New Lignans and Iridoid Glycosides from Dipsacus asper Wall

Abstract

Six new compounds, including four new lignans, dipsalignan A (1), B–D (3–5), and two new bis-iridoid glycoside dimmers, dipsanosides M (7) and N (8), together with two known compounds (2) and (6), have been isolated from the roots of Dipsacus asper Wall. Their structures were established on the basis of spectroscopic data (MS, 1D, 2D NMR, and CD) and chemical methods. All the isolated compounds were tested against human immunodeficiency virus-1 (HIV-1) integrase inhibition activities, and only compounds 1, 2, 7, and 8 displayed weak activities.

An Efficient Method for Determining the Relative Configuration of Furofuran Lignans by 1H NMR Spectroscopy

“…To review the relative configurations of 8-OH-type furofuran lignans, 1-hydroxypinoresinol ( 10 ), pseuderesinol ( 11 ), , (+)-1-hydroxy-6-epipinoresinol ( 12 ), (+)-6-epifraxiresinol 4′,4″-di- O -methyl ether ( 13 ), (1 R *,2 R *,5 R *,6 R *)-2,6-bisphenyl-1-hydroxy-3,7-dioxabicyclo­[3.3.0]­octane ( 14 ), (+)-gmelinol ( 15 ), 1-hydroxyfurofuran ( 16 ), neogmelinol ( 17 ), (+)-1-hydroxy-2,6-bisepipinoresinol ( 18 ), and dipsalignan A ( 19 ) (Figure ) were selected as model compounds. The configuration of 14 was determined from its single-crystal X-ray crystallography .…”

“…The configuration of 14 was determined from its single-crystal X-ray crystallography . Since their 7,9′:7′,9-diepoxy moiety also possesses a cis -fused configuration, − these compounds can be classified into four groups according to the orientations of the two aromatic rings: (IV) 7-H/8-OH trans , 7′-H/8′-H trans ( 10 , 11 ); (V) 7-H/8-OH trans , 7′-H/8′-H cis ( 12 – 15 ); (VI) 7-H/8-OH cis , 7′-H/8′-H cis ( 16 ); and (VII) 7-H/8-OH cis , 7′-H/8′-H trans ( 17 – 19 ).…”

A New Ionone Glycoside and Three New Rhemaneolignans from the Roots of Rehmannia glutinosa

“…The relative configuration of 2 was determined by analysis of the coupling constants. The H-7′ possessed a β-orientation on the basis of the observed J value of 6.0 Hz between H-7′ and H-8′, indicating that H-7′ and H-8′ were in a trans -configuration [11]. The NOESY correlations from H-8′ to H-7′ further supported the conclusion (Figure 3).…”

Comparative Proteomic Analysis of Dipsacus asperoides Roots from Different Habitats in China

“…However, due to the different growth environments, the accumulated active components and the quality of D. asperoides have shown marked differences in different cultivation bases [2][3][4]. At present, research on D. asperoides has primarily focused on chemical composition [5], cultivation [6], pharmacology [7], and transcriptomics [1].…”