Plant proanthocyanidins. Part I. Introduction; the isolation, structure, and distribution in nature of plant procyanidins

Thompson, RS; Dougnon, Jacques; Haslam, Edwin; Tanner, R. J. N.

doi:10.1039/p19720001387

Cited by 465 publications

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“…29) One possible reason for this apparent discrepancy is that the rich organic acids in Chinese hawthorn might enhance procyanidin decomposition or inhibition of polymerization. 13) HP is an ethyl acetate extract from HE. The total content of the 13 polyphenols in HP was 21.4%, i.e., almost 8.5-fold of that in HE, and 38-fold of that in a standardized extract of fresh Crataegus berries.…”

Section: Contents Of Organic Acid and Polyphenolsmentioning

confidence: 99%

“…12) These crude extracts contain many undesirable substances, such as carbohydrates, organic acids, and moisture, which not only reduce the concentration of active constituents but also hasten procyanidin decomposition in an environment of moist acidity. 13) Hence we developed a new extraction procedure 14) that uses ethyl acetate treatment of HE to prepare a sugarless extract, which we call hawthorn polyphenol (HP). Using this procedure, the side-products of concentrated hawthorn juice (HJ) and hawthorn dietary fiber can also be prepared.…”

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Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Cui

Nakamura

Tian

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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Hawthorn polyphenol (HP) was prepared by ethyl acetate treatment of the ethanol extract (HE) of Chinese hawthorn fruit. The concentrations of 15 polyphenols in the HP, HE, extraction residue (HJ), and a hawthorn leaf extract (HF) were determined by HPLC. For HP, the total content of the 15 polyphenols was 21.4%, comprised of 19.7% of procyanidins, 1.21% of chlorogenic acid, and 0.48% of flavonoids, compared to 2.55% for the HE. The yields of procyanidin monomer, dimer, trimer, tetramer, and pentamer were 50.5%, 30.3%, 23.0%, 14.6%, and 12.5% respectively, and the mean degree of polymerization was reduced to 1.39 (HP) from 1.65 (HE). Seven different physiological actions of the four extracts were investigated. The HP showed strong O 2 À and OH scavenging capacities (IC 50 values of 6.3 g/ml and 1.1 g/ml respectively), as well as selective prolyl endopeptidase inhibition (IC 50 of 60 g/ml). The active constituents appeared to be procyanidins.Key words: Crataegus pinnatifida; HPLC; procyanidin; antioxidant; free radicalsIn Europe, standardized extracts of the leaves and flowers of Crataegus oxyacantha and Crataegus monogyna are used in the therapy for moderate (NYHA II) congestive heart failure. 1,2) These extracts exert several pharmacological and clinical effects, such as antiischemia/reperfusion-injury, anti-arrhythmic, hypolipidemic, and hypotensive effects. 1,2) Flavonoids and procyanidins are considered to be the two main active constituents. 2) Species of Chinese hawthorn, particularly Crataegus pinnatifida and Crataegus pinnatifida Bge. var. major NE Br., have also been used as herbal medicines. 2,3) Studies indicate that Chinese hawthorn extracts have beneficial effects, such as antioxidant, 4,5) anti-inflammatory, 6) and hypolipidemic effects, 7) as well as protective effects on the brain and vascular endothelium 8,9) and endothelium-dependent relaxation. 10) Recently, we analyzed 37 major cultivars of Chinese hawthorn using high performance liquid chromatography (HPLC), and found that procyanidins, which were present in high concentrations, were the main phenolic active constituents in these fruits. 11) In general, the hawthorn found in China is an edible fruit that is popular for its special acidic taste. It is bigger than its European counterpart. Since the content of organic acid in Chinese hawthorn fruits can be up to 5% (fresh weight), they are used to produce various foods, such as jams, jellies, juices, tinned foods, wines, and various sweet foods. However, the high sugar content of these fruits counteracts the benefits of polyphenols for consumers of advanced age or for those who suffer from hypertension, cardiovascular disease, or diabetes. Hence, it is desirable to separate the polyphenol and sugar components. Previously, hawthorn extract (HE) for medical applications were ethanol-extracted from the dried fruit of the Chinese hawthorn. 12) These crude extracts contain many undesirable substances, such as carbohydrates, organic acids, and moisture, which not only reduce the concentration of acti...

