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New dibenzocyclooctadiene lignans from Kadsura induta with their anti-inflammatory activity.

ABSTRACT: Five new dibenzocyclooctadiene lignans, named kadsuindutains A-E (1-5), and three known ones schizanrin F (6), schizanrin O (7), and schisantherin J (8) were isolated from the stems of Kadsura induta. Their structures were determined by analyses of HR-ESI-MS, NMR, and ECD spectra. Compounds 1-5 contain a 2',4'-dioxygenated-2',3'-dimethylbutyryl moiety which is rarely reported for dibenzocyclooctadiene lignans. Molecular docking predicted that compounds 1-8 displayed good binding affinity to the active site of iNOS and TNF-α proteins but unstable binding to the active site of COX-2 protein. Additionally, in vitro experiments showed that compounds 1-8 inhibited NO production in LPS-activated RAW264.7 cells with IC₅₀ values from 10.7 μM to 34.0 μM, compared to the positive control L-NMMA (IC₅₀ = 31.2 μM).

SUBMITTER: Tai BH

PROVIDER: S-EPMC9451003 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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New dibenzocyclooctadiene lignans from <i>Kadsura induta</i> with their anti-inflammatory activity.

Tai Bui Huu BH Yen Pham Hai PH Hoang Nguyen Huy NH Thanh Huong Phan Thi PT Dung Nguyen Viet NV Van Thanh Bui B Cuong Nguyen The NT Bang Ngo Anh NA Nhiem Nguyen Xuan NX Van Kiem Phan P

RSC advances 20220907 39

Five new dibenzocyclooctadiene lignans, named kadsuindutains A-E (1-5), and three known ones schizanrin F (6), schizanrin O (7), and schisantherin J (8) were isolated from the stems of <i>Kadsura induta</i>. Their structures were determined by analyses of HR-ESI-MS, NMR, and ECD spectra. Compounds 1-5 contain a 2',4'-dioxygenated-2',3'-dimethylbutyryl moiety which is rarely reported for dibenzocyclooctadiene lignans. Molecular docking predicted that compounds 1-8 displayed good binding affinity ...[more]

PMID: 36199356

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Project description:In vitro cultures of scarlet flax (Linum grandiflorum L.), an important ornamental flax, have been established as a new possible valuable resource of lignans and neolignans for antioxidant and anti-inflammatory applications. The callogenic potential at different concentrations of α-naphthalene acetic acid (NAA) and thidiazuron (TDZ), alone or in combinations, was evaluated using both L. grandiflorum hypocotyl and cotyledon explants. A higher callus induction frequency was observed on NAA than TDZ, especially for hypocotyl explants, with a maximum frequency (i.e., 95.2%) on 1.0 mg/L of NAA. The presence of NAA (1.0 mg/L) in conjunction with TDZ tended to increase the frequency of callogenesis relative to TDZ alone, but never reached the values observed with NAA alone, thereby indicating the lack of synergy between these two plant growth regulators (PGRs). Similarly, in terms of biomass, NAA was more effective than TDZ, with a maximum accumulation of biomass registered for medium supplemented with 1.0 mg/L of NAA using hypocotyls as initial explants (DW: 13.1 g). However, for biomass, a synergy between the two PGRs was observed, particularly for cotyledon-derived explants and for the lowest concentrations of TDZ. The influence of these two PGRs on callogenesis and biomass is discussed. The HPLC analysis confirmed the presence of lignans (secoisolariciresinol (SECO) and lariciresinol (LARI) and neolignan (dehydrodiconiferyl alcohol [DCA]) naturally accumulated in their glycoside forms. Furthermore, the antioxidant activities performed for both hypocotyl- and cotyledon-derived cultures were also found maximal (DPPH: 89.5%, FRAP 866: µM TEAC, ABTS: 456 µM TEAC) in hypocotyl-derived callus cultures as compared with callus obtained from cotyledon explants. Moreover, the anti-inflammatory activities revealed high inhibition (COX-1: 47.4% and COX-2: 51.1%) for extract of hypocotyl-derived callus cultures at 2.5 mg/L TDZ. The anti-inflammatory action against COX-1 and COX-2 was supported by the IC50 values. This report provides a viable approach for enhanced biomass accumulation and efficient production of (neo)lignans in L. grandiflorum callus cultures.

Project description:Cancer remains one of the leading causes of mortality worldwide. The search for novel and effective anticancer agents has been a significant area of research. Dibenzocyclooctadiene lignans (DBCLS), derived from the Schisandra genus plants like: S. chinensis, S. sphenanthera, S. henryi, S. rubriflora, S. grandiflora, S. propinqua, and S. glabra, have been traditionally used in various medicinal systems and are known for their myriad health benefits, including anticancer properties. This comprehensive review aimed to collate and critically analyse the recent literature on the anticancer properties of DBCLS, focusing on their mechanistic approaches against different cancer types. An exhaustive literature search was performed using databases like PubMed/MedLine, Scopus, Web of Science, Embase, TRIP database and Google Scholar from 1980 to 2023. Peer-reviewed articles that elucidated the mechanistic approach of these lignans on cancer cell lines, in vivo models and preliminary clinical studies were included. Studies were assessed for their experimental designs, cancer types studied, and the mechanistic insights provided. The studies demonstrate that the anticancer effects of DBCLS compounds are primarily driven by their ability to trigger apoptosis, arrest the cell cycle, induce oxidative stress, modulate autophagy, and disrupt essential signaling pathways, notably MAPK, PI3K/Akt, and NF-κB. Additionally, these lignans have been shown to amplify the impact of traditional chemotherapy treatments, suggesting their potential role as supportive adjuncts in cancer therapy. Notably, several studies also emphasise their capacity to target cancer stem cells and mitigate multi-drug resistance specifically. DBCLS from the Schisandra genus have showcased significant potential as anticancer agents. Their multi-targeted mechanistic approach makes them promising candidates for further research, potentially leading to developing of new therapeutic strategies in cancer management.

Dataset Information

New dibenzocyclooctadiene lignans from Kadsura induta with their anti-inflammatory activity.

Publications

New dibenzocyclooctadiene lignans from <i>Kadsura induta</i> with their anti-inflammatory activity.

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