Anti-invasive and cytotoxic evaluation of a (+)-pinoresinol-based semisynthetic library against glioblastoma

• Chen Zhang,
• Kah Yean Lum,
• Jonathan M. White,
• Paul I. Forster,
• Nicholas Booth,
• Sunita A. Ramesh and
• Rohan A. Davis

Beilstein J. Org. Chem. 2026, 22, 691–704, doi:10.3762/bjoc.22.54

• reported. In this study, we chemically investigated the seeds of Eremophila maculata for the first time, which led to the isolation and characterization of two known plant metabolites, (+)-salicifoliol and (+)-pinoresinol. Due to the reported biological properties of the lignan natural product

• (+)-pinoresinol and its high abundance from the seeds of E. maculata, we synthesized five analogues for biological evaluations. Preliminary cytotoxicity evaluations of the semisynthetic pinoresinol-based library against two human glioblastoma cell lines, U251MG and KNS42, showed (+)-4,4'-di(3,3-dimethylbutanoyl

• ; glioblastoma; (+)-pinoresinol; seeds; semisynthesis; Introduction Since ancient times, natural products have played a crucial role in the development of medicines for various diseases [1][2][3][4]. A recent review by Newman et al. has identified that over the past four decades, >30% of therapeutic drugs

Efficient solid-phase synthesis and structural characterization of segetalins A–H, J and K

• Liangyu Liu,
• Wanqiu Lu,
• Quanping Guo and
• Zhaoqing Xu

Beilstein J. Org. Chem. 2025, 21, 2612–2617, doi:10.3762/bjoc.21.202

• unique conformational constraints imposed by cyclization and diverse biological activities [1][2][3]. Specifically, plant-derived cyclopeptides represent a valuable source of potential lead compounds for drug discovery [4]. Segetalins A–H, J and K (1–10), isolated from the seeds of Vaccaria segetalis

A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids

• Zhiyang Zhang,
• Jialei Hu,
• Hanfeng Ding,
• Li Zhang and
• Peirong Rao

Beilstein J. Org. Chem. 2025, 21, 926–934, doi:10.3762/bjoc.21.75

• involving limonoids. Krishnolides A and C (7 and 8, respectively; Scheme 1A) were identified by Wu and co-workers from the seeds of a Krishna mangrove Xylocarpus moluccensis [26]. These two molecules belong to khayanolides, a class of rearranged phragmalin limonoids characterized by a structurally intricate

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

• ]+ calcd for C15H14FN2OS, 289.0811; found, 289.0806. Biology and biochemistry In vivo greenhouse screening: Seeds of mono- and dicotyledonous weed plants and crop plants were sown in plastic or organic planting pots in sandy loam and covered with soil (replicates: n = 10, i.e., 10 monocotyledonous weed

• seeds were grown per pot or n = 5, i.e., 5 dicotyledonous weed seeds were grown per pot). The 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines described above (e.g., 7a–c, 13a–c, 14a–c, 16a–f, and 17a–b), formulated in the form of wettable powder (WP) , were applied to the surface of the covering soil as

• seeds per pot depending on the plant species (10 seeds for corn and wheat spectrum). The harmful plants and crops used in greenhouse tests were the following species: Alopecurus myosuroides (ALOMY), resistant Alopecurus myosuroides (ALOMY_R, origin: Germany), Apera spica-venti (APESV), Brachiaria

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

• explored screening methanol and hexane extracts of various parts of the A. mexicana plant (seeds, leaves, inner vs outer roots) for biological activity with the outer root methanol extract showing the highest activity against Gram-positive bacteria as well as inhibitory effects against human colon cancer

Navigating and expanding the roadmap of natural product genome mining tools

• Friederike Biermann,
• Sebastian L. Wenski and
• Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

• trained on a set of known precursor genes to detect RiPP precursor genes semi-independently of their subclass. Subsequently, a pan-genome analysis is performed to identify the corresponding BGCs with the putative RiPP precursor genes as seeds. Putative NP BGCs are identified that are organized in operon

Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone

• Motoyuki Isoda,
• Kazuyuki Sato,
• Kenta Kameda,
• Kana Wakabayashi,
• Ryota Sato,
• Hideki Minami,
• Yukiko Karuo,
• Atsushi Tarui,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2022, 18, 1642–1648, doi:10.3762/bjoc.18.176

• antimicrobial activity. Moreover, antiviral activity was also confirmed for aggregatin B [52] containing a 7-membered lactone ring, in which the β-position hydroxy group was dehydrated (Figure 1). Monocrotaline is a kind of pyrrolizidine alkaloid and was isolated from seeds of Crotalaria spectabilis in 1935 [53

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

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

• cherry stones show for example less ash content compared to grape seeds. Olive wastes and bagasse results in activated carbons with high surface areas, whereas straw is less suitable to produce high surface areas [19]. Yahya et al. mentioned that the yields of the activated carbons prepared from these

• ruptured surface obtained [46]. SEM micrographs also allow the determination of different types of pores. The group of Okman showed SEM investigations on activated carbons prepared from grape seeds by activation with KOH. The sponge-like surface of the activated carbon indicates a microporous structure [56

