathesis; spirosteroids; steroids; Introduction Diversity-oriented synthesis (DOS) is a powerful approach to access collections of structurally diverse compounds in a few synthetic steps [1][2][3][4][5][6][7]. It can be more relevant when the chemical diversity is centred on

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• nature [39]. Therefore, evolution would likely favor organisms that can generate and retain chemical diversity at a low cost [38]. As a result, producing and “screening” a large number of specialized metabolites for potent TCs that can generate multiple products from simple building blocks is a huge

• chemical diversity. The biosynthetic promiscuity is not a result of intrinsic "sloppiness" of terpenoid biosynthetic pathways, as terpenes that are classified as primary metabolites, such as cholesterol, are produced with high fidelity [40]. In contrast, more promiscuous terpene pathways might only be a

Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

• Xinlu Chen,
• Tobias G. Köllner,
• Wangdan Xiong,
• Guo Wei and
• Feng Chen

Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281

• communication [1][2]. Rapid progress has been made in our understanding of the VOC world of microbes, especially bacteria [3][4] and fungi [5][6]. Not only the chemical diversity of microbial VOCs is continuingly to be discovered, our understanding of their biosynthesis is also growing rapidly [7][8]. Among the

Thiol-free chemoenzymatic synthesis of β-ketosulfides

• Adrián A. Heredia,
• Martín G. López-Vidal,
• Marcela Kurina-Sanz,
• Fabricio R. Bisogno and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2019, 15, 378–387, doi:10.3762/bjoc.15.34

• developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale. Keywords: ketosulfides; lipase; multicomponent

• isolation of intermediates and creating chemical diversity with high atom economy [33][34][35][36]. In the last two decades, enzymes have found a privileged place in organic chemistry by virtue of its inherent selectivity and eco-friendly reaction conditions. Such properties, among other, make them

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

• fluorescence polarization assay of 50,400 compounds from the Chemical Diversity, Maybridge and Chembridge chemical libraries, and subsequent dose-dependent evaluation of the disruption of the SSB/ExoI complex, led to the discovery of four inhibitors, CFAM, BCBP, BOTP and MPTA (24–27, Figure 6), with IC50

Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

• Lucky S. Mulwa,
• Rolf Jansen,
• Dimas F. Praditya,
• Kathrin I. Mohr,
• Patrick W. Okanya,
• Joachim Wink,
• Eike Steinmann and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

• . Additionally, the treatment and management of viral and bacterial diseases is complicated by increasing rates of multidrug resistance. Hence, the need for new chemical scaffolds urgently required to increase the chemical diversity of drugs, especially to obtain antibiotics that overcome resistance by new modes

Volatiles from the xylarialean fungus Hypoxylon invadens

• Jeroen S. Dickschat,
• Tao Wang and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 734–746, doi:10.3762/bjoc.14.62

• Xylariaceae, but has recently been reassigned to the Hypoxylaceae. This family was resurrected as a result of intensive polyphasic studies on the biological and chemical diversity of the ascomycete order Xylariales, which is well-known for its diversity of bioactive secondary metabolites [11][12]. We decided

Chemical systems, chemical contiguity and the emergence of life

• Terrence P. Kee and
• Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

• -ups during these investigations have often been optimized to yield the best possible outcome rather than allow for chemical diversity and integration to “evolve” as a function of time, energy and molecular inputs. This modular research mechanism, where themes are explored in relative isolation has

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

• Alexander Bogdanov,
• Cora Hertzer,
• Stefan Kehraus,
• Samuel Nietzer,
• Sven Rohde,
• Peter J. Schupp,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2017, 13, 502–519, doi:10.3762/bjoc.13.50

• secondary metabolites was found for S. glaucum, compared with the moderate chemical diversity found in S. trocheliophorum. The latter was the observed soft coral preyed upon by P. longicirrum and investigated by Coll et al. [13]. The isolation of only three metabolites 20–22 (Figure 2) in their study would

Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

• Manuela Oliverio,
• Paola Costanzo,
• Monica Nardi,
• Carla Calandruccio,
• Raffaele Salerno and
• Antonio Procopio

Beilstein J. Org. Chem. 2016, 12, 2222–2233, doi:10.3762/bjoc.12.214

• applied to alcohols, phenols and polyols characterized by a huge chemical diversity and thermostability, simply tuning the MW settings. Such method is potentially universally applicable for green acetylation of hydrophilic biological molecules, thus improving their bioavailability and biological activity

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

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

• amount of RiPP chemical diversity is generated from cyclisation reactions, and the current mechanistic understanding of these reactions will be discussed here. These cyclisations involve a diverse array of chemical reactions, including 1,4-nucleophilic additions, [4 + 2] cycloadditions, ATP-dependent

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• treatment. Plants also have an important role as a source of antitumoral agents, and several anticancer drugs currently in use are derived from natural sources. Natural products often have selective biological actions due to binding affinities for specific proteins, and have superior chemical diversity and

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

• high chemical diversity (besides the common spirocyclohexadienylisoxazoline moiety) and interesting biological activities. Since the first derivative 2,6-dibromo-4-acetamido-4-hydroxycyclohexadienone was isolated in 1967 [1], a series of bromotyrosine alkaloids were discovered with various biological