Nortriterpenoids from Schisandra chinensis and their absolute configurational assignments by electronic circular dichroism study

Shi, Yi‐Ming; Wang, Liyan; Zou, Xi-Sheng; Li, Xiaonian; Shang, Shan‐Zhai; Gao, Zhong‐Hua; Liang, Cheng-Qin; Luo, Huai‐Rong; Li, Honglin; Xiao, Wei‐Lie; Sun, Han‐Dong

doi:10.1016/j.tet.2013.12.023

Cited by 34 publications

(21 citation statements)

References 37 publications

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“…Propindilactone Q (6) was recently isolated from the stem and leaves of this plant. 15) All isolates obtained in the present study were evaluated for their cytotoxicity against endometrial cancer cells (Ishikawa) using 3-4,5-dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide (MTT) assays. As a result, all compounds isolated, including new dibenzocyclooctadiene lignan glucosides 1-4, were found to be inactive (IC 50 values >50 µM) in this assay system.…”

Section: Resultsmentioning

confidence: 99%

Schisandrosides A–D, Dibenzocyclooctadiene Lignan Glucosides from the Roots of <i>Schisandra chinensis</i>

Kim

Ryu

Lee

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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Four new dibenzocyclooctadiene lignan glucosides, schisandrosides A-D (1-4), as well as two known rare nortriterpenoids, micrandilactone C (5) and propindilactone Q (6), were isolated from the roots of Schisandra chinensis BAILLON (Schisandraceae). The structure of compounds 1-4 were elucidated by physical and spectroscopic data interpretation. To the best of our knowledge, schisandrosides A-D (1-4) represent the first example of a dibenzocyclooctadiene lignan glycoside.

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Section: Resultsmentioning

confidence: 99%

Schisandrosides A–D, Dibenzocyclooctadiene Lignan Glucosides from the Roots of <i>Schisandra chinensis</i>

Kim

Ryu

Lee

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In recent years, other valuable biological properties have been demonstrated for some dibenzocyclooctadiene lignans, such as: inhibition of platelet aggregation, the action of inhibiting the proliferation of human immunodeficiency virus (HIV) (Shi et al 2014a) and adjuvant action in cancer treatment by: inhibiting early oncogenic activation of the Epstein-Barr virus (EBV-EA) (Chen et al 2002), reversing multidrug resistance dependent on P-glycoprotein (Pgp-MDR) in tumor cells (Fong et al 2007), and sensitization of liver cancer cells to the effects of doxorubicin (Hou et al 2015; Li et al 2006). …”

Section: Main Biological Modes Of Action Of Dibenzocyclooctadiene Ligmentioning

confidence: 99%

Current knowledge of Schisandra chinensis (Turcz.) Baill. (Chinese magnolia vine) as a medicinal plant species: a review on the bioactive components, pharmacological properties, analytical and biotechnological studies

Szopa

Ekiert²

2016

Phytochem Rev

262

215

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Schisandra chinensis Turcz. (Baill.) is a plant species whose fruits have been well known in Far Eastern medicine for a long time. However, schisandra seems to be a plant still underestimated in contemporary therapy still in the countries of East Asia. The article presents latest available information on the chemical composition of this plant species. Special attention is given to dibenzo cyclooctadiene lignans. In addition, recent studies of the biological activity of dibenzocyclooctadiene lignans and schisandra fruit extracts are recapitulated. The paper gives a short resume of their beneficial effects in biological systems in vitro, in animals, and in humans, thus underlining their medicinal potential. The cosmetic properties are depicted, too. The analytical methods used for assaying schisandra lignans in the scientific studies and also in industry are also presented. Moreover, special attention is given to the information on the latest biotechnological studies of this plant species. The intention of this review is to contribute to a better understanding of the huge potential of the pharmacological relevance of S. chinensis.

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“…Initially, because of the glycosidic bond between rhamnose and benzofuran in 1 , which can cause various changes in conformation during energy-minimized structure calculation, we carefully analyzed ROESY correlations between the sugar and aglycone to obtain a most probable conformation (see Supplementary Information ). After the calculation of the energy-minimized structure from the conformation based on the ROESY correlation, we calculated ECD spectra [ 16 , 17 ]. The ECD spectra based on the conformation were calculated for the 8 S and 8 R configurations.…”

Section: Resultsmentioning

confidence: 99%

A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.

et al. 2014

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Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 1–3 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116.

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Nortriterpenoids from Schisandra chinensis and their absolute configurational assignments by electronic circular dichroism study

Cited by 34 publications

References 37 publications

Schisandrosides A–D, Dibenzocyclooctadiene Lignan Glucosides from the Roots of <i>Schisandra chinensis</i>

Schisandrosides A–D, Dibenzocyclooctadiene Lignan Glucosides from the Roots of <i>Schisandra chinensis</i>

Current knowledge of Schisandra chinensis (Turcz.) Baill. (Chinese magnolia vine) as a medicinal plant species: a review on the bioactive components, pharmacological properties, analytical and biotechnological studies

A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.

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