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Section: Contents Of Organic Acid and Polyphenolsmentioning

confidence: 99%

mentioning

confidence: 99%

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Cui

Nakamura

Tian

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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“…In general, the 4S-linkage between two flavan units produces negative Cotton effects at 220-240 and 275 nm in the CD spectra. [22][23][24][25][26][27] Such negative Cotton effects can be observed in the spectrum of compound 9a, in addition to a positive Cotton effect at 255 nm. The latter effect is (probably) due to the S-configuration of the phenylpropanoid substituent.…”

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Phenylpropanoid substituted flavan-3-ols from Trichilia catigua and their in vitro antioxidative activity

Resende¹,

Rodrigues‐Filho²,

Luftmann³

et al. 2011

J. Braz. Chem. Soc.

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O novo flavan-3-ol contendo um substituinte fenilpropanoide apocinina E, juntamente com oito substâncias conhecidas, epicatequina, procianidina B2, procianidina B4, procianidina C1, cinchonaína Ia, cinchonaína Ib, cinchonaína IIb e cinchonaína IIa foram isoladas a partir do extrato acetona-H 2 O das cascas secas de Trichilia catigua. As substâncias cinchonaína Ib e cinchonaína IIb foram reavaliadas em relação à sua estereoquímica. Todas as substâncias foram caracterizadas por análises espectroscópicas incluindo ressonância magnética nuclear (NMR) 1D e 2D e espectrometria de massa (MS) de seus derivados acetilados. A configuração absoluta do substituinte fenilpropanoide foi determinada por espectropolarimetria de dicroísmo circular (CD) e pela análise do efeito anisotrópico empregando modelo de Dreiding, e por experimento de espectroscopia de efeito nuclear Overhauser (NOESY NMR). As nove substâncias mostraram maior atividade sobre o sequestro de radical livre e poder de redução do que o ácido ascórbico e Trolox frente ao radical livre 2,2-difenil-1-picrilhidrazila e no sistema do teste de redução do ferro (Fe 3+ -Fe 2+ ).The new phenylpropanoid substituted flavan-3-ol apocynin E, together with eight known compounds, epicatechin, procyanidin B2, procyanidin B4, procyanidin C1, cinchonain Ia, cinchonain Ib, cinchonain IIb, and cinchonain IIa were isolated from an acetone-H 2 O extract of the air-dried stem bark of Trichilia catigua. The cinchonain Ia e Ib were reevaluated to its estereochemistry. All the compounds were characterized by spectroscopic analysis including 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS) of their peracetate derivatives. The absolute configuration of the phenylpropanoid moiety was determined by circular dichroism (CD) spectra and by analyzing the anisotropic effects in the Dreiding model and nuclear Overhauser effect (NOESY NMR) experiments. The nine isolated compounds showed higher radical scavenging activity and reducing power than ascorbic acid and Trolox in the free-radical 2,2-diphenyl-1-picrylhydrazyl and Fe 3+ -Fe 2+ reduction assay systems. Keywords:Trichilia catigua, Meliaceae, cinchonains, proanthocyanidins, antioxidative activity IntroductionTrichilia catigua A. Juss. (Meliaceae), commonly known as "catuaba", is a plant native to South and Central America and widely distributed in Brazil. 1 However, the identity of the plant source is often uncertain, and stem barks from several different species of Erythroxylum or Anemopaegma, all regionally known as "catuaba", are sold commercially. Marques 2 described the differences among the species known as "catuaba" and Phenylpropanoid Substituted Flavan-3-ols from Trichilia catigua J. Braz. Chem. Soc. 2088 determined that T. catigua is the main species that is sold as "catuaba" in Brazil. The same conclusion was reached by Kletter et al. 3 and Daolio et al. 4 The bark of T. catigua has been traditionally used as a health and mental tonic, and especially as a sexual stimulant. 3,5 Some pharmacological studies o...

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“…All of the above migrated to some extent in the BAW solvent. RF values were slightly higher with Haslam's solvent mixture containing less H20 and 2-butanol instead of 1-butanol (11). The "overlap" between the catechin components in the 5% HOAc and the subsequent MeOH:5% HOAc (20:80) fraction was minimized by a more exhaustive extraction (15 ml rather than 3 ml) with 5% HOAc.…”

Section: Methodsmentioning

confidence: 89%

“…Isolation of MeOH2-soluble procyanidins by chromatography on paper or Sephadex LH-20 columns (11) or by precipitation with ethyl acetate (7) led to forms that did not migrate in a BAW mixture and streaked on 5% HOAc in twodimensional chromatography. These problems have now been partially resolved with the development of a rapid small-scale ' This research was supported by National Science Foundation Grant PCM-76-84392.…”

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Procyanidins (Condensed Tannins) in Green Cell Suspension Cultures of Douglas Fir Compared with Those in Strawberry and Avocado Leaves by Means of C₁₈-Reversed-phase Chromatography

Stafford¹,

Lester²

1980

Plant Physiol.

