Two New Phenolic Glycosides from the Barks of<i>Hydnocarpus annamensis</i>and their Anti-Inflammatory and Anti-Oxidation Activities

H, Shi; Wen, Jing; Jia, Chen; Jin, Wei; Zhang, Xiufeng; Yao, Zhi-Rong; Tu, Peng‐Fei

doi:10.1055/s-2006-946678

Cited by 16 publications

(6 citation statements)

References 9 publications

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“…Together, these results question whether the G glycerol units are solely due to oxidation. Alternatively, guaiacylglycerol might be synthesized intracellularly, as it was isolated as only one enantiomeric form, the D-threo-isomer, from Zantedeschia aethiopica (Della Greca et al, 1998), and guaiacylglycerol glucosides were detected in leaves of Juniperus phoenicea (Comte et al, 1997), in roots and rhizomes of Sinopodophyllum emodi (Zhao et al, 2001), in stems of Hydnocarpus annamensis (Shi et al, 2006) and Xylosma controversum (Xu et al, 2008), and in leaves and branches of Camellia amplexicaulis (Tung et al, 2009). …”

Section: Discussionmentioning

confidence: 99%

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Morreel

Dima²,

Kim³

et al. 2010

Plant Physiol.

171

213

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Although the primary structure of proteins, nucleic acids, and carbohydrates can be readily determined, no sequencing method has been described yet for the second most abundant biopolymer on earth (i.e. lignin). Within secondary-thickened plant cell walls, lignin forms an aromatic mesh arising from the combinatorial radical-radical coupling of monolignols and many other less abundant monomers. This polymerization process leads to a plethora of units and linkage types that affect the physicochemical characteristics of the cell wall. Current methods to analyze the lignin structure focus only on the frequency of the major monomeric units and interunit linkage types but do not provide information on the presence of less abundant unknown units and linkage types, nor on how linkages affect the formation of neighboring linkages. Such information can only be obtained using a sequencing approach. Here, we describe, to our knowledge for the first time, a sequencing strategy for lignin oligomers using mass spectrometry. This strategy was then evaluated on the oligomers extracted from wild-type poplar (Populus tremula 3 Populus tremuloides) xylem. In total, 134 lignin trimers to hexamers were observed, of which 36 could be completely sequenced. Interestingly, based on molecular mass data of the unknown monomeric and dimeric substructures, at least 10 unknown monomeric units or interunit linkage types were observed, one of which was identified as an arylglycerol end unit.Lignin is an aromatic heteropolymer that is mainly present in secondary-thickened plant cell walls, allowing the transport of water and nutrients and providing the necessary strength for the plant to grow upwardly Vanholme et al., 2008Vanholme et al., , 2010. In angiosperms, lignin is predominantly composed of guaiacyl (G) and syringyl (S) units that are derived from combinatorial radical-radical coupling of the monolignols coniferyl and sinapyl alcohol, respectively Fig. 1A). Following oxidation of the monolignols by peroxidase and/or laccase, the resulting electron-delocalized radical has unpaired electron density at its 1-, 3-, O-4-, 5-, and 8-positions (Fig. 1B); note that much of the lignin literature uses Greek letters for the side chain, a, b, and g for the 7-, 8-, and 9-positions. As radical coupling at the 8-position is favored, coupling with another monolignol radical affords, after rearomatization, a mixture of dehydrodimers with 8-8-, 8-5-, and 8-O-4-linkages (Fig. 1C). Following dimerization, polymerization will continue by the coupling of the 8-position of an incoming monolignol radical to the O-4-position of the dimer's phenolic end. In the case of a G dimer, coupling can also occur, albeit at a lower frequency, to the 5-position. Thus, chain elongation creates 8-5-and 8-O-4-linkages (Adler, 1977). Besides the monolignols and other monomers that are present in minor amounts , the plasticity of lignin polymerization permits the incorporation of any phenolic that enters the lignification site, subject to its chemical cross-coupling propensit...

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Section: Discussionmentioning

confidence: 99%

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Morreel

Dima²,

Kim³

et al. 2010

Plant Physiol.

