Effect of Momordica charantia Administration on Anthropometric Measures and Metabolic Profile in Patients with Obesity: A Pilot Clinical Trial

Marisol Cortez-Navarrete,Miriam Mendez-del Villar,Esperanza Martınez-Abundis,Luis D. Lo´pez-Murillo,Miriam de J. Escobedo-Gutie´rrez,Lizet Y. Rosales-Rivera,Karina G. Perez-Rubio 한국식품영양과학회 2022 Journal of medicinal food Vol.25 No.6

The aim of this study was to evaluate the effect of Momordica charantia (MC) administration on anthropometric measures in patients with obesity. A randomized, double-blind, placebo-controlled pilot clinical trial was carried out in 24 patients with obesity. Twelve patients randomly received MC (2000 mg/day) for 12 weeks, and 12 patients received placebo. Body weight (BW), body mass index (BMI), waist circumference (WC), body fat percentage, as well as clinical and laboratory determinations, were evaluated before and after the intervention. Results showed that while reductions in BW, BMI, WC, and body fat percentage were observed in the MC group, these differences did not reach statistical significance. Significant decreases in triglycerides (TG) (1.9 ± 0.6 mM vs. 1.7 ± 0.7 mM, P ≤ .05) and very low-density lipoprotein (VLDL) (0.4 ± 0.1 mM vs. 0.3 ± 0.1 mM, P ≤ .05) levels were found after the intervention with MC. In contrast, significant increases in BW (83.0 ± 10.7 kg vs. 84.6 ± 9.1 kg, P ≤ .05) and BMI (31.9 ± 1.5 kg/m2 vs. 33.0 ± 1.3 kg/m2, P ≤ .05) were observed in the placebo group. In conclusion, no significant reductions in BW, BMI, WC, and body fat percentage were observed after MC administration; however, MC significantly decreased TG and VLDL levels. The protocol was registered at ClinicalTrials.gov with the identifier NCT04916379.

Push–Pull Type Oligo(<i>N</i>-annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties

Zeng, Zebing,Lee, Sangsu,Son, Minjung,Fukuda, Kotaro,Burrezo, Paula Mayorga,Zhu, Xiaojian,Qi, Qingbiao,Li, Run-Wei,Navarrete, Juan T. Ló,pez,Ding, Jun,Casado, Juan,Nakano, Masayoshi,Kim, Dongho American Chemical Society 2015 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.137 No.26

<P>Research on stable open-shell singlet diradicaloids recently became a hot topic because of their unique optical, electronic, and magnetic properties and promising applications in materials science. So far, most reported singlet diradicaloid molecules have a symmetric structure, while asymmetric diradicaloids with an additional contribution of a dipolar zwitterionic form to the ground state were rarely studied. In this Article, a series of new push pull type oligo(N-annulated perylene)quinodimethanes were synthesized. Their chain length and solvent-dependent ground states and physical properties were systematically investigated by various experimental methods such as steady-state and transient absorption, two-photon absorption, X-ray crystallographic analysis, electron spin resonance, superconducting quantum interference device, Raman spectroscopy, and electrochemistry. It was found that with extension of the chain length, the diradical character increases while the contribution of the zwitterionic form to the ground state becomes smaller. Because of the intramolecular charge transfer character, the physical properties of this push pull system showed solvent dependence. In addition, density functional theory calculations on the diradical character and Hirshfeld charge were conducted to understand the chain length and solvent dependence of both symmetric and asymmetric systems. Our studies provided a comprehensive understanding on the fundamental structure and environment property relationships in the new asymmetric diradicaloid systems.</P>

Kinetically Blocked Stable Heptazethrene and Octazethrene: Closed-Shell or Open-Shell in the Ground State?

Li, Yuan,Heng, Wee-Kuan,Lee, Byung Sun,Aratani, Naoki,Zafra, José,L.,Bao, Nina,Lee, Richmond,Sung, Young Mo,Sun, Zhe,Huang, Kuo-Wei,Webster, Richard D.,Ló,pez Navarrete, Juan T.,Kim, Dongh American Chemical Society 2012 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.134 No.36

<P>Polycyclic aromatic hydrocarbons with an open-shell singlet biradical ground state are of fundamental interest and have potential applications in materials science. However, the inherent high reactivity makes their synthesis and characterization very challenging. In this work, a convenient synthetic route was developed to synthesize two kinetically blocked heptazethrene (<B>HZ-TIPS</B>) and octazethrene (<B>OZ-TIPS</B>) compounds with good stability. Their ground-state electronic structures were systematically investigated by a combination of different experimental methods, including steady-state and transient absorption spectroscopy, variable temperature NMR, electron spin resonance (ESR), superconducting quantum interfering device (SQUID), FT Raman, and X-ray crystallographic analysis, assisted by unrestricted symmetry-broken density functional theory (DFT) calculations. All these demonstrated that the heptazethrene derivative <B>HZ-TIPS</B> has a closed-shell ground state while its octazethrene analogue <B>OZ-TIPS</B> with a smaller energy gap exists as an open-shell singlet biradical with a large measured biradical character (<I>y</I> = 0.56). Large two-photon absorption (TPA) cross sections (σ<SUP>(2)</SUP>) were determined for <B>HZ-TIPS</B> (σ<SUP>(2)</SUP><SUB>max</SUB> = 920 GM at 1250 nm) and <B>OZ-TIPS</B> (σ<SUP>(2)</SUP><SUB>max</SUB> = 1200 GM at 1250 nm). In addition, <B>HZ-TIPS</B> and <B>OZ-TIPS</B> show a closely stacked 1D polymer chain in single crystals.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2012/jacsat.2012.134.issue-36/ja304618v/production/images/medium/ja-2012-04618v_0015.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja304618v'>ACS Electronic Supporting Info</A></P>

Stable Tetrabenzo-Chichibabin’s Hydrocarbons: Tunable Ground State and Unusual Transition between Their Closed-Shell and Open-Shell Resonance Forms

Zeng, Zebing,Sung, Young Mo,Bao, Nina,Tan, Davin,Lee, Richmond,Zafra, José,L.,Lee, Byung Sun,Ishida, Masatoshi,Ding, Jun,Ló,pez Navarrete, Juan T.,Li, Yuan,Zeng, Wangdong,Kim, Dongho,Huang American Chemical Society 2012 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.134 No.35

<P>Stable open-shell polycyclic aromatic hydrocarbons (PAHs) are of fundamental interest due to their unique electronic, optical, and magnetic properties and promising applications in materials sciences. Chichibabin’s hydrocarbon as a classical open-shell PAH has been investigated for a long time. However, most of the studies are complicated by their inherent high reactivity. In this work, two new stable benzannulated Chichibabin’s hydrocarbons <B>1-CS</B> and <B>2-OS</B> were prepared, and their electronic structure and geometry in the ground state were studied by various experiments (steady-state and transient absorption spectra, NMR, electron spin resonance (ESR), superconducting quantum interference device (SQUID), FT Raman, X-ray crystallographic etc.) and density function theory (DFT) calculations. <B>1-CS</B> and <B>2-OS</B> exhibited tunable ground states, with a closed-shell quinoidal structure for <B>1-CS</B> and an open-shell biradical form for <B>2-OS</B>. Their corresponding excited-state forms <B>1-OS</B> and <B>2-CS</B> were also chemically approached and showed different decay processes. The biradical <B>1-OS</B> displayed an unusually slow decay to the ground state (<B>1-CS</B>) due to a large energy barrier (95 ± 2.5 kJ/mol) arising from severe steric hindrance during the transition from an orthogonal biradical form to a butterfly-like quinoidal form. The quick transition from the quinoidal <B>2-CS</B> (excited state) to the orthogonal biradicaloid <B>2-OS</B> (ground state) happened during the attempted synthesis of <B>2-CS</B>. Compounds <B>1-CS</B> and <B>2-OS</B> can be oxidized into stable dications by FeCl<SUB>3</SUB> and/or concentrated H<SUB>2</SUB>SO<SUB>4</SUB>. The open-shell <B>2-OS</B> also exhibited a large two-photon absorption (TPA) cross section (760 GM at 1200 nm).</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2012/jacsat.2012.134.issue-35/ja3050579/production/images/medium/ja-2012-050579_0017.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja3050579'>ACS Electronic Supporting Info</A></P>

(Semi)ladder-Type Bithiophene Imide-Based All-Acceptor Semiconductors: Synthesis, Structure-Property Correlations, and Unipolar n-Type Transistor Performance

Wang, Yingfeng,Guo, Han,Harbuzaru, Alexandra,Uddin, Mohammad Afsar,Arrechea-Marcos, Iratxe,Ling, Shaohua,Yu, Jianwei,Tang, Yumin,Sun, Huiliang,Ló,pez Navarrete, Juan Teodomiro,Ortiz, Rocio Ponce American Chemical Society 2018 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.140 No.19

<P>Development of high-performance unipolar n-type organic semiconductors still remains as a great challenge. In this work, all-acceptor bithiophene imide-based ladder-type small molecules BTI<I>n</I> and semiladder-type homopolymers PBTI<I>n</I> (<I>n</I> = 1-5) were synthesized, and their structure-property correlations were studied in depth. It was found that Pd-catalyzed Stille coupling is superior to Ni-mediated Yamamoto coupling to produce polymers with higher molecular weight and improved polymer quality, thus leading to greatly increased electron mobility (μ<SUB>e</SUB>). Due to their all-acceptor backbone, these polymers all exhibit unipolar n-type transport in organic thin-film transistors, accompanied by low off-currents (10<SUP>-10</SUP>-10<SUP>-9</SUP> A), large on/off current ratios (10<SUP>6</SUP>), and small threshold voltages (∼15-25 V). The highest μ<SUB>e</SUB>, up to 3.71 cm<SUP>2</SUP> V<SUP>-1</SUP> s<SUP>-1</SUP>, is attained from PBTI1 with the shortest monomer unit. As the monomer size is extended, the μ<SUB>e</SUB> drops by 2 orders to 0.014 cm<SUP>2</SUP> V<SUP>-1</SUP> s<SUP>-1</SUP> for PBTI5. This monotonic decrease of μ<SUB>e</SUB> was also observed in their homologous BTI<I>n</I> small molecules. This trend of mobility decrease is in good agreement with the evolvement of disordered phases within the film, as revealed by Raman spectroscopy and X-ray diffraction measurements. The extension of the ladder-type building blocks appears to have a large impact on the motion freedom of the building blocks and the polymer chains during film formation, thus negatively affecting film morphology and charge carrier mobility. The result indicates that synthesizing building blocks with more extended ladder-type backbone does not necessarily lead to improved mobilities. This study marks a significant advance in the performance of all-acceptor-type polymers as unipolar electron transporting materials and provides useful guidelines for further development of (semi)ladder-type molecular and polymeric semiconductors for applications in organic electronics.</P> [FIG OMISSION]</BR>

Benzo-thia-fused [ <i>n</i> ]thienoacenequinodimethanes with small to moderate diradical characters: the role of pro-aromaticity <i>versus</i> anti-aromaticity

Shi, Xueliang,Quintero, Estefaní,a,Lee, Sangsu,Jing, Linzhi,Herng, Tun Seng,Zheng, Bin,Huang, Kuo-Wei,Ló,pez Navarrete, Juan T.,Ding, Jun,Kim, Dongho,Casado, Juan,Chi, Chunyan Royal Society of Chemistry 2016 Chemical Science Vol.7 No.5

<▼1><P>Pro-aromatic <B>Th<I>n</I>-TIPS</B> exhibits distinctly different physical properties from anti-aromatic <B>S<I>n</I>-TIPS</B>.</P></▼1><▼2><P>Open-shell singlet diradicaloids have recently received much attention due to their unique optical, electronic and magnetic properties and promising applications in materials science. Among various diradicaloids, quinoidal π-conjugated molecules have become the prevailing design. However, the need for a fundamental understanding on how the fusion mode and pro-aromaticity/anti-aromaticity affect their diradical character and physical properties remains unaddressed. In this work, a series of pro-aromatic benzo-thia-fused [<I>n</I>]thienoacenequinodimethanes (<B>Th<I>n</I>-TIPS</B> (<I>n</I> = 1–3) and <B>BDTh-TIPS</B>) were synthesized and compared with the previously reported anti-aromatic bisindeno-[<I>n</I>]thienoacenes (<B>S<I>n</I>-TIPS</B>, <I>n</I> = 1–4). The ground-state geometric and electronic structures of these new quinoidal molecules were systematically investigated by X-ray crystallographic analysis, variable temperature NMR, ESR, SQUID, Raman, and electronic absorption spectroscopy, assisted by DFT calculations. It was found that the diradical character index (<I>y</I><SUB>0</SUB>) increased from nearly zero for <B>Th1-TIPS</B> to 2.4% for <B>Th2-TIPS</B>, 18.2% for <B>Th3-TIPS</B>, and 38.2% for <B>BDTh-TIPS</B>, due to the enhanced aromatic stabilization. Consequently, with the extension of molecular size, the one-photon absorption spectra are gradually red-shifted, the two-photon absorption (TPA) cross section values increase, and the singlet excited state lifetimes decrease. By comparison with the corresponding anti-aromatic analogues <B>S<I>n</I>-TIPS</B> (<I>n</I> = 1–3), the pro-aromatic <B>Th<I>n</I>-TIPS</B> (<I>n</I> = 1–3) exhibit larger diradical character, longer singlet excited state lifetime and larger TPA cross section value. At the same time, they display distinctively different electronic absorption spectra and improved electrochemical amphotericity. Spectroelectrochemical studies revealed a good linear relationship between the optical energy gaps and the molecular length in the neutral, radical cationic and dicationic forms. Our research work discloses a significant difference between the pro-aromatic and anti-aromatic quinoidal compounds and provides guidance for the design of new diradicaloids with desirable properties.</P></▼2>