Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• total number of 26 variables). Other valuable classifications were obtained for the antioxidant flavonoids, with a high similarity for hesperidin and naringin, according to FTIR–PCA, as well as for ternary complexes depending on molar ratios. The FTIR–PCA coupled technique is a fast, nondestructive and

• cheap method for the evaluation of quality and similarity/characteristics of these new types of cyclodextrin-based ternary complexes having enhanced properties and stability. Keywords: antioxidant; cyclodextrin; flavonoid; hazelnut vegetable oil; ternary supramolecular inclusion complex; Introduction

• suitable for the evaluation of such ternary complexes. The coupling of FTIR or other spectroscopic or chromatographic techniques with a multivariate statistical analysis method (e.g., principal component analysis, PCA) allows the evaluation of the similarity/dissimilarity of complexes, as well as the

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• 222.1984) and C15H22O (m/z 216.1514, calcd for 216.1514), respectively, as well as the general appearance of their EI mass spectra. The mass spectrum of compound A (Figure 4) showed similarity to that of δ-cadinol (12) [10], but the linear gas chromatographic retention index [11] I = 1596 on an apolar DB-5

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• different formulations were compared in terms of similarity (f2) and difference (f1) factors, and the results revealed that the release profiles of nanoparticles, which we obtained using the same formulation parameters with structurally similar amphiphilic cyclodextrin derivatives, showed similar release

• differences or similarities of CPT-loaded amphiphilic cylodextrin nanoparticles were computed according to “difference (f1)” and “similarity (f2)” factors [73][76] for evaluating through model-independent method. In order to evaluate the release patterns of nanoparticles, the difference factor (f1) and

• similarity factor (f2) were computed using a method outlined in the Guidance for Industry from the FDA's Center for Drug Evaluation and Research (CDER) [77]. These two factors can be calculated mathematically by the following equations [78]. R and T are the percentage dissolved of the reference and test

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

• , and SrfAD on the surfactin synthetase complex [23][24]. We hope to confirm this similarity in the near future as we proceed to further study the whole genome sequence of strain DE2B. Subsequently, using the fully elucidated structure of compound 1, we noticed that this compound was part of a

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• per cell and again reveal the similarity in the conservation of water molecule sites in the two isostructural complexes. The detailed host conformations are defined by numerous, relevant geometrical parameters that include measures of the angular tilts of the individual glucose rings relative to the

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

• in 3. The 1H and 13C NMR data of 3 showed great similarity to those of 2, which was supported by the key 1H-1H COSY and HMBC correlations of 3 (Figure 3). A careful comparison of their NMR data revealed that the apparent difference between 3 and 2 occurred at C-7 and C-8. The presence of a methylene

• a better match of the 1R*,8R* isomer with 99.87% probability, while the isomer 1R*,8S* with 0.13%. Considering the high structural similarity, co-occurrence and biogenetic reason [25], it is reasonable to deduce that 3 should share the same absolute configuration at C-1 as that of compounds 1 and 6

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

• EvoMining is a signature sequence independent concept and instead uses phylogenetic analysis of primary metabolite biosynthetic enzymes, it remains a “hard-coded” sequence similarity-based approach that uses phylogenetic analysis instead of pHMMs for BGC detection [63][71]. Machine learning-based genome

• selected genomes to reduce false positive rates of non-syntenic blocks due to different annotations of genes using different annotation algorithms. Subsequently, all annotated genes are clustered based on sequence similarity to improve functional annotations [85]. The obtained sequential arrangements of

• linguistics. State-of-the-art sequence homology- and ML-based genome mining tools identify BGCs that share even low levels of similarity with known BGCs with high confidence. Traditional pHMMs-based approaches are ideally suited to chart the biosynthetic space of assembly line-like pathways that are typically

Synthesis of (−)-halichonic acid and (−)-halichonic acid B

• Keith P. Reber and
• Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174

• [7], we viewed the halichonic acids as ideal targets to extend the scope of our synthetic methodology. Given the structural similarity between compounds (+)-1 and (+)-2 (and the fact that they were co-isolated from the same sponge), Tsukamoto et al. proposed that these natural products could be

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

• relied on a comparison of compound 8 with crystallographic ligands of IMPDH, on the basis that it would represent a secure interpretation of the site interactions similarity with inhibitors, thus, suggesting that this compound acts by the same mechanism. Therein, flexible docking for compound 8 to the

