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Plants of the Schisandraceae family have a rich and medicinal history dating back to ancient times. Many of them are used as folk medicine in the treatment of chronic coughs, asthma, nocturnal emission, spontaneous sweating, night sweats, palpitation, insomnia and thirst.The current review is carried out on triterpenoids from the Schisandraceae family, aiming to comprehensively summarize their phytochemistry, pharmacology and synthesis and provide new insights to the chemical and pharmacological study and rational utilization on medicinal plants of the Schisandarceae family.The information was searched from the scientific literature published from June 2014 to November 2021 on the online databases (including PubMed, CNKI, Elsevier, SciFinder and Web of Science) and other bibliography (e.g. the Chinese Pharmacopoeia, 2020 edition, Chinese herbal books). The scientific literature related to phytochemistry, pharmacology, biological activites and synthesis of triterpenoids from the Schisandraceae family was gathered.From June 2014 to November 2021, there were approximately 211 novel triterpenoids isolated and identified from 18 species of the Schisandraceae family. These compounds exhibit tremendous diversity in their structures, and some of them possess promising pharmacological activities, including anti-viral, anti-tumor, anti-inflammatory, hepatoprotective, immunosuppressive activities and neuroprotective effects. In the attempt to synthesize active compounds, the total synthesis of 13 schinortriterpenoids belonging to five structural types was successfully completed.Studies of triterpenoids from the Schisandraceae family are well documented in this review (from June 2014 to November 2021), and it is also well acknowledged that they are valuable resources with medicinal efficacy. However, relevant pharmacological studies are limited to in vitro tests, and data from in vivo studies and toxicology are lacking or unavailable. Fortunately, there is growing interest in the synthesis of active compounds, which should serve as an approach for accessing active compounds to develop in vivo or toxicity studies, with a view of clarifying their in vitro and vivo mechanisms for more effective and safe natural drugs.

The roots of Kadsura coccinea is commonly used in Tujia ethnomedicine, named “heilaohu”, having the effect of treating rheumatic arthritis (RA). Chemical investigation on the ethanol extract of heilaohu led to the isolation of one undescribed cuparane sesquiterpenoid, heilaohusesquiterpenoid A, one undescribed carotane sesquiterpenoids, heilaohusesquiterpenoid B, and eighteen sesquiterpene derivatives. Their structures were subsequently determined based on their 1D and 2D-NMR, HR-ESI-MS, and ECD spectroscopic data. Gaultheriadiolide was the most cytotoxic compound against the proliferation of rheumatoid arthritis-fibroblastoid synovial (RA-FLS) cells with an IC50 value of 9.37 μM. In the same line, nine compounds exhibited significant inhibition effects against TNF − α and IL-6 release in the LPS-induced RAW264.7 cells with IC50 values ranging between 1.03 and 10.99 μM. The potential molecular mechanisms of the active compounds against RA were established through pharmacological network analysis based on the initial screening results. Experimental validation showed that gaultheriadiolide suppressed inflammation by inhibiting the NF-kB and JAK2/STAT3 pathways. This study enriches the structural diversity of sesquiterpenes in K. coccinea and lays a foundation for further anti-RA and anti-inflammatory studies.

Both Schisandra sphenanthera (S. sphenanthera) and Schisandra chinensis (S. chinensis) are used as traditional Chinese medicines, but they have different medicinal properties. Because S. sphenanthera is cheaper, it is often used as a counterfeit product for S. chinensis. In the present study, an electronic tongue (e-tongue) was used for discrimination of the two Schisandraceae species. In addition, the contents of schisandrin, schizandrol B, schisantherin A, deoxyschizandrin, and schisandrin B were determined simultaneously by ultra-performance liquid chromatography. Principal component analysis (PCA) and discriminant factor analysis (DFA) were used to establish the mathematical models for species identification, and the classification rates for both methods reached 100%. The e-tongue coupled with multivariate analysis exhibited the excellent performance and classification accuracy, and this was validated by the ultra-performance liquid chromatography results. This simple e-tongue technique could be useful for rapid and accurate identification of S. sphenanthera and S. chinensis.

