Four benzofuran glycosides from Styrax officinalis

Anıl, Hüseyın

doi:10.1016/s0031-9422(00)83973-4

Cited by 37 publications

(20 citation statements)

References 9 publications

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“…The compounds styraxlignolide B-F (14-18), taraxerol (19), syringin (20) Pastorova et al, 1997;Djerassi et al, 1955;Schroeder, 1968;Reinitzer, 1914Reinitzer, , 1921 Yoshikawa et al, 2000;Nakano et al, 1967aNakano et al, , b, 1969Kitagawa et al, 1974aKitagawa et al, , b, 1975Kitagawa et al, , 1980Sugiyama et al, 1967a, b Segal et al, 1964;Zehavi et al, 1986;Yayla et al, 2002;Anil, 1979 seeds 7-9, 54-59, 66, 67, 72, 124-130 Anil, 2003a, b;Anil, 1980;Segal et al, 1967;Ulubelen et al, 1976 S. paralleloneurum resin Reynolds, 1982;Schroeder, 1968;Reinitzer, 1914Reinitzer, , 1921Huang, 1999;Wang et al, 2006a,b to the control. Therefore the effect of compounds on the expression of type I procollagen, and the MMP-1 proteins (matrix metalloproteinases) in cultured human dermal fi broblasts was examined, and 23 increased the type I procollagen protein expression level by 518.9 18.0%, and decreased the MMP-1 protein expression level signifi cantly by an average of 62.1 8.3 % at 10 M, compared with the vehicle-treated controls cells.…”

Section: Bioactivity Of Metabolitesmentioning

confidence: 99%

The Styracaceae

Pauletti¹,

Teles²,

Silva³

et al. 2006

Rev. bras. farmacogn.

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RESUMO: "Styracaceae". Styracaceae possui 11 gêneros e aproximadamente 160 espécies, sendo árvores e arbustos, distribuídos nas regiões tropicais e subtropicais. Esta família é conhecida principalmente devido ao gênero Styrax, que é notório pela produção de um material resinoso, produto patológico, coletado a partir de incisões realizadas no caule. Esta goma é usada em perfumes, como anti-séptico, expectorante, incenso e material fumegante. Este artigo reúne os estudos fi toquímicos e biológicos realizados em 11 espécies desta família. Foram consultados 92 artigos e levantadas 130 substâncias, que indicaram que Styrax é o maior gênero desta família e o único que foi extensivamente investigado.Unitermos: Styracaceae, Styrax, lignanas, tritepenenos, revisão. ABSTRACT:The Styracaceae contains 11 genera and approximately 160 species consisting of small trees and shrubs, mostly native to tropical and subtropical regions. This family is well-known by the genus Styrax, which is notorious due to the production of resinous material, a pathological product, harvested by making incisions into the tree's bark. The gum is used in perfumes, as antiseptic, expectorant, incense, and fumigating material. This paper reviews the phytochemical and biological studies carried out on 11 species of this family. A total of 92 papers were consulted, and 130 compounds were described, thus these data indicate that Styrax is by far the largest genus in the family, and the only which has been extensively investigated.

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Section: Bioactivity Of Metabolitesmentioning

confidence: 99%

The Styracaceae

Pauletti¹,

Teles²,

Silva³

et al. 2006

Rev. bras. farmacogn.

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“…4) The EtOH extract of the fresh fruiting bodies of the fungus was separated by reversed-phase HPLC with 40-70% MeOH to give two new compounds, masutakeside I (1) and masutakic acid A (2), in addition to five known compounds. The structures of the known compounds, egonol (3), demethoxyegonol (4), egonol glucoside (5), egonol gentiobioside (6), 5,6) and 2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-hydroxymethyl-5-benzofuranpropanol, 7) were determined by a combination of spectroscopic analysis and comparison with reported data.…”

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confidence: 99%

A Benzofuran Glycoside and an Acetylenic Acid from the Fungus Laetiporus sulphureus var. miniatus.