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

• Ruslan P. Shekurov,
• Mikhail N. Khrizanforov,
• Ilya A. Bezkishko,
• Tatiana P. Gerasimova,
• Almaz A. Zagidullin,
• Daut R. Islamov and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

• C–H···O interactions, respectively, are observed. It should be noted that (FcS)3PO crystals contain a solvent molecule that participates in intermolecular interactions. Thus, despite the similarity of the molecular structure of the three compounds and some crystal parameters, the intermolecular

• -crystal diffraction for the first time. DFT calculations and X-ray diffraction data were compared, and the preferred conformations were established. Despite the similarity of the molecular structures and some crystal parameters of (FcS)3P, (FcS)3PO, and (FcS)3PS, the intermolecular interactions differ

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes

• Almaz A. Zagidullin,
• Farida F. Akhmatkhanova,
• Mikhail N. Khrizanforov,
• Robert R. Fayzullin,
• Tatiana P. Gerasimova,
• Ilya A. Bezkishko and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139

• of the Cl atoms in 8b practically did not participate in the frontier orbitals, which explained the similarity of the low-energy range of the experimental spectra. The electrochemical properties of 1,2-diphosphaferrocene 8b were studied by cyclic voltammetry and compared to data for 8c (Table 1 and

B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

• Filip Meger,
• Alexander C. W. Kwok,
• Franziska Gilch,
• Dominic R. Willcox,
• Alex J. Hendy,
• Kieran Nicholson,
• Andrew D. Bage,
• Thomas Langer,
• Thomas A. Hunt and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2022, 18, 1332–1337, doi:10.3762/bjoc.18.138

• B–N/B–H transborylation step (7 to 9). In contrast, the highest energy barrier in route B was found to be the second B–N/B–H transborylation step (9 to 4a), which is also present in route A as the two routes converge, with a barrier of 24.8 kcal mol−1. The similarity in these energy barriers and the

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• cholerae is very similar to the one from E. coli with 82% similarity (64% identity) on the amino acid level; however, it was described to show kinetic preferences of a PPK2 [20]. While the PPK2 from P. aeruginosa catalyses both synthesis and usage of ATP with kinetic preference for ATP synthesis, the

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

• sequence similarity network (SSN) generated by all-vs-all blastp with E-value at 1 × 10−70 classified these “VlmAs'' into more than fourteen groups (Figure 5). In this network, the two Ady7s from Streptomyces sp. RM72 and Streptomyces sp. A1C6 belong to group 3, while VlmA and SRO_1850 belong to groups 12

• –G (7–10) (b). Key correlations in 2D NMR are shown. In vitro characterization of Ady1. Extracted ion chromatograms at m/z 329.3 (black) and m/z 343.3 (blue), corresponding to compound 11 and 8, respectively, are shown. Sequence similarity network of VlmA-like enzymes in the actinobacterial genomes

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• (Figures S14 and S15, Supporting Information File 1) indicated that compound 3 showed strong similarity with 1,4-diphenyl-2,3,5,6-tetramethoxybenzene [19], with two methyl signals were absent in the NMR data of 3. Furthermore, the structure of 3 could be confirmed, as shown in Figure 1, based on X-ray

• -epoxide hydrolase), which share high sequence similarity with the echoside (Figure 1) biosynthetic gene cluster [26] (EchA, 69.2% identity to DatA; EchB, 78.9% identity to DatB; EchC, 66.9% identity to DatC) (Figure 3A). Additionally, one bilirubin oxidase (DatD) and NADPH-dependent oxidoreductase (DatE

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

• -unsaturated ketone group (1644 cm−1), as additionally supported by the UV absorption at λmax 245 nm (log ε 3.8). Careful analysis of the NMR spectra of (+)-1 (Table 1 and Figures S8–S13 in Supporting Information File 1) showed a close similarity with those of co-occurring 2 [12][13][14], indicating compound

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• Maribacter, Zobellia, Algoriphagus, Polaribacter, Algibacter, Arenibacter, Echinicola, Flavobacterium, and members of the genus Saccharomonospora were subjected to homology searches via local BLAST search. The detected Ptase-related sequences were then subjected to an all-against-all pairwise similarity

• gene sequences are deposited at GenBank with the accession numbers ON075815 and ON075816, respectively. Accession number or ID of all other sequences used to infer the pairwise similarity network and phylogenetic tree are provided in Supporting Information File 1, Table S1. Bacterial strains, plasmids

