Complete assignments of 1H and 13C NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia

Liu, Haitao; Xu, Lijia; Peng, Yong; Yang, Jun‐Shan; Yang, Xiu‐Wei; Xiao, Pei‐Gen

doi:10.1002/mrc.2430

Cited by 12 publications

(5 citation statements)

References 9 publications

(9 reference statements)

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“…Kadsura longipedunculata (KL) has been used for the treatment of a variety of diseases, including tumors, hepatitis [5,6], inflammation [7], immunosuppression [8], and insomnia [9,10], for thousands of years. Its therapeutic effects on insomnia are highly related to the lignans, which are the main constituents of Kadsura [6,11–13]. Despite its definite curative effects on insomnia, only a few studies have aimed at revealing the sedative mechanism of KL, and the sedative mechanism of KL remains unclear and requires further careful evaluation.…”

Section: Introductionmentioning

confidence: 99%

In silico Analysis and Experimental Validation of Lignan Extracts from Kadsura longipedunculata for Potential 5-HT1AR Agonists

Zheng

Feng

et al. 2015

PLoS ONE

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Objectives Kadsura longipedunculata (KL) has been widely used for the treatment of insomnia in traditional Chinese medicine. The aim of this study was to explore the mechanism of the sedative and hypnotic effects of KL.Materials and MethodsThe content of KL was evaluated by HPLC-TOF-MS, and a potential target was found and used to construct its 3D structure to screen for potential ligands among the compounds in KL by using bioinformatics analysis, including similarity ensemble approach (SEA) docking, homology modeling, molecular docking and ligand-based pharmacophore. The PCPA-induced insomnia rat model was then applied to confirm the potential targets related to the sedative effects of KL by performing the forced swimming test (FST), the tail suspension test (TST) and the measurement of target-related proteins using western blotting and immunofluorescence.ResultsBioinformatics analysis showed that most of lignan compounds in KL were optimal ligands for the 5-HT1A receptor (5-HT1AR), and they were found to be potential targets related to sedative effects; the main lignan content of KL extracts was characterized by HPLC-TOF-MS, with 7 proposed lignans detected. Administration of KL could significantly reduce FST and TST immobility time in the PCPA-induced 5HT-depleted insomnia rat model. The expressions of proteins related to the 5-HT1AR pathway were regulated by extracts of KL in a concentration-dependent manner, indicating that extracts of KL had 5-HT1AR agonist-like effects.Conclusion In silico analysis and experimental validation together demonstrated that lignan extracts from KL can target 5-HT1AR in insomniac rats, which could shed light on its use as a potential 5-HT1AR agonist drug.

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Section: Introductionmentioning

confidence: 99%

In silico Analysis and Experimental Validation of Lignan Extracts from Kadsura longipedunculata for Potential 5-HT1AR Agonists

Zheng

Feng

et al. 2015

PLoS ONE

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“…The 1 H-NMR signals at δ H 2.43 (m, H-2′), 1.40 (m, H-3′), 1.62 (m, H-3′), 0.86 (t, J = 7.4, H-4′), 1.02 (d, J = 7.0, H-5′) and 13 C-NMR signals at δ C 173.1 (C-1), 41.5 (C-2′), 26.8 (C-3′), 11.7 (C-4′), and 16.9 (C-5′) were assignable to a 2-methylbutyryloxy group. Comparison of the NMR data of 2 with a known lignan, kadoblongifolins A, showed great similarity [ 14 ]. The only difference was the presence of a 2-methylbutyryloxy ( O -isovaleryl) group at C-1 in 2 .…”

Section: Resultsmentioning

confidence: 99%

“…Dibenzocyclooctadiene (two benzene rings sharing an eight membered ring neighborhood) is the most common basic skeleton in Heilaohu. Methoxy, hydroxyl and methylenedioxy are the most frequently found substituents at benzene rings, while other important substituents including acetyl-, angeloyl-, tigloyl-, propanoyl-, benzoyl-, cinnamoyl- and butyryl- groups are invariably presented at C-1, C-6 or C-9 [ 13 , 14 , 15 ]. Spirobenzofuranoid dibenzocyclooctadienes are rare in other genera and can be considered as the characteristic chemical constituents of genus Kadsura .…”

