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Journal articles on the topic '1D and 2D NMR (¹H'

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Published: 7 June 2025

Last updated: 17 July 2025

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1

Li, Chuanjiang, Hui Wang, Manuel Juárez та Eric Dongliang Ruan. "Structural Characterization of Amadori Rearrangement Product of Glucosylated Nα-Acetyl-Lysine by Nuclear Magnetic Resonance Spectroscopy". International Journal of Spectroscopy 2014 (17 квітня 2014): 1–6. http://dx.doi.org/10.1155/2014/789356.

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Maillard reaction is a nonenzymatic reaction between reducing sugars and free amino acid moieties, which is known as one of the most important modifications in food science. It is essential to characterize the structure of Amadori rearrangement products (ARPs) formed in the early stage of Maillard reaction. In the present study, the Nα-acetyl-lysine-glucose model had been successfully set up to produce ARP, Nα-acetyl-lysine-glucose. After HPLC purification, ARP had been identified by ESI-MS with intense [M+H]+ ion at 351 m/z and the purity of ARP was confirmed to be over 90% by the relative intensity of [M+H]+ ion. Further structural characterization of the ARP was accomplished by using nuclear magnetic resonance (NMR) spectroscopy, including 1D 1H NMR and 13C NMR, the distortionless enhancement by polarization transfer (DEPT-135) and 2D 1H-1H and 13C-1H correlation spectroscopy (COSY) and 2D nuclear overhauser enhancement spectroscopy (NOESY). The complexity of 1D 1H NMR and 13C NMR was observed due to the presence of isomers in glucose moiety of ARP. However, DEPT-135 and 2D NMR techniques provided more structural information to assign the 1H and 13C resonances of ARP. 2D NOESY had successfully confirmed the glycosylated site between 10-N in Nα-acetyl-lysine and 7′-C in glucose.

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2

Zhuravleva, Olesya I., Maria P. Sobolevskaya, Vladimir A. Denisenko, et al. "New 6,6-Spiroketal from the Alga-Derived Fungus Penicillium Lividum." Natural Product Communications 11, no. 2 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100219.

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The new 6,6-spiroketal, sargassopenilline H (1), and known peneciraistin C (2) have been isolated from an EtOAc extract of the marine-derived fungus PenicilliumlividumKMM 4663. The structure of the new metabolite was determined by HR ESIMS and 1D and 2D NMR spectroscopy. Sargassopenilline H (1) in non-cytotoxic concentration inhibited colony formation of RPMI-7951 and MDA-MB-231 cell lines.

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3

W., KRAUS, MAILE R., VOGLER B., and WUNDRAK B. "1-Tigloyl-3-acetylazadirachtol, a New Limonoid from the Marrango Tree, Azadirachta excelsa Jack (Meliaceae)." Journal of Indian Chemical Society Vol. 74, Nov-Dec 1997 (1997): 870–73. https://doi.org/10.5281/zenodo.5900395.

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Department of Chemistry. University of Hohenheim. Garbenstr 30, D-70593, Stuttgart, Germany <em>Manuscript received 1 September 1997</em> The structure of a new  limonoid from the Marrango tree, <em>Azadirachta excelsa</em> Jack, has been established as 1-ticloyl-acetylazadirachtol (4) by 1D and 2D <sup>1</sup>H and <sup>13</sup>C nmr spectra.

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4

Shan, Wei-Guang, Yuan Wang, Lie-Feng Ma, and Zha-Jun Zhan. "A new pyrrole alkaloid from the mycelium of Inonotus obliquus." Journal of Chemical Research 41, no. 7 (2017): 392–93. http://dx.doi.org/10.3184/174751917x14967701766941.

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Inotopyrrole B, a new pyrrole alkaloid, was isolated from the mycelium of Inonotus obliquus together with two known ones, inotopyrrole and 5-(hydroxymethyl)-1 H-pyrrole-2-carboxaldehyde. The structure of the new compound was established via detailed analyses of the spectroscopic data, in particular, 1D and 2D NMR and HRESIMS.

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5

Wu, Zhao-Yuan, Hong-Mei Li, Yuan-Dan Li, and Rong-Tao Li. "Grayanane Diterpenoids from the Fruits of Pieris formosa." Zeitschrift für Naturforschung B 67, no. 2 (2012): 171–75. http://dx.doi.org/10.1515/znb-2012-0210.

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Four new acylated grayanane diterpenoids, pierisformosins E-H (1 - 4), together with two known ones, pierisformosins B and C (5, 6), were isolated from the fruits of Pieris formosa. The structures and relative configurations of the new compounds were elucidated by means of spectroscopic methods, including 1D and 2D NMR and mass spectrometry.

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6

Huang, Ting-Hong, Jie Yan, Ye-Feng Liu, Yun-Tao Xie, and Chen Jia. "Synthesis, Structural Characterisation, and Spectroscopic Properties of Copper(I) Complexes and their Applications to Dye-Sensitised Solar Cells." Australian Journal of Chemistry 68, no. 7 (2015): 1144. http://dx.doi.org/10.1071/ch14562.

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Based on the ligand 1,4-bis(2-(diphenylphophino)benzylideneamino)benzene (pbb), two complexes, [Cu2(pbb)(2,2′-bipyridine)2](BF4)2 (1) and [Cu2(pbb)(phen)2](BF4)2 (2), have been prepared and characterised by IR, 1H NMR, 31P NMR, 19F NMR, and 11B NMR spectroscopy and X-ray crystal structure analysis. Structural analysis reveals that complexes 1 and 2 contain 1D infinite chains and 2D supramolecular networks constructed by C–H···π and π···π interactions, and an ordered-layer-lattice of BF4– is located between these 2D networks. The results show that C–H···π and π···π interactions play an important role in the formation of 2D supramolecular networks. The UV-vis absorption peaks of complexes 1 and 2 display intraligand charge transfer and metal to ligand charge transfer (MLCT) absorption. Complexes 1 and 2 display efficient luminescent emission assigned to MLCT excited states, and the maximum emissions of these complexes in acetonitrile solution are different from those of the solid-state samples. In addition, complexes 1 and 2 have been exploited as sensitisers in dye-sensitised solar cells, and efficiencies are also observed.

