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

• diphosphate substrates MSTSs from plants Substrate-promiscuous TSs are widely spread in plants, which mainly produce linear terpenoids such as linalool (6), (E)-nerolidol (7) and (E,E)-α-farnesene (8) (Figure 2) [14][15]. Most plant MSTSs accept two prenyl substrates: C5 and C10 [16], C10 and C15 [17][18][19

• different subcellular compartments may facilitate the generation of multiple terpenoids in plants. Recently, in addition to linear terpenoid-producing TSs, MSTSs that form cyclic terpenoids have been discovered in plants, further increasing our understanding of chemodiversity and biosynthesis of plant

• terpenoids. LcTPS2 from Leucosceptrum canum was characterized as a versatile TS that generated six macrocyclic sesterterpenoids (11–16) and two macrocyclic diterpenoids (17,18), representing the first macrocyclic terpenoids isolated from plants (Table 1, Figure 2) [19]. In addition to linear prenyl

Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria

• Kara A. Strickland,
• Brenda Martinez Rodriguez,
• Ashley A. Holland,
• Shelby Wagner,
• Michelle Luna-Alva,
• David E. Graham and
• Jonathan D. Caranto

Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75

• producers and of NNG is unknown. Additionally, NNG’s physiological function is unknown, but it is toxic to plants, mice, and Gram-negative bacteria [25][26]. While there is no direct evidence of the mechanism of this toxicity, NNG has been shown to competitively inhibit succinate dehydrogenase, a component

• , reductively decomposes the nitramine functionality of RDX to form •NO2 [38], a toxic reactive nitrogen species. Additionally, NNG is a structural analog of another natural product 3-nitropropionate (3NP) found in plants and fungi [39]. This highly toxic compound inhibited succinate dehydrogenase and other

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

• University, Nanjing 211198, China 10.3762/bjoc.20.73 Abstract Drimane-type sesquiterpenoids (DMTs) are characterized by a distinctive 6/6 bicyclic skeleton comprising the A and B rings. While DMTs are commonly found in fungi and plants, their presence in bacteria has not been reported. Moreover, the

• performs a similar role to DrtB, engaging two P450s (AncE and AncB) to synthesize (+)-isoantrocin and (−)-antrocin [18]. Notably, the P450s identified in fungi and plants predominantly modify the B-ring of DMTs [15][16][18]. DMTs are commonly found in plants and fungi [6][9][13][15]. While enzymes

• derivatives 7–9. This study marks the first discovery of natural DMTs from bacteria and unveils the role of CavA in a novel late-stage modification pathway, expanding DMT biosynthesis beyond fungi and plants. Results and Discussion Discovery of three DMTs in S. clavuligerus S. clavuligerus is notably

Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• environment in order to activate silent genes in actinomycetes. Actinomycetes mainly inhabit soils, but they are widely symbiotic with plants [103], insects [104], and other organisms [105][106], and there are reports of their secondary metabolites controlling their own physiological functions or functioning

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

• -inflammatory properties, hepatorenal protection, and anticancer activity. They are often used as coloring and seasoning agents. Due to the limited content of crocins in plants and the high cost of chemical synthesis, the supply of crocins is insufficient to meet current demand. The biosynthetic pathways for

• , which complicates matching supply to demand. Engineering microbial strains for the heterologous production of rare natural products has emerged as a promising approach [18][19]. With the elucidation of the biosynthetic pathways for crocins in plants, the heterologous production of crocin and crocetin

• roots of plants. The content varies significantly among different plant species and different parts within the same plant. For instance, in C. sativus, crocins are predominantly accumulated in the stigma, but in G. jasminoides, they are primarily stored in the pulp. The traditional methods for

Genome mining of labdane-related diterpenoids: Discovery of the two-enzyme pathway leading to (−)-sandaracopimaradiene in the fungus Arthrinium sacchari

• Fumito Sato,
• Terutaka Sonohara,
• Shunta Fujiki,
• Akihiro Sugawara,
• Yohei Morishita,
• Taro Ozaki and
• Teigo Asai

Beilstein J. Org. Chem. 2024, 20, 714–720, doi:10.3762/bjoc.20.65

• TCs subsequently catalyze the second cyclization to construct the polycyclic scaffold of natural products [5]. In plants, two independent αβγ tri-domain TCs, ent-CPP synthase (CPS) and ent-kaurene synthase (KS), are often used for this conversion [6], and a single bifunctional enzyme that successively

• employed [8]. In fungi, only bifunctional enzymes consisting of αβγ tri-domains have been identified to date [9][10][11][12][13]. In the evolutionary aspects, fungal bifunctional TCs are proposed to have been acquired from plants by a horizontal gene transfer event [14] and eukaryotic tri-domain TCs are

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• other than variochelins, including vacidobactin from V. paradoxus S110, variobactin from V. paradoxus P4B, and imaqobactin from Variovorax sp. RKJM285, suggesting their significant role in interactions with both plants and other microbes in near-surface soil through iron photocycling [5][11][12]. In