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The procyanidins (the most common type of proanthocyanidin or condensed tannin) from cell suspension cultures derived from cotyledons of Douglas Fir have been compared with those isolated from leaves of strawberry and avocado. Seventy per cent methanol (v/v) extracts from 100 milligrams fresh weight samples were analyzed by a combination of C18-reversed-phase columns with high-performance liquid chromatography, and normal phase paper chromatography. (-)-Epicatechin and its oligomers were generally retarded longer on C18 columns than the corresponding units made of (+)-catechin when eluted with solvents made up of 5% acetic acid alone or mixed with methanol up to 15% (v/v). Douglas fir preparations contained the most complex set of procyanidins and consisted of oligomers of catechin and epicatechin, whereas strawberry and avocado contained mainly (+)-catechin and (-)-epicatechin derivatives, respectively.Proanthocyanidins (polymeric phenolic compounds also called condensed tannins) are found in numerous gymnosperms and angiosperms in amounts up to 40% of the fresh weight of the tissues extracted. It is assumed that they are generalized chemical defense mechanisms against animal predators and attack by microorganisms (10). The most common type produce cyanidin upon acid hydrolysis and are called procyanidins. They are believed to be formed by the condensation of a precursor diol or a carbocation with already formed catechin or epicatechin monomers or oligomers (5, 9). One example of a dimer is shown in Figure 1.Recent investigations of the procyanidins in green cell suspension cultures derived from cotyledons of Douglas fir were hampered by apparent low levels of lower mol wt oligomers of procyanidins. Isolation of MeOH2-soluble procyanidins by chromatography on paper or Sephadex LH-20 columns (11) or by precipitation with ethyl acetate (7) led to forms that did not migrate in a BAW mixture and streaked on 5% HOAc in twodimensional chromatography. These problems have now been partially resolved with the development of a rapid small-scale ' This research was supported by National Science Foundation Grant PCM-76-84392. MATERIALS AND METHODSThe three major tissues or cells studied were chamber-grown at about 25 C. The cell suspension cultures of Douglas fir (Pseudotsuga menziesii, Franco) were derived from cotyledons (9). The strawberry leaves and green fruits were from an unidentified cultivar of Fragaria chiloensis var. ananassa, Bailey. Avocado plants (Persea gratissima, Gaertn.) were grown from seeds of commercial origin.

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Plant proanthocyanidins. Part I. Introduction; the isolation, structure, and distribution in nature of plant procyanidins

Abstract: The isolation and determination of structure of some plant procyanidins in their free phenolic forms are described. The distribution of procyanidins in the tissues of twenty-nine plant species has been examined and the biogenetic implications of this study are briefly discussed.

Cited by 465 publications

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Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Phenylpropanoid substituted flavan-3-ols from Trichilia catigua and their in vitro antioxidative activity

Procyanidins (Condensed Tannins) in Green Cell Suspension Cultures of Douglas Fir Compared with Those in Strawberry and Avocado Leaves by Means of C₁₈-Reversed-phase Chromatography

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Plant proanthocyanidins. Part I. Introduction; the isolation, structure, and distribution in nature of plant procyanidins

Abstract: The isolation and determination of structure of some plant procyanidins in their free phenolic forms are described. The distribution of procyanidins in the tissues of twenty-nine plant species has been examined and the biogenetic implications of this study are briefly discussed.

Cited by 465 publications

References 0 publications

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Phenylpropanoid substituted flavan-3-ols from Trichilia catigua and their in vitro antioxidative activity

Procyanidins (Condensed Tannins) in Green Cell Suspension Cultures of Douglas Fir Compared with Those in Strawberry and Avocado Leaves by Means of C18-Reversed-phase Chromatography

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Procyanidins (Condensed Tannins) in Green Cell Suspension Cultures of Douglas Fir Compared with Those in Strawberry and Avocado Leaves by Means of C₁₈-Reversed-phase Chromatography