A comprehensive phytochemical investigation of the stems and leaves of Schisandra chinensis (Turcz.) Baill. resulted in isolation of seventeen compounds, including five lignans: meso-dihydroguaiaretic acid (1), licarin-A (2), pregomisin (3), gomisin A (4), acutissimanide (5), three phenylpropanoids: 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol (6), 2-methoxy-4-(2-propenyl) phenyl β-D-glucopyranoside (7), erigeside 2 (8), six sesquiterpenoids: 7′-hydroxy-abscisic acid (9), burmannic acid (10), (3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one (11), 3-Cyclohexene-1,2-diol, 4-(3-hydroxybutyl)- 3, 5, 5-trimethyl- (12), (−)-loliolide (13), (3Z,5R,8R,11R)-Caryophyll-3-ene-5,8,15-triol (14), one monoterpenoid: (6R,3Z)-6,7-dihydroxy-3,7-dimethyl-2-octenoic acid (15) and two other compounds: methyl shikimate (16), 4-Hydroxydodec-2-enedioic acid (17). Their chemical structures were confirmed through NMR, HRESIMS and comparison with the data in the literature. This is the first report of compounds 5, 6, 8–15, 17 from the family Schisandraceae and compounds 2, 16 from the genus Schisandra. Furthermore, we performed a chemotaxonomic study of the separated compounds.

Phytochemical study on a non-medicinal part of a plant material for herbal medicine, the roots of Schisandra chinensis, was conducted to isolate five new triterpenes, schinensins A–D (1–4) and 3-O-methylchangnanic acid (5), together with 21 known compounds including 10 triterpenes, one sterol, two sesquiterpenes, seven lignans, and one flavonoid. The structures of new triterpenes (1–5) were assigned on the basis of spectroscopic analyses aided with TDDFT ECD calculations. Schinensin A (1) was a dinortriterpene possessing 28-norschiartane skeleton, while schinensins B–D (2–4) were assigned as 3,4:9,10-disecocycloartane, 3,4-secocycloartane, and cycloartane triterpenes, respectively. In an evaluation of antiproliferative activities against human cancer cell lines, some triterpenes exhibited significant activities against human breast carcinoma MCF-7 cells as compared to the other cell lines (A549, HeLa, and RPMI8226).

Schisantherin A (SchA) is a dibenzocyclooctadiene lignan isolated from the fruit of Schisandra sphenanthera. The role of SchA in liver injury induced by ischemia and reperfusion (I/R) has not yet been elucidated. The present study hypothesized the protective effects of SchA in hepatic I/R model. Either sham laparotomy or hepatic I/R was induced in C57BL/6 male mice after SchA or vehicle administration. Liver function, histological damage, oxidative/nitrosative stress, inflammatory infiltration, cytokine production, cell apoptosis, cell autophagy, and I/R-associated intracellular signaling pathway were assessed to evaluate the impact of SchA pretreatment on I/R-induced liver injury. After liver I/R injury, the mice pretreated with appropriate SchA displayed significantly preserved liver function, less histological damage, ameliorated oxidative/nitrosative stress, attenuated inflammatory state, and reduced cell apoptosis. However, no differences in the autophagic response were detected after SchA pretreatment. The underlying protective mechanism putatively involves the inhibition of mitogen-activated protein kinase (MAPK) signaling pathway. Based on the beneficial effects, SchA pretreatment may serve as a potential prophylactic measure to prevent liver I/R injury related to various clinical conditions.

An extensive phytochemical study on the stems and leaves of Schisandra viridis A. C. Smith led to the isolation of two novel highly oxygenated schinortriterpenoids, pre-schisanartanin P ( 1 ) and wuweizidilactone Q ( 2 ), together with four known ones ( 3–6 ). Their structures with absolute configurations were established on the basis of comprehensive spectroscopic methods, including HRESIMS, 1D and 2D NMR analyses and ECD experiments. All isolates were evaluated for their in vitro cytotoxicities against HepG2, MCF-7 and HT-29 cancer cell lines, none of them showed significant activities.

Phytochemical investigations on the fresh fruits of Kadsura coccinea (Lem.) A. C. Sm. have led to the isolation of fourteen undescribed 2,2′-cyclolignans named heilaohuguosus A-N, four undescribed aryltetrahydronaphthalene lignans, heilaohuguosus O-R and one tetrahydrofuran lignan, heilaohuguosu S, with twenty-seven previously described lignan analogues. Their structures and absolute configurations of heilaohuguosus A-S were established by spectroscopic methods including 1D and 2D-NMR techniques and CD experiments. All isolated compounds were evaluated for their hepatoprotective activity against APAP-induced toxicity in HepG-2 cells, four 2,2′-cyclolignans, heilaohuguosus A and L, tiegusanin I and kadsuphilol I showed good hepatoprotective activities against APAP toxicity in HepG-2 cells with cell survival rates of 53.5 ± 1.7%, 55.2 ± 1.2%, 52.5 ± 2.4%, and 54.0 ± 2.2% (positive control bicyclol, 52.1 ± 1.3%) at 10 μM, respectively.