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7

Zeng, Yan-Bo, Shan-Shan Ma, Zhi-Kai Guo, Bei Jiang, Wen-Li Mei, and Hao-Fu Dai. "A New Degraded Sesquiterpene from the Twigs of Trigonostemon Lutescens." Natural Product Communications 11, no. 3 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100312.

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A new degraded sesquiterpene, tectoionol C (1), together with five known compounds wilsonol F (2), heterodendrin (3), epi-heterodendrin (4), 7-deoxogeayine (5), and 1 H-indole-3-carboxylicacid, methyl ester (6), was isolated from the twigs of Trigonostemon lutescens. Their structures were determined by spectroscopic methods including 1D and 2D NMR techniques, as well as by comparison with published data.

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8

Bennevault, V., C. Huin, P. Guégan, K. Evgeniya, X. P. Qiu та F. M. Winnik. "Temperature sensitive supramolecular self assembly of per-6-PEO-β-cyclodextrin and α,ω-di-(adamantylethyl)poly(N-isopropylacrylamide) in water". Soft Matter 11, № 32 (2015): 6432–43. http://dx.doi.org/10.1039/c5sm01293g.

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The host/guest interactions in water of a star polymer consisting of a β-cyclodextrin core bearing six PEO arms linked to the C<sub>6</sub> positions of β-CD (5K) and α,ω-di-(adamantylethyl)PNIPAM-12K were studied by 1D and 2D <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, isothermal calorimetry, and light scattering.

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9

Mzozoyana, Vuyisa, Fanie R. van Heerden, and Craig Grimmer. "Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds." Beilstein Journal of Organic Chemistry 16 (February 10, 2020): 190–99. http://dx.doi.org/10.3762/bjoc.16.22.

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4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (J FH = 2.6 Hz) and 13C NMR suggested that this C–F···H–C coupling is a through-space interaction. The 2D 19F-{1H} HOESY and 1H-{19F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C–F···H–C interaction.

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10

Roxin, Áron, Thomas D. MacDonald, and Gang Zheng. "Synthesis and characterization of a new natural product analog, 132-173-bacteriochlorophyllone a." Journal of Porphyrins and Phthalocyanines 18, no. 03 (2014): 188–99. http://dx.doi.org/10.1142/s1088424613501058.

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Here we show the facile synthesis of 132-173-bacteriochlorophyllone a (12), with a distinct seven-membered exocyclic F-ring formed by 132-173-cyclization of bacteriopheophorbide a(16). This is the latest reported bacteriochlorin with such an exocyclic F-ring since 1975 (132-173 cyclobacteriopheophorbide a-enol, 11), and is an analog of previously described natural exocyclic F-ring-containing porphyrins (1–4) and chlorins (5–10). The structure of 12 was confirmed using a combination of 1D 1 H NMR, 2D COSY 1 H NMR, Jmod 13 C NMR and HRMS analysis. The biological activity of 12 was explored, and we found that this compound does not possess strong antioxidant activity like its natural product counterparts, but is a capable photosensitizer for photodynamic therapy.

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11

Khalid, Rozida Mohd, Md Lip Jabit, Faridah Abas, Johnson Stanslas, Khozirah Shaari, and Nordin H. Lajis. "Cytotoxic Xanthones from the Leaves of Garcinia Urophylla." Natural Product Communications 2, no. 3 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200309.

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Two new xanthones, 7-hydroxydesoxymorellin (1) and isocaledonixanthone D (2), and four known ones, gaudichaudione H, 1,7-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, 1,5-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, and 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone, as well as lupeol were isolated from the leaves of Garcinia urophylla (Guttiferae). Their structures were determined using a combination of 1D (1H NMR, 13C NMR, DEPT) and 2D (COSY, gHSQC, gHMBC) NMR spectroscopic techniques. Among the isolates, 7-hydroxydesoxymorellin (1), gaudichaudione H, 1,5-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, and 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone demonstrated cytotoxic activities against breast (MCF-7), prostate (DU-145), and lung (NCI-H460) human cancer cell lines.

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12

Becerra, Diana, Jaime Portilla, and Juan-Carlos Castillo. "2-Oxo-2H-chromen-7-yl 4-chlorobenzoate." Molbank 2021, no. 3 (2021): M1279. http://dx.doi.org/10.3390/m1279.

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We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester 3 was completely characterized by mass spectrometry, IR, UV–Vis, 1D, and 2D NMR spectroscopy.

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13

Ali, Liaqat, Lubna Al-Kharusi, and Ahmed Al-Harrasi. "Two New Sulfonoglycolipids from the Green Alga Codium dwarkense." Natural Product Communications 12, no. 4 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200429.

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Two new sulfonoglycosides named Codioside E (1) and Codioside F (2) have been isolated from the MeOH extract of the marine green alga Codium dwarkense collected from the coastal areas of the Gulf of Oman. The structures of these secondary metabolites were elucidated by combined analysis of 1D (1H- and 13C-) and 2D (H–C correlations; HSQC and HMBC) NMR spectroscopic and MS data.

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14

Lee, Azizan, Lo, Tan, and Tiekink. "2-{[Bis(propan-2-yl)carbamothioyl]sulfanyl}acetic acid." Molbank 2019, no. 4 (2019): M1082. http://dx.doi.org/10.3390/m1082.

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The title compound, (iPr)2NC(=S)SCH2C(=O)OH (1), was synthesized by conventional methods and its X-ray crystal structure was determined by X-ray crystallography. The compound was further characterized by analytical, IR, UV, 1D NMR (1H and 13C{1H}), and 2D NMR (DEPT-135) spectroscopy, and density functional theory (DFT) methods. X-ray crystallography on 1 confirms the formulation and reveals a nearly orthogonal relationship between the planar NCS2 and C2O2 residues. In the crystal, hydroxyl-O–H⋯O(carbonyl) hydrogen bonds lead dimers via an eight-membered {⋯OCOH}2 ring.

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15

Nirwan, N., C. Pareek, A. K. Chohadia, and K. K. Verma. "Synthesis, Antibacterial, and Antifungal Activities of 3-(4,5-Diphenyl-1<i>H</i>-Imidazol-2-yl)-1<i>H</i>-Indole Derivatives." Journal of Scientific Research 15, no. 1 (2023): 159–70. http://dx.doi.org/10.3329/jsr.v15i1.59004.

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Indolylimidazole ring-containing natural and synthesized compounds have shown vast biological activities. These indolylimidazole compounds contain both indole and imidazole rings. The indolylimidazole structure resembling compounds 1a-1d and 2a-2d were synthesized by a green and efficient one-pot four components condensation of indole-3-carbaldehyde, benzil, ammonium-acetate, and substituted amines under microwave irradiation using Amberlyst A-15 as a recyclable catalyst. The structures of synthesized compounds were characterized by FTIR, 1H NMR, and Mass spectrometric studies. These compounds' antibacterial and antifungal activities were screened and compared with the standard drug. The compound 1c was found to be the most active derivative in these compounds, with a minimum inhibitory concentration in the range of 09.9 to 12.5 μg/mL. Compound 1d also showed potent activity against Candida albicans. The sensitivity order of compounds was found 1a<1b<1c>1d against Staphylococcus aureus, Staphylococcus epidermidis, and Escherichia coli and 1a<1b<1c<1d for C. albicans. Compound 2a showed good antimicrobial activity against E. coli and C. albicans.

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16

Tarakci, Deniz Kutlu, İlke Gürol, and Vefa Ahsen. "2,2,3,3-Tetrafluoropropoxy substituted oxo-titanium phthalocyanines axially ligated with common MALDI matrix materials." Journal of Porphyrins and Phthalocyanines 17, no. 06n07 (2013): 548–54. http://dx.doi.org/10.1142/s1088424613500399.

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The synthesis of tetra and octa 2,2,3,3-tetrafluoropropoxy substituted oxo-titanium phthalocyanines (TiOPc) are reported. Using strongly chelating oxygen donor ligands, the reactions of TiOPc with catecholate (1a, 2a), 4-nitrocatecholate (1b, 2b) and caffeic acid (1c, 2c), ellagic acid (1d, 2d) and chlorogenic acid (1e, 2e) are described. The new compounds were characterized by mass, 1 H NMR, FT-IR, and UV-vis spectroscopic techniques as well as elemental analysis.

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17

Zhang, Zhan-Xin, Hui-Hong Li, Gai-Xia Fan, et al. "A Novel Norclerodane Diterpenoid from the Roots of Croton crassifolius." Natural Product Communications 10, no. 11 (2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001128.

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A chemical investigation of Croton crassifolius afforded a novel norclerodane diterpenoid (1) with an unprecedented six-membered oxygen ring between C-1 and C-12, together with three known compounds. The structure of the new compound was elucidated based on spectroscopic (IR, 1D, and 2D NMR) and HR-ESI-MS techniques. This report describes the first example of a natural norclerodane with a 4 H-chromene ring system.

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18

Tijjani, MA, GM Magaji, AH Yaro, et al. "Quercetin from n-butanol Soluble Fraction of Crude Ethanol Leaf Extract of Cadaba Farinosa Forssk." Chemistry Research Journal 2, no. 5 (2017): 270–74. https://doi.org/10.5281/zenodo.13952123.

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The plant <em>Cadaba farinosa </em>Forssk (Capparaceae) is distributed throughout the world in mostly tropical and sub-tropical regions. It is used in treatment of pains, dysentery, rheumatism, cough, fever, as antidote and neurological disorders. Phytochemical screening of the leaf revealed the presence of alkaloids, anthraquinones, carbohydrates, cardiac glycosides, flavonoids, glycosides, saponins and tannins. Silica gel column chromatography of the <em>n-</em>butanol soluble fraction (NBU) followed by gel filtration using sephadex LH-20 and PTLC led to isolation of a Flavonol aglycone characterised as Quercetin by spectroscopic techniques. The complete <sup>1</sup>H and <sup>13</sup>C NMR spectral assignments of the isolated compound is reported herewith on the basis of 1D (<sup>1</sup>H and <sup>13</sup>C) and 2D (COSY, NOESY, HSQC, HMBC) NMR.

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19

Cuc, Nguyen Thi, Hoang Le Tuan Anh, Dan Thi Thuy Hang, et al. "Sesquiterpenes from the Vietnamese Marine Sponge Dysidea Fragilis." Natural Product Communications 10, no. 8 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000804.

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Two new sesquiterpenes, named dysinidins A-B (3, 4) along with two known sesquiterpenes, furodysinin lactone (1) and O-methyl furodysinin lactone (2), were isolated from the Vietnamese marine sponge Dysidea fragilis. Their structures were determined by 1D- and 2D-NMR spectroscopies and HR ESI MS, as well as by comparison with reported literature data. None of compounds showed inhibitory growth of human lung cancer cell lines, A-549 and H-1975 (IC50 > 30μM).

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20

Tabakmakher, Kseniya M., Tatyana N. Makarieva, Vladimir A. Denisenko, et al. "Normonanchocidins G and H, New Pentacyclic Guanidine Alkaloids from the Far-Eastern Marine Sponge Monanchora pulchra." Natural Product Communications 12, no. 7 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200707.

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Two new pentacyclic guanidine alkaloids, normonanchocidins G (1) and H (2) containing an unusual ω-2-hydroxy fatty acid moiety were isolated from the Far-Eastern marine sponge Monanchora pulchra. The structures of 1 and 2 were determined by 1D- and 2D-NMR spectroscopic and mass spectrometric data interpretation. Compounds 1 and 2 exhibit potent cytotoxic activities against human leukemia THP-1, HL-60 cells, human cervical epithelioid carcinoma HeLa cells and also have high impact on ability of HeLa cells to migrate.

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21

Kim, Tuyen Pham Nguyen, Tram Phan Thi Mai, and Phung Nguyen Kim Phi. "Two New Compounds from Hedyotis lindleyana." Natural Product Communications 10, no. 7 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000701.

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One new sodium salt of an iridoid acid, sodium 6- O-methyldeacetylasperulosidate (1) and one new heterocyclic compound, 1,3,6-trimethylpyrano[2,3- d]imidazole-2,5(1 H,3 H)-dione (2) were isolated from Hedyotis lindleyana Hook. (Rubiaceae), together with seven known compounds, oleanolic acid (3), ursolic acid (4), teneoside D (5), 6 β-hydroxygeniposide (6), deacetylasperulosidic acid sodium salt (7), liquiritin (8), and 3,3′,4′-tri- O-methylellagic acid (9). The structures were established by spectroscopic (1D, 2D NMR) and HR-ESI-MS analysis, as well as by comparison with data reported in the literature.

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22

Zhu, Qinfeng, Beibei Gao, Qian Chen, Tiantian Luo, Guobo Xu, and Shanggao Liao. "Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring." Beilstein Journal of Organic Chemistry 18 (October 7, 2022): 1410–15. http://dx.doi.org/10.3762/bjoc.18.146.

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One new lignan sinensiol H (1) and two new bisnorlignans, sinensiols I and J (2 and 3), along with three known compounds were isolated from the whole plants of Selaginella sinensis. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopy as well as high-resolution mass spectrometry. The absolute configuration of 1 was established by ECD calculation. Compounds 2 and 3 represent rare examples of naturally occurring 9,9'-bisnorlignans. All the isolated compounds were assayed for their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages.

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23

Monteiro, Carlos J. P., Mariette M. Pereira, Nuno P. F. Gonçalves, et al. "Separation and atropisomer isolation of ortho-halogenated tetraarylporphyrins by HPLC: Full characterization using 1D and 2D NMR." Journal of Porphyrins and Phthalocyanines 16, no. 03 (2012): 316–23. http://dx.doi.org/10.1142/s1088424612500368.

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The separation and isolation of the four atropisomers of ortho-halogenated tetraarylporphyrins by semi-preparative HPLC is described. Full characterization and assignment of all 1 H and 13 C resonances of 5,10,15,20-tetrakis(2-fluoro or 2-chlorophenyl)porphyrins and 5,10,15,20-tetrakis(2-fluoro or chloro-5-N-ethylsulfamoylphenyl)porphyrins by 1D and 2D NMR techniques is reported. The outcome is an unequivocal evidence of the chlorosulfonation of meso-tetra(2-haloaryl)porphyrins on the 5′-position.

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24

Thao, Tran Thi Phuong, Nguyen Vu Anh, Ho Ngoc Anh, Tran Duc Quan, and Tran Van Sung. "Study on Chemical Constituents of the Vietnamese Medicinal Plant Fissistigma petelotii." Zeitschrift für Naturforschung B 64, no. 3 (2009): 323–27. http://dx.doi.org/10.1515/znb-2009-0312.

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A new bisabolene derivative (1S*, 2R*, 4R*, 7R*, 10R*)-1,7,10,11-tetrahydroxy-1,7,11-trimethyl- 4,10(H)-2-O-cinnamoyl-bisabol-8(9)-ene (1), together with cinnamic acid (2), methyl cinnamate (3), sodium cinnamate (4) and methyl elaidate (5) have been isolated from the leaves and barks of Fissistigma petelotii. Sodium cinnamate (4) was isolated for the first time from the nature. The structures of these compounds were elucidated by analysis of their IR, MS, 1D and 2D NMR spectra.

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25

Boulacel, Ibtissem, Lakhdar Djarri, Salima Azzouzi, et al. "Phytochemical studies and antibacterial activity of the aerial parts of Physospermum verticillatum." Bangladesh Journal of Pharmacology 12, no. 2 (2017): 6. http://dx.doi.org/10.3329/bjp.v12i2.29668.

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<p class="Abstract">In this study, we focused on the isolation and identification of the main compounds, triterpene, sterol, phenolic and fatty acid from the aerial parts of Physospermum verticillatum, which has not been previously reported. Dichloromethane, ethyl acetate and n-butanol extracts led to the isolation of ß-amyrin (1), 3,11-dihydroxy-12-oleanene (2), pentadecanoic acid (3), spina-sterol (4), spinasterol-3-O-ß-D-glucopyranoside (5) and saikochromic acid (6). These compounds were determined by means of the combined systems with high resolution tandem mass spectrometry (HPLC-TOF/MS), 1D NMR (<sup>1</sup>H NMR, <sup>13</sup>C NMR) and 2D NMR(COSY, HSQC and HMBC). Further, the extracts demonstrated significant antibacterial activity.</p>

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26

Wood, Jordan, David R. Morgan, Kimberly Ange-van Heugten, et al. "Observable Metabolites and Metabolomic Sampling Protocols for Managed African Savanna Elephant (Loxodonta africana) Whole Blood Using H-NMR Spectroscopy." Metabolites 12, no. 5 (2022): 400. http://dx.doi.org/10.3390/metabo12050400.

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We used nuclear magnetic spectroscopy (NMR) to evaluate the metabolomics of heparinized whole blood drawn from six African savanna elephants (Loxodonta africana) maintained on a well characterized diet. Whole blood samples obtained under behavioral restraint, then quickly frozen in liquid nitrogen, were stored at −80 °C until analysis. Frozen samples were thawed under controlled conditions and extracted with methanol and chloroform to separate the polar and non-polar metabolites. We identified 18 polar metabolites and 14 non-polar lipids using one-dimensional (1D) and two-dimensional (2D) NMR spectra. Despite unexpected rouleaux formation in the thawed frozen samples, spectra were consistent among animals and did not vary dramatically with age or the sex of the animal.

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27

Chen, Huiqin, Georgios Daletos, Festus Okoye, Daowan Lai, Haofu Dai, and Peter Proksch. "A New Cytotoxic Cytochalasin from the Endophytic Fungus Trichoderma harzianum." Natural Product Communications 10, no. 4 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000412.

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The new natural product 4′-hydroxy-deacetyl-18-deoxycytochalasin H (1), together with the known deacetyl-18-deoxycytochalasin H (2) and 18-deoxycytochalasin H (3) were obtained from the endophytic fungus Trichoderma harzianum isolated from leaves of Cola nitida. The structure of the new compound was unambiguously determined by 1D and 2D NMR spectroscopy, and by HRESIMS measurements, as well as by comparison with the literature. Compounds 1-3 showed potent cytotoxic activity against the murine lymphoma (L5178Y) cell line and against human ovarian cancer (A2780 sens and A2780 CisR) cell lines (IC50 0.19–6.97 μM). The A2780 cell lines included cisplatin-sensitive (sens) and -resistant (R) cells.

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28

Liu, Qingqing, Feiyi Sun, Yulin Deng, Rongji Dai, and Fang Lv. "HPLC-ESI-MSn Identification and NMR Characterization of Glucosyloxybenzyl 2R-Benzylmalate Deriva-Tives from Arundina Graminifolia and Their Anti-Liver Fibrotic Effects In Vitro." Molecules 24, no. 3 (2019): 525. http://dx.doi.org/10.3390/molecules24030525.

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Four new glucosyloxybenzyl 2R-benzylmalate derivatives, named Arundinoside H (2), I (5), J (6), K (8) as well as four known compounds Arundinoside D (1), G (3), F (4), E (7) were isolated and characterized by a combination of chemical and spectroscopic methods, including HR-ESI-MS, 1D and 2D NMR experiments. Besides, 24 unreported compounds were inferred from ESI-MSn data. The anti-liver fibrotic activities of the isolates were determined as proliferation inhibition of lipopolysaccharide (LPS)-induced activation of rat hepatic stellate cells (HSC-T6). The result suggested Arundinosides D, H, F, I and K showed moderate inhibitory effects in vitro.

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29

Sajkowska-Kozielewicz, Joanna J., Paweł Kozielewicz, Katerina Makarova, Marcin Stocki, Nicholas M. Barnes, and Katarzyna Paradowska. "Geissospermiculatine, a New Alkaloid from Geissospermum reticulatum Bark." Molecules 26, no. 1 (2020): 143. http://dx.doi.org/10.3390/molecules26010143.

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A new alkaloid, geissospermiculatine was characterized in Geissospermum reticulatum A. H. Gentry bark (Apocynaceae). Here, following a simplified isolation protocol, the structure of the alkaloid was elucidated through GC-MS, LC-MS/MS, 1D, and 2D NMR (COSY, ROESY, HSQC, HMBC, 1H-15N HMBC). Cytotoxic properties were evaluated in vitro on malignant THP-1 cells, and the results demonstrated that the cytotoxicity of the alkaloid (30 μg/mL) was comparable with staurosporine (10 μM). Additionally, the toxicity was tested on zebrafish (Danio rerio) embryos in vivo by monitoring their development (0–72 h); toxicity was not evident at 30 μg/mL.

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30

Xu, Qiao, Miao-Miao Zhang, Shu-Zhen Yana, et al. "Two Dibenzoquinones from the Fungus Acremonium cavaraeanum." Natural Product Communications 12, no. 11 (2017): 1934578X1701201. http://dx.doi.org/10.1177/1934578x1701201129.

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Two symmetrical dibenzoquinone derivatives were isolated from solid cultures of the fungus Acremonium cavaraeanum. Compound 1 was new and identified as 2,7-dihydroxy-3,6,9-trimethyl-9 H-xanthene-1,4,5,8-tetraone. Compound 2 was 3,3’,6,6’-tetrahydroxy-4,4’-dimethyl-1,1’-bi- p-benzoquinone, i.e. oosporein, which was reported from A. cavaraeanum for the first time. The structure of the dibenzoquinone (1) was unambiguously elucidated using a combination of MS, IR, 1D- and 2D-NMR, and the dibenzoquinone (2) was further determined by single-crystal X-ray diffraction.

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31

Hajib, Sara, Salaheddine Boukhssas, Younas Aouine, et al. "4,4-Bis(hydroxymethyl)-2-phenyl-2-oxazoline." Molbank 2020, no. 4 (2020): M1163. http://dx.doi.org/10.3390/m1163.

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The title compound, 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline 2, a well-known substance, was resynthesized in high yields through a conventional method. The structure of compound 2 was characterized for the first time by a single-crystal X-ray structure determination. The compound was further established through NMR spectroscopy (1D and 2D). In the molecular packing, two molecules of 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline interact through H-Bonds to define “dimers” in which phenyl groups interact especially using π…π contact.

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32

Allam, Ahmed E., Alaa M. Nafady, Mohamed A. El-Shanawany, Fumide Takano, and Tomihisa Ohta. "New secoiridoid ester of swertiamarin and secoxyloganic acid with hepatoprotective activity from Centaurium spicatum L." Journal of Pharmacy & Pharmacognosy Research 3, no. 1 (2015): 69–76. http://dx.doi.org/10.56499/jppres15.058_3.3.69.

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Context: Centaurium spicatum (L.) Fritsch (Gentianaceae) is an annual herb occurring in Southern Europe and Northern Africa where it is used in traditional medicine for treatment of numerous illness. Aims: To isolate compounds from C. spicatum having hepatoprotective activity. Methods: Structure elucidation of the new compound was established on the basis of 1D and 2D NMR analyses including 1H-, 13C- NMR, DEPT-135 NMR, HMQC, HMBC and H- H HOHAHA experiments in addition to FAB+ and HRFAB+ Mass spectrometry. In vivo transaminases inhibition activity was carried out. Results: A new ester of swertiamarin and secoxyloganic acid (1) was isolated from C. spicatum in addition to its known components secoiridoids swertiamarin (2) and secoxyloganic acid (3). All tested secoiridoids have transaminases inhibition activity with different values for each compound 1, 2, 3 (86, 83, 81%) for SGOT and (96, 93, 91%) for SGPT, respectively. Conclusions: The new ester compound from C. spicatum has hepatoprotective activity over than its components.

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33

Le Tuan Anh, Hoang, Nguyen Thi Thu Hien, Dan Thi Thuy Hang, et al. "ent-Kaurane Diterpenes from Annona glabra and Their Cytotoxic Activities." Natural Product Communications 9, no. 12 (2014): 1934578X1400901. http://dx.doi.org/10.1177/1934578x1400901204.

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A new ent-kaurane glycoside, annoglabasin H (1), and three known ent-kauranes, annoglabasin E (2), annoglabasin B (3), and 19-nor- ent-kaurent-4-ol-17-oic acid (4) were isolated from the fruits of Annona glabra. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparison with the NMR data reported in the literature. The cytotoxic activities of these compounds were evaluated on four human cancer cell lines, LU-1, MCF-7, SK-Mel2, and KB. Compound 1 exhibited significant cytotoxic activity on all tested human cancer cell lines with IC50 values ranging from 3.7 to 4.6 μM.

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34

Li, Renfeng, Ximei Zhao, Baojun Shi, et al. "Insecticidal Pregnane Glycosides from the Root Barks of Periploca sepium." Natural Product Communications 11, no. 10 (2016): 1934578X1601101. http://dx.doi.org/10.1177/1934578x1601101003.

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To explore novel lead compounds for botanical pesticides from natural sources, a new pregnane glycoside (periplocoside) P2 as well as its isomer, a known pregnane glycoside P1, were isolated from the root barks of Periploca sepium using a bioactivity-guided method, and their structures were confirmed by 1D NMR, 2D NMR, IR, ESI-MSn and HRMS. Their insecticidal activities were evaluated against 3rd instar larvae of M. separata, and the results indicated that P2 exhibited excellent insecticidal activity with LC50 values of 2.9 and 2.2 mg/mL after 24 and 48 h, respectively, much lower than those of the positive control celangulin-V (24.7 and 21.0 mg/mL after 24 and 48 h, respectively). This work demonstrated that pregnane glycosides from Periploca sepium could be promising lead compounds for developing botanical pesticides urgently needed in agriculture.

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35

Ma, Lie-Feng, Hao-Ying Qian, Yang Zheng, et al. "The structures of xenorine A–C from the entomopathogenic bacterium Xenorhabdus indica." Journal of Chemical Research 41, no. 5 (2017): 262–65. http://dx.doi.org/10.3184/174751917x14925986241016.

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Three new compounds, xenorine A-C, along with six known compounds were isolated from the cultured broth of Xenorhabdus indica. The chemical structures of these compounds were elucidated mainly by analysis of 1D and 2D NMR and MS data. The major metabolites were dioxopiperazines. In addition, 5,6,11,11a-tetrahydro-1 H-imidazo[1′,5′:1,6]pyrido[3,4- b]indole-1,3(2 H)-dione, previously described as synthetic product, was isolated as a natural product. The absolute configuration was determined using quantum chemical time-dependent density functional theory calculations. The six known compounds showed weak in vitro immunosuppressive activity towards concanavalin-A- and lipopolysaccharide -induced proliferation of mice splenocytes.

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36

Shin, Hee Jae, Chang-Su Heo, Cao Van Anh, Yeo Dae Yoon, and Jong Soon Kang. "Streptoglycerides E–H, Unsaturated Polyketides from the Marine-Derived Bacterium Streptomyces specialis and Their Anti-Inflammatory Activity." Marine Drugs 20, no. 1 (2022): 44. http://dx.doi.org/10.3390/md20010044.

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Four new streptoglycerides E–H (1–4), with a rare 6/5/5/-membered ring system, were isolated from a marine-derived actinomycete Streptomyces specialis. The structures of 1–4 were elucidated by detailed analysis of HRESIMS, 1D and 2D NMR data and ECD spectra as well as comparison of their spectroscopic data with those reported in literature. Compounds 1–4 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production in Raw 264.7 cells with IC50 values ranging from 3.5 to 10.9 µM. Especially, 2 suppressed mRNA expression levels of iNOS and IL-6 without cytotoxicity.

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37

Li, Guo-Li, Hui-Min Qi, Yi-Lin He, Yu-Kai Shen, and Tong Shen. "Concanamycin H from the soil actinomycete Streptomyces sp. R1706-8." Journal of Chemical Research 46, no. 4 (2022): 174751982211091. http://dx.doi.org/10.1177/17475198221109161.

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The actinomycete strain R1706-8 is isolated from a soil sample collected from the nest of the horned-face bee ( Osmia cornifrons) and identified as Streptomyces sp. based upon the results of 16SrRNA sequence analysis. Two concanamycin derivatives obtained from the solid fermentation have been determined by analysis of the infrared, high-resolution electrospray ionization mass spectrometry, 1D and 2D NMR spectra as well as by comparison with literature data. Of the two derivatives, one is a new compound, named concanamycin H, and the other is the known compound, concanamycin G. These compounds are assayed for antibacterial activity, with concanamycins H and G displaying inhibitory activity against Bacillus subtilis (minimum inhibitory concentration = 0.625 µg mL−1).

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38

Yamada, Takeshi, Ayano Fujii, and Takashi Kikuchi. "New Diterpenes with a Fused 6-5-6-6 Ring System Isolated from the Marine Sponge-Derived Fungus Trichoderma harzianum." Marine Drugs 17, no. 8 (2019): 480. http://dx.doi.org/10.3390/md17080480.

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New diterpenes, namely, trichodermanins F–H, with a fused 6-5-6-6 ring system were isolated from the fungus Trichoderma harzianum OUPS-111D-4 separated from a marine sponge Halichondria okadai. These chemical structures were elucidated by 1D and 2D NMR as well as high-resolution fast atom bombardment mass spectrometry (HRFABMS) spectral analyses. We established their absolute stereostructures by application of the modified Mosher’s method or circular dichroism (CD) spectroscopy. In addition, their cytotoxicities were assessed using several cancer cell lines, with 1 and 2 exhibiting modest activities.

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39

Niemevz, Fernando, and Graciela Y. Buldain. "Phenyl biliverdin isomers obtained by chemical oxidation of iron(III) complex of 5-phenyl protoporphyrin IX." Journal of Porphyrins and Phthalocyanines 08, no. 07 (2004): 989–95. http://dx.doi.org/10.1142/s1088424604000350.

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Oxidative cleavage of synthetic 5-phenyl protohemin IX in pyridine solution in the presence of ascorbic acid (coupled oxidation), followed by esterification of the products with boron trifluoride-methanol rendered mainly three isomeric biliverdins. These were identified by MS and 1D and 2D 1 H NMR as 15-phenyl biliverdin IXβ (1), 10-phenyl biliverdin IXγ (2) and 5-phenyl biliverdin IXδ (3) dimethyl esters. The fact that biliverdin IXα dimethyl ester derivative is not obtained indicates that oxidation fails to occur in the α-meso-carbon bearing the phenyl group.

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40

Phan, Thanh-Tung, Hoang-Khang Le, Thuy-Duong Ngo Thi, Hoang-Long Ngo, Kim-Thuy Tran, and That-Quang Ton. "Chemical constituents of the methanol extract of Hibiscus sabdariffa (Linn) seeds." Tạp chí Khoa học - Trường Đại học Sư phạm Hà Nội 2 1, no. 2 (2022): 76–80. http://dx.doi.org/10.56764/hpu2.jos.2022.1.2.76-80.

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The flower of Hibiscus sabdariffa Linn (Malvaceae) is used in food preparation in sauces, jams, juices, jellies, syrups, flavoring, and has some medicinal uses. Most of the bioactivities of H. sabdariffa L. is antioxidant which has a large amount of phenolic compounds. The phytochemical investigation of the ethyl acetate extract from the flowers led to the isolation of five compounds named 1-O-Acetylglycerol (1), 4-Hydroxybenzaldehyde (2), 3-C-(hydroxymethyl)-β-D- erythrofuranoside (3). Their structures were elucidated by 1D-, 2D-NMR spectra as well as by comparison with those reported in the literature.

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41

Li, Guoli, Zhengyu Liu, Jiacheng Xie, et al. "Chemical Constituents of Oxytropis ochrocephala." Molecules 30, no. 12 (2025): 2489. https://doi.org/10.3390/molecules30122489.

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A new lignan (1) and a new phenolic glycoside (2), together with eighteen known compounds (3–20), were isolated from Oxytropis ochrocephala. Their structures were unambiguously elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR), and HR-ESI-MS analysis, as well as by comparison with the literature. The insecticidal activity of these compounds was evaluated against Tetranychus urticae Koch, and the results showed that compounds 3, 9, 15, and 16 had a weak inhibitory effect at a concentration of 1 mg/mL after treatment for 24 h.

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42

Vemulapalli, Sahithya Phani Babu, Juan Carlos Fuentes-Monteverde, Niels Karschin, Tatsuo Oji, Christian Griesinger, and Klaus Wolkenstein. "Structure and Absolute Configuration of Phenanthro-perylene Quinone Pigments from the Deep-Sea Crinoid Hypalocrinus naresianus." Marine Drugs 19, no. 8 (2021): 445. http://dx.doi.org/10.3390/md19080445.

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Two new water-soluble phenanthroperylene quinones, gymnochrome H (2) and monosulfated gymnochrome A (3), as well as the known compounds gymnochrome A (4) and monosulfated gymnochrome D (5) were isolated from the deep-sea crinoid Hypalocrinus naresianus, which had been collected in the deep sea of Japan. The structures of the compounds were elucidated by spectroscopic analysis including HRMS, 1D 1H and 13C NMR, and 2D NMR. The absolute configuration was determined by ECD spectroscopy, analysis of J-couplings and ROE contacts, and DFT calculations. The configuration of the axial chirality of all isolated phenanthroperylene quinones (2–5) was determined to be (P). For gymnochrome H (2) and monosulfated gymnochrome A (3), a (2′S,2″R) configuration was determined, whereas for monosulfated gymnochrome D (5) a (2′R,2″R), configuration was determined. Acetylated quinones are unusual among natural products from an echinoderm and gymnochrome H (2) together with the recently reported gymnochrome G (1) represent the first isolated acetylated phenanthroperylene quinones.

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43

Henderson, William, Obinna Okpareke, Ainnul Azizan та Edward Tiekink. "[Dicyclohexyl(sulfanylidene)-λ5-phosphanyl]methanol". Molbank 2019, № 3 (2019): M1069. http://dx.doi.org/10.3390/m1069.

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The title compound, [dicyclohexyl(sulfanylidene)-λ5-phosphanyl]methanol, Cy2P(=S)CH2OH (1), was obtained from the reaction between [Cy2P(CH2OH)2]Cl with one molar equivalent of NaOH and an excess of elemental sulfur (powdered). Characterization was by a single-crystal X-ray structure determination as well as IR, and 1D-NMR (1H, 13C{1H}, 31P{1H}), and 2D-NMR (DEPT-135 and HSQC) spectroscopy, ESI mass spectrometry, and elemental analysis. X-ray crystallography on Compound 1 shows the phosphorus atom to be tetrahedrally coordinated within a non-symmetric C3S donor set but with relatively minor distortions from the ideal geometry. In the molecular packing, hydroxyl-O–H⋯S(thione) hydrogen bonds led to supramolecular helical chains along the b-axis direction.

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44

El-Shazly, Assem, Afaf El-Sayed, and Eman Fikrey. "Department of Pharmaceutical Care, General Hospital of Chinese PLA, Beijing, 100853, P. R. China." Zeitschrift für Naturforschung C 67, no. 7-8 (2012): 353–59. http://dx.doi.org/10.1515/znc-2012-7-801.

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Column chromatography of the light petroleum fraction from the methanolic extract of the stem bark of Salix tetrasperma Roxb. (Salicaceae) resulted in the isolation of β-sitosterol acetate, friedelin, 3β-friedelinol, β-amyrin, β-sitosterol, β-sitosterol-O-glucoside in addition to palmitic acid. From the dichloromethane fraction of the leaves, catechol and tremulacin were isolated. Salicin and its derivatives tremuloidin and 2’-O-p-(E)-coumaroyl salicin were isolated from the ethyl acetate fraction of the leaves. The isolated compounds were identified by MS, and 1D NMR (1H and 13C) and 2D NMR (H-H COSY, HSQC, and HMBC) spectral analyses. The total methanolic extract exhibited significant anti-inflammatory activity (rat hind paw oedema). The extract with a content of 120 mg/kg body weight produced 52% inhibition equivalent to the standard diclofenac sodium (54% inhibition). The antioxidant (DPPH free radical scavenging) and analgesic activities, respectively, were also evaluated.

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45

Arfan, Muhammad, Khaled A. Shaaban, Anja Schüffler, and Hartmut Laatsch. "Furanone Derivatives from Terrestrial Streptomyces spp." Natural Product Communications 7, no. 9 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700925.

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Chemical investigation of the terrestrial Streptomyces sp. isolates GT2005/020 and ANK148 led to the isolation of two microbial furanone derivatives, 5-hydroxy-4-methylnaphtho[1,2-b]furan-3-one (1) and 4-hydroxy-5-methyl-furan-3-one (2), respectively, which have some similarity to quorum sensing molecules of the AI-2 type. In addition, the known compounds chalcomycin, ferulic acid, indole-3-acetic acid, uracil, thymine, 2′-deoxy-thymidin, monensin B (3), phencomycin, and 1-acetyl-β-carboline were isolated. The structures of 1 and 2 were deduced from extensive studies of NMR (1D and 2D) and mass spectra. Additionally, the complete NMR shift assignments for monensin B (3) using H-H COSY, HMQC and HMBC experiments are reported here for the first time. We are describing the taxonomy and fermentation of the producing strains, the structure elucidation of the new metabolites and their bioactivity.

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46

Chen, De-Li, Xu-Dong Xu, Rong-Tao Li, et al. "Five New Cucurbitane-Type Triterpenoid Glycosides from the Rhizomes of Hemsleya penxianensis with Cytotoxic Activities." Molecules 24, no. 16 (2019): 2937. http://dx.doi.org/10.3390/molecules24162937.

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Five new cucurbitane-typetriterpenoid glycosides, named Xuedanoside F–J (1–5), were obtained from the rhizomes of Hemsleya penxianensis (Xue dan), which belongs to the family of Cucurbitaceae. These new compounds were elucidated byspectroscopic analysis, including 1D, 2D NMR, and HR-ESI-MS spectra. Additionally, all the isolates were evaluated for cytotoxicity against three human cancer cell lines (Hela, MCF-7, and A-549) with the IC50 ranging from 2.25 to 49.44 µM in vitro with treatment 48 h and showed low cytotoxicity in human normal liver L-02 cells (IC50 > 50 µM). Compound 5 showed the most significant cytotoxic activity with the IC50 value of 2.25, 4.72, and 5.33 µM in 48 h, respectively.

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47

Hasin, Ohad, and Shmuel Carmeli. "Isolation and Structure Elucidation of Secondary Metabolites from a Microcystis sp. Bloom Material Collected in Southern Israel." Natural Product Communications 13, no. 10 (2018): 1934578X1801301. http://dx.doi.org/10.1177/1934578x1801301020.

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The hydrophilic extract of Microcystis sp. bloom material collected from Bror Hayil Reservoir in southern Israel afforded four new metabolites, (2 S,3 S)-3-hydeoxy-1,4-diphenylbutan-2-yl-acetate, aeruginosins BH604, BH462A and BH462B, and two known metabolites cyanopeptolins S and SS. The planar structure of 1–4 was established by analyses of their 1D and 2D NMR data and mass spectrometric data. The absolute configurations of the chiral centers of 1 were established by Mosher method and analysis of the coupling constants between H-2 and H-3, and those of 2–4 by Merfay's method and advanced Merfay's method and chiral HPLC. The compounds do not inhibit the serine proteases trypsin and thrombin.

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48

Rajana, Nagaraju, Dharamasoth Rama Devi, Dinne Naresh Kumar Reddy, J. Moses Babu, K. Basavaiah, and K. Balakumaran. "Characterization of Five Oxidative Degradation Impurities and One Process Impurity of Suvorexant Drug Substance by LC-MS/MS, HR-MS and 1D, 2D NMR: Validation of Suvorexant Drug Substance and Process Impurities by HPLC and UPLC." Journal of Chromatographic Science 58, no. 5 (2020): 433–44. http://dx.doi.org/10.1093/chromsci/bmaa003.

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Abstract During the oxidative (10% H2O2) degradation of suvorexant drug substance, around 1.0% of one impurity and less than 1.0% four impurities were found by a new high-performance liquid chromatography (HPLC) assay and related substance method. The mass numbers of 1.0% impurity was 469 [M + H]+, remaining four impurities were 172 [M + H]+, 467 [M + H]+, 483 [M + H]+ and 485 [M + H]+. The 469 [M + H]+, 485[M + H] and 172 [M + H]+ impurities were characterized by using the LC-MS/MS, HR-MS and 1D, 2D NMR spectroscopic data. The 172 [M + H]+ impurity was prepared synthetically and co-injected in HPLC. The retention time of synthesized 172 [M + H]+ impurity was matching with the unknown degradation impurity in HPLC. The developed mass compatible HPLC and ultra performance liquid chromatography methods were validated for drug substance and process impurities by following ICH Q2 (R1) guidelines.

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49

Agarkov, Artem S., Anna A. Nefedova, Elina R. Gabitova, et al. "(2-Hydroxy-3-Methoxybenzylidene)thiazolo[3,2-a]pyrimidines: Synthesis, Self-Assembly in the Crystalline Phase and Cytotoxic Activity." International Journal of Molecular Sciences 24, no. 3 (2023): 2084. http://dx.doi.org/10.3390/ijms24032084.

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A series of new 2-hydroxy-3-methoxybenzylidenethiazolo[3,2-a]pyrimidines with different aryl substituents at the 5 position are synthesized and characterized by 1H/ 13C NMR and IR-spectroscopy and mass-spectrometry, as well as single crystal X-ray diffraction (SCXRD). It was demonstrated that the type of hydrogen bonding can play a key role in the chiral discrimination of these compounds in the crystalline phase. The hydrogen bond of the O–H...N type leads to 1D supramolecular heterochiral chains or conglomerate crystallization in the case of the formation of homochiral chains. The hydrogen bond of O–H...O type gave racemic dimers, which are packed into 2D supramolecular layers with a parallel or angular dimers arrangement. Halogen bonding of the N...Br or O...Br type brings a new motif into supramolecular self-assembly in the crystalline phase: the formation of 1D supramolecular homochiral chains instead 2D supramolecular layers. The study of cytotoxicity against various tumor cells in vitro was carried out. It was found that 2-hydroxy−3-methoxybenzylidenethiazolo[3,2-a]pyrimidines with 3-nitrophenyl substituent at C5 carbon atom demonstrated a high efficiency against M-HeLa (cervical adenocarcinoma) and low cytotoxicity against normal liver cells.

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50

Tabakmakher, Kseniya M., Tatyana N. Makarieva, Vladimir A. Denisenko, et al. "New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities." Marine Drugs 17, no. 8 (2019): 445. http://dx.doi.org/10.3390/md17080445.

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Seven new unusual polysulfated steroids—topsentiasterol sulfate G (1), topsentiasterol sulfate I (2), topsentiasterol sulfate H (3), bromotopsentiasterol sulfate D (4), dichlorotopsentiasterol sulfate D (8), bromochlorotopsentiasterol sulfate D (9), and 4β-hydroxyhalistanol sulfate C (10), as well as three previously described—topsentiasterol sulfate D (7), chlorotopsentiasterol sulfate D (5) and iodotopsentiasterol sulfate D (6) have been isolated from the marine sponge Halichondria vansoesti. Structures of these compounds were determined by detailed analysis of 1D- and 2D-NMR and HRESIMS data, as well as chemical transformations. The effects of the compounds on human prostate cancer cells PC-3 and 22Rv1 were investigated.

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