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

• Fei You,
• Xing He,
• Song Gao,
• Hong-Ru Li and
• Liang-Nian He

Beilstein J. Org. Chem. 2020, 16, 351–361, doi:10.3762/bjoc.16.34

• industry [4]. Especially, the characteristics of non-volatility and biodegradability make plant oil the most promising material to develop functional polymeric materials with superior performance [5][6][7]. Castor oil is one kind of nonedible oil and can be extracted from the seeds of the castor bean plant

• . Globally, around one million tons of castor seeds are produced every year and the leading producing areas are India, China, and Brazil [8]. The castor oil has long been used as purgative or laxative to counter constipation and nowadays it is used commercially as a highly renewable resource for the chemical

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

• conditions of the corresponding sample sites. At this stage the trapped organisms are separated from each other, but connected to their original environment via semipermeable membranes. This way the fungal seeds are provided with growth factors exclusively found in their natural habitat. The device was

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

• ) λmax 3334, 2927 and 1045 cm−1; 1H and 13C NMR data, see Table 1; HRESIMS m/z: [M + H − 2H2O]+ calcd for C15H25O2+, 237.1849; found, 237.1859. Phytotoxicity assays The phytotoxicity assays on wheat leaves and seeds were carried out as previously reported [37]. Briefly, the leaves of 17-days-old wheat

• were examined for the presence of necrosis or chlorosis after 24 h and 48 h. The control consisted of 30 µL of 0.2% MeOH/H2O without dissolved compound. Two wheat seeds (sterilised by 10% EtOH) were placed on top of the agar (1.5% agar in 1 mL of tap water) containing 100 ppm of compound. The control

• was agar containing 30 µL of MeOH. The seeds were monitored for the progress of germination on day 5 and day 7. Calculation of ECD spectra Structures were initially subjected to a LowModeMD conformational search using the Molecular Operating Environment 2019.0101 package. The lowest energy geometry

Isolation and characterisation of irinans, androstane-type withanolides from Physalis peruviana L.

• Annika Stein,
• Dave Compera,
• Bianka Karge,
• Mark Brönstrup and
• Jakob Franke

Beilstein J. Org. Chem. 2019, 15, 2003–2012, doi:10.3762/bjoc.15.196

• analysis. Chemical studies support a model that these compounds are formed by an oxidative process. We propose the name androwithanolides for this withanolide subclass. Experimental General experimental procedures Seeds of Physalis peruviana were obtained from FloraSelf, Sperli and Quedlinburger Saatgut

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• studied by us and others, there are only scarce reports on the biological activity of archangelolide. Here we present the preparation of its fluorescent derivative based on a dansyl moiety using azide–alkyne Huisgen cycloaddition having obtained the two sesquiterpene lactones from the seeds of Laserpitium

• [12] was described, we aimed to develop a facile method for the isolation of these SLs from the seeds of Laserpitium archangelica Wulfen using supercritical CO2 extraction (SCE; for advantages of this method, see Supporting Information File 1, section 8). In our experience, any part of the plant may

• be used for extraction of compound 1, while the roots and seeds give much higher yields than other parts. Utilization of SCE gives improved efficiency of the extraction and shortens the work-up in contrast with classical methods. By the abovementioned methodology, we obtained sufficient amounts of

Reversible end-to-end assembly of selectively functionalized gold nanorods by light-responsive arylazopyrazole–cyclodextrin interaction

• Maximilian Niehues,
• Patricia Tegeder and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2019, 15, 1407–1415, doi:10.3762/bjoc.15.140

• used were rinsed with aqua regia before use. A 0.1 M aqueous solution of CTAB was prepared by gentle heating and sonication. Au seeds were prepared as follows: An aqueous solution of HAuCl4·3H2O (250 μL, 0.01 M) was added to an aqueous solution of CTAB (9.75 mL, 0.1 M) in a round-bottomed flask. The

• solution was stirred at 25 °C for 10 min. Then, a freshly prepared ice-cold aqueous solution of NaBH4 (600 μL, 0.01 M, prepared by diluting an 0.1 M solution) was added in one portion under vigorous stirring. After 10 min, stirring was slowed down to 200 rpm and continued at 25 °C. The seeds were kept at

Understanding the unexpected effect of frequency on the kinetics of a covalent reaction under ball-milling conditions

• Ana M. Belenguer,
• Adam A. L. Michalchuk,
• Giulio I. Lampronti and
• Jeremy K. M. Sanders

Beilstein J. Org. Chem. 2019, 15, 1226–1235, doi:10.3762/bjoc.15.120

• concentration of 1-2. This increase in 1-2 was only observed with aged NG and LAG samples that contained more than 2 mol % of 1-2 seeds. Higher concentrations of 1-2 seeds in the initial sample led to a higher overall conversion with aging. Importantly, we stress that the detectable increase in 1-2 with time

Chemical structure of cichorinotoxin, a cyclic lipodepsipeptide that is produced by Pseudomonas cichorii and causes varnish spots on lettuce

