Anti-inflammatory and PTP1B inhibitory sesquiterpenoids from the twigs and leaves of Aglaia lawii

Xia, Mingjun; Zhang, Meng; Li, Song-Wei; Cai, Zhe-Fei; Zhao, Tiansheng; Liu, Aihong; Luo, Jun; Zhang, Haiyan; Li, Jia; Guo, Yue‐Wei; Wang, Bin; Mao, Shui-Chun

doi:10.1016/j.fitote.2022.105260

Cited by 7 publications

(25 citation statements)

References 32 publications

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“…L. doyonensis, compounds 1-9 were evaluated at 20 μg/mL for their PTP1B inhibitory activities with oleanolic acid as the positive control, as described previously [11,13,24]. Compounds 3, 4, 7, and 8 exhibited promising activities with inhibition rates of >60%, including three compounds (4, 7, and 8)…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Therefore, PTP1B is considered to be a promising therapeutic target for the treatment of type 2 diabetes mellitus and obesity [23]. Given the PTP1B inhibitory effects of the EtOH extract of L. doyonensis, compounds 1-9 were evaluated at 20 µg/mL for their PTP1B inhibitory activities, with oleanolic acid as the positive control, as described previously [11,13,24]. Compounds 3, 4, 7, and 8 exhibited promising activities, with inhibition rates of > 60 %, including three compounds (4, 7, and 8) with inhibition rates of > 90 % (▶ Table 2).…”

Section: Posimentioning

confidence: 99%

“…Considering the anti-inflammatory properties of the EtOH extract of L. doyonensis, the potential inhibitory activities of compounds 1-9 were evaluated against LPS-induced NO production in BV-2 microglial cells. Resveratrol served as the positive control, as previously described [24]. As shown in ▶ Fig.…”

Section: Posimentioning

confidence: 99%

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Lyonensinols A – C, 24-Norursane-Type Triterpenoids from the Twigs and Leaves of Lyonia doyonensis and Their Potential Anti-inflammatory and PTP1B Inhibitory Activities

et al. 2023

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Lyonia doyonensis is a deciduous shrub native to high-altitude regions of Asia. So far, there is no report on any chemical and biological properties of L. doyonensis. An EtOH extract of L. doyonensis twigs and leaves showed inhibitory activities on PTP1B and lipopolysaccharide (LPS)-induced inflammation in BV-2 microglial cells. Phytochemical investigation of this extract led to the isolation of a, so far only ambiguously described, 24-norursane-type triterpenoid, now named lyonensinol A (1), along with its two new derivatives, lyonensinols B and C (2 and 3), and six known triterpenoids (4–9). Their structures were elucidated by detailed analysis of spectroscopic data. A combination of chemical conversions, ECD, and Mo2(OAc)4-induced ECD was used to confirm their absolute configurations. Lyonensinols B (2) and C (3) represent the first examples of norursane-type triterpenoids acylated with a p-coumaroyl moiety. The potential anti-inflammatory and PTP1B inhibitory activities of all the isolates were evaluated. Compounds 3, 7, and 8 at 10 μM showed potent inhibitory activities on LPS-induced NO production in BV-2 microglial cells with NO levels decreased to 31.5%, 41.9%, and 27.1%, respectively, while compounds 3, 4, 7, and 8 exhibited notable inhibitory activities against PTP1B with IC50 values ranging from 1.7 to 18.2 μM. Interestingly, compounds 3 and 8 bearing a C-3 trans-p-coumaroyl group showed not only more potent anti-inflammatory effects, but also exhibited stronger PTP1B inhibition, than their respective stereoisomers (2 and 7) with a cis-p-coumaroyl group.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Section: Posimentioning

confidence: 99%

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Lyonensinols A – C, 24-Norursane-Type Triterpenoids from the Twigs and Leaves of Lyonia doyonensis and Their Potential Anti-inflammatory and PTP1B Inhibitory Activities

