Dibenzocyclooctadiene lignans from the family Schisandraceae: A review of phytochemistry, structure-activity relationship, and hepatoprotective effects

Liu, Shiqi; Yang, Yupei; Hussain, Nusrat; Jian, Yuqing; Li, Bin; Qiu, Yixing; Yu, Haichao; Wang, Huizhen; Wang, Wei

doi:10.1016/j.phrs.2023.106872

Cited by 4 publications

(3 citation statements)

References 194 publications

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“…For the 52 agents listed above, we found the structures of the compounds corresponding to 41 of them through literature search (Fig. 5 ) and analyzed them for drug likeness by using Python’s rdkit package (Goodwin et al 2017 ; Lazic et al 2022 ; Liu et al 2023a ; Liu et al 2022b ). Commonly, the drug properties of chemical molecules can be initially determined according to Lipinski’s rule V. Lipinski’s rule V is defined as a molecular weight not exceeding 500 Dalton, octanol–water partition coefficient [log P] not exceeding 5, hydrogen bond acceptor not exceeding 10, and hydrogen bond donor not exceeding 5 (Lipinski et al 2001 ).…”

Section: Drug Likeness Analysismentioning

confidence: 99%

Recent advances of NFATc1 in rheumatoid arthritis-related bone destruction: mechanisms and potential therapeutic targets

Zheng,

Liu,

Deng

et al. 2024

Mol Med

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Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease characterized by inflammation of the synovial tissue and joint bone destruction, often leading to significant disability. The main pathological manifestation of joint deformity in RA patients is bone destruction, which occurs due to the differentiation and proliferation of osteoclasts. The transcription factor nuclear factor-activated T cell 1 (NFATc1) plays a crucial role in this process. The regulation of NFATc1 in osteoclast differentiation is influenced by three main factors. Firstly, NFATc1 is activated through the upstream nuclear factor kappa-B ligand (RANKL)/RANK signaling pathway. Secondly, the Ca2+-related co-stimulatory signaling pathway amplifies NFATc1 activity. Finally, negative regulation of NFATc1 occurs through the action of cytokines such as B-cell Lymphoma 6 (Bcl-6), interferon regulatory factor 8 (IRF8), MAF basic leucine zipper transcription factor B (MafB), and LIM homeobox 2 (Lhx2). These three phases collectively govern NFATc1 transcription and subsequently affect the expression of downstream target genes including TRAF6 and NF-κB. Ultimately, this intricate regulatory network mediates osteoclast differentiation, fusion, and the degradation of both organic and inorganic components of the bone matrix. This review provides a comprehensive summary of recent advances in understanding the mechanism of NFATc1 in the context of RA-related bone destruction and discusses potential therapeutic agents that target NFATc1, with the aim of offering valuable insights for future research in the field of RA. To assess their potential as therapeutic agents for RA, we conducted a drug-like analysis of potential drugs with precise structures.

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Section: Drug Likeness Analysismentioning

confidence: 99%

Recent advances of NFATc1 in rheumatoid arthritis-related bone destruction: mechanisms and potential therapeutic targets

Zheng,

Liu,

Deng

et al. 2024

Mol Med

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“…Figure S5 shows a cluster of 45 features, potentially corresponding to dibenzocyclooctadienes. These compounds were identified using an in-house database compiled from previously identified dibenzocyclooctadienes in the Schisandraceae family, along with molecular formula and fragmentation patterns [10]. For example, compound B31 displayed a [M + Na] + ion peak at m/z 595.21489, suggesting a molecular formula of C 30 H 36 O 11 , consistent with kadsurarin in the in-house database.…”

Section: Identification Of Lignan and Triterpenoid Derivatives In F2mentioning

confidence: 99%

“…Xuetongsu (schisanlactone E), a triterpenoid found in the highest concentration in Xuetong, has shown remarkable dose-dependent effects in terms of analgesia, anti-inflammatory properties, and anti-rheumatoid arthritis (RA) activity [9]. The dibenzocyclooctadiene in Xuetong has a protective effect on liver damage caused by various factors such as drugs, chemicals, alcohol, and viruses [10]. These components also showcase a diverse array of pharmacological activities, encompassing anti-inflammatory, analgesic, anti-HIV, anticancer, and anti-hepatitis B actions [6].…”

