Gas Chromatography/Mass Spectrometry of the Lignans in Resin of Callitris preissii

Abstract

The total extract of resin from Callitris preissii was analyzed by gas chromatography/mass spectrometry and 34 lignans, underivatized and as trimethylsilyl ether derivatives, were identified by interpretation of the mass spectra. The lignans in the resin include 13 new lignans, i.e., four secoisolariciresinol derivatives, four lariciresinol derivatives, 3῏,4῏-methylenedioxy-7῏-hydroxylariciresinol, 3,4-methylenedioxypinoresinol isomer, and two matairesinol derivatives. Furthermore, 17 lignans of the resin are characterized by methylenedioxy substitution on either or both guaiacylpropyl units or the syringylpropyl unit: i.e., five secoisolariciresinol derivatives, three lariciresinol derivatives, 3῏,4῏-methylenedioxy-7῏-hydroxylariciresinol, three pinoresinol derivatives, and five matairesinol derivatives, have methylenedioxy structures. Eleven lignans, including two secoisolariciresinol derivatives, four lariciresinol derivatives, two pinoresinol derivatives, and three matairesinol derivatives, contain a syringyl moiety.

Terpenoid Compositions of Resins from Callitris Species (Cupressaceae)

“…Callitrisol (V), ferruginol (VI), and sandaracopimara-8(14),15-dien-3β-ol (VII) are minor hydroxylated components in some samples. In addition, C. preissii resin contains dominant lignans, as already reported [31]. Three sesquiterpenoids, i.e., callitrisin (I), columellarin (II), and dihydrocolumellarin (III), are present here only in resin of C. preissii (Figure 1c).…”

“…In this study only C. preissii contains numerous known and novel lignans in the total resin extract. They are a complex mixture, including seco -lariciresinols, lariciresinols, pinoresinols, and matairesinol with many syringyl moieties, and their mass spectra as the derivatized compounds with interpretations have been published [31].…”

Non-host disease resistance response in pea (Pisum sativum) pods: Biochemical function of DRR206 and phytoalexin pathway localization

“…S1B) to the authentic standard ( Fig. S1A) (Yamamoto et al, 2010). Following its purification using reversed-phase HPLC (see "Experimental") and chiral HPLC, the pinoresinol (3) isolate was found to be in 84% e.e.…”

Metabolite Profiling of Two Maple-Derived Products Using Dereplication Based on High-Performance Liquid Chromatography–Diode Array Detector–Electrospray Ionization-Time-of-Flight-Mass Spectrometry: Sugar Maple Bark and Bud Hot-Water Extracts

“…MS peaks at m / z 613 [M – H – 196] − , 565 [M – H – 196 – 18 – 30] − (dehydrated guaiacylglycerol fragment loss followed by H 2 O loss and FL) and at [183] + justified the occurrence of a S­(8-8)­S resinol genin fragment. Dereplication led to a match of the chemical formula of compound bk89 with several lignan formulas, inter alia, 3­(,3′),4­(,4′)-(di)­methylenedioxylated derivatives of resinol-type lignans found in Acer . , Considering the limited spectral data, bk89 was simply labeled as lignan (λ max = 258 nm and positive MS fragment at m / z 183, either S residue or dihydroconiferyl alcohol).…”