Ethnopharmacological relevance Kadsura heteroclita (Roxb.) Craib (traditionally known as “Xue Tong”) is an important member of the economically and medicinally important plant family Schisandraceae. “Xue Tong” is an imperative ingredient of the Tujia ethnomedicine, traditionally used for the treatment of rheumatoid arthritis (RA), hepatitis, and muscles and joint spasm. The plant is known to be a rich source of lignans and triterpenoids. These classes of natural products have been known to possess various pharmacological activities. Aim of review This review was motivated by the importance of K. heteroclita in traditional Chinese medicine (TCM). It aims to compile the available information on its botanical distribution and description, traditional uses, phytochemistry, pharmacological activities, toxicity, and quality control to provide a solid base for further research and development. Materials and methods Relevant literature was collected by several scientific databases including PubMed, CNKI, Scifinder, The Plant List, Google Scholar, Baidu Scholar, Books (Tujia pharmaceutical records, Guangxi Chinese herbal medicine, Hunan pharmaceutical records and Field identification manual of Chinese herbal medicine) and other literature sources (Flora of China, Pharmacopoeia of the People’s Republic of China) which helped in collecting maximum data about the studied species. Results Traditional uses of K. heteroclita have proven its medicinal importance, providing a rationale for scientific research. Phytochemical studies on the stem of K. heteroclita resulted in the identification of 187 chemical constituents, among which lignans and triterpenoids are the predominant groups. The isolates and crude extracts have been found to exhibit a wide spectrum of in vivo and in vitro pharmacological activities such as anti-RA, anti-inflammatory and analgesic, hepatoprotection, anti-HIV, anti-cancer and anti-HBV. Schisanlactone E (xuetongsu), a triterpenoid, is one of the major components of K. heteroclita exhibiting anti-cancer, neuroprotective and anti-neuroinflammation activities. Interestingly and luckily, this plant has been found to be safe and non-toxic within the therapeutic dose range. Conclusion Pharmacological investigations have validated the use of K. heteroclita in traditional Chinese medicine (TCM). Literature review has demonstrated that lignans and triterpenoids are possibly responsible for most of the biological activities exhibited by this plant. To conclude, this plant shows immense potential for the discovery of more potent bioactive secondary metabolites and therefore further phytochemical and biological studies on other parts of K. heteroclita need to be conducted and more compounds need to be tested regarding their biological activities to completely explore its value as a tremendously important medicinal plant species.

Five new triterpenoids, named schiglausins P-T (1–5), together with twelve known analogues (6–17), were isolated from the fruit of Schisandra glaucescens Diels. Their structures were determined by various spectroscopic methods, including HRESIMS, 1D and 2D NMR spectra and CD experiment. Additionally, all these compounds were tested for their cytotoxicities against B16 mouse melanoma cell line. Compounds 8, 11, 14, and 15 exhibited moderate anti-proliferative effects against B16 cells with IC50 values ranging from 3.64 to 27.00 μM.

Six undescribed triterpenoids, schincarins A‒F, categorized as the preschisanartane (schincarin A), 3,4-secocycloartane (schincarins B‒D), 3,4; 9,10-disecocycloartane (schincarin E), and 3,4-secolanostane (schincarin F) classes, along with twelve known analogues, were obtained from the stems and leaves of Schisandra incarnata Stapf. Their structures were elucidated on the basis of extensive spectroscopic analyses. The absolute configuration of schincarin A was corroborated by analysis of the experimental ECD spectrum, and single-crystal X-ray diffraction with Mo Kα irradiation. Schincarin A represented the first example of preschisanartane-type triterpenoid with two oxa-bridged hemiketals. Among the selected compounds which were evaluated for immunosuppressive activities, schincarin C and kadsudilactone A showed potential inhibition against ConA-induced T-cell proliferation with IC50 values of 5.83 and 6.32 μM, and LPS-induced B cell proliferation with IC50 values of 10.21 and 11.49 μM, respectively.