Section: Introductionmentioning

confidence: 99%

Targeted Offline Two-Dimensional HPLC and UHPLC-Orbitrap-MS Combined with Molecular Networking Reveal the Effect of Processing on Chemical Constituents of Xuetong (the Stem of Kadsura heteroclita)

Yuan,

Su,

Liang

et al. 2024

Separations

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Xuetong, the dried stem of Kadsura heteroclita (Roxb.) Craib, is a traditional Tujia medicine extensively used to treat rheumatoid arthritis (RA). All traditional Chinese medicines (TCMs) necessitate a processing stage called “Paozhi” before clinical application. However, there is a dearth of research concerning the processing methods employed for Xuetong. To investigate the impact of vinegar and wine processing on the chemical constituents of Xuetong, this study devised a targeted offline two-dimensional (2D) high-performance liquid chromatography (HPLC) and ultra-high-performance liquid chromatography-orbitrap mass spectrometry (UHPLC-orbitrap-MS) method. By incorporating various MS data-processing techniques, such as molecular networking technology, fragment-ion similarity searching (FISh), online and offline database matching, and fragmentation pattern analysis, a total of 158 components were identified in Xuetong. Among them, 14 were verified by comparison with the reference standards. Notably, aside from triterpenoids and lignans, catechin derivatives were found to be the predominant constituents of Xuetong, and their levels exhibited a significant decrease following processing. This method significantly improved peak capacity and resolution, overcoming the limitations of 1D LC in simultaneously analyzing highly polar catechin derivatives and less polar triterpenoids and lignans. Moreover, the developed method shows promise for Xuetong’s quality control.

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Hepatoprotective Lignan Glycosides from the Leaves and Stems of Symplocos cochinchinensis (Lour.) S. Moore

Giang,

Park,

Lee

et al. 2024

Chemistry & Biodiversity

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This study investigates Symplocos cochinchinensis (Lour.) S. Moore leaves and stems, commonly known as Symplocos, a plant indigenous to Asia renowned for its traditional use in holistic medicine. A comprehensive phytochemical analysis of S. cochinchinensis led to the isolation of two new lignans, namely symplolignans A and B (1 and 2) along with eleven known lignan glucosides: nortrachelogenin 4‐O‐β‐D‐glucopyranoside (3), nortracheloside (4), matairesinol 4‐O‐β‐D‐glucopyranoside (5), lariciresinol 4′‐O‐β‐D‐glucopyranoside (6), balanophonin 4‐O‐β‐D‐glucopyranoside (7), dehydrodiconiferyl alcohol 4‐O‐β‐D‐glucopyranoside (8), dehydrodiconiferyl alcohol γ'‐O‐β‐D‐glucopyranoside (9), 3‐(β‐D‐glucopyranosyloxymethyl)‐2‐(4‐hydroxy‐3‐methoxyphenyl)‐5‐(3‐hydroxypropyl)‐7‐methoxy‐(2R,3S)‐dihydrobenzofura (10), and pinoresinol 4′‐O‐β‐D‐glucopyranoside (11). Their chemical structures were elucidated using 1D‐ and 2D‐NMR, mass spectrometry, and their spectroscopic data were compared with those reported in literatures. Furthermore, all compounds were evaluated for their hepatoprotective effects using the Resazurin reduction assay in HepG2 hepatocellular carcinoma cells. Compounds 1, 5, 7, and 8 exhibited notable hepatoprotective efficacy, with cell viability ranging from 105.0 ± 2.6 to 109.2 ± 3.3 at a concentration of 10 µM. This research highlights the therapeutic potential of these compounds and enhanced to the understanding of lignans and neolignans in liver cell proliferation.

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Dibenzocyclooctadiene lignans from the family Schisandraceae: A review of phytochemistry, structure-activity relationship, and hepatoprotective effects

Cited by 4 publications

References 194 publications

Recent advances of NFATc1 in rheumatoid arthritis-related bone destruction: mechanisms and potential therapeutic targets

Recent advances of NFATc1 in rheumatoid arthritis-related bone destruction: mechanisms and potential therapeutic targets

Targeted Offline Two-Dimensional HPLC and UHPLC-Orbitrap-MS Combined with Molecular Networking Reveal the Effect of Processing on Chemical Constituents of Xuetong (the Stem of Kadsura heteroclita)

Hepatoprotective Lignan Glycosides from the Leaves and Stems of Symplocos cochinchinensis (Lour.) S. Moore

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