et al. 2023

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“…However, the medicinal values of A. lawii have not been comprehensively explored, and the chemical ingredients and pharmacological activities of one remain elusive. [2][3][4] Our team has isolated triterpenoids and limonoids from Meliaceae plants (e. g., Cipadessa baccifera, Melia toosendan and Toona ciliata) and found that they possess antitumor, anti-inflammatory and anti-bacterial effects. [5][6][7] As part of our ongoing work, the structurally novel and biologically active ethanol extract of the branches and leaves of Alawl was investigated and afforded three previously undescribed limonoids (1)(2)(3) and one new natural product, azedaralide (4), together with nine known analogues (5-13) (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…[2][3][4] Our team has isolated triterpenoids and limonoids from Meliaceae plants (e. g., Cipadessa baccifera, Melia toosendan and Toona ciliata) and found that they possess antitumor, anti-inflammatory and anti-bacterial effects. [5][6][7] As part of our ongoing work, the structurally novel and biologically active ethanol extract of the branches and leaves of Alawl was investigated and afforded three previously undescribed limonoids (1)(2)(3) and one new natural product, azedaralide (4), together with nine known analogues (5-13) (Figure 1). Their structures were characterized by comprehensive sectroscopic data analysis, ECD calculations and X-ray crystallography.…”

Section: Introductionmentioning

confidence: 99%

Limonoids from the Branches and Leaves of Aglaia lawii and Their Cytotoxic Activities

Dong,

Liu,

Wang

et al. 2023

Chemistry & Biodiversity

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Three undescribed limonoids (1–3), named aglaians G–I, and one new natural product azedaralide (4), together with nine known analogues (5–13) were isolated from the branches and leaves of Aglaia lawii by RP C18 column, silica gel column, Sephadex LH‐20 column chromatography and preparative HPLC. The structures of the new compounds were elucidated by IR, HRESIMS, 1D, 2D NMR, electronic circular dichroism (ECD) calculations and X‐ray crystallography diffraction analysis. The results of bioassay showed that the compound 12 exhibited potential inhibitory activity against six human tumor cell lines (MDA‐MB‐231, MCF‐7, Ln‐cap, A549, HeLa and HepG‐2) with IC50 values as 8.0–18.6 μM.

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The genus Aglaia: Diversity in chemical structure and biological activity

Bang,

Tai,

Yen

et al. 2024

Vietnam Journal of Chemistry

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The Meliaceae family has been investigated comprehensively because of their structurally multifarious, and biologically active components. The genus Aglaia has the highest amount in this family, including around 150 species. These species are widespread throughout tropical regions, particularly in Southeast Asia and Australia. They have been used in traditional medicine for treating various diseases. This article summarizes 370 metabolites, which have been isolated from several parts such as the bark, roots, seeds, and leaves of Aglaia species in over fifty years from the first investigation in 1965 to 2024, originating from the flavagline, triterpenoid, sesquiterpenoid, steroid, alkaloid, and limonoid, while flavagline is the largest group. The components isolated from the genus Aglaia are analyzed for potential biological activities, like cytotoxicity, anti‐inflammatory, insecticidal, antiviral, antituberculosis, and antifungal effects. In addition, the flavagline was reported to show a high potential for cytotoxic and insecticidal activities and was confirmed to be used as the chemical marker for this species. Therefore, these reports indicate that Aglaia species may hold potential as a valuable source for producing biologically active compounds.

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Anti-inflammatory and PTP1B inhibitory sesquiterpenoids from the twigs and leaves of Aglaia lawii

Cited by 7 publications

References 32 publications

Lyonensinols A – C, 24-Norursane-Type Triterpenoids from the Twigs and Leaves of Lyonia doyonensis and Their Potential Anti-inflammatory and PTP1B Inhibitory Activities

Lyonensinols A – C, 24-Norursane-Type Triterpenoids from the Twigs and Leaves of Lyonia doyonensis and Their Potential Anti-inflammatory and PTP1B Inhibitory Activities

Limonoids from the Branches and Leaves of Aglaia lawii and Their Cytotoxic Activities

The genus Aglaia: Diversity in chemical structure and biological activity

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