Five 3,4-seco-cycloartane triterpenoids were isolated from the stems of Kadsura ananosma, two of which had rearranged 5/6 consecutive carbocycle rings C/D (trivially named ananosins A (1) and B (2)), one had a migrated CH3-18 (named ananosins C (3)), and two were analogs, ananosins D (4) and E (5). Their structures were characterized by comprehensive spectroscopic analysis, especially using 2D NMR spectra. A biogenetic pathway to 1 was proposed. These 5 compounds, together with 5 known analogs isolated from the same origin, were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549, PANC-1, and SK-BR-3 human cancer cells, but were inactive.

Aim To study the chemical constituents of the roots and stem bark of Kadsura coccinea . Method Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and finally purified by prep-HPLC. Their structures were elucidated by extensive spectroscopic methods, including 1D- and 2D-NMR, and HR-ESI-MS. Results Two compounds were determined as (7′ S ,8′ S ,8 R )-(8β,8′α)-dimethyl-4,4′-dihydroxy-5,3′-dimethoxy-5′-cyclolignan glucoside ( 1 ) and micrandiactone H ( 2 ), respectively. Conclusion Compunds 1 and 2 are new and neither showed inhibitory effects on nitric oxide (NO) production in lipopolysaccharide-induced RAW264.7 macrophages.

Three new lignans 14-O-demethyl polysperlignan D (1), kadsurindutin E (16), coccilignan A (17), and fifteen known lignan compounds (2–15 and 18) were isolated from the roots of Kadsura coccinea. Their structures were elucidated on the basis of detailed spectroscopic analyses (IR, ESIMS, HR-ESIMS, 1D and 2D NMR, and CD). The NO production inhibitory activities of these isolated lignans were also evaluated.

Four dibenzocyclooctadiene lignans, schisanchinins A-D, and 10 known compounds were isolated from the EtOAc extract of fruits of Schisandra chinensis (Turcz.) Baill. Structures of compounds 1-4 were elucidated using a combination of spectroscopic techniques, including MS, UV and IR, NMR ((1)H NMR, (13)C NMR, HMQC, HMBC). The stereochemistry of the chiral centers and the biphenyl configuration were determined using NOESY, as well as analysis of CD spectra. In vitro activity assays showed that 11 of the 14 compounds exhibited inhibitory activity on lipopolysaccharide (LPS)-induced NO release in primary murine BV2 microglia cells.

Genus Kadsura Kaempf. ex Juss. includes important medicinal plants widely used in the south and southwest of China. The stems and roots are effective in activating blood and resolving stasis, promoting qi circulation to relieve pain, dispelling wind and eliminating dampness, in which lignans and triterpenoids are the major bioactive constituents. Here we summarized the chemical constituents isolated from genus Kadsura Kaempf. ex Juss., which would provide a primary and strategic platform for further exploiting the medicinal value and resources of genus Kadsura Kaempf. ex Juss.

Phytochemical investigation of ethanolic extract from the fruits of Schisandra chinensis led to the isolation of four new sesquiterpenes (1-4); their structures were determined by a combination of NMR (1D and 2D) and MS spectroscopic techniques. In addition, all these isolates were screened for their cytotoxic activities against MCF-7, Caco-2, Hela, Lncap, Hep G2 and MDA-MB231 cancer cell lines. Results indicated that compounds 2 and 3 displayed potent cytotoxic activity against Caco2 cell lines with IC50 values of 17.10 μg/mM and 16.46 μg/mM, respectively.

