Search

Two new dibenzocyclooctane lignans, schisanwilsonins H ( 1 ) and I ( 2 ), together with eight known compounds gomisin J ( 3 ), wulignan A 1 ( 4 ), gomisin S ( 5 ), tigloylgomisin P ( 6 ), gomisin O ( 7 ), (-)-gomisin K 1 ( 8 ), rubschisantherin ( 9 ) and wuweizisu C ( 10 ) were isolated from the 95% ethanol extract of the fruits of Schisandra wilsoniana . 7 exhibited anti-HBV activity with potency against HBsAg and HBeAg secretion by 37.1% and 32.6%, respectively, at 50 μg/ml. 10 exhibited anti-HIV activity with EC 50 and therapeutic index (TI) values of 2.10 μg/ml and 11.98, respectively.

Three new phenolic glycosides, carvacrol-2- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (1: ), 1-methyl-3-isopropylphenol-4- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (2: ), p -methoxythymol-5- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (3: ), and a pair of new 8- O -4' neolignan enantiomers (5A: /5B: ), together with 26 known compounds (4, 6:  - 30: ) were isolated from the roots of Lilium dauricum . The structures of the new compounds were elucidated based on extensive spectroscopic and chemical methods, and the absolute configurations of 5A: and 5B: were established by electronic circular dichroism analysis. Nine compounds (1, 3, 4, 8, 9, 17, 25, 29,: and 30: ) exhibited potent α -glucosidase inhibitory activity with IC 50 values ranging from 73.4 µM to 988.2 µM. Besides, compound 19: displayed strong anticomplementary activity (CH 50 : 71.6 µM)., Competing Interests: The authors declare that they have no conflict of interest., (Thieme. All rights reserved.)

A new dibenzocyclooctadiene lignan, renchangianin E (1) was isolated from the stems of Kadsura renchangiana. Its structure and stereochemistry were elucidated by spectroscopic methods, including 2D-NMR techniques.

Aim: To study the dibenzocylooctadiene lignans from the stems of Kadsura heteroclita., Method: Chromatographic separations of silica gel and semi-preparative HPLC were used. All of the structures were elucidated on the basis of spectroscopic analysis, including 2D-NMR and HR-MS techniques., Results: Four dibenzocylooctadiene lignans were isolated from K. heteroclita. Their structures were identified as heteroclitin R (1), heteroclitin S (2), gonisin O (3), and schisanlignone A (4)., Conclusion: Heteroclitin R (1) and heteroclitin S (2) are new natural lignans., (Copyright © 2014 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.)

Context: The diethyl ether extract of the stems of Schisandra pubescens Hemsl. et Wils. (Schisandraceae) was found to exhibit cytotoxic activity in vitro. However, investigations of the bioactive constituents of this plant have been very limited., Objective: Elucidation of the cytotoxic constituents of S. pubescens was performed., Methods: Repeated silica gel column chromatography and preparative TLC were used for the chemical investigation of the diethyl ether extract of S. pubescens stems. All isolates were evaluated for their in vitro cytotoxicity against A549, PC-3, KB and KBvin human cancer cell lines., Results: Nine known compounds were obtained, including four lignans, epischisandrone (1), tigloylgomisin P (2), cagayanone (3) and (-)-gomisin L₂ (4), together with five triterpenoids, micranoic acid B (5), lancifodilactone H (6), coccinic acid (7), schisanlactone B (8) and anwuweizonic acid (9). Compounds 2-6 and 8 showed moderate to marginal cytotoxicity, with GI₅₀ values of 11.83-35.65 μM., Conclusion: The isolation of 1-9 from S. pubescens and the cytotoxicities of 3-6 are first reported. Compounds 2-6 and 8 could be the active principles responsible for the anticancer effects of S. pubescens.

Five new dibenzocyclooctane lignans, schisanwilsonins K-O, together with eighteen known lignans were isolated from the stems of Schisandra wilsoniana. The structures of these new compounds were elucidated by spectroscopic methods, including 2D-NMR techniques. Several compounds were found to show anti-HIV and anti-HBV activity., (Georg Thieme Verlag KG Stuttgart · New York.)

