Hyperelatosides A–E, biphenyl ether glycosides from <i>Hypericum elatoides</i>, with neurotrophic activity

Yan, Xiaohai; An, Zhen; Tang, Dan; Peng, Guang-Rui; Cao, Chenyu; Xu, Yuanzhen; Li, Chun-Huan; Liu, Peiliang; Jiang, Zaimin; Gao, Jin‐Ming

doi:10.1039/c8ra05322g

Cited by 14 publications

(4 citation statements)

References 65 publications

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“…Hypericum elatoides , a perennial herb, is distributed primarily at an altitude range of 540–1600 m in the Shaanxi and Gansu provinces of northwestern China. Previous studies reported the isolation of polycyclic polyprenylated acylphloroglucinol, xanthones, biphenyl ether glycosides, and phenolic metabolites from this plant. , In the present study, four novel δ- and γ-lactone derivatives, hyperelatolides A–D ( 1 – 4 ), were obtained from the aerial parts of H. elatoides . The structures and absolute configurations of 1 – 4 were established via extensive analyses of spectroscopic data, single-crystal X-ray diffraction using Cu Kα radiation, calculated NMR chemical shifts coupled with a statistical procedure (DP4+), and electronic circular dichroism (ECD) calculations.…”

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confidence: 68%

Hyperelatolides A–D, Antineuroinflammatory Constituents with Unusual Carbon Skeletons from Hypericum elatoides

Xie,

Wang,

Liu

et al. 2023

J. Nat. Prod.

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Four new δand γ-lactone derivatives, hyperelatolides A−D (1−4, respectively), were discovered from the aerial portions of Hypericum elatoides R. Keller. Their structures were elucidated by analysis of NMR spectra, HRESIMS, quantum chemical calculations of NMR and ECD spectra, and X-ray crystallographic data. Hyperelatolides A (1) and B (2) represent the first examples of δ-lactone derivatives characterized by a (Z)-(5,5-dimethyl-2-(2-oxopropyl)cyclohexylidene)methyl moiety and a benzoyloxy group attached to the βand γ-positions of the δlactone core, respectively, while hyperelatolides C (3) and D (4) are unprecedented γ-lactone derivatives featuring substituents similar to those of 1 and 2. All compounds were tested for their inhibitory effects on NO production in LPS-activated BV-2 cells. Lactones 1 and 2 exhibited considerable antineuroinflammatory activity, with IC 50 values of 5.74 ± 0.27 and 7.35 ± 0.26 μM, respectively. Moreover, the mechanistic study revealed that lactone 1 significantly suppressed nuclear factor kappa B signaling and downregulated the expression of inducible nitric oxide synthase and cyclooxygenase-2 in LPS-induced cells, which may contribute to its antineuroinflammatory activity.

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confidence: 68%

Hyperelatolides A–D, Antineuroinflammatory Constituents with Unusual Carbon Skeletons from Hypericum elatoides

Xie,

Wang,

Liu

et al. 2023

J. Nat. Prod.

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“…Hypericum elatoides , a member of the genus Hypericum (Hypericaceae), is a perennial herb mainly distributed in Shaanxi and Gansu Provinces, northwestern China. In our ongoing search for novel and bioactive natural products from this plant 12 – 14 , five uncommon PPAPs, hyperelanitriles A–D ( 1 – 4 ) and hyperelamine A ( 5 ), were isolated from the aerial parts of H. elatoides . Their structures, including absolute configurations, were elucidated based on a combination of extensive spectroscopic data analysis, 13 C NMR calculations coupled with DP4+ probability analysis, ECD calculations, single-crystal X-ray diffraction, and chemical synthesis.…”

Section: Introductionmentioning

confidence: 99%

Discovery from Hypericum elatoides and synthesis of hyperelanitriles as α-aminopropionitrile-containing polycyclic polyprenylated acylphloroglucinols

Xie,

Li,

Yan

et al. 2024

Commun Chem

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The search for lead compounds with anti-neuroinflammatory activity from structurally ‘optimized’ natural products is a crucial and promising strategy in the quest to discover safe and efficacious agents for treating neurodegenerative diseases. A phytochemical investigation on the aerial portions of Hypericum elatoides led to the isolation of five nitrogenous polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperelanitriles A–D (1–4) and hyperelamine A (5). Their structures were determined by spectroscopic analysis, ECD and NMR calculations, and X-ray crystallography. To the best of our knowledge, compounds 1–4 represent the first examples of acylphloroglucinols featuring an α-aminonitrile moiety, while 5 is a rare enamine-containing PPAP. Further, the synthesis of these naturally occurring PPAP-based nitriles or amines was accomplished. Compound 5 exhibited inhibitory activity against LPS-activated NO production in BV-2 cells, potentially through the suppression of TLR-4/NF-κB signaling. Here we show the isolation, structural elucidation, synthesis, and bioactive evaluation of compounds 1–5.

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“…The latter were selected as many phenolics have been reported to enhance neurite outgrowth. [21][22][23] Moreover, extracellular Aβ aggregation is closely connected with declines in cell adhesion and neurite outgrowth. [24] Thus, the promotion of neurite may see a reversal or may serve as a prevention of Aβ aggregation.…”

Section: Introductionmentioning

confidence: 99%

The Discovery of Benzylidene‐Indenone as Selective Butyrylcholinesterase Inhibitor with Choline Acetyltransferase Gene and Neurite Promoting Abilities

Ooi,

San Tang,

Tan

et al. 2024

ChemistrySelect

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Alzheimer's disease (AD) is a multifactorial and progressive neurodegenerative disease, associated with aging. A total of forty benzylidene‐indenone derivatives were synthesized in search of multi‐target‐directed ligands (MTDL) against AD. Compound 9 was found as the most promising MTDL in this study. It was demonstrated to selectively inhibit human butyrylcholinesterase, increase the gene expression of choline acetyltransferase (CHAT), and promote neurite outgrowth in SH‐SY5Y cells. The compound was also predicted to be able to permeate across the lipid‐infused bilayer, indicating its ability to cross the blood‐brain barrier. The abovementioned findings show compound 9 and its analogs warrant further exploration as potential MTDL anti‐AD agents.

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Hyperelatosides A–E, biphenyl ether glycosides from Hypericum elatoides, with neurotrophic activity

Abstract: Five new biphenyl ether glycosides, hyperelatosides A–E, one new benzoate glycoside, hyperelatoside F, were isolated from Hypericum elatoides. Hyperelatosides A, B, and D–F significantly enhanced NGF-induced neurite outgrowth in PC12 cells.

Cited by 14 publications

References 65 publications

Hyperelatolides A–D, Antineuroinflammatory Constituents with Unusual Carbon Skeletons from Hypericum elatoides

Hyperelatolides A–D, Antineuroinflammatory Constituents with Unusual Carbon Skeletons from Hypericum elatoides

Discovery from Hypericum elatoides and synthesis of hyperelanitriles as α-aminopropionitrile-containing polycyclic polyprenylated acylphloroglucinols

The Discovery of Benzylidene‐Indenone as Selective Butyrylcholinesterase Inhibitor with Choline Acetyltransferase Gene and Neurite Promoting Abilities

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