Ethnopharmacological relevance Rheumatoid arthritis (RA) is a chronic autoimmune disease characterized by failure of spontaneous resolution of inflammation. The stem of Kadsura heteroclite (KHS) is a well-known anti-arthritic Tujia ethnomedicinal plant, which named Xuetong in folk, has long been used for the prevention and treatment of rheumatic and arthritic diseases. Aim of the study The analgesic and anti-inflammatory effects and the potential mechanisms behind such effects of KHS would be investigated by using different animal models. Materials and methods The abdominal writhing episodes of mice induced by intraperitoneal injection of acetic acid and the tail-flick response induced by radiant heat stimulation were used to evaluate the analgesic effect of KHS. The number of abdominal writhing episodes of mice and the latency of tail-flick in rats were measured and recorded. In acute inflammatory models, the ear edema of mice was induced by applying xylene on the ear surface, while the paw edema of male and female rats was induced by subcutaneous injection of carrageenan into the right hind paws of animals. The carrageenan-induced paw swelling in rats were selected as an anti-acute inflammatory mechanism of KHS. Serum levels of interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor (TNF-α) were measured by ELISA, and protein expression of cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were detected by Western blot. Results The maximal tolerated single dose of KHS was determined to be 26 g/kg in both sexes of mice. Pharmacological studies showed that KHS at the dose of 200 mg/kg significantly prolonged the reaction time of rats to radiant heat stimulation and suppressed abdominal writhing episodes of mice induced by intraperitoneal injection of acetic acid. KHS at the dose of 200, 400, and 800 mg/kg, showed dose-dependent inhibition of xylene-induced ear swelling in mice. KHS at the dose of 100, 200, 400, and 800 mg/kg demonstrated dose- and time-dependent suppression of paw edema induced by subcutaneous injection of carrageenan in both all rats. Mechanistic studies revealed that the anti-inflammatory effect of KHS was associated with inhibition of the production of pro-inflammatory cytokines IL-1β, IL-6, and TNF-α and effectively decreased the expression of COX and iNOS proteins in the carrageenan-injected rat serum, paw tissues and inflammatory exudates. The positive reference drug, rotundine at a dosage of 100 mg/kg and indomethacin at a dosage of 10 mg/kg were used in both mice and rat models. Conclusion These results suggested that KHS has significant effects on analgesia and anti-inflammation with decreasing the pro-inflammation cytokines of IL-1β, IL-6, and TNF-α and inhibiting the proteins expression of COX-2 and iNOS.

Human immunodeficiency virus integrase (HIV-1 IN) inhibitors that are currently approved or are in advanced clinical trials specifically target the strand transfer step of integration. However, considerable cross-resistance exists among some members of this class of IN inhibitors. Intriguingly, though, HIV-1 IN possesses multiple sites, distinct from those involved in the strand transfer step, that could be targeted to develop new HIV-1 IN inhibitors. We have developed a fluorescent HIV-1 IN DNA binding assay that can identify small molecules termed IN binding inhibitors (INBIs) that inhibit IN binding to viral DNA. This assay has been optimized with respect to concentrations of each protein, long terminal repeat (LTR) DNA substrate, salt, and time, and has been used successfully to measure the HIV-1 IN DNA binding activity of a well-characterized INBI termed FZ41. In addition, we have used the assay to screen a small library of natural products, resulting in the identification of nigranoic acid as a new INBI. The proposed fluorescence assay is easy and inexpensive, and provides a high-throughput detection method for determination of HIV-1 IN DNA binding activity, monitoring of enzyme kinetics, and high-throughput screening for the identification of new INBIs. (C) 2013 Elsevier B.V. All rights reserved.

Six new lignans, schisphenlignans F-K (1-6), together with ten known ones, were isolated from the leaves and stems of Schisandra sphenanthera. Their structures were elucidated on the basis of spectroscopic methods, including extensive NMR, MS and CD spectra. In addition, some compounds were tested for their acute activity on insulin sensitivity in 3T3-L1 differentiated adipocytes and anti-HIV-1 activity. (C) 2013 Elsevier B.V. All rights reserved.

Ethnopharmacological relevance The fruits of Schisandra chinensis (Trucz.) Baill. (Schisandraceae) which have been used as a tonic especially for kidney yin deficiency in Chinese traditional medicine are recently receiving attention for its preventive activity on age-related neurodegenerative diseases. A variety of studies demonstrated the cognitive-enhancing effects of Schisandra chinensis through animal tests and also in clinical trials. Aim of study In this study, we attempted to investigate the effects of the lignan-riched extract of Schisandra chinensis fruits (ESP-806) on neurotoxicity and memory impairment induced by Aβ 1–42 injection in mice. Materials and methods The fruits of Schisandra chinensis were extracted with the mixture of n -hexane:ethanol (9:1), which is riched with bioactive dibenzocyclooctadiene lignans, schizandrin, gomisin N, wuweigisu C. After oral treatment of ESP-806 (100 mg/kg body weight) followed by injection of Aβ 1–42 (2 μg/mouse, i.c.v. ), novel object recognition and passive avoidance tests were evaluated. To verify the cognition enhancing effects of ESP-806, we examined the effects of ESP-806 on the activities of β -secretase and acetylcholinesterase, and the contents of Aβ and the reduced glutathione within the cortex and hippocampus of Aβ-injected mice. Results Oral treatment of ESP-806 (100 mg/kg body weight) significantly attenuated Aβ 1–42 -induced memory impairment evaluated by behavioral tests. Furthermore, the treatment of ESP-806 attenuated the elevation of β -secretase activity accompanying the reduced level of Aβ 1–42 in the cortex and hippocampus of the brain. ESP-806 also significantly inhibited the acetylcholinesterase activity in the hippocampus and increased the content of the reduced glutathione in the cortex and hippocampus of mouse brain. Conclusions These data suggested that the extract of Schisandra chinensis fruits riched with dibenzocyclooctadiene lignans may be useful in the prevention and treatment of Alzheimer's disease.

