Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

• again from A. alternata [138], from A. brassicae [262], and further A. spp. [215][263], from Ulocladium sp. [210], Colletotrichum capsica [264], Setosphaeria sp. [265], Phyllosticta capitalensis [266], and from Fusarium guttiforme [267]. Isoaltenuene showed some phytotoxicity on tomato leaves at 20 µg

• ], and from Fusarium guttiforme [267]. No biological activities could be determined for this compound. The natural products depicted in Figure 15 are 9-O-demethylated derivatives of altenuene diastereomers. Alternolides B and C (58 and 59) were isolated from Alternaria alternata and their structures

Enhancing structural diversity of terpenoids by multisubstrate terpene synthases

• Min Li and
• Hui Tao

Beilstein J. Org. Chem. 2024, 20, 959–972, doi:10.3762/bjoc.20.86

• convert natural substrates into cyclic skeletons. According to a phylogenetic tree constructed using 51 well-characterized class I TSs, clade III is of particular interest because most characterized di- and sester-TSs are enriched in this clade [28]. Two clade III TSs, FgMS and FgGS, from Fusarium

(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

Confirmation of the stereochemistry of spiroviolene

• Yao Kong,
• Yuanning Liu,
• Kaibiao Wang,
• Tao Wang,
• Chen Wang,
• Ben Ai,
• Hongli Jia,
• Guohui Pan,
• Min Yin and
• Zhengren Xu

Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77

• from Fusarium graminearum GJ1012 [11], have been reported almost at the same time. The discrepancy of the stereochemistry at C3 between 1' and 2 was first noticed by Snyder and co-workers [12]. The conserved stereochemistry of spiroviolene and 2 at C3 was later confirmed by the conversion of a

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• gloeosporioides, Coniothyrium diplodiella, Curvularia spicifera, Fusarium proliferatum, and Penicillium digitatum) (Table 2). In the antibacterial screening, none of the compounds displayed potent activity against the tested strains (MIC ≥ 32 μg/mL). The antifungal assays showed that compounds 1–3 exhibited

• , Alternaria brassicae QDAU-11, Penicillium digitatum QDAU-14, Coniothyrium diplodiella QDAU-15, Curvularia spicifera QDAU-18, and Fusarium proliferatum QDAU-19) were determined by a serial dilution technique using 96-well microtiter plates [21] with minor modifications as our previously report [22]. Briefly

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

• in other foodstuff such as fish and coffee contaminations with 1 are perceived as unpleasant flavor constituents [15][16][17][18]. Despite its occurrence in fungi, 1 also has moderate antifungal activity as observed for its inhibition of mycelial growth and sporulation in Fusarium moniliforme [19

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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

• 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

• on Fusarium graminearum induces several metabolites, of which especially the bisnaphthopyrone pigment aurofusarin (3) was shown to have antifeedant effects not only on springtails but also on mealworm Tenebrio molitor and woodlouse Trichorhina tomentosa. Not only Fusarium species produce

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

• known endophytic volatiles, sesquiterpenes have gained much attention in recent years as they can play an important role in plant–plant, plant–microbe, and microbe–microbe interactions [39][40]. Weikl et al., for instance, analyzed the volatile emission of Alternaria alternata and Fusarium oxysporum in

• , Cladosporium, Fusarium, Sordaria, and Stemphylium (Table 1). One unidentified species was also included in the volatile analysis. All the identified fungi belong to the Ascomycota, the largest fungal phylum. Endophytic fungi emit typical plant VOCs Altogether, we detected 77 volatile compounds in the

• ), and α-muurolene (8). However, monoterpenes were completely absent from the volatile bouquets of the endophytic species in our study. Weikl et al. who compared the volatiles released from Alternaria alternata and Fusarium oxysporum also did not detect any monoterpenes [41]. However, other studies on

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

• program from marine fungi, two new aromatic polyketides karimunones A (1) and B (2) and five known compounds (3–7) were isolated from sponge-associated Fusarium sp. KJMT.FP.4.3 which was collected from an Indonesian sponge Xestospongia sp. The structures of these compounds were determined by the analysis

• polyketide; Fusarium; marine fungus; secondary metabolite; sponge; Introduction Marine organisms have been known as a potential source of prospective bioactive compounds, and sponges are particularly emphasized as the most promising source among all marine invertebrates [1][2]. However, the collection of