Section: Introductionmentioning

confidence: 99%

“…The chemical investigation led to the isolation and characterization of three new ( 1 – 3 ) and twenty known ( 4 – 23 ) lignans. The three new Kadsura lignans A–C ( 1 – 3 ) and seventeen known lignans, schizandrin ( 4 ) [ 16 ], binankadsurin A ( 5 ) [ 17 ], acetylbinankadsurin A ( 6 ) [ 18 ], isobutyroylbinankadsurin A ( 7 ) [ 19 ], isovaleroylbinankadsurin A ( 8 ) [ 19 ], kadsuralignan I ( 9 ) [ 20 ], kadsuralignan J ( 10 ) [ 20 ], kadsuralignan L ( 11 ) [ 21 ], kadsulignan N ( 12 ) [ 22 ], longipedunin B ( 13 ) [ 15 ], schisantherin F ( 14 ) [ 23 ], schizanrin D ( 15 ) [ 23 ], acetylgomisin R ( 16 ) [ 24 ], intermedin A ( 17 ) [ 25 ], kadsurarin ( 18 ) [ 14 ], kadsutherin A ( 19 ) [ 25 ] and kadsuphilol A ( 20 ) [ 26 ] possessed dibenzocyclooctadiene skeletons. Similarly, meso-dihydroguaiaretic acid dimethyl ( 21 ) [ 27 ] had a diarylbutane type.…”

Section: Introductionmentioning

confidence: 99%

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Lignans from Tujia Ethnomedicine Heilaohu: Chemical Characterization and Evaluation of Their Cytotoxicity and Antioxidant Activities

et al. 2018

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Heilaohu, the roots of Kadsura coccinea, has a long history of use in Tujia ethnomedicine for the treatment of rheumatoid arthritis and gastroenteric disorders, and a lot of work has been done in order to know the material basis of its pharmacological activities. The chemical investigation led to the isolation and characterization of three new (1–3) and twenty known (4–23) lignans. Three new heilaohulignans A-C (1–3) and seventeen known (4–20) lignans possessed dibenzocyclooctadiene skeletons. Similarly, one was a diarylbutane (21) and two were spirobenzofuranoid dibenzocyclooctadiene (22–23) lignans. Among the known compounds, 4–5, 7, 13–15 and 17–22 were isolated from this species for the first time. The structures were established, using IR, UV, MS and NMR data. The absolute configurations of the new compounds were determined by circular dichroism (CD) spectra. The isolated lignans were further evaluated for their cytotoxicity and antioxidant activities. Compound 3 demonstrated strong cytotoxic activity with an IC50 value of 9.92 µM, compounds 9 and 13 revealed weak cytotoxicity with IC50 values of 21.72 µM and 18.72 µM, respectively in the HepG-2 human liver cancer cell line. Compound 3 also showed weak cytotoxicity against the BGC-823 human gastric cancer cell line and the HCT-116 human colon cancer cell line with IC50 values of 16.75 µM and 16.59 µM, respectively. A chemiluminescence assay for antioxidant status of isolated compounds implied compounds 11 and 20, which showed weak activity with IC50 values of 25.56 µM and 21.20 µM, respectively.

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“…Thus, the structure of compound 7 was established as shown. The known compounds 8-18 were identified as propinquanin A (8) [14], schisantherin I (9) [25], propinquanin D (10) [14], propinquanin B (11) [14], schisantherin H (12) [25], propinquanin C (13) [14], schizandrin J (14) [26], kadoblongifolin C (15) [27], kadsuphilins B (16) [28], schisantherin F (17) [29], and henricine B (18) [24] by comparison of their NMR spectral data with literature values. Inhibitory effects on lymphocyte proliferation of isolated compounds were examined using a lymphocyte transformation assay (LT assay).…”

Section: Supporting Informationmentioning

confidence: 99%

Lignans from Schisandra propinqua with Inhibitory Effects on Lymphocyte Proliferation

et al. 2012

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Seven new dibenzocyclooctadiene lignans, named propinquain E-K, together with 11 known lignans were isolated from the ethanol extract of the roots of Schisandra propinqua subsp. sinensis. The structures of the new compounds were elucidated by spectroscopic methods, including ¹H- and ¹³C-NMR, 2D-NMR, HR ESI-MS, and CD spectra. Two dibenzocyclooctadienes revealed inhibitory effects on lymphocyte proliferation.

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Complete assignments of ¹H and ¹³C NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia

Cited by 12 publications

References 9 publications

In silico Analysis and Experimental Validation of Lignan Extracts from Kadsura longipedunculata for Potential 5-HT1AR Agonists

In silico Analysis and Experimental Validation of Lignan Extracts from Kadsura longipedunculata for Potential 5-HT1AR Agonists

Lignans from Tujia Ethnomedicine Heilaohu: Chemical Characterization and Evaluation of Their Cytotoxicity and Antioxidant Activities

Lignans from Schisandra propinqua with Inhibitory Effects on Lymphocyte Proliferation

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