Construction of 6/7 fused bicycles featuring C/D rings of micrandilactone C and rubrifloradilactone B is reported through IMDA reaction of properly designed substrates. Also a route to the construction of a tricycle having A/B ring of nortriterpenoids of schisandra family is reported using RCM and a bromonium ion initiated cycloetherification reaction as the key steps.

A new dibenzocyclooctane lignan, schisanbicolorin A, together with fifteen known lignans, were isolated from the stems of Schisandra bicolor Cheng. Their structures were identified as (aS,6R,7S)-5,6,7,8-tetrahydro-2,3,13-trimethoxy-6,7-dimethyldibenzo[3,4]cycloocta [1,2-f][1,3]benzodioxol-1-ol ( 1 ), neglschisandrin C ( 2 ), angeloylgomisin R ( 3 ), schisantherin D ( 4 ), gomisin F ( 5 ), schisantherin B ( 6 ), tigloylgomisin Q ( 7 ), gomisin G ( 8 ), interiotherin B ( 9 ), schisandrin ( 10 ), angeloylgomisin H ( 11 ), benzoylgomisin H ( 12 ), gomisin H ( 13 ), angeloyl−(+)−gomisin K 3 ( 14 ), deoxyschizandrin ( 15 ), and (+)-gomisin K 3 ( 16 ), respectively, based on spectroscopic analysis and by comparison of their spectral data with those reported previously in the literature.

Aim To study the chemical constituents of the aerial parts of Schisandra propinqua var. propinqua . Method Silica gel, C 18 reversed phase silica gel and HPLC were used. The structures were elucidated by extensive spectroscopic methods. Result Two new triterpenoids, propinic lactone A ( 1 ) with 3, 4- seco -cycloartane skeleton, and propinic lactone B ( 2 ) possessing 3, 4:9, 10- seco -cycloartane skeleton, together with a known typical cycloartane triterpenoid, schizandronic acid ( 3 ), have been isolated and identified. Conclusion These two new triterpenoids serve as two important bridge intermediates from cycloartane triterpenoids to Schisandra nortriterpenoids biogenetically.

Illiciaceae and Schisandraceae, together with other members of Austrobaileyales have been identified as one of the earliest diverging lineages of angiosperms, within the ANITA grade The specialized Illiciaceae and Schisandraceae comprise a clade defined by apomorphic characters including pollen grains with three or six colpate apertures. In both these families, pollen apertures and exine sculpture were found to be very informative when considered in the context of recent understanding of evolutionary patterns In the current study, pollen grains of 21 taxa from Illicraceae and Schisandraceae were investigated. These data, together with palynological data for taxa previously studied, were mapped into recent molecular phylogenetic trees to re-evaluate the existing classification and phylogenetic relationships in the two families Palynological data were found to be relatively congruent with recent molecular phylogenies, while traditional delimitations of infra-generic taxa were somewhat conflicting and did not reflect phylogeny and evolution The evolution of pollen morphology in the two families, together with other members of Austrobaileyales, is discussed in comparison with the molecular phylogenies (C) 2009 Elsevier GmbH. 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 class of C 29 triterpene dilactones ( 1 – 6 ) featuring 18(13→14)- abeo -schiartane skeleton have been isolated from the stems of Schisandra propinqua var. propinqua . The structures of new compounds, propindilactones K–O ( 1 – 5 ), were determined on the basis of comprehensive spectroscopic means. Biogenetic pathway of 1 – 6 was proposed and then chemically mimicked. The absolute stereochemistries of new compounds were established on biosynthetic consideration coupled with CD experiments. Compound 2 showed promising anti-HBV activity in vitro.

