Oligomeric Hydrolyzable Tannins From Liquidambar Formosana and Spectral Analysis of the Orientation of Valoneoyl Groups in Their Molecules

Hatano, Tsutomu; Okonogi, Akira; Okuda, Takuo

doi:10.1007/978-1-4615-3476-1_11

Cited by 4 publications

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“…In addition, 11 known hydrolyzable tannins, pedunculagin, casuarinin, 1,4,6-tri- O -galloyl-β- d -glucose, 2,4,6-tri- O -galloyl- d -glucose, 1,2,4,6-tetra- O -galloyl-β- d -glucose, guavin C, pterocarinin A, and isorugosins A ( 4 ), B ( 5 ), D ( 6 ), and G ( 7 ) (Figure ), were also identified. Among these known hydrolyzable tannins, 2,4,6-tri- O -galloyl- d -glucose, guavin C, and pterocarinin A were isolated for the first time from this plant source.…”

Section: Resultsmentioning

confidence: 99%

“…The orientations of both of the valoneoyl groups were determined to be of the isorugosin type (Figure ), and as shown in Table , the 1 H NMR chemical shifts of glucose-II signals of 1 coincided with the corresponding signals of 6 , while the H-3 signal of glucose-I of 1 was shielded (Δδ H 0.23) relative to that of 6 . This shift was attributed to the anisotropic effect of the galloyl moiety of the valoneoyl group . The electronic circular dichroism (ECD) spectrum of 1 exhibited a strong positive Cotton effect in the short-wavelength region ([θ] 225 +2.7 × 10 5 ), indicating that the absolute configuration of both valoneoyl groups was (a S ) .…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H NMR spectrum showed the presence of two valoneoyl groups by the two following three-proton sets [δ H 7.16 (1H, s, valoneoyl-H C ), 6.62 (1H, s, valoneoyl-H A ), 6.156 (1H, s, valoneoyl-H B ) and δ H 7.18 (1H, s, valoneoyl-H C ), 6.63 (1H, s, valoneoyl-H A ), 6.162 (1H, s, valoneoyl-H B )] . Proton signals due to the six galloyl groups (δ H 7.10, 7.08, 7.01, 6.97, 6.89, and 6.88) and an HHDP group (δ H 6.70 and 6.61) were also present in the aromatic region . The aliphatic region of the 1 H NMR spectrum displayed three seven-spin systems assignable to the protons of three glucose cores (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…Its leaves and fruits are used in traditional Chinese medicine to treat enteritis, dysentery, and rheumatic arthralgia . In addition to several constituents including flavonoids and terpenes, hydrolyzable tannins have been isolated from the leaves. − …”

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Structures and Antibacterial Properties of Isorugosins H–J, Oligomeric Ellagitannins from Liquidambar formosana with Characteristic Bridging Groups between Sugar Moieties

et al. 2017

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Three new ellagitannin oligomers, isorugosins H (1), I (2), and J (3), together with 11 known hydrolyzable tannins were isolated from an aqueous acetone extract of the fresh leaves of Liquidambar formosana. Their chemical structures were elucidated based on spectroscopic data and chemical conversion into known hydrolyzable tannins. The bridging mode of the valoneoyl groups between their sugar moieties has been identified only in this plant species. Additionally, the effects of the isorugosins isolated from this species on drug-resistant bacteria were evaluated and showed that isorugosin A (4) exhibited the most potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The isorugosins also had a suppressing effect on pigment formation in Pseudomonas aeruginosa. The isorugosin-protein complexes were analyzed using size-exclusion chromatography and polyacrylamide gel electrophoresis to clarify the relationship of their antibacterial properties with their protein interaction potency as hydrolyzable tannins. The results suggested that the antibacterial properties of hydrolyzable tannins are not simply a result of their binding activity to proteins, but are due to other factors such as the accessibility of polyphenolic acyl groups to bacterial membranes.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Structures and Antibacterial Properties of Isorugosins H–J, Oligomeric Ellagitannins from Liquidambar formosana with Characteristic Bridging Groups between Sugar Moieties