171

213

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“…HMBCs (l " Fig. 2) from H-6′′ to C-1′′, C-5′′, and a carboxyl (δ C = 172.6); from H-1′′ to C-4′′, C-5′′, and C-3′′; and from H-7′′ to C-3′′, C-4′′, C-5′′, and C-6′′ constructed a highly oxygenated lactone bridge ring (2-oxabicyclo [2,2,1]heptan-3-one-4,5,6-trihydroxy-5-formacyl), and the key HMBC from H-7 to another carboxyl carbon (δ C = 172.6) established this lactone ring moiety attached at C-7. The position of the hydroxy group at the quaternary carbon (C-4′′) lying at the bridgehead suggested its relative β-configuration, and the coupling constants J H-6′′/H-1′′ = 2.0 indicated that they have a large dihedral angle between 0°and 90°, suggesting that C-6′′-OH and the carboxyl (C-3′′) were in the trans orientation, which is in accordance with the obvious correlation of H-6′′ with H-1′′, as well as with the weak correlation of H-6′′ with H-7′′α observed in the NOESY spectrum of 3.…”

Section: Hr-esi-ms Analysis Of Compound 3 Gave An [M + H]mentioning

confidence: 99%

“…We previously reported the phenolic and flavonoid glycosides from the leaves of S. chinensis [5] and some known compounds from its stems [8]. Herein, we describe the isolation and structure elucidation of three new phenolic glycosides, scolochinenosides C-E (1)(2)(3), and a new triterpenoid scolopianate A (4) (l " Fig. 1), together with 15 known compounds in a continued investigation toward the stems.…”

mentioning

confidence: 94%

Three New Phenolic Glycosides and a New Triterpenoid from the Stems ofScolopia chinensis

Lu¹,

Chai²,

Xu³

et al. 2009

Planta Med

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Three new phenolic glycosides, scolochinenosides C-E ( 1- 3), and a new triterpenoid, scolopianate A ( 4), were isolated from the stems of SCOLOPIA CHINENSIS, along with 15 known compounds. The structures of the new compounds were elucidated by means of extensive spectroscopic and chemical methods. Compound 3 contains a novel highly oxygenated lactone bridge ring attached at the aglycone. Six lanostane triterpenoids ( 10- 15) were discovered for the first time in a species other than GANODERMA LUCIDUM (Polyporaceae). In addition, the phenolic glycosides were evaluated for their inhibitory activity against snake venom phosphodiesterase I.

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“…The Bark, seed, leaf and stem of Hydnocarpus have been used for treating leprosy and other skin disorders for thousands of years in India, China and southeast Asia (Cole and Cardoso, ; Cole and Ht, ; Nayer, ; Chellappandian et al ., ). In recent pharmacological studies, extracts of Hydnocarpus demonstrated a variety of in vitro and in vivo activities including anti‐diabetic (Jong‐Anurakkun et al ., ; Lee et al ., ) anti‐inflammatory (Wang, ), hypolipidemic (Sharma and Hall, ), antimicrobial (Bueno Pérez et al ., ) and antioxidant activities (Shi et al ., ), and this has attracted much attention. Furthermore, significant inhibitory activity on the growth of the human glioma cell line U251 has been reported for the ethanol extract of Hydnocarpus hainanensis , and its use as an antitumor drug has been suggested.…”

Section: Introductionmentioning

confidence: 99%

An efficient in vitro and in vivo HPLC method for hydnocarpin in nanomicelles formulation

Feng

Sun

Omari‐Siaw

et al. 2015

Biomedical Chromatography

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For quantitative and other related bioactive studies of hydnocarpin, there is a need to establish an efficient, specific and sensitive analytical method (in vitro and in vivo). In this paper, an efficient HPLC method has been established and validated to analyze hydnocarpin in a nanomicelle formulation for the first time. Various chromatographic conditions for in vitro and in vivo determinations were investigated, with the application examined by pharmacokinetics and tissue distribution studies. The analysis was carried out using an HPLC system with a Waters symmetry C18 column (4.6 × 150 mm, 5 µm) at 25°C with a detecting wavelength of 342 nm. Eluting at a rate of 1.0 mL/min, a 65% methanol and 35% acetic acid solution (0.1%) served as the mobile phase for the in vitro determinations while a 62% methanol and 38% acetic acid solution (0.1%) was used for in vivo analysis with isoliquiritigenin as internal standard. The established in vitro linearity range for hydnocarpin was 0.2-20 µg/mL (R(2) = 0.9996), with the biological (in vivo) samples following the same trend. The accuracy of the method was >99% (in vitro) and 92.4-105.3% (in vivo). Also, the precision met the acceptance criterion. These results indicate that the established method exhibited high specificity, accuracy, linearity and precision. Additionally, this efficient HPLC method was applied to pharmacokinetics and tissue distribution studies.

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Two New Phenolic Glycosides from the Barks ofHydnocarpus annamensisand their Anti-Inflammatory and Anti-Oxidation Activities

Cited by 16 publications

References 9 publications

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Three New Phenolic Glycosides and a New Triterpenoid from the Stems ofScolopia chinensis

An efficient in vitro and in vivo HPLC method for hydnocarpin in nanomicelles formulation

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