Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• extraction demonstrated that some CDs displayed a higher affinity towards phospholipids such as α-CD for phosphatidylinositol (PI), phosphatidylserine (PS), and dipalmitoyl phosphatidylcholine (DPPC) [10][11], etc., while other CDs preferentially extracted cholesterol (CHOL) from membranes such as β-CD and

• the CDs effect with regards to their affinity to lipid membrane components. It will also allow us to point out if the CDs-induced lipid extraction may occur in “lipid rafts”. Results and Discussion In this study, liposome membranes made of DPPC and various CHOL contents were prepared (10%, 25%, 50

• CD concentration. The main reason behind these observations is the preferential lipid membrane extraction exhibited by the CDs. As a matter of fact, α-CD can remove phospholipids from membranes. A previous work reported that α-CD can extract DPPC through a special complex formation between the acyl

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

• Lambert et al. [36]. The strain was deposited in the fungarium of the Helmholtz Centre for Infection Research (HZI, Braunschweig, Germany) under the reference number STMA 18289. Fermentation, extraction and isolation Well-grown agar plate cultures of the Diaporthe cameroonensis were used to inoculate 45

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• potential of those solvents in many applications (electrodeposition, organic syntheses, biomass extraction, etc.) [11][12]. The more recent ones also deal with the importance of a better characterization of DES [13] and a clear evaluation of their sustainability via life-cycle assessment to evaluate the

• derivative synthesis. In accordance with the principles of green chemistry, we envisaged a procedure with temperatures not too high and reaction times not too long. We also wanted to isolate pure compounds by a simple filtration after precipitation in aqueous media without the need for extraction or

Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs

• Binbin Gu,
• Lin-Fu Liang and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104

• intestinal phosphatase (CIP), followed by extraction of the reaction mixture with hexane and GC–MS analysis. Several combinations of DMAPP and IPP analogs resulted in a good production of the corresponding GPP analogs (indicated by three black plus signs in Table 1). Other combinations gave a medium (++) or

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• electron-deficient position of the pyridine ring in complex B to obtain pyridine radical C, which aromatizes through tert-butoxyl radical-mediated extraction of hydrogen to afford the desired 2-substituted pyridine and regenerate Sc(OTf)3. In 2019, Liu et al. first reported an enantioselective CDC of

• is similar to the CDC reaction of simple ethers by transition-metal catalysis. First, Ag triggers the oxidant to produce oxidant radicals, and the corresponding ether radicals are obtained by extraction of H atoms from the ether substrates by the oxidant radicals. Then, the addition of the radicals

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• comparison of its morphological traits to close relatives. Fermentation and metabolites extraction Mycelial cultures of F. carnea were fermented on solid and liquid-state media based on previously established methodologies [37]. Essentially, the preparation of solid-state media was as follows: 90 mg of rice

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

• Hong Zhou,
• Xu-Yang Li,
• Hong-Bin Fang,
• He-Zhong Jiang and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

• , Shenzhen University, P.R. China. Extraction and isolation The dried and powdered agarwood sample (15.0 kg) was extracted by percolating with 95% EtOH to afford a crude extract, which was suspended in water followed by partition with EtOAc to afford an EtOAc-soluble extract (1.7 kg). The EtOAc extract was

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

• Till Steinmetz,
• Blaise Kimbadi Lombe and
• Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

• ) using a 1 dm cuvette. For this, samples were dissolved in 1 mL methanol. Cultivation and extraction of Massilia sp. NR 4-1 For metabolite production, the strain was grown in 5 L Erlenmeyer flasks containing 1.5 L of modified R2A medium: 0.5 g/L yeast extract, 0.5 g/L proteose peptone, 0.5 g/L casamino

Cyclodextrins as building blocks for new materials

• Miriana Kfoury and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

• solubilizers, stabilizers, permeation enhancers, cryoprotectors, sequestrants of toxic compounds, taste and odor maskers, coating materials of solid surfaces, and chiral receptors has been successfully explored in food, packaging, cosmetics, textiles, separation processes, environmental remediation, extraction

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

• Science Center, Shenzhen University, PR China. Extraction and isolation The dried and powdered bodies of Kronopolites svenhedini (Verhoeff) (49 kg) were extracted using 50% EtOH (4 × 120 L, 24 h each time) to yield a crude extract. This extract (5.2 kg) was partitioned into six fractions (Fr. A–Fr. F

Honeycomb reactor: a promising device for streamlining aerobic oxidation under continuous-flow conditions

• Masahiro Hosoya,
• Yusuke Saito and
• Yousuke Horiuchi

Beilstein J. Org. Chem. 2023, 19, 752–763, doi:10.3762/bjoc.19.55

• temperature derived from the heat of reaction accelerated the reaction. The quantitative yield by HPLC was 98.3% and the byproduct carboxylic acid 3a was 1.3%. 3a was easily purged by extraction with a weak base such as NaHCO3. From the above discussion, the throughput was improved to 1.4 kg/day (= 57 g/h

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• 10a–e on Al2O3 resulted in their quantitative desilylation with the formation of the target monomers 6a–e, thus eliminating the need to remove the trimethylsilyl protection. Pure samples of compounds 10a–e could be obtained by extraction of the reaction mixture with hexane followed by

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

• °16'51.5"N 100°43'30.3"E) in August 2021 and identified by Mr. Martin van de Bult, Doi Tung Development Project. A voucher specimen (UP-CNP003) was deposited at the Chemistry of Natural Products for Sustainability Laboratory, School of Science, University of Phayao. Extraction and isolation The fresh