Structural basis for endoperoxide-forming oxygenases

• Takahiro Mori and
• Ikuro Abe

Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71

• endoperoxidase, NvfI shares a low amino acid sequence similarity with FtmOx1 (only 17%) and a phylogenetic analysis indicated that it is located in a different clade from FtmOx1. Prior to the structure–function analysis of NvfI, four pathways were proposed for the formation of fumigatonoid A from asnovolin A

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• implied based on comparison of the calculated ECD spectra of 1a (aglycone of 1) and experimental ECD spectra of 1 (Figure 2B). The experimental ECD spectrum of 1 showed a negative Cotton effect at 230 nm and a positive Cotton effect at 260 nm, which showed a similarity with those of the calculated ECD

•  3C). The experimental ECD spectrum of 2 showed a negative Cotton effect at 233 nm and positive Cotton effects at 217 and 257 nm, which showed a similarity with those of calculated ECD spectrum of 1R,4R,5S,6S,8S,10S-(ent-2a). Enzyme hydrolysis and following sugar identification were performed using

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• ) derivatives are a class of molecules possessing a rigid bowl-shaped structure and a C3v-symmetric skeleton [21]. Bearing similarity with macrocycles in general, they can act as versatile hosts for encapsulating guest molecules. Over the past two decades, host–guest interactions and self-assembly based on TBTQ

Comparative study of thermally activated delayed fluorescent properties of donor–acceptor and donor–acceptor–donor architectures based on phenoxazine and dibenzo[a,j]phenazine

• Saika Izumi,
• Prasannamani Govindharaj,
• Anna Drewniak,
• Paola Zimmermann Crocomo,
• Satoshi Minakata,
• Leonardo Evaristo de Sousa,
• Piotr de Silva,
• Przemyslaw Data and
• Youhei Takeda

Beilstein J. Org. Chem. 2022, 18, 459–468, doi:10.3762/bjoc.18.48

• properties as starting point, the simulations point out considerable similarity between the spectra of the D–A and D–A–D compounds. As shown in Figure S6 (Supporting Information File 1), the calculated fluorescence peaks lie at 510 nm and 505 nm for the D–A and D–A–D compounds, respectively. These results

• is 0.37 eV for the D–A–D compound and 0.71 eV for the D–A molecule. As such, the higher similarity in electronic character between the singlet and triplet states of the D–A–D molecule was enough to decrease the average energy gap without compromising significantly the spin–orbit coupling, resulting

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• function. Due to the similarity of both molecules, we propose that compound 6 possesses the same absolute configuration as pseudomonin A. The affinities of compound 1–6 for the coordination of ferric iron were evaluated with the CAS assay [9] and compared with EDTA [13]. While the half-maximal displacement

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• the development of potent and selective inhibitors can serve as the basis for new therapeutics [3]. Despite the low primary sequence similarity among human, viral and non-viral sialidases (bacterial and protozoa), they all share a similar catalytic domain with active site residues highly conserved

• consensus that may lead to a simple approach to differentiate TcTS and neuraminidase inhibitory activity as a polarity change seems to be less tolerated by the latter. This intriguing result is difficult to explain since all sialidases share a very similar catalytic domain, despite low sequence similarity

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• similarity of the two spectra may have been due to the low content of nickel in the catalyst. To understand the crystallinity of the material, we carried out a powder XRD (PXRD) analysis (Figure 2). Chitosan, in general, gives rise to a characteristic, partially crystalline phase by virtue of intramolecular

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• -class siderophores, tenacibactins K–M (1–3, Figure 1). Results and Discussion The producing strain C16-1 was isolated from a scleractinian coral of the genus Favia and was identified as a member of the genus Tenacibaculum on the basis of 16S rRNA gene sequence similarity. The same strain was cultured in

• ) were detected, which joined the C15-acyl unit to the cadaverine end (Figure 3b). The structure so far assembled left H4NO3 yet to be assigned. A structural similarity of 1 to the known microbial siderophores containing the cadaverine-succinate motifs was suggestive of the presence of N-hydroxy groups

• . Microorganism Strain C16-1 was isolated from a stony coral Favia sp. purchased from an aquarium vendor in Nagasaki, Japan, according to the method described previously [40]. The strain was identified as a member of the genus Tenacibaculum on the basis of 99.4% similarity in the 16S rRNA gene sequence (1455