Nortriterpenoids, sphenadilactone C (1) and sphenasin A (2), together with four known lignans (3-6), were isolated from the leaves and stems of Schisandra sphenanthera. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data and compound 2 was further confirmed by single-crystal X-ray diffraction. Compound 1 features a partial enol moiety and an acetamide group in its structure. In addition, compounds 1, 3-6 showed weak anti-HIV-1 activity with EC(50) values in the range of 15.5-29.5 microg/mL.

Sheng-Mai-San (SMS) is a famous traditional Chinese medicine (TCM) recipe, containing Radix Ginseng (Panax ginseng C.A. Mey., Araliaceae), Radix Ophiopogonis (Ophiopogon japonicus (Thunb.) Ker-Gawl., Liliaceae) and Fructus Schisandrae (Schisandra chinensis (Turcz.) Baill., Magnoliaceae), and has been used more than one thousand years. In this research, pharmacokinetics of one component of this TCM recipe was studied. Schizandrin is the main absorbed effective ingredient of Fructus Schisandrae and its pharmacokinetics were studied following oral administration of pure schizandrin, Fructus Schisandrae aqueous extract, and SMS decoction in rats with approximately the same dose of 5mg/kg. At different time points (0, 0.083, 0.25, 0.5, 1, 1.5, 2, 3, 4, 6, 8, 10 and 12h) after administration, the concentrations of schizandrin in rat plasma were determined by LC-MS, and main pharmacokinetic parameters were estimated. It was found that both AUC0-tn and T1/2 of schizandrin in Fructus Schisandrae aqueous extract and in SMS decoction were increased significantly (p

In order to explore the role of cytochrome P-450 (P-450) in schisandrin B (Sch B)-induced antioxidant and heat shock responses, the effect of 1-aminobenzotriazole (ABT, a broad spectrum inhibitor of P-450) on hepatic mitochondrial glutathione antioxidant status (mtGAS) and heat shock protein (Hsp)25/70 expression was examined in Sch B-treated mice. The non-specific and partial inhibition of cytochrome P-450 (P-450) by ABT pretreatment significantly caused a protraction in the time-course of Sch B-induced enhancement in hepatic mitGAS and Hsp25/70 expression in mice. Using mouse liver microsomes as a source of P-450, Sch B, but not dimethyl diphenyl bicarboxylate (a non-hepatoprotective analog of Sch B), was found to serve as a co-substrate for the P-450-catalyzed NADPH oxidation reaction, with a concomitant production of oxidant species. Taken together, the results suggest that oxidant species generated from P-450-catalyzed reaction with Sch B may trigger the antioxidant and heat shock responses in mouse liver.

Following an initial cleaning-up step on the D101 macroporous resin, a preparative high-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of n-hexane–ethyl acetate–methanol–water (1:0.9:0.9:1, v/v) was used to isolate and separate schizandrin and gomisin A from Schisandra chinensis. A total of 107 mg schizandrin and 36 mg gomisin A with purities of 99.5% and 99.1% were obtained from 400 mg crude extract in one-step elution and less than 3 h, and the structure identification was performed by UV, IR, MS, 1 H NMR and 13 C NMR.

The host plant, Schisandra chinensis (Turcz.) Baill. (Schisandraceae), of the weevil Dendrobaris maculata (Roelofs) (Madarini) is reported for the first time. The larvae grow in the lower stem of S. chinensis at the soil surface. Host plants are up to 5 years old. Redescription, photos of habitus, and genitalia of the weevil and damage and biological data of the host plant are provided.

Six major lignans (schizandrin, gomisin A, deoxyschizandrin, y-schizandrin, gomisin N, wuweizisu C) in the caulomas and leaves of Schizandra chinensis (Turcz.) Baill., and cinnamic acid in the leaves of the plant, were quantitatively analysed by high-performance liquid chromatography in reversed-phase mode with UV detection. Resolution of the determined lignans was evaluated for two multistep gradients applied. Samples for HPLC analysis were prepared by extraction with supercritical carbon dioxide at pressures of 20-27 MPa and temperatures of 40-60 degrees C. Kinetics of the extraction of individual components was measured and simulated with a model.