• -associated fungi from Indonesia are still underevaluated. Therefore, exploration of novel compounds from fungi associating with Indonesian sponges is currently a major subject in our research group [16][17][18]. Along this line of study, Fusarium sp. KJMT.FP.4.3 was isolated from a sponge Xestospongia sp

Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• axenic. From experiment 1, 39 isolates were microscopically identified as belonging to genera common in soil, e.g., Fusarium, Penicillium or Trichoderma and thus were not further processed. The addition of antibiotics prevented bacterial contamination in all marine samples. However, a few antibiotic

Genome mining in Trichoderma viride J1-030: discovery and identification of novel sesquiterpene synthase and its products

• Xiang Sun,
• You-Sheng Cai,
• Yujie Yuan,
• Guangkai Bian,
• Ziling Ye,
• Zixin Deng and
• Tiangang Liu

Beilstein J. Org. Chem. 2019, 15, 2052–2058, doi:10.3762/bjoc.15.202

• that has received considerable attention as an effective biocontrol agent against two fungal pathogens, Fusarium oxysporum f. sp. adzuki and Pythium arrhenomanes, infecting soybean. This fungus is a competent mycoparasite and strong producer of secondary metabolites [22][23]. However, T. viride

Bipolenins K–N: New sesquiterpenoids from the fungal plant pathogen Bipolaris sorokiniana

• Chin-Soon Phan,
• Hang Li,
• Simon Kessler,
• Peter S. Solomon,
• Andrew M. Piggott and
• Yit-Heng Chooi

Beilstein J. Org. Chem. 2019, 15, 2020–2028, doi:10.3762/bjoc.15.198

• effects on cells infected with respiratory syncytial virus [22][23], induction of aerial mycelium formation in Fusarium culmorum [24], and as an inhibitor of ubiquinol-cytochrome c reductase binding protein, blocking mitochondrial ROS-mediated vascular endothelial growth factor receptor type 2 signalling

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• ) skeletons. These azasteroids, in which one or more nitrogen atoms are present in the side chain, were designed as promising compounds since such classes of antifungal steroids were known in the literature. Some of the resulting azasteroids showed inhibitory effects on the growth of fungi such Fusarium

• lateritium (causal agent of chlorotic leaf distortion in sweet potato) and Fusarium virguliforme (causal agent of sudden death syndrome in soy bean), without exerting in vitro toxicity on mammalian cells. Another interesting result came out from the comparison of the biological activity between homologous

• library of androstanic derivatives 21 (Figure 2B) and their reduced analogues bearing the 3β-hydroxy group were biologically tested showing antifungal activity against Fusarium virguliforme and Fusarium solani. The generation of this compound library suffered from the formation of the Passerini reaction

Mechanistic investigations on multiproduct β-himachalene synthase from Cryptosporangium arvum

• Jan Rinkel and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2019, 15, 1008–1019, doi:10.3762/bjoc.15.99

• truncatula with at least 27 products [7], γ-humulene synthase from Abies grandis with 52 products [8], and also the long known trichodiene synthase from Fusarium sporotrichioides produces at least 15 sesquiterpenes [9]. Some TSs can even accept multiple chain length substrates [10], a concept which seems to

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

• ). A phylogenetic analysis of 878 fungal terpene synthase homologs (Figure S1 in Supporting Information File 1) demonstrates that this enzyme is closely related to the bifunctional ent-copalyl diphosphate synthase/ent-kaurene synthase from Fusarium fujikuroi [33]. The N-terminal domain shows the DXDD

• sesquiterpenes arising via cation A with the main product trichodiene was previously reported from Fusarium [34]. The compounds 10 and 11 are directly formed from this cation by deprotonation. A 1,3-hydride shift to B and deprotonation yields 8 and γ-curcumene (C). Instead of the latter compound its autoxidation

• the formation of one of the two groups of sesquiterpenes with the main compounds α-acoradiene (15) and daucene (19). The enzyme XP_001262485 is closely related to the α-acorenol synthase from Fusarium fujikuroi [37] (Figure S1 in Supporting Information File 1) that produces α-acorenol (16) by

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

• ] reported that a fungal strain (Fusarium equiseti M41) was able to introduce a 7β-hydroxy group into LCA by hydroxylation forming UDCA directly. Later, many other microorganisms with a 7β-hydroxylating activity were discovered in strains of actinobacteria and filamentous fungi [96][97]. The key-enzyme in