An ultra performance liquid chromatography (UPLC) coupled with quadrupole time-of-flight mass spectrometry (QTOF-MS) procedure is designed for the first simultaneous analysis of nortriterpenoids and lignans in Schisandra samples. The method consists of three individual mass spectrometric experiments, including the full scan MS, MS/MS experiment and in-source collision induced dissociation (CID) MS/MS, which enable the identification of diagnostic fragmentation pathways of nortriterpenoids and lignans. As such, a total of 6 nortriterpenoids and 10 lignans were unequivocally identified, and one nortriterpenoid and 20 lignans were tentatively identified from different Schisandra samples within 12.5 min. In addition, 6 nortriterpenoids and 10 lignans were quantified in 48 samples of S. chinensis and S. sphenanthera using an extract ion chromatogram (XIC) of the full scan MS experiment. Dataset obtained from UPLC-MS was processed with principal component analysis (PCA) and orthogonal partial least squared discriminant analysis (OPLS-DA) to compare the difference between the two Schisandra species., (Copyright © 2011 Elsevier B.V. All rights reserved.)

Seven new dibenzocyclooctane lignans, schisanwilsonins A-G (1-7), were isolated from the fruits of Schisandra wilsoniana, together with five known lignans (8-12). The structures of these new compounds were elucidated by spectroscopic methods including 2D-NMR techniques. The 12 lignans were tested for anti-hepatitis B virus (HBV) activity in vitro. Schisanwilsonin D (4), schisantherin C (9), deoxyschizandrin (10) and (+)-gomisin K(3) (11) showed anti-HBV activity. 9 exhibited the most potent anti-HBV activity with potency against HBsAg and HBeAg secretion by 59.7% and 34.7%, respectively, at 50 microg/mL.

Wuweizi (Fructus Schisandrae) is classified in traditional Chinese medicine as a superior drug, and has been used for thousands of years. Modern pharmacological research has demonstrated that most of the biological actions and pharmacological effects of Wuweizi can be attributed to its lignan constituents, particularly the dibenzocyclooctadiene-type lignans, which can lower the serum glutamate-pyruvate transaminase (SGPT) level, inhibit platelet aggregation, and show antioxidative, calcium antagonism, antitumor-promoting, and anti-HIV (human immunodeficiency virus) effects. The dried ripe fruits of both Schisandra chinensis and Schisandra sphenanthera have long been used as Wuweizi, although their chemical constituents and contents of the bioactive components are quite different. Since 2000, they have been accepted as two different crude drugs, Bei-Wuweizi and Nan-Wuweizi, respectively, by the Chinese Pharmacopoeia. In order to provide a useful reference for good quality control of Wuweizi, many studies on the chemical constituents, pharmacological effects, identification and quality control methods of the two drugs have been reported in the literature and are summarized herein. Particular attention was given to the different methodologies developed for the qualitative and quantitative analysis of the major bioactive lignans. In our opinion, thin-layer chromatography (TLC) is the most simple and convenient method for identification of these two crude drugs, and high-performance liquid chromatography with UV detection (HPLC-UV) is the preferred method for quantitative analysis based on the bioactive lignans. Some newly developed methods, particularly hyphenated chromatographic-analytical techniques, are effective in determination of the lignans that occur in low content and those difficult to be fully separated with HPLC.

A new dibenzocyclooctadiene lignan, kadsutherin D (1), together with 12 known lignans, kadsurin (2), heteroclitin C (3), interiotherin C (4), schisanlignone A (5), binankadsurin A (6), angeloyl binankadsurin A (7), gomisin U (8), heteroclitin D (9), interiorin (10), schiarisanrin C (11), heteroclitin G (12) and meso-dihydroguaiaretic acid (13) were isolated from the stems of Kadsura species. Their structures were elucidated by spectroscopic methods including 2D-NMR techniques.

