Highly Oxygenated Dimeric Grayanane Diterpenoids as Analgesics: <scp>TRPV1</scp> and <scp>TRPA1</scp> Dual Antagonists from <i>Rhododendron molle</i>

Huang, Lang; Zheng, Guijuan; Yang, Feng; Jin, Pengfei; Gao, Biao; Zhang, Hanqi; Ma, Xiaomin; Zhou, Junfei; Yao, Guangmin

doi:10.1002/cjoc.202200348

Cited by 13 publications

(11 citation statements)

References 44 publications

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“…2). [45][46][47][48] The experimental ECD spectrum of our synthetic 5 matched well with the calculated spectrum of (3S,4aS,5R,11R,11aR)-5, while being opposite to that of (3R,4aR,5S,11S,11aS)-5. Thus, the absolute configuration of our synthetic 5 was assigned 3S,4aS,5R,11R,11aR.…”

Section: Resultssupporting

confidence: 73%

Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

Wang,

Xu,

Yan

et al. 2024

Org. Chem. Front.

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Section: Resultssupporting

confidence: 73%

Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

Wang,

Xu,

Yan

et al. 2024

Org. Chem. Front.

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“…DP4+ probability analysis has been proved to be a powerful method to determine the relative configuration of complex natural products. − To assign the full relative configuration of 1 , the 13 C NMR data of four potential isomers ( 1a–1d ) (Figure S3) were calculated by the GIAO method at the B3LYP/IEFPCM/6-311G(d,p) level using Gaussian 09 software, and (3′ R *,5‴ R *)- 1a had a better correlation coefficient ( R 2 = 0.9950) between the experimental and calculated 13 C NMR chemical shifts than three other isomers (Figures A and S4). Further DP4+ probability analysis suggested the (3′ R *,5‴ R *)-configuration of 1 with a high probability of 97.77% (Figures A and S5).…”

Section: Resultsmentioning

confidence: 99%

Piericones A and B as Potent Antithrombotics: Nanomolar Noncompetitive Protein Disulfide Isomerase Inhibitors with an Unexpected Chemical Architecture

Zheng

Huang

et al. 2023

J. Am. Chem. Soc.

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Extracellular protein disulfide isomerase (PDI) is a promising target for thrombotic-related diseases. Four potent PDI inhibitors with unprecedented chemical architectures, piericones A–D (1–4), were isolated from Pieris japonica. Their structures were elucidated by spectroscopic data analysis, chemical methods, quantum 13C nuclear magnetic resonance DP4+ and electronic circular dichroism calculations, and single-crystal X-ray diffraction analysis. Piericones A (1) and B (2) were nanomolar noncompetitive PDI inhibitors possessing an unprecedented 3,6,10,15-tetraoxatetracyclo[7.6.0.04,9.01,12]pentadecane motif with nine contiguous stereogenic centers. Their biosynthetic pathways were proposed to include a key intermolecular aldol reaction and an intramolecular 1,2-migration reaction. Piericone A (1) significantly inhibited in vitro platelet aggregation and fibrin formation and in vivo thrombus formation via the inhibition of extracellular PDI without increasing the bleeding risk. The molecular docking and dynamics simulation of 1 and 2 provided a novel structure basis to develop PDI inhibitors as potent antithrombotics.

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“…The electronic CD (ECD) spectra of (5″R)-1 and its enantiomer were calculated at the LC-wPBE/6-311G (d,p) level with Gaussian 09 software. 30 The calculation method referred to the reported article with appropriate modifications, 31 and the specific steps are shown in the Supporting Information.…”

Section: Synthesis and Isolationmentioning

confidence: 99%

Novel Flavonol Alkaloids in Green Tea: Synthesis, Detection, and Anti-Alzheimer’s Disease Effect in a Transgenic Caenorhabditis elegans CL4176 Model

Chen,

Yang,

et al. 2024

J. Agric. Food Chem.

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Novel N-ethy-2-pyrrolidinone-substituted flavonols, myricetin alkaloids A−C (1−3), quercetin alkaloids A−C (4a, 4b, and 5), and kaempferol alkaloids A and B (6 and 7), were prepared from thermal reaction products of myricetin, quercetin, kaempferol�L-theanine, respectively. We used HPLC-ESI-HRMS/MS to detect 1−7 in 14 cultivars of green tea and found that they were all present in "Shuchazao," "Longjing 43", "Fudingdabai", and "Zhongcha 108" green teas. The structures of 1−4 and 6 were determined by extensive 1D and 2D NMR spectroscopies. These flavonol alkaloids along with their skeletal flavonols were assessed for anti-Alzheimer's disease effect based on molecular docking, acetylcholinesterase inhibition, and the transgenic Caenorhabditis elegans CL4176 model. Compound 7 strongly binds to the protein amyloid β (Aβ 1−42 ) through hydrogen bonds (BE: −9.5 kcal/mol, K i : 114.3 nM). Compound 3 (100 μM) is the strongest one in significantly extending the mean lifespan (13.4 ± 0.5 d, 43.0% promotion), delaying the Aβ 1−42 -induced paralysis (PT 50 : 40.7 ± 1.9 h, 17.1% promotion), enhancing the locomotion (140.0% promotion at 48 h), and alleviating glutamic acid (Glu)-induced neurotoxicity (153.5% promotion at 48 h) of CL4176 worms (p < 0.0001).

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Highly Oxygenated Dimeric Grayanane Diterpenoids as Analgesics: TRPV1 and TRPA1 Dual Antagonists from Rhododendron molle

Cited by 13 publications

References 44 publications

Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids

Piericones A and B as Potent Antithrombotics: Nanomolar Noncompetitive Protein Disulfide Isomerase Inhibitors with an Unexpected Chemical Architecture

Novel Flavonol Alkaloids in Green Tea: Synthesis, Detection, and Anti-Alzheimer’s Disease Effect in a Transgenic Caenorhabditis elegans CL4176 Model

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