• Fusarium merismoides VKM F-2310. The possibility to access that kind of chemical and chemo-enzymatic reactions pave the way for the design of other unexplored routes for the production of UDCA (example in Figure 8). In addition, other reported enzymes can eventually play a role in the cascade reaction

Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)

• Tao Wang,
• Kathrin I. Mohr,
• Marc Stadler and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9

• roqueforti [7][8][9], trichodiene (4) is the parent hydrocarbon of the trichothecene family of mycotoxins in various Trichothecium and Fusarium strains [10], and the diterpene ent-kaurene (5) is the precursor of gibberellins, a class of plant hormones that are produced in large amounts by the rice pathogen

• Fusarium fujikuroi and other fusaria [11][12]. The potential beneficial bioactivity and role in the intra- or interspecies communication as well as the possible function as markers for toxin production recently resulted in an increasing interest in volatile secondary metabolites in the scientific community

The direct oxidative diene cyclization and related reactions in natural product synthesis

• Juliane Adrian,
• Leona J. Gross and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

• isolated from the mould fungus Fusarium solani as a phytotoxin against barnyardgrass and duckweed in 1996 [30]. The Donohoe group presented a total synthesis in 2003 using an Os(VIII)-catalyzed oxidative cyclization as the key step [31] (Scheme 4). Several other total syntheses of that natural product did

Mechanistic investigations on six bacterial terpene cyclases

• Patrick Rabe,
• Thomas Schmitz and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 1839–1850, doi:10.3762/bjoc.12.173

• the substrate FPP is converted with a strict stereochemical course with respect to the fate of the diastereotopic methyl groups in FPP. These findings are in agreement with those reported for several other terpene cyclases [58][59][60], while the (1R,4R,5S)-guaia-6,10(14)-diene synthase from Fusarium

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

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

• niger (AJ117374, MIC: 12.5 μg mL−1) and Fusarium sp. (AJ177167, MIC: 6.3 μg mL−1). These MIC values were in a similar range as those of known antifungal compounds such as amphotericin B or nystatin against the same fungi (MIC: 3.1 μg mL−1 for both compounds). Recently, the 9.4 Mb genome of H. ochraceum

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• kill their prey [45][46]. Fusapyrone (32) and the derivative deoxyfusapyrone (33) had been isolated from Fusarium semitectum [39]. These compounds show considerable antifungal activity, e.g., a minimum inhibitory concentration against Botrytis cinerea, Aspergillus parasiticus, and Penicillium brevi

• crop diseases which can occur while storing the crops [47]. From another strain of this fungal genus, i.e., Fusarium fujikuroi, the gibepyrones A–F (39–44) were isolated (Figure 8) [48]. The activity of these compounds was tested against bacterial and fungal strains. However, the activities were

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• challenged by invading fungal species such as Escovopsis, Fusarium, and Trichoderma (Ascomycota). To clean the garden, ants apply mechanical grooming [71] and secrete antimicrobial compounds, such as 3-hydroxydecanoic acid, from their metapleural glands [72]. As a second line of defense, the ants are

• not nearly been explored to the same extent as bacterial protagonists, which is surprising as fungi have a vast biosynthetic potential and are a rich source of antibiotics (Figure 8). As early as 1982, Nakashima et al. investigated the fungal cultivar (Fusarium sp.) of the ambrosia beetle Euwalecea

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• avenae subsp. Citrulli, Erwinia amylovora, Pseudomonas syringae pv. Lachrymans, Clavibacter michiganense subsp. Sepedonicus, and Pectobacterium carotovorum subsp. carotovorum) and fungi (Rhizoctonia solani Kühn, Rhizotonia cerealis van der Hoeven, Phytophthora capsici Leonian, Fusarium moniliforme Sheld

• , Alternaria solani Jones et Grout, Sclerotinia sclerotiorum de Bary, Fusarium graminearum Schw., Fusarium coeruleum Sacc., and Botrytis cinerea Pers.) were tested. Aspergiloid I (1) showed no antibacterial or antifungal activity at a concentration of 20 μg/mL. It also had no antifungal activity against

• Candida albicans (ATCC 10231) or Fusarium oxysporum f. sp. cubense race 4 at concentrations as high as 20 mg/mL. Conclusion In summary, guided by 1H NMR detection, we isolated and characterized a novel norditerpenoid, aspergiloid I (1), from the liquid fermentation broth of the endophytic Aspergillus sp