Bioactivity-directed fractionation of an ethanolic extract of the fruits of Schisandra rubriflora led to the isolation and identification of dibenzocyclooctadiene lignans including the new lignans rubrisandrins A (1a + 1b) and B (2) and the known lignans gomisin J (3), (+/-)-gomisin M1 (4), (+)-gomisin M2 (5), schisanhenol (6), deoxyschisandrin, schisantherin B, schisandrin, tigloylgomisin P, gomisin O, angeloylgomisin P, and epigomisin O. Their structure and stereochemistry were determined by spectroscopic methods, including 2D-NMR techniques. Compounds 1 and 3-6 were active as anti-HIV agents. (+/-)-Gomisin M1 (4) exhibited the most potent anti-HIV activity, with EC50 and therapeutic index (TI) values of <0.65 microM and >68, respectively.

Three new lignans, longipedunins A (1), B (2) and C (3), together with three known compounds, benzoyl-binankadsurin A (4), acetyl-binankadsurin A (5) and schisanlactone A (6), were isolated from Kadsura longipedunculata. Their structures and stereochemistry were determined by spectral and single-crystal X-ray analyses. Compounds 1 and 6 showed appreciable inhibitory activity against HIV-1 protease with IC50 values of 50 and 20 microM, respectively.

Objective: To determinate the contents of lignans in the stems, roots and fruits of Schisandra medicinal plants., Method: HPLC was applied to determine the contents of schisandrin, gomisin A, schisantherin A, deoxyschizandrin, d-epigalbacine, (+)-anwulignan, wuweizisu B, 6-O-benzoylgomisin O and wuweizisu C in the stems, roots and fruits of Schisandra., Result: The percent contents of 9 lignans in the fruits of 5 species were 0.52% - 1.96%, and 0.02% - 1.51% in the stems of 11 species. The lignans in the fruits of S. micrantha were similar to that of S. sphenanthera, especially with high content of deoxyschizandrin. The lignans of S. viridis were similar to that of S. chinensis and with high content of schisandrin, gomisin A and wuweizisu B. (+)-Anwulignan was present in the fruits of S. henryi and S. sphenanthera, in the stems of S. micrantha and S. pubescens var. pubinervis, and in the roots of S. bicolor with percentages of 0.77%, 0.42%, 0.50%, 0.26% and 0.38% respectively. d-Epigalbacine was present in the stems of S. pubescens var. pubinervis, S. pubescens and S. glaucescens with percentages of 0.89%, 1.51% and 0.17% respectively., Conclusion: The lignans contents in the fruits of Schisandra were higher than that in the roots and stems. The fruits of S. henryi and S. sphenanthera, the stems of S. micrantha and S. pubescens var. pubinervis and the roots of S. bicolor, the stems of S. pubescens var. pubinervis, S. pubescens and S. glaucescens may be served as the resources plants of (+)-anwulignan and d-epigalbacine respectively.

Two new lignans, interiotherins C (1) and D (2), together with the known compounds interiorin (3), heteroclitin F (4), neokadsuranin (5), heteroclitin D (6), kadsurin (7), gomisin A (8), schisandrin C (9), interiotherin A (10), angeloylgomisin R (11), gomisin G (12), interiotherin B (13), and gomisin C (14), were isolated from the stems of Kadsura interior. The structures and stereochemistries of the new compounds were determined from mass, CD, and NMR spectral data. Fourteen neolignans were screened as potential antitumor promoters by examining their ability to inhibit Epstein-Barr virus early antigen (EBV-EA) activation (induced by 12-O-tetradecanoylphorbol-13-acetate) in Raji cells. Neokadsuranin (5) and schisandrin C (9) were the most potent compounds. These data suggest that some neolignans might be valuable antitumor promoters or chemopreventors.

Anti-complementary activity-guided fractionation led to the isolation of a new abietane diterpene (1) and twenty-five known compounds (2–26) from the twigs and leaves of Juniperus tibetica. All the compounds were isolated from J. tibetica for the first time. The structure of 1 was assigned by spectroscopic data and X-ray crystallography analysis. Five lignans (2, 3, 7, 9 and 10), two flavones (19 and 22), and one coumarin (23) exhibited anti-complementary activity with CH50 values ranging from 0.3 to 3.69 mM. [ABSTRACT FROM AUTHOR]