• Hidekazu Komatsu,
• Takashi Shirakawa,
• Takeo Uchiyama and
• Tsutomu Hoshino

Beilstein J. Org. Chem. 2019, 15, 299–309, doi:10.3762/bjoc.15.27

• . cichorii YM8705 was cultured in YPD medium (polypeptone (10 g, Nippon Shinyaku Ltd), dry yeast extract (5 g, Oxoid Ltd.), NaCl (3 g) and mannitol (5 g, Wako Ltd.) in 1000 mL of H2O). Precultured seeds were grown at 28 °C for 24 h in 100 mL of YPD medium using a 500 mL Sakaguchi flask with reciprocal

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• plants [34][35][36][37][38][39] as well as components of complex molecules produced by different species [40][41][42]. 3,4-Dihydroxyglutamic acid (4) of unknown stereochemistry was identified as a constituent of seeds of Lepidum sativum and leaves of Rheum rhaponticum and later on in other species [43

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• solution to receive functionalised polymers. It is a naturally occurring flavonoid, which is abundantly found in citrus fruits, herbs, vegetables, seeds, tea, nuts, and red wine [24][25][26]. It is considered to be a strong antioxidant due to its ability to scavenge free radicals and bind transition metal

Synthesis of ergostane-type brassinosteroids with modifications in ring A

• Vladimir N. Zhabinskii,
• Darya A. Osiyuk,
• Yuri V. Ermolovich,
• Natalia M. Chaschina,
• Tatsiana S. Dalidovich,
• Miroslav Strnad and
• Vladimir A. Khripach

Beilstein J. Org. Chem. 2017, 13, 2326–2331, doi:10.3762/bjoc.13.229

• the contrary, no correlation was observed between the corresponding protons in compound 22, which is consistent with the α-orientation of the epoxide ring. 2β,3β-, 2β,3α- and 2α,3β-diols of type 6–8 Experiments on the identification of steroidal phytohormones in immature seeds of Phaseolus vulgaris

• opening of the 2α,3α-epoxides 4 [22][23][24] or 2β,3β-epoxides 5 [24]. The preparation of the diequatorial derivatives 8 requires more effort. The synthesis of 3,24-diepicastasterone (29), identified in immature seeds of Phaseolus vulgaris as a natural BS [25], started from the diol 14 (Scheme 5). The

An improved preparation of phorbol from croton oil

• Alberto Pagani,
• Simone Gaeta,
• Andrei I. Savchenko,
• Craig M. Williams and
• Giovanni Appendino

Beilstein J. Org. Chem. 2017, 13, 1361–1367, doi:10.3762/bjoc.13.133

• ; Introduction Croton oil is obtained by pressing or solvent extraction from the seeds of Croton tiglium L., a small tree native to the Far East [1]. The oil is toxic to all living organisms, from bacteria to insects and vertebrates, and its irritancy and cathartic properties are legendary [2]. Croton oil was

Detection of therapeutic radiation in three-dimensions

• John A. Adamovics

Beilstein J. Org. Chem. 2017, 13, 1325–1331, doi:10.3762/bjoc.13.129

• radiation in which a cavity is created in the dosimeter for placement of radioactive seeds, deformable dosimetry in which the elastic properties of the dosimeter are manipulated to mimic those of human tissue, and reusable dosimetry [39][43][44]. Clinical research dosimeter adaptions have also made possible

Isoxazole derivatives as new nitric oxide elicitors in plants

• Anca Oancea,
• Emilian Georgescu,
• Florentina Georgescu,
• Alina Nicolescu,
• Elena Iulia Oprita,
• Catalina Tudora,
• Lucian Vladulescu,
• Marius-Constantin Vladulescu,
• Florin Oancea and
• Calin Deleanu

Beilstein J. Org. Chem. 2017, 13, 659–664, doi:10.3762/bjoc.13.65

• of both NO and ROS was proven by fluorescence microscopy using specific fluorescence indicators that help to exactly define the sites of generation. We used Arabidopsis thaliana wild type seeds, cultivated for six weeks in laboratory in Arasystem [60]. Arabidopsis thaliana was selected as model

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• subsequently isolated from the seeds of the legume Lonchocarpus sericeus [3][4]. It was found to inhibit seedling germination of lettuce [5] and did not exhibit any significant effect on the inhibition of protein production in rat hepatoma cells [6]. L-(5) and D-β-hydroxyenduracididine (6) were first resolved

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

• -mediated bidirectional oxidative cyclization approach [99]. Membranacin and membrarollin Membranacin (55) and membrarollin (62) are typical adjacent bis-THF acetogenins having a threo-cis-threo-cis-erythro configured core (Scheme 12 and Scheme 13). They were isolated from the seeds of the fruit tree

• has originally been isolated from the seeds of Asimina triloba [118] but has also been found in extracts of the bark of Goniothalamus giganteus (Annonaceae) [119] by McLaughlin and co-workers [120][121]. In 1999, Wang and Shi et al. disclosed the first total synthesis of (–)-asimilobin (74) and its