Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

• Jana M. Boysen,
• Nauman Saeed and
• Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

• ; non-ribosomal peptides; polyketides; secondary metabolism; virulence; Introduction To thrive in their natural habitats all organisms from bacteria and fungi to plants and animals need access to sufficient nutritional sources and have to defend themselves against both, competitors and predators

• the form of naturally grown truffles (e.g., Tuber melanosporum) or recently cultivated meat alternatives like Quorn® (Fusarium venenatum) [15][16][17]. Species of Aspergillus, such as Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger can affect the health of humans, plants and lifestock

• -melanin Melanins are a heterogenous group of hydrophobic phenolic polymers that are found in a range of organisms including bacteria, plants, fungi and even animals. The melanin pigments are of mostly dark colours like black or brown and are associated with virulence in plant- and animal-pathogenic fungi

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• volatile blends of plants consist of different compound classes, including green leaf volatiles, benzenoids, terpenoids, and nitrogen-containing compounds [5][6][7]. Among these, terpenoids represent the largest and most diverse group of compounds. In poplar trees, large amounts of terpenoids can be

• precursors GPP, FPP, and GGPP into the different terpene skeletons [42][43][44]. However, our knowledge on terpene synthases of endophytic fungi is scarce, specifically in comparison to the vast knowledge on these enzymes in plants and bacteria [44][45]. Typical monoterpenes like limonene and linalool (5

• endophytic fungi qualitatively overlap with the VOC bouquets produced by numerous plant species [53][54][55][56] including black poplar (Populus nigra) [57][58][59]. Thus, the question arises whether endophytes found in plants contribute significantly to the overall plant volatile blend by expression of

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• degradation of antiviral RNA molecules. The present work demonstrates that VLPs (virus-like particles) allow efficient delivery of dsRNAi as antiviral therapy in shrimp. In particular, VLPs derived from a virus that infects plants, such as cowpea chlorotic mottle virus (CCMV), in which the capsid protein (CP

• ) has been extensively studied and characterized, due to its potential applications in nanomedicine [33][36][39][40][41]. Native CCMV has a positive single-stranded RNA. It is a Bromoviridae family member that infects cowpea (Vigna unguiculata) plants. The CCMV VLPs with heterologous RNA has already

• purification. The plant virus CCMV was produced in California cowpea plants (Vigna ungiculata). The plants were mechanically inoculated with a solution containing the virus. After two weeks, the infected leaves were collected and ground in a virus extraction buffer (0.5 M sodium acetate, 0.08 M magnesium

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

• Chinese medicinal plants Dichroa febrifuga Lour., and (+)-halofuginone (134), which is a pharmaceutical candidate developed from febrifugine for the treatment of human scleroderma (Scheme 36). The reaction of chiral imine 135 with Grignard reagents in THF took also place with high diastereoselectivity

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• of this family, berberine (1a) is a natural product and may be isolated from different plants such as berberis vulgaris, hydrastis canadensis or coptidis rhizome [2]. Particularly, the latter is established in traditional Chinese medicine as source for anti-inflammatory extracts [2]. Berberine has

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

• -volatile precursor that is stored in garlic and related plants and only degraded into sulfur volatiles upon wounding by the pyridoxal phosphate (PLP) dependent alliinase (Scheme 1B) [7]. This initial enzyme-catalyzed reaction yields one equivalent of allylsulfenic acid (10), pyruvic acid (11), and ammonia

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

• Joon Min Cha,
• Dong Hyun Kim,
• Lalita Subedi,
• Zahra Khan,
• Sang Un Choi,
• Sun Yeou Kim and
• Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

• [11]. As a part of the continuing studies to identify bioactive constituents from the Korean medicinal plants [13][16][17][18][19][20], previous phytochemical investigations on the MeOH extract of the twigs of C. sinensis have led to the isolation and characterization of triterpenoids [13], biphenyls

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

• nutrient availability and geochemical features [9]. Therefore, soil consists of microbial hotspots, indicating faster process rates than the average soil [10]. One such microbial hotspot is the rhizosphere, harbouring microbial communities where various interactions between bacteria, fungi, and plants take

• , Bacillus amyloliquefaciens (now identified as Bacillus velezensis), and Bacillus cereus to the roots of broccoli plants led to species-dependent changes in the diversity, evenness, and relative abundances of endophytic bacterial communities [32]. Like many other soil bacteria, B. subtilis and other

On the mass spectrometric fragmentations of the bacterial sesterterpenes sestermobaraenes A–C

• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2020, 16, 2807–2819, doi:10.3762/bjoc.16.231

• related techniques the volatiles from many bacteria, fungi, and plants have been investigated [8][9][10], which provides rapid information about the production of volatile terpenes. This information is particularly useful in the combination with the genome sequences of the producing organism, because it

