ChiralityPub Date : 2026-05-01DOI: 10.1002/chir.70106
Aleksandra Cebrat, Kevin Martin, Pingo Mutombo, Manfred Parschau, Narcis Avarvari, Karl-Heinz Ernst
{"title":"Beyond the Solid Solution: Ordered Enantiomerically Unbalanced Packing in Surface-Confined Tetrahelicene Monolayers.","authors":"Aleksandra Cebrat, Kevin Martin, Pingo Mutombo, Manfred Parschau, Narcis Avarvari, Karl-Heinz Ernst","doi":"10.1002/chir.70106","DOIUrl":"10.1002/chir.70106","url":null,"abstract":"<p><p>The two-dimensional crystallization and on-surface chemistry of chiral polycyclic aromatic hydrocarbons provide access to surface-confined symmetry breaking and novel covalently bonded nanostructures. Here, we investigate the self-assembly of racemic 2,3-dicarbonitrile tetrahelicene on Ag(111). Using low-temperature scanning tunneling microscopy in combination with density functional theory calculations, we resolve the evolution of molecular organization as a function of coverage. After room-temperature deposition at submonolayer coverage, the tetrahelicene moiety spontaneously resolves into extended homochiral Kagomé domains upon cooling. The resulting monolayer consists of hexameric dimer motifs arranged in a porous network. These mirror-related supramolecular enantiomorphs are characteristic of two-dimensional conglomerate crystallization. As the surface coverage increases, the system undergoes a transition toward denser packing. At saturation, compact domains form that retains long-range lattice order while exhibiting a regular yet enantiomerically unbalanced distribution of both handednesses. The nonrandom incorporation of enantiomers distinguishes this phase from a racemic solid solution and instead indicates a compositionally biased, structurally ordered mixed phase.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 5","pages":"e70106"},"PeriodicalIF":2.4,"publicationDate":"2026-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13128537/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147764080","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2026-05-01DOI: 10.1002/chir.70101
Guanghui Gou, Wenli Bao, Liu Liu, Jun Li
{"title":"Isolation and Identification of Bioactive Fatty Acid Amides From Piper longum Fruits.","authors":"Guanghui Gou, Wenli Bao, Liu Liu, Jun Li","doi":"10.1002/chir.70101","DOIUrl":"10.1002/chir.70101","url":null,"abstract":"<p><p>Four pairs of previously undescribed fatty acid amide enantiomers [(+)-1/(-)-1 - (+)-4/(-)-4] bearing a trans-epoxide, and 12 known compounds (5-14) were isolated from the fruits of Piper longum L. Their structures were elucidated using spectroscopic methods, including HRMS and NMR, and by comparing with literatures. The absolute configuration of the novel compounds was determined through electronic circular dichroism (ECD) calculations. The bioactivity of all isolated compounds was evaluated, revealing that compounds (+)-4 and (+)-7 exhibited significant anti-inflammatory activity, with IC<sub>50</sub> values of 10.62 ± 0.80 and 8.93 ± 0.59 μM, respectively (IC<sub>50</sub> value of the positive control, andrographolide, was 5.85 ± 0.26 μM). In the cytotoxicity assay, compound 10 demonstrated a potent cytotoxic effect against HT-29 cells with an IC<sub>50</sub> value of 6.43 ± 0.36 μM; compounds 6, (+)-7, and 9 displayed moderate cytotoxic activity against HT-29 cells with IC<sub>50</sub> values between 10 and 20 μM (IC<sub>50</sub> value of the positive control, doxorubicin, was 0.22 ± 0.02 μM). These findings suggested that fatty acid amides from P. longum possess promising anti-inflammatory and cytotoxic properties.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 5","pages":"e70101"},"PeriodicalIF":2.4,"publicationDate":"2026-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147721708","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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