et al. 2017

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“…Namun untuk pemula, membuat analisis spektrum MS dan NMR adalah pekerjaan yang relatif sulit. Teknik yang dapat digunakan untuk MS, misalnya FAB-MS (fast atom bombardement-MS) (Hatano et al, 1992). Sedangkan untuk NMR baik H-NMR maupun C-NMR, antara lain COSY, NOESY, HMQC, dan HMBC (Lin et al, 2001).…”

Section: Analisis Biokimiaunclassified

REVIEW: Ellagitannin; biosynthesis, isolation, and biological activities

et al. 2003

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Ellagitannin is one of the bioactive groups produced by some of medicinal plants. Ellagitannin is a hydrolysable tannin compound biosynthesized via shikimic acid â€“ gallic acid â€“ pentagalloilglucose pathway. Ellagitannin can be isolated by cascade extraction procedures followed by column chromatography method and preparative HPLC method. The biological activities of ellagitannin are caused by molecular bond between ellagitannin and some other compound, especially protein that makes complex compound and changes physiological processes in cells or tissues of the livingthinks. Biological activities of ellagitannin included anti-diabetic, anti-microbes, anti-viruses, anti-hypertension, antioxidative, and anti-cancer or anti-tumor.

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The Chemistry and Chemical Ecology of Ellagitannins in Plant–Insect Interactions: From Underestimated Molecules to Bioactive Plant Constituents

Salminen

2014

Recent Advances in Polyphenol Research

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This chapter reviews our current knowledge of the chemistry and chemical ecology of ellagitannins (ETs), placing particular emphasis on the role these under-appreciated polyphenols play in plant-herbivore interactions. Instead of the traditional tannin-linked activity that comes from their complex formation with proteins, it discusses tannins' less well-known pro-oxidant activity. ETs are likely the most active tannin pro-oxidants. Plant cells synthesize ETs via the shikimate pathway, utilizing the enzymatic conversion of dehydroshikimic acid into gallic acid and further to galloyl glucoses. During the biosynthetic steps from monogalloyl glucose towards pentagalloyl glucose, the pro-oxidant activity of the polyphenols decreases, but it begins to increase again as soon as pentagalloyl glucose is transformed to glucopyranose-based ETs and further to very active C-glycosidic ETs. Thus, the tannin-based pro-oxidant capacity of a plant cell is highly dependent on the total and relative concentrations of different types of products or intermediates of the hydrolyzable tannin pathway. Within plant species that accumulate different types of galloyl glucoses and ETs differing in pro-oxidant activities, this balance typically varies significantly. The situation is further complicated by the variation in ETs observed seasonally and between individual plants. In addition, ETs may also derive their antiherbivore activities via their hydrolysis products, which is largely an unexplored area of research. Historically, ETs have not been taken specifically into account as plant-defense compounds, mainly due to difficulties in their compound-specific analysis from the plant cell. Recent developments in tannin chemistry have diminished these problems and the joint effort of ecologists and

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Oligomeric Hydrolyzable Tannins From Liquidambar Formosana and Spectral Analysis of the Orientation of Valoneoyl Groups in Their Molecules

Cited by 4 publications

References 14 publications

Structures and Antibacterial Properties of Isorugosins H–J, Oligomeric Ellagitannins from Liquidambar formosana with Characteristic Bridging Groups between Sugar Moieties

Structures and Antibacterial Properties of Isorugosins H–J, Oligomeric Ellagitannins from Liquidambar formosana with Characteristic Bridging Groups between Sugar Moieties

REVIEW: Ellagitannin; biosynthesis, isolation, and biological activities

The Chemistry and Chemical Ecology of Ellagitannins in Plant–Insect Interactions: From Underestimated Molecules to Bioactive Plant Constituents

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