Stachysetin, a diapigenin-7-glucoside-p,p′-dihydroxy-truxinate from Stachys aegyptiaca

El-Ansari, Mohamed A.; Nawwar, Mahmoud A.M.; Saleh, Nabiel A.M.

doi:10.1016/0031-9422(95)00395-n

Cited by 61 publications

(39 citation statements)

References 9 publications

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“…Dextran 70T was obtained from Amersham Pharmacia Biotech AB (Uppsala, Sweden). Naringin was isolated from Rhizoma drynariae (Gusuibu), and naringenin was hydrolyzed from naringin, which were characterized by 1 H NMR on Bruker Ultrashied TM 400 MHz Plus spectrometer, and their spectra were identical to following literature reports, respectively (El-Ansari et al, 1995;Pereira et al, 2007). E 2 assaying kit (enzyme-linked immunosorbent assay (ELISA) was bought from Shanghai Hufeng Biology and Technology Co., Ltd. All the cell lines in the article were provided by China Centre for Type Culture Collection (Wuhan).…”

Section: Methodsmentioning

confidence: 99%

Double directional adjusting estrogenic effect of naringin from Rhizoma drynariae (Gusuibu)

Guo

Wang

et al. 2011

Journal of Ethnopharmacology

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Section: Methodsmentioning

confidence: 99%

Double directional adjusting estrogenic effect of naringin from Rhizoma drynariae (Gusuibu)

Guo

Wang

et al. 2011

Journal of Ethnopharmacology

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“…We have previously reported the isolation and structure elucidation of diapigenin 7-O-(6″-trans-6″-cis-p,p′dihydroxy-µ-truxinyl)glucoside [stachysetin] [2] and hypoluetin 7-[6″-acetylallosyl-(1→2)-3″-acetyl-glucoside, along with 24 known flavonoid aglycones and glycosides [3]. Also, the acetylated isoscutellarein glucoside was reported [4].…”

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confidence: 99%

A new flavone glucoside from Stachys aegyptiaca

2007

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Key words: Stachys aegyptiaca, Lamiaceae, new flavone glucoside.Stachys aegyptiaca is a perenninal plant growing wild in the Sinai desert [1] and proved to be a rich source for flavonoids. We have previously reported the isolation and structure elucidation of diapigenin 7-O-(6″-trans-6″-cis-p,p′dihydroxy-µ-truxinyl)glucoside [stachysetin] [2] and hypoluetin 7-[6″-acetylallosyl-(1→2)-3″-acetyl-glucoside, along with 24 known flavonoid aglycones and glycosides [3]. Also, the acetylated isoscutellarein glucoside was reported [4]. In continuation of our study on the phenolic constituents of S. aegyptiaca, the present communication describes the further isolation and structure elucidation of a new flavone glycoside, the structure of which was identified as luteolin 3′,4′-dimethylether-7-Oglucoside from the aerial parts of the same plant.The methanol extract of the aerial parts of S. ageyptiaca was fractionated on a polyamide column with H 2 O as eluent with increasing amounts of MeOH. Isolation and purification were achieved by combination of PPC, TLC on silica gel and Sephadex LH-20.Flavonoid 1 was isolated as a yellowish white amorphous powder. Acid hydrolysis of 1 afforded glucose, which was identified by co-chromatography with authentic samