Dataset Information

Xylopidimers A-E, Five New Guaiane Dimers with Various Carbon Skeletons from the Roots of Xylopia vielana.

ABSTRACT: Five new guaiane dimers, xylopidimers A-E (1-5), were isolated and identified from the roots of Xylopia vielana. The structures of 1-5 were elucidated by spectroscopic analysis and further confirmed by single-crystal X-ray diffraction. On the basis of the results of single-crystal X-ray analysis, 1-5 showed different carbon skeletons. Among these compounds, the unique connecting patterns of 1 and 2 caused significant differences on their carbon skeletons, which have not been reported. Moreover, 3-5 were also three new guaiane dimers. Among these compounds, 4 exhibited potent inhibitory activity against the production of nitric oxide with an IC₅₀ value of 4.59 ?M in RAW264.7 cells stimulated by lipopolysaccharide.

SUBMITTER: Guo YG

PROVIDER: S-EPMC6648509 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Xylopidimers A-E, Five New Guaiane Dimers with Various Carbon Skeletons from the Roots of Xylopia vielana.

Guo Yi-Gong YG Xie Yang-Guo YG Wu Guo-Jing GJ Cheng Tao-Fang TF Zhu Sheng-Lan SL Yan Shi-Kai SK Jin Hui-Zi HZ Zhang Wei-Dong WD

ACS omega 20190125 1

Five new guaiane dimers, xylopidimers A-E (1-5), were isolated and identified from the roots of Xylopia vielana. The structures of 1-5 were elucidated by spectroscopic analysis and further confirmed by single-crystal X-ray diffraction. On the basis of the results of single-crystal X-ray analysis, 1-5 showed different carbon skeletons. Among these compounds, the unique connecting patterns of 1 and 2 caused significant differences on their carbon skeletons ...[more]

PMID: 31459455

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Project description:Nicotinamide adenine dinucleotide (NAD) is a central molecule in cellular metabolism that has been implicated in human health, the aging process, and an array of human diseases. NAD is well known as an electron storage molecule, cycling between NAD and the reduced NADH. In addition, NAD is cleaved into nicotinamide and Adenine diphosphate ribose by NAD-consuming enzymes such as sirtuins, PARPs and CD38. There are numerous pathways for the biosynthesis of NAD to maintain a baseline concentration and thus avoid cellular death. The NAD salvage pathway, a two-step process to regenerate NAD after cleavage, is the predominant pathway for humans. Nicotinamide PhosphribosylTransferase (NAMPT) is the rate-limiting enzyme within the salvage path. Exposure to pharmacological modulators of NAMPT has been reported to either deplete or increase NAD levels. This study used a curated set of virtual compounds coupled with biochemical assays to identify novel activators of NAMPT. Autodock Vina generated a ranking of the National Cancer Institute's Diversity Set III molecular library. The library contains a set of organic molecules with diverse functional groups and carbon skeletons that can be used to identify lead compounds. The target NAMPT surface encompassed a novel binding location that included the NAMPT dimerization plane, the openings to the two active site channels, and a portion of the known binding location for NAMPT substrate and product. Ranked molecules were evaluated in a biochemical assay using purified recombinant NAMPT enzyme. Two novel carbon skeletons were confirmed to stimulate NAMPT activity. Compound 20 (NSC9037) is a polyphenolic xanthene derivative in the fluorescein family, while compound 2 (NSC19803) is the polyphenolic myricitrin nature product. Micromolar quantities of compound 20 or compound 2 can double NAMPT's product formation. In addition, natural products that contain high concentrations of polyphenolic flavonoids, similar to myricitrin, also stimulate NAMPT activity. Confirmation of a novel binding site for these compounds will further our understanding of the cellular mechanism leading to NAD homeostasis and better human health outcomes.

Dataset Information

Xylopidimers A-E, Five New Guaiane Dimers with Various Carbon Skeletons from the Roots of Xylopia vielana.

Publications

Xylopidimers A-E, Five New Guaiane Dimers with Various Carbon Skeletons from the Roots of <i>Xylopia vielana</i>.

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