Different aspects of the pharmacology of Schisandra chinensis fruit and dibenzo- wx a,c cyclooctene lignans from this plant are reviewed focusing in particular on the antihepa- totoxic, antioxidant and antitumoural activities, and on the effects on physical performance and on the central nervous system. Q 1999 Elsevier Science B.V. All rights reserved.

Three new dibenzocyclooctadiene lignans, named angustifolin A, B and C, were isolated from the stems of Kadsura angustifolia. Their structures and stereochemistries were elucidated by spectral studies. (C) 1998 Elsevier Science Ltd. All rights reserved.

An electrospray high-performance liquid chromatography-mass spectrometry interface coupled with a photodiode-array detector has been applied successfully to the identification of a number of lignan constituents from an ethanol extract of the fruits of Schisandra chinensis Baill. A total of fifteen peaks were identified, six of them unambiguously identified as schisandrin (1), schisantherin A (19), schisantherin B (20), schisanhenol (4), deoxyschisandrin (3) and γ-schisandrin (11), based on their abundant [M+H] + , [M+Na] + ions, UV spectra and retention times, compared with those data of reference compounds. Another nine peaks were tentatively identified, based on their intense [M+H] + and [M+Na] + ions and UV spectra.

Two new dibenzocyclooctadiene lignans, angeloylbinankadsurin B, acetylbinankadsurin B, and a known lignan, deangeloylschisantherin F, were isolated from the fruits of Kadsura japonica. Their structures were determined on the basis of chemical and spectral studies.

Five new lignans, schisantherins LO and acetylschisantherin L, were isolated from the seeds of Kadsura coccinea . Their structures, including absolute configurations, were elucidated by spectroscopic analysis and chemical conversions.

Four new lignans, kadsulignan H, I, J and K were isolated from the seeds of a Kadsura sp., of which kadsulignan K possesses a novel benzobicyclooctane skeleton. Their structures, including absolute configurations, were elucidated by 2D 1 H- 13 C long range COSY spectra and chemical conversions.

Three new lignans, kadsulignans E-G, with a spirodienone structure were isolated from the root bark of Kadsura longipedunculata. Their structures were elucidated by 2D 1H-13C long range COSY experiments and chemical conversions. The structures and mechanism of formation of their hydrolysis products are discussed.

From the stems of Kadsura heteroclita, new dibenzocyclo-octadiene lignans, named heteroclitins A-E, were isolated together with the known compounds, kadsurin and interiorin. Their structures were determined by spectroscopic means.

Summary Three lignans, which had antagonistic activities of [ 3 H]PAF to washed rabbit platelet receptor binding, were isolated from the fruits of Schisandra chinensis . Schisandrin A showed most potent antagonistic activity against PAF in this group.

Four new dibenzocyclooctadiene lignans possessing a spirobenzofuranoid skeleton, named propoxyl-, acetoxyl-, benzoyl oxokadsurane and isovaleroyl oxokadsuranol were isolated from the stems of Kadsura coccinea. Their chemical structures were elucidated by spectral and chemical analysis and their absolute configuration determined by a circular dichroic exciton chirality method. Propoxyl oxokadsuranol and benzoyl oxokadsuranol were obtained by hydroxylation of propoxyl oxokadsurane and benzoyl oxokadsurane.

From the fruit of Schisandra sphenanthera , we have isolated a new triterpenoid, named schisanol, as well as the four known lignans, wuweizisu A, schisantherin A and D, and (+)-gomisins K 3 . The structure of schisanol was determined on the basis of spectral data.

A new triterpenoid, named kadsulactone A, was isolated from the methanol extract of stems of Kadsura heteroclita . Its structure was determined by spectroscopic means.

A new dibenzocyclooctadiene lignan, isoschizandrin was isolated from the fruits of Schizandra chinensis . The structure was elucidated on the basis of the spectral analysis and chemical correlation with schizandrin and (+)− deoxyschizandrin. In experiments using rats, schizandrin and its derivatives, including isoschizandrin, showed inhibitory effects on stress-induced gastric ulceration (p.o.).

A new lignan, enshicine, isolated from the fruit of Schisandra henryi , is shown to be 1-oxy-2 S ,3 S -dimethyl- 4 R -(3-methoxy-4-hydroxyphenol)-6,7-methylenedioxytetralin, by means of spectral analysis and chemical correlations.