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

Abstract

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.

Inhibitory Effects of Schisandra Lignans on Cytochrome P450s and Uridine 5′-Diphospho-Glucuronosyl Transferases in Human Liver Microsomes

“…Chemical structures of the isolated compounds were determined by NMR. All structures were consistent with previously published data [ 28 ]. Gomisin B (95%) and gomisin C (98%) were purchased from Toronto Research Chemical (Toronto, ON, Canada) and Sigma-Aldrich, respectively.…”

Lignans and Terpenoids from the Leaves of Schisandra chinensis

“…Combined with DEPT‐135, HSQC and 13 C‐NMR data, compound 1 exhibited signals for 32 carbons, including 12 aromatic carbons ( δ C 153.2, 152.6, 151.2, 143.3, 141.9, 140.7, 136.3, 136.2, 125.4, 124.3, 114.2, 116.6), four methoxy groups ( δ C 61.9, 61.3, 61.1, 56.6), two methyl groups ( δ C 29.6, 16.4), one oxymethine signals ( δ C 73.8), a glucose group ( δ C 102.6, 78.0, 78.0, 75.1, 71.4, 62.5), as well as an angeloyl group ( δ C 167.0, 139.5, 128.7, 20.7, 15.8; Table ), indicating that compound 1 belonged to the C 18 ‐dibenzocyclooctadiene lignan with a glucose moiety and an angeloyl group. Compared the 1D NMR data of compound 1 with literatures, it was found that compound 1 was similar to schisandroside B ( 7 ) . The obvious difference between them was that a methoxy group in schisandroside B was substituted by an angeloyl group at C‐12 in 1 .…”

“…In addition, thirteen known compounds 3 – 15 were identified as gomisin F ( 3 ), (−)‐tigloyldeangeloylgomisin F ( 4 ), angeloylgomisin Q ( 5 ), schisandrin ( 6 ), schisandroside B ( 7 ), schisandroside A ( 8 ), pregomisin ( 9 ), 8,8′‐dihydroxypinoresinol ( 10 ), 8‐hydroxypinoresinol ( 11 ), ( R )‐ p ‐cymene 9‐ O ‐ α ‐ d ‐arabinofuranosyl‐(1→6)‐ β ‐ d ‐glucopyranoside ( 12 ), 15‐hydroxy‐ α ‐cadinol ( 13 ), guaidiol ( 14 ), 3 β ‐hydroxy‐5 α ,6 α ‐epoxy‐ β ‐ionone ( 15 ), by comparing the NMR data with the published data in the literatures. Compounds 13 – 15 were isolated firstly from Schisandraceae, and they might provide some new insights to biosynthetic pathway of other compounds, such as triterpenoids or schinortriterpenoids.…”

Chemical Constituents of the Roots of Schisandra chinensis

“…[1] Until now, there are little research were conducted on the chemical compounds of the roots of S. chinensis, which led to isolated lignans and triterpenoids from the roots, while pharmacology studies were displayed that this plant has anti-inflammatory, anti-tumor activities, and so on. [2][3][4] In summary, the roots of S. chinensis have extremely high research value. Therefore, in this study, we have separated one new phenylpropanoid schineolignin D (1), one new sesquiterpene (À )-(7S,10S)-3,11,12,13-tetrahydroxycalamenene (2), one new quinic acid 4-(E)-O-coumaroylquinic acid ethyl ester (3), and seven known compounds (4 -10) from the roots of S. chinensis (Figure 1).…”

“…To promote further studies on the plant, many phytochemistry and pharmacology studies focus on the different parts of S. chinensis [1] . Until now, there are little research were conducted on the chemical compounds of the roots of S. chinensis , which led to isolated lignans and triterpenoids from the roots, while pharmacology studies were displayed that this plant has anti‐inflammatory, anti‐tumor activities, and so on [2–4] …”