Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• run over 50 min at a flow rate of 9 mL/min; 60 fractions (60 × 1 min) were collected and resulted in the purification of the known sterol, aplysterol (8, 0.9 mg, tR 12–13 min, 0.009% dry wt). The extraction and isolation process described above was repeated twice more (identical scale) to obtain

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

• polyketides, alkaloids, sterol derivatives, terpenoids, and macrolides, with polyketides and alkaloids comprising 40% and 32% of the total, respectively. Alkaloids are a diverse group of compounds with multiple pharmacological activities, including anti-inflammatory, antibacterial, antiviral, insecticidal

Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants

• Karan Malhotra and
• Jakob Franke

Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135

• steroids in plants as a starting point for future research. Keywords: biosynthesis; CYPs; cytochrome P450 monooxygenases; plants; steroid; sterol; triterpene; triterpenoid; Introduction Triterpenoids are a large class of natural products derived from precursors containing 30 carbon atoms and composed of

• sterol scaffolds have drastically different three-dimensional shapes. For this reason, CYPs are typically specific to a certain group of triterpenoid scaffolds. Hence, we summarised our list of 149 triterpenoid/steroid CYPs (Table 1) according to their target scaffold. Figure 3 covers plant CYPs acting

• ) function as sterol 14α-demethylases in green plants [24][25][98]. These enzymes catalyse oxidation of the C14α methyl group to trigger elimination of formic acid [24][25]. The sister subfamily CYP51H, on the other hand, is only found in monocots. AsCYP51H10 from Avena sativa (oat) is a multifunctional CYP

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

• Elias Christoforides,
• Andreas Papaioannou and
• Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

• plane of the glucosidic O4n atoms of the hosts forming an angle of 83.18 (16)° with it. The sterol group of the guest is tightly fitted inside the hydrophobic cavity of the host A whereas its aliphatic ‘tail’ is located inside the hydrophobic cavity of the other host (host B) and characterized by high

• B also form C–H···O bonds with the O63C primary hydroxy group (partially occupied site, sof = 0.4) and the glycosidic O46A atom, respectively. The tight fit of the sterol group of the guest in host A hydrophobic cavity, is further enhanced by the H···H interactions between the hydrogens of the C19

• the sterol group, forming C–H···O bonds with the partially occupied primary hydroxy group O61D (sof = 0.2) of host B, disordered water molecules located in the dimers’ interspace and the primary hydroxy group O66A of host A of the adjacent dimer (1+x, y, -1+z). Supporting Information File 1, Table S2

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• products [26]. In contrast, when glycosyl sulfoxide donor 1 was preactivated with Tf2O at −78 °C, followed by the addition of sterol 2 and 2,6-di-tert-butyl-4-methylpyridine (DTBMP) as an acid scavenger, the desired compound 3 was obtained in an excellent 86% yield (Scheme 2). While this method has not

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• the sterol and fatty acid biosynthetic pathways were activated in the MSCs, and subsequent experiments validated the model predictions of increased levels of proteins in these pathways and the formation of lipid rafts on the cell membranes. In silico sparse feature selection thus revealed a hitherto

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• Abstract Compared to cholesterol, hydroxycholesterols contain an additional hydroxy group in the alkyl chain and are able to efficiently cross the brain–blood barrier. Therefore, they are responsible for the sterol transfer between brain and circulation. The current study compares the membrane properties

• barrier function. Interestingly, not only modifications in the tetracyclic sterol ring system lead to pronounced changes of the molecular membrane architecture and of the interactions between the respective sterol and membrane lipids and proteins [14][15][16][17], but also the iso-branched side chain of

• close to the pure lipid membrane but significant smaller for a cholesterol containing membrane. Influence of hydroxylcholesterols on membrane permeability The permeability of POPC membranes in the absence and in the presence of the respective sterol (molar ratio 0.8:0.2) was measured by using a

N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• pharmacological activities. For example, abafungin (Figure 1) is an antifungal drug marketed worldwide for the treatment of dermatomycoses. It works by inhibiting the enzyme sterol 24-C-methyltransferase [1][2][3][4]. Febuxostat, also known by its brand name adenuric is a xanthine oxidase inhibitor that helps to