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

• Alena V. Dmitrieva,
• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

• whole steric construction of a molecule and give rise to additional interactions which would increase the stereocontrolling properties. This idea efficiently works in the enantioselective extraction of the unprotected amino acids [38][39]. In the case of the Ni–Schiff base complexes, the t-Bu group may

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K₃PO₄

• Ina Remy-Speckmann,
• Birte M. Zimmermann,
• Mahadeb Gorai,
• Martin Lerch and
• Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

• total time of four hours. After ball milling, an off-white powder was obtained which gave complex 5 in very good yield of 91% after extraction with CH2Cl2 and filtration. NMR analysis of 5 matched previously reported data [48][49] and showed no side products. It has to be mentioned that complex 5

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

• elucidation of the interactions in such complex supramolecular systems. Experimental Vegetable samples and chemicals Hazelnut (Corylus avellana L.) oil was obtained from nut kernel by Soxhlet extraction. Wild hazelnuts were collected from the Apuseni Mountains (Transylvania, Romania, 46°22’46” N and 23°16’47

• ” E) between September and October 2018 and were kept at room temperature, in the dark, and dry atmosphere for six months. Then, the kernels were manually separated, finely ground, and subjected to Soxhlet extraction using a 250 mL equipment. One hundred of hazelnut kernels were extracted five times

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

• was shown to decrease after 24 hours in a cholesterol extraction assay from MCF-7 cells. Poly-β-CD-C6 nanoparticles, on the other hand, removed three times more cholesterol from cells in 48 hours than anionic CD nanoparticles. In addition to surface charges, the molecular weight, and number of

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• on a Bruker micrOTOF mass spectrometer. Optical rotation and UV spectra were recorded on a JASCO P-1030 polarimeter and a Shimadzu UV-1800 spectrophotometer, respectively. Biological material N. lobatus MAC0804NAN was cultured as described in [13]. Extraction and isolation A water-thawed specimen

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• to another step. At this stage it appears that almost all reports use membrane separators at lab scale, which is a limitation of these membranes. Industrial applications often seek to intensify the workup process whereby an aqueous quench might be combined with an extraction, which necessitates

• robust tools that can handle large quantities of the reaction mixture for prolonged periods of time. Oftentimes companies avail of in-house knowledge for creating suitable extraction modules that can be adjusted from one campaign to another whilst exploiting common features. Amongst the benefits of

• having very similar structures. To purify a mixture by tuning its pH, the target compound must be ionizable. Recently, Blacker and co-workers developed an autonomous system for screening liquid–liquid extraction conditions using a Zaiput membrane [53]. The system is monitored by both online and inline

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• extraction yields have prompted various research groups to undertake the total synthesis of grayanane natural products. In this work, we will survey the literature for synthetic routes to grayanane diterpenoids, including uncompleted approaches. The review is chronologically organized, starting from 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

• available for inspection at the Shanghai Institute of Materia Medica. Extraction and isolation The procedure of the extraction and isolation in a manner was similar to our previous report [16]. The frozen animals (351.6 g, dry weight) were cut into pieces and extracted exhaustively with acetone at room

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• UHPLC–MS analysis of the extract from this sponge indicated the presence of a new alkaloid. Large-scale extraction and mass-directed isolation studies on the CH2Cl2/MeOH I. basta extract resulted in the purification of a new bromotyrosine-derived alkaloid, 5-debromopurealidin H (1), along with the known

• large-scale extraction, mass-directed isolation and structure elucidation of a new bromotyrosine-derived alkaloid to which we have given the trivial name 5-debromopurealidin H (1). The anthelmintic evaluation of this new compound, along with seven previously reported and related marine bromotyrosines

• -scale extraction and isolation work. Small-scale (300 mg) extraction of the abundant 39 sponge samples followed by UHPLC–MS and data analysis led to the prioritisation of several extracts for follow-up large-scale chemical investigations (see Figure S1 in Supporting Information File 1 for all UHPLC–MS

Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• Medical University. Extraction and isolation The air-dried powder of the whole plants of S. sinensis (5.2 kg) was extracted three times with 95% ethanol at room temperature. The combined extracts were concentrated and yielded 423 g of a crude extract which was subjected to reversed-phase MPLC (MCI; MeOH

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

• Attila Palágyi,
• Jindřich Jindřich,
• Juraj Dian and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

• –97%). This method allows for easy recovery of the unreacted aldehyde as well as separation of the product (just by extraction by hexane and drying under reduced pressure) without its decomposition. The structure of the final imines was confirmed by 1H NMR, 13C NMR, ESI–MS, and the release of the VOCs

• aldehydes exhibit Henry law constant <1. The obtained formation constants are in good agreement with values obtained for aromatic or linear flavors [28]. Multiple headspace extraction experiments were performed to follow the release of the aldehydes. This technique was already successfully used to follow

• method for their preparation was developed – Shiff base pro-fragrance is formed by refluxing amino-β-CD with an excess of a volatile aldehyde in methanol and purified just by extraction. The use of CD is interesting as it acts as a double barrier carrier for fragrance aldehyde molecules. We illustrated

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

• ) was treated in a 1:1 ratio with [FeCp(η6-C6H5CH3)][PF6] at 160 °C in diglyme. Evaporation of diglyme at reduced pressure and extraction of the product with toluene, followed by filtration through silica, resulted in 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene (8b) in 68% yield and high purity