Yoshikawa

Bando

Arihara

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new benzofuran glycoside, masutakeside I (1) and a new C 10 acetylenic acid, masutakic acid A (2) were isolated from the fruiting bodies of the fungus Laetiporus sulphureus var. miniatus. Their structures were established by spectroscopic and chemical methods. The known compounds 3-6 were also obtained and identified as egonol, demethoxyegonol, egonol glucoside and egonol gentiobioside. Some of these compounds exhibited cytotoxicity against Kato III cells.

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“…[16][17][18][19][20] In our laboratory, a series of benzofuran derivatives ( Fig. 1) was isolated from Styrax perkinsiae and Styrax macranthus 4,18 and, to our knowledge, these compounds have not been studied by ESI-MS/MS.…”

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confidence: 99%

Analysis of benzofuran derivatives using electrospray ionization ion trap and electrospray ionization quadrupole time‐of‐flight mass spectrometry

Han²,

Chen

et al. 2010

Rapid Comm Mass Spectrometry

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Analysis of benzofuran derivatives using electrospray ionization ion trap and electrospray ionization quadrupole time-of-flight mass spectrometry Benzofurans and their analogues constitute a major group of naturally occurring compounds 1 and exhibit anti-tumor activity, 2 anti-complement activity, 3 cytotoxic activity, 4 activity against human leukaemic cells, 5 and antifungal and antibacterial activity. 6,7 Their broad range of biological activities has attracted the attention of synthetic organic chemists, 8,9 and such potential applications point to the need for reliable, fast and low-cost analysis of this class of compounds.Mass spectrometry (MS), especially tandem mass spectrometry (MS/MS), has been one of the important physicochemical methods for the identification of trace natural products due to its rapidity, sensitivity, and low levels of sample consumption, 10-13 and some benzofuran derivatives have been rapidly analyzed using electrospray ionization (ESI)-MS. 14,15 Seeds of the Styracaceae family are known to contain various benzofuran derivatives. [16][17][18][19][20] In our laboratory, a series of benzofuran derivatives ( Fig. 1) was isolated from Styrax perkinsiae and Styrax macranthus 4,18 and, to our knowledge, these compounds have not been studied by ESI-MS/MS. To obtain information on the structural elucidation of this class of compounds, such as their degradation products, metabolites and biosynthesis intermediates, the detailed fragmentation patterns of benzofuran derivatives were studied using ESI-MS n in positive ion mode. For several representative benzofuran derivatives, the elemental compositions of most of the product ions were confirmed by low-energy ESI-MS/MS using a quadrupole time-of-flight (QTOF) instrument.HPLC-grade methanol was purchased from Fisher Scientific (Pittsburgh, PA, USA). The MS n experiments were performed on a Esquire 6000 ion trap (IT) mass spectrometer (Bruker, Bremen, Germany). The capillary voltage was set at 4 kV and the source temperature was maintained at 3008C. High-purity nitrogen gas was used as the nebulizer gas at a pressure of 20 psi. Tandem mass spectra were obtained by collision-induced dissociation (CID) of selected precursor ions with helium as the collision gas, by applying collision voltages between 0.3 and 0.5 V. High-resolution experiments were performed on a Bruker micrOTOF Q (quadrupole time-of-flight) mass spectrometer in positive ion mode. The Agilent (Agilent Technologies, Santa Clara, CA, USA) ESI-MS tuning mixture (ES Tuning Mix, PN G2421A), with reference masses at m/z 322.0481, 622.0290 and 922.0098, was used to calibrate the instrument in positive ion mode. Helium was used as the collision gas and highpurity nitrogen as the nebulizer and drying gas at a pressure of 30 psi. The samples were introduced into the mass spectrometer at a flow rate of 115 mL/h. The ESI source conditions were as follows: capillary voltage, À4500 V; end plate voltage, À4000 V; capillary exit voltage, 120 V; and drying gas temperature, 1508C. The collision energ...

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Four benzofuran glycosides from Styrax officinalis

Cited by 37 publications

References 9 publications

The Styracaceae

The Styracaceae

A Benzofuran Glycoside and an Acetylenic Acid from the Fungus Laetiporus sulphureus var. miniatus.

Analysis of benzofuran derivatives using electrospray ionization ion trap and electrospray ionization quadrupole time‐of‐flight mass spectrometry

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