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• inclusion complex because of the driving force of complexation: hydrophobic interaction. Despite there is no information on the binding constant observed for the inclusion of cholesterol in γ-CD, the cavity internal diameter of the β-CD and its derivatives perfectly matches the size of the sterol molecules

• phosphatidylcholine (SOPC) or SOPC/cholesterol. In the steady state under such conditions where a negligible fraction of the sterol is bound to CD (i.e., in the presence of submillimolar concentrations), β- and γ-CDs accelerate considerably the rate of cholesterol transfer between lipid vesicles (63- and 64-fold

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

• degradation of a sterol, leading to the tricyclic core structure. Compounds 27 and 30 have shown inhibitory activity towards A. crystallopoietes (MIC value of 8 and 4 μg mL−1, respectively). Since salimabromide is a novel structure of putatively assigned PKS origin, our research group sequenced the genome of

3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates

• Aneta M. Tomkiel,
• Adam Biedrzycki,
• Jolanta Płoszyńska,
• Dorota Naróg,
• Andrzej Sobkowiak and
• Jacek W. Morzycki

Beilstein J. Org. Chem. 2015, 11, 162–168, doi:10.3762/bjoc.11.16

• leads to sterol glycoconjugates. Initially, the reaction of cholesterol (1) with various sugars was studied. During anodic oxidation of cholesterol in dichloromethane (the choice of solvent is crucial as the reaction course may be different in other solvents) [1], splitting of the carbon–oxygen bond in

• -steroid ethers are frequently prepared for simultaneous protection of both 3β-ol and Δ5 groups in sterols. The cycloreversion that occurs under acidic conditions allows to recover sterol functions. We thought that such highly energetic i-steroid ethers would easily generate the mesomeric carbocation

• substrates (sterol donors, sugar alcohol) and the resulting glycoconjugate, the possibility that side processes will occur increases as the anode potential is more positive and the glycoconjugate concentration grows. A series of blank experiments proved that the electrochemical activation of i-steroidal

New tridecapeptides of the theonellapeptolide family from the Indonesian sponge Theonella swinhoei

• Annamaria Sinisi,
• Barbara Calcinai,
• Carlo Cerrano,
• Henny A. Dien,
• Angela Zampella,
• Claudio D’Amore,
• Barbara Renga,
• Stefano Fiorucci and
• Orazio Taglialatela-Scafati

Beilstein J. Org. Chem. 2013, 9, 1643–1651, doi:10.3762/bjoc.9.188

• treasure troves of secondary metabolites. The chemical diversity of the isolated compounds ranges from unusual steroids (exemplified by the 4-methylene sterol theonellasterol [2][3] and truncated side-chain sulfated steroids [4]), to complex macrocyclic polyketides (as the well-known swinholide A, now a

Chemical–biological characterization of a cruzain inhibitor reveals a second target and a mammalian off-target

• Jonathan W. Choy,
• Clifford Bryant,
• Claudia M. Calvet,
• Patricia S. Doyle,
• Shamila S. Gunatilleke,
• Siegfried S. F. Leung,
• Kenny K. H. Ang,
• Steven Chen,
• Jiri Gut,
• Juan A. Oses-Prieto,
• Jonathan B. Johnston,
• Michelle R. Arkin,
• Alma L. Burlingame,
• Jack Taunton,
• Matthew P. Jacobson,
• James M. McKerrow,
• Larissa M. Podust and
• Adam R. Renslo

Beilstein J. Org. Chem. 2013, 9, 15–25, doi:10.3762/bjoc.9.3

• activities of 4 and 8 suggest TcCYP51 as a relevant target of these compounds. To assess inhibition of TcCYP51 in live parasites we analyzed the sterol composition of intracellular T. cruzi parasites treated with test compounds 3–8, 1, or posaconazole as a positive control. The analysis was performed by

• relative abundance of TcCYP51 substrates lanosterol (f) and eburicol (h) and accordingly, a reduction in the abundance of downstream sterols such as fecosterol (e) and cholesta-7,24-dien-3β-ol (a), among others. Treatment with 1 had little effect on sterol composition as expected, whereas treatment with