Introduction of a human- and keyboard-friendly N-glycan nomenclature

• Friedrich Altmann,
• Johannes Helm,
• Martin Pabst and
• Johannes Stadlmann

Beilstein J. Org. Chem. 2024, 20, 607–620, doi:10.3762/bjoc.20.53

• always the same core. Years later, colleagues from in- and outside my institution engaged in “humanization” of plant N-glycans, which at first entailed removal of the plant-typical residues α1,3-fucose and xylose [32][33]. Later, the glyco-engineering of plants with the introduction of human features

• strictly always in α1,6. If you only work with mammalian samples you may content yourself with this simplification. However, as insect cells and plants are of relevance as biotechnological expression systems for pharmaceutical glycoproteins, we must consider that here fucose may also be found in the α1,3

• plants and some non-vertebrate animals [43][44], the β-mannosyl residues may instead be decorated with a xylose residue, for which the letter X is added after the term for the 3-arm (Figure 4). Fucose on antennae Lewis fucoses introduce branching of the antenna. IUPAC nomenclature uses square brackets to

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• , and anticancer properties [6][7]. Historically, most alkaloids were isolated from higher plants, with a significant number found in the Apocynaceae family. Notable examples such as vinblastine, vinorelbine, vincristine, and vindesine have gained prominence as effective anticancer drugs [6][7][8][9][10

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• with emphasis on the structural diversity of small-molecule ligands. In this context, acyl-acyl carrier protein (acyl-ACP) thioesterase inhibitors have shown a remarkable variability. Fatty acid thioesterase (FAT) enzymes represent a family of proteins exclusively found in higher plants. They mediate

• 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, i.e., 13a–c, and 7a–c, the acylated analogues 14a–c and 16a–f, as well as selected aminoboranes 17d and 17e, were tested for target affinity in dedicated in vitro tests, as well as for herbicidal effects in vivo upon preemergence application to plants. Based

• on our experience with thiazolopyridine-based FAT inhibitors [12][13], five representative grass weeds (ALOMY, ECHCG, LOLRI, POAAN, and SETVI) were chosen as model plants to assess initial preemergence activity using a dose rate of 320 g/ha, whereas in vitro tests were carried out using FAT A

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• and fungi at 20 µg per disc in the paper disc diffusion method. Dihydroxybenzoic acid (DHBA) plays a role in anti-inflammatory, antihyperglycemic, antiapoptotic, and antioxidant processes [14]. 2,3-DHBA is found in nature and is produced by various plants (e.g., Gentiana rigerscense and Vinca minor

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• infects a great number of agricultural plants, causing great harm to production by evolving to resist most of the existing drugs. Thus, BIMs have emerged as a new natural alternative class of antiviral agents, surpassing commonly used drugs such as ribavirin that has been observed to damage the DNA

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

• Jon Lundstrøm,
• Emilie Gillon,
• Valérie Chazalet,
• Nicole Kerekes,
• Antonio Di Maio,
• Ten Feizi,
• Yan Liu,
• Annabelle Varrot and
• Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

• biology, and biomedicine. These carbohydrate-binding proteins boast a range of functions, acting as recognition modules in cell–molecule and cell–cell interactions, thereby playing vital roles in immune defense, regulation of growth, and apoptosis [1]. In plants, they serve as essential components in

• abovementioned applications are R-type lectins, especially those derived from plants. Examples include SNA (from Sambucus nigra, binding Neu5Acα2-6 [14]) or RCA1 (from Ricinus communis, binding terminal β-linked galactose [15]). Yet, despite the extensive studies on plant lectins, particularly R-type lectins

• in which its preferred binding motifs occur (O-glycans, milk glycans, GAGs) are absent from most plants, including melons. We thus hypothesize that the role of this lectin might be to recognize non-self epitopes, such as for protection against pathogens, which is a common function in plant lectins [3

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• (Figure 14). Indirubin (26) is a purple colored dye that can be found in Isatis tinctoria and Indigofera tinctoria plants along with indigo and its derivatives or can be obtained as a metabolism product of some bacteria [68]. Given to the wide range of biological activities, including anticancer and anti

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• well as the HMBC correlations of H2-2 with C-3 and C-17, this substituent was identified as a (2-amino-2-oxoethyl)thio group. This substituent has been reported in several alkaloids isolated from plants in the Aristolochiaceae family [17][18]. Compound 3 had a β orientation for the sulfur-containing

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• ; endophytic fungi; hemiketal polyketide; Introduction Endophytic fungi are organisms that reside almost ubiquitously inside the fresh healthy tissue of plants, and they may increase the resistance of the host tropical trees to survive in extreme conditions [1]. As the global diversity of endophytic fungi is

