Conifer Seed Cone Proanthocyanidin Polymers: Characterization by 13C NMR Spectroscopy and Determination of Antifungal Activities

Eberhardt, Thomas L.; Young, Richard M.

doi:10.1021/jf00044a023

Cited by 63 publications

(45 citation statements)

References 13 publications

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“…Our results on the seed cones can be compared to the study of Eberhardt and Young (1994), who analyzed purified condensed tannins from five Pinus spp. seed cones with 13 C-NMR spectroscopy.…”

Section: Cones and Seedpodsmentioning

confidence: 86%

Tannin signatures of barks, needles, leaves, cones, and wood at the molecular level 1 1Associate editor: C. Arnosti

Hernes

Hedges

2004

Geochimica et Cosmochimica Acta

108

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Section: Cones and Seedpodsmentioning

confidence: 86%

Tannin signatures of barks, needles, leaves, cones, and wood at the molecular level 1 1Associate editor: C. Arnosti

Hernes

Hedges

2004

Geochimica et Cosmochimica Acta

108

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“…For example, Fukushima et al (2002) reported that di-and triterpenes from Chamaecyparis obtusa cones had antifeedant activity against Spodoptera litura. Eberhardt and Young (1994) isolated proanthocyanidins from the seed cones of white spruce and pines, and demonstrated their antifungal activities against Ceratocystis coerulescens and Schizophyllum commune. Mono-, sesqui-, and diterpenes have been found in the seed cones of T. distichum (Hirasawa et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Antifungal Abietane-Type Diterpenes from the Cones of Taxodium distichum Rich

et al. 2010

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The chemical composition of Taxodium distichum cones and the antifungal activities of twelve diterpenoids against two wood decay fungi, Trametes versicolor (white-rot) and Fomitopsis palustris (brown-rot) were examined. The chemical composition of the major extractive fraction, the n-C(6)H(14) extract, was evaluated and its antifungal properties were identified. Twelve diterpenoids including ten abietane-type components were isolated from the n-C(6)H(14) extract: 6,7-dehydroferruginol (1), ferruginol (2), 6,7-dehydroroyleanone (3), sandaracopimaric acid (4), taxodione (5), taxodal (6), taxodone (7), sugiol (8), xanthoperol (9), salvinolone (10), 5,6-dehydrosugiol (11), and 14-deoxycoleon U (12). Compounds 5 and 12 were highly active against both wood-decay fungi. In particular, the activities of these compounds against F. palustris were potent. The results suggest that the position and the number of hydroxyl groups on abietane-type structures may be related to antifungal activities against T. versicolor and F. palustris.

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“…As the literature reported that the C2-C3 of cis-structure or C2-C3 of trans-structure can be determined through the distinct differences in the C2 chemical shifts, which is in the region between 70 and 90 ppm. [31,32] In the 13 C NMR spectra, C2 gives resonances of 77 ppm and 84 ppm for the cis (procyanidin B1) and trans (procyanidin B3) form, respectively. C3 of both cis and trans isomers occurs at 73 ppm.…”

Section: Structural Identifications Of the Isolated Compoundsmentioning

confidence: 99%

Separation and Purification of Four Flavan-3-ols FromIris LacteaPall.var. Chinensis(Fisch.) Koidz by High-Speed Counter-Current Chromatography with Flow-Rate Gradient

Ouyang

Wang

et al. 2015

Journal of Liquid Chromatography & Related Technologies

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In this study, we established a flow-rate gradient separation method to isolate four flavan-3-ol compounds with high purity from the seed coat extracts of Iris lactea by high-speed counter-current chromatography (HSCCC). First, the ethyl acetate extract was pre-separated by silica column chromatography fractionation to obtain the enriched flavan-ols sample (EFS). Then, the EFS was separated by HSCCC with a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (0.75:12.5:1:12.5, v/v/v/v) by increasing the flow rate of the mobile phase from 1.5 to 3.0 mL/min after 120 min. The separation temperature was 30°C, the detection wavelength was 280 nm and the revolution speed was 900 rpm. By the optimized HSCCC method, 300 mg of the EFS was separated, yielding 58 mg of procyanidin B3, 72 mg of procyanidin B1, 52 mg of catechin, and 18 mg of procyanidin B7, at a purity of 98.23%, 99.05%, 99.03%, and 96.34% in 240 min. In this work, the flavan-3-ols in I. lactea are partly reviewed and the results can provide evidence to look for other rich source of procyanidins.

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Conifer Seed Cone Proanthocyanidin Polymers: Characterization by 13C NMR Spectroscopy and Determination of Antifungal Activities

Cited by 63 publications

References 13 publications

Tannin signatures of barks, needles, leaves, cones, and wood at the molecular level 1 1Associate editor: C. Arnosti

Tannin signatures of barks, needles, leaves, cones, and wood at the molecular level 1 1Associate editor: C. Arnosti

Antifungal Abietane-Type Diterpenes from the Cones of Taxodium distichum Rich

Separation and Purification of Four Flavan-3-ols FromIris LacteaPall.var. Chinensis(Fisch.) Koidz by High-Speed Counter-Current Chromatography with Flow-Rate Gradient

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