Two new diphenyl ethers from Acanthopanax senticosus (Rupr. &amp; Maxim.) Harms with PTP1B inhibitory activity

Li, Na; Lee, Hyun-Sun; Zhang, Nan; Sun, Yanan; Li, Jialin; Shen, Xing; Chen, Jianguang; Cui, Long

doi:10.1016/j.phytol.2015.07.006

Cited by 15 publications

(4 citation statements)

References 21 publications

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“…Seven known compounds with inhibitory active on NF-κB were identified by the spectroscopic and physico-chemical analyses and comparison with literature values including 24-( Z )-3-oxo-dammar-20(21), 24-dien-27-oic acid [1] ( 17 ), 22(S)-3-oxodammar-20, 24-dien-26, 22-lactone [2] ( 17 ), 3-[3',5'-dihydroxy-4'-(4''-hydroxymethyl-3'', 5''-dimethoxy-phenoxy)-phenyl)-propenal [3] ( 6 ), 3-[3'-methoxy-4'-(4''-formyl-2'',6''-dimethoxy-phenoxy)-phenyl)-propenal [4] ( 6 ), 3β-hydroxy-28-norolean-12-ene-16-one 3-O-β-ᴅ-glucopyranoside [5] ( 18 ), 3β,17β-dihydroxy-28-norolean-12-ene-16-one 3-O-β-ᴅ-glucopyranoside [6] ( 18 ), 3β-hydroxy-olean-12-ene-16,28-lactone 3-O-β-ᴅ-glucopyranoside [7] ( 18 ) ( Figure 10 ). The inhibitory activity of those seven active compounds on NF-κB was showed in Table 1 .…”

Section: Resultsmentioning

confidence: 99%

“…Harms, also known as edible tonic in China, is a shrub which widely distributes in Northeast Asia and Siberia. It possesses a wide range of active compounds, such as diterpenoids, triterpenoids, lignans and phenylpropanoids ( 5 , 6 ). In addition, it has been traditionally used as a folk medicine for treating rheumatism, diabetes and hepatitis ( 7 , 8 ).…”

Section: Introductionmentioning

confidence: 99%

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Ethanol extract of Acanthopanax senticosus (Rupr. & Maxim.) Harms induces liver cancer cell apoptosis through inhibiting NF-κB

Zhao¹,

Zhu²,

Han³

et al. 2020

Transl Cancer Res TCR

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Background: Acanthopanax senticosus (Rupr. & Maxim.) Harms, a traditional Chinese medicine, has been used to treat various diseases, including ischemic, heart diseases, hepatocellular carcinoma (HCC), hypertension and neurasthenia. The purpose of this study was to investigate the anticancer activity of A. senticosus (ASE).Materials: MTT assay, clonogenicity, reverse transcription-polymerase chain reaction (RT-PCR), flow cytometry and Western blot were employed to evaluate the viability and invasion of liver cancer cells. In addition, luciferase assay was used to delineate the inhibitory activity of ethanol extract against NF-κB.Results: Our results showed that the ethanol extract of ASE could decrease the viability of cancer cells. In addition, the ethanol extract could decrease the protein levels of Matrix metalloproteinase-2 (MMP-2), MMP-9, t-protein kinase B (Akt) and p-Akt, but increase those of E-cadherin. Nuclear factor kappa beta (NF-κB)-Luciferase assay showed the ethanol extract could effectively inhibit the activity of NF-κB. Furthermore, fourteen compounds including seven active compounds were isolated and activities against NF-κB were investigated.Conclusions: This study confirmed that the ASE could be as an alternative or complementary therapy to treat liver cancer.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ethanol extract of Acanthopanax senticosus (Rupr. & Maxim.) Harms induces liver cancer cell apoptosis through inhibiting NF-κB

Zhao¹,

Zhu²,

Han³

et al. 2020

Transl Cancer Res TCR

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“…Naturally occurring biphenyl ethers have been reported to be in some fungi in recent years, especially Aspergillus species, 25 but are rarely found in plants. 26 In fungi, these kinds of compounds are formed biosynthetically from the anthraquinone emodin, via sulochrin, and the grisandienes such as geodin was previously reported. 27 However, these intermediates of desmethylsulochrin, sulochrin, dihydrogeodin, and geodin are rarely as the plant metabolites.…”

Section: Resultsmentioning

confidence: 94%

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

Yan

Tang

et al. 2018

RSC Adv.

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“…Based on the physicochemical and chromatographic properties, spectral analyses (UV, 1 H, and DEPT‒Q NMR), as well as comparison with the literature and some authentic samples, the compounds isolated (Figure 2) from the ethanolic extract of P. odorata bark afforded the new tetrahydrofurofurnan lignan 35 , along with the known 4 β -hydroxyasarinin-1- o - β -glucopyranoside 36 [18], 1,5 α -dihydroxypinoresinol 37 [22], premnadimer-A 38 [18], 3-[3′-methoxy-4′-(4′’-formyl-2′’,6′’-dimethoxy-phenoxy)-phenyl]-propenal 39 [23], sinapaldehyde 40 [24], 3,5-dimethoxybenzaldehyde 41 [24], apigenin 42 , luteolin 43 , diosmetin 44 , vitexin 45 [5], orientin 46 [25],vicenin-2 47 [16], schaftoside-2 48 [17], and apigenin-6,8-di- c - α - l -arabinopyranoside 49 (Figure 2) [25]. All characterized compounds ( 37 , 39 – 41 , 46 – 49 ) were isolated herein for the first time from the genus Premna , while compounds 36 , 38 were isolated for the first time from the Premna species.…”

Section: Resultsmentioning

confidence: 99%

Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco

et al. 2019

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Metabolomic profiling of different Premna odorata Blanco (Lamiaceae) organs, bark, wood, young stems, flowers, and fruits dereplicated 20, 20, 10, 20, and 20 compounds, respectively, using LC–HRESIMS. The identified metabolites (1–34) belonged to different chemical classes, including iridoids, flavones, phenyl ethanoids, and lignans. A phytochemical investigation of P. odorata bark afforded one new tetrahydrofurofuran lignan, 4β-hydroxyasarinin 35, along with fourteen known compounds. The structure of the new compound was confirmed using extensive 1D and 2D NMR, and HRESIMS analyses. A cytotoxic investigation of compounds 35–38 against the HL-60, HT-29, and MCF-7 cancer cell lines, using the MTT assay showed that compound 35 had cytotoxic effects against HL-60 and MCF-7 with IC50 values of 2.7 and 4.2 µg/mL, respectively. A pharmacophore map of compounds 35 showed two hydrogen bond acceptor (HBA) aligning the phenoxy oxygen atoms of benzodioxole moieties, two aromatic ring features vectored on the two phenyl rings, one hydrogen bond donor (HBD) feature aligning the central hydroxyl group and thirteen exclusion spheres which limit the boundaries of sterically inaccessible regions of the target’s active site.

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Two new diphenyl ethers from Acanthopanax senticosus (Rupr. & Maxim.) Harms with PTP1B inhibitory activity

Cited by 15 publications

References 21 publications

Ethanol extract of Acanthopanax senticosus (Rupr. & Maxim.) Harms induces liver cancer cell apoptosis through inhibiting NF-κB

Ethanol extract of Acanthopanax senticosus (Rupr. & Maxim.) Harms induces liver cancer cell apoptosis through inhibiting NF-κB

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

Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco

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