• those exclusive to their host plants, is not only important from a biomolecular standpoint but also from an ecological perspective. In continuation of our interest to explore secondary metabolites of rare and hitherto unexplored fungi hosted in Cameroonian medicinal plants [5][6], we investigated the

• cereals [31]. The isolation of the alternariol compound in this study is not surprising because it has been reported that dibenzo-α-pyrones are also found in mycobionts, plants, some animal dung, and endophytes [32][33]. Although the toxicity of dibenzo-α-pyrones is not fully understood and varies amongst

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• have been found to possess antimicrobial resistance genes [6]. With the persistent increase in drug-resistant microbial strains, there is a pressing need to continuously explore new and alternative drug candidates. Plants naturally produce many compounds that can be used to treat a variety of human

Functional characterisation of twelve terpene synthases from actinobacteria

• Anuj K. Chhalodia,
• Houchao Xu,
• Georges B. Tabekoueng,
• Binbin Gu,
• Kizerbo A. Taizoumbe,
• Lukas Lauterbach and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100

• = +95.9 (c 0.55, CH2Cl2) pointed to the same enantiomer as is known from the plants Pinus sibirica ([α]D20 = +118.4) and Torreya nucifera ([α]D18 = +118.6) [34], and from the fungus Xylobolus frustulatus ([α]D25 = +99.9 (c 0.6, CHCl3)) [35]. This finding is rather unusual, as more and more cases were

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• position of the glycerol) [8], protozoa [9], marine and land animals [10][11], but they are, according to the current scientific knowledge, absent in yeast [12] and plants [4]. It is estimated that ether lipids account for 10 to 20% of all the glycerophospholipids in humans. However, their tissue

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors

• Grace A. Lowe

Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88

• been used in artificial photosynthesis research to model different key photosynthesis processes. In plants, photosynthesis is a complex process where light-harvesting reactions are carried out in two photosystems to split water and recycle NADH and ADP. NADPH and ATP are then consumed in the Calvin

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• exhibit a variety of biological activity. Their application is known in pharmacy [1][2][3][4] and agro-industry [5][6][7][8]. Especially such compounds are used to protect plants from insects and weeds (Figure 1). Thus, pinoxaden is a commercially available inhibitor of acetyl-CoA carboxylase and affects

• the biosynthesis of fatty acids in plants, which leads to herbicidal activity [9]. Pyraclonil is used as a protoporphyrinogen oxidase inhibitor for weed control. Such inhibitors not only block the production of chlorophyll and gem in plant pests, but also lead to the formation of highly reactive

• : deposit@ccdc.cam.ac.uk). Examples of bioactive pyrazoles for the protection of cultivated plants and drugs containing a thiocarbonyl group. Structures of starting materials. Syntheses of 4,5-diamino- and 4-thiocarbamoyl-5-aminopyrazoles. Synthesis of 3,5-diaminopyrazoles 4а–с and thiocarbamoyl-NH

CO₂ complexation with cyclodextrins

• Cecilie Høgfeldt Jessen,
• Jesper Bendix,
• Theis Brock Nannestad,
• Heloisa Bordallo,
• Martin Jæger Pedersen,
• Christian Marcus Pedersen and
• Mikael Bols

Beilstein J. Org. Chem. 2023, 19, 1021–1027, doi:10.3762/bjoc.19.78

• processes or power plants, transporting it to a storage site, and storing it underground or consuming it by forming polymers [4] or fuels from CO2 [5][6]. However, the implementation of CCS technologies faces many challenges, including high costs, energy consumption, and the need for large-scale

Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

• Yuan-Nan Yuan,
• Jin-Qiang Li,
• Hong-Bin Fang,
• Shao-Jun Xing,
• Yong-Ming Yan and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59

• long carbon chain. Thus far, the structure of compound 8 was identified as shown in Figure 1 and named as kronoponoid B. Of note, the structures of compounds 2–4 are common in plants but rare in animals. Whether these compounds originate from plants or animals so far remains unknown. In addition to the

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

• Sarot Cheenpracha,
• Ratchanaporn Chokchaisiri,
• Lucksagoon Ganranoo,
• Sareeya Bureekaew,
• Thunwadee Limtharakul and
• Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

• 50200, Thailand Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai 57100, Thailand 10.3762/bjoc.19.47 Abstract Two new cassane diterpenoids, 14β

• exhibit diverse biological properties, including anti-inflammatory [12], antimalarial [13], antitumor [14], antiviral [15], antibacterial [16], antiproliferative [13], and immunomodulatory [17] activities. As part of our studies on Thai medicinal plants, an investigation of the fruits of P. macropterum

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• ” (macrocyclic diaryl ethers) series found in plants present on the African and Asian continent [15]. The first report of this class of compounds was made by Pettit and co-workers when they isolated combretastatin D-1 (1) from a CH2Cl2/MeOH extract of Combretum caffrum, a South African tree [16]. From 77 kg of