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

• Florian Mann,
• Daiane Szczerbowski,
• Lisa de Silva,
• Melanie McClure,
• Marianne Elias and
• Stefan Schulz

Beilstein J. Org. Chem. 2020, 16, 2776–2787, doi:10.3762/bjoc.16.228

• studies on speciation (species formation), as species often consist of multiple subspecies diverging for a number of adaptive traits, such as color pattern or host plants, which can then cause reproductive isolation. As such, they offer an excellent system to study the mechanisms underlying

• various plants [9]. These alkaloids are transformed into the alkaloid and pheromone precursor lycopsamine (1, Scheme 1) [10][11][12] that can then be converted either into necine base derived compounds such as methyl hydroxydanaidoate (2), or into necic acids derived ones, e.g., ithomiolide A (3) [10][11

• that all individuals devoid of 3 simply had no access to PAs and/or that its absence is a specific trait of I. s. derasa. In contrast, elemol/hedycaryol (8) is specific to the latter subspecies. Although sesquiterpenes are common in plants, the occurrence of a single sesquiterpene might indicate

Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of ¹J_C,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites

• Md. Rokon Ul Karim,
• Enjuro Harunari,
• Amit Raj Sharma,
• Naoya Oku,
• Kazuaki Akasaka,
• Daisuke Urabe,
• Mada Triandala Sibero and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222

• found in association with marine organisms such as invertebrates and plants [4][5]. Marine actinomycetes show unique physiological adaptations distinct from their terrestrial counterparts in terms of pressure, salinity, or low-temperature tolerance, which might affect their metabolic ability in their

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

• downloading at http://www.rings.t.soka.ac.jp/downloads.html. GlycanBuilder2 is a newer version of GlycanBuilder [20] with additional features. This version is capable of supporting various ambiguous glycans consisting of monosaccharides from plants and bacteria. The tool uses the SNFG notation to display

How and why plants and human N-glycans are different: Insight from molecular dynamics into the “glycoblocks” architecture of complex carbohydrates

• Carl A. Fogarty,
• Aoife M. Harbison,
• Amy R. Dugdale and
• Elisa Fadda

Beilstein J. Org. Chem. 2020, 16, 2046–2056, doi:10.3762/bjoc.16.171

• undetected because of their intrinsic structural disorder. In this work we use molecular dynamics (MD) simulations to provide insight into N-glycans’ 3D structure by analysing the effects of a set of very specific modifications found in plants and invertebrate N-glycans, which are immunogenic in humans. We

• glycans sequence can alter their 3D structure and conformational dynamics, ultimately regulating recognition [19]. In this work we use molecular dynamics (MD) simulations to analyse the effects of the inclusion of motifs typically found in plants and invertebrates N-glycans and immunogenic in mammals [20

• ][21][22][23]. More specifically, we investigate how core α(1-3)-linked fucose (Fuc) and β(1-2)-linked xylose (Xyl) affect the structure and dynamics of plants N-glycoforms [23] and of hybrid constructs with mammalian N-glycoforms [24]. At first glance plants protein N-glycosylation [23] is quite

Synthesis of the tetrasaccharide repeating unit of the O-specific polysaccharide of Azospirillum doebereinerae type strain GSF71^T using linear and one-pot iterative glycosylations

• Arin Gucchait,
• Pradip Shit and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2020, 16, 1700–1705, doi:10.3762/bjoc.16.141

• cause environmental pollution, resistance in plant pathogens as well as high production costs of crops [1][2][3]. Varieties of crop plants have symbiotic relationships with microorganisms by hosting them in their roots and utilize their beneficial effects such as improving the quality of soil and

• is quite pertinent to study the effect of the cell-wall polysaccharides of rhizobacteria on the growth of leguminous plants. As a consequence, the structural elucidation of a variety of cell-wall polysaccharides of several strains of Azospirillum have been reported in the past [14][15][16][17][18][19

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

• Dandan Li,
• Naoya Oku,
• Yukiko Shinozaki,
• Yoichi Kurokawa and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

• in liquid production cultures, quenched hydroxy radical-induced chemiluminescence emitted by luminol by 86%. Because some Burkholderia species are pathogenic to plants and animals, the above result suggests that 1 is a potential antioxidant to counteract reactive oxygen species-based immune response

• in the host organisms. Keywords: antioxidant; Burkholderia sp; quinolone; soil bacterium; Zn2+ enrichment culture; Findings 4-Hydroxy-2(1H)-quinolone (3) is a unique structural motif mostly found in alkaloids from rutaceous plants (family Rutaceae) [1][2]. This motif has several tautomeric forms

• rutaceous plants [9]. Examples from microbes include chymase inhibitors SF2809-I to VI from an actinomycete of the genus Dactylosporangium [10], a quorum sensing signaling molecule 2,4-dihydroxyquinoline (DHQ, 4) from Gram-negative bacteria Pseudomonas aeruginosa and Burkholderia thailandensis, [7], and 4-O

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• and agriculture are well-suited for this purpose [15]. Wood is mainly composed of cellulose (40 to 55 wt %), hemicelluloses (mostly xylan in hardwoods with 20 to 35 wt %) and lignin (18 to 35 wt %). Cellulose maintains the structure of the cell walls of plants and is the most abundant raw material

• with a production of 1011–1012 tons per year, followed by lignin as second most abundant raw material [16]. Lignin is a three-dimensional phenolic polymer and is responsible for the cementation of cellulose fibres in plants [17]. Hemicelluloses, predominantly xylan, are non-cellulosic polysaccharides

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

• Dragana Vuk,
• Irena Škorić,
• Valentina Milašinović,
• Krešimir Molčanov and
• Željko Marinić

Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

• numerous biologically active natural compounds (Figure 1) [4][5][6][7], their strenuous isolation procedures from plants, as well as their complicated multistage synthesis due to the complexity of their structure, encouraged us to develop a simple one-step synthetic procedure based on a photochemical

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• , our focus in this part of the review is the use of porphyrins as photocatalysts, but we decided to select another relevant example using chlorophyll a (a chlorin-type derivative) for artemisinin preparation. Gilmore and co-workers have shown that the extract in toluene from Artemisia annua plants

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku,
• Nobuyasu Matsuura,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

• fatty acids bearing a keto group in the middle of the carbon chain are relatively limited in their distribution in nature. Many of such natural keto fatty acids were found in plants, mainly as a constituent of seed oil [21][22][23][24][25][26][27][28][29]. Among them, rabdosia acids [30] and (10E,12E)-9

• NBRC14554, a causative agent of crown gall disease of plants [41]. The MIC values for 1 against T. maritimum and R. radiobacter were 50 and 6.2 µg/mL, respectively, while 2 was more potent against T. maritimum, with a MIC of 12.5 µg/mL, and less against R. radiobacter, with a MIC of 50 µg/mL, presenting an

Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

• Ken-ichi Nakashima,
• Junko Tomida,
• Takao Hirai,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

• first time in over 50 years. Keywords: absolute configuration; endophytic fungus; glauconic acid; Talaromyces; tetrahydroxanthone; xanthenedione; Introduction The xanthones, which are a class of phenolic compounds produced by many different organisms, including plants, lichens, fungi, and bacteria

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

• Man-Man Wang,
• Hao Huang,
• Lei Shu,
• Jian-Min Liu,
• Jian-Qiu Zhang,
• Yi-Le Yan and
• Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

• is found in microbes, mammals, and plants, and has different functions in different organisms [1]. In the catalytic process of HPPD, 4-hydroxyphenylpyruvic acid (HPPA) and FeII form a chelate complex, from which the HPPA substrate is converted into homogentisic acid (HGA). The generally accepted

• catalytic mechanism for this process is shown in Scheme 1 [2][3][4][5][6]. The HPPD amino acid sequence homologies in plants and mammals are significantly different [7][8], and this difference affects the binding stability between an inhibitor and HPPD, leading to inhibitor activities that differ among

• various species and genera and providing a theoretical basis for the design of inhibitors that are highly selective and safe [2]. In plants, HPPD inhibitors competitively restrain HPPA from chelating to FeII. The production of plastoquinone is inhibited and phytoene is accumulated when the transformation

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

• Jucleiton J. R. Freitas,
• Queila P. S. B. Freitas,
• Silvia R. C. P. Andrade,
• Juliano C. R. Freitas,
• Roberta A. Oliveira and
• Paulo H. Menezes

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

• factor) [31]. Within this context, the development of solvent-free methods is highly desirable since the difficult for solvent recycling in academic laboratories and chemical manufacturing plants is universal. In addition, a reliable method for the propargylation reaction which could involve the use of

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

• metabolites on the planet. To date more than 70,000 terpenoids (dictionary of natural products) have been characterized and grouped into more than 400 structural families – the vast majority of which have been isolated from plants and fungi [1]. Their structural diversity reflects the breadth of their

• reported [40]. In fact, different pathways have evolved in plants, fungi, and bacteria for this fascinating compound family in an extreme case of convergent evolution [41][42]. While the plant and fungal biosynthetic pathways are well studied [42], the bacterial pathway was studied to a lesser degree until

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

• and gene expression patterns, the products of most DdTPSs were released as volatiles from D. discoideum at the multicellular developmental stage [14][15]. TPS genes previously were known to exist only in bacteria, fungi, and plants [13][17][18]. The identification of TPS genes in dictyostelid social

• different prenyl diphosphate substrates, or require different conditions for catalysis. It is also possible that they become inactive genes in the process of pseudogenization. What are the biological functions of volatile terpenoids emitted from P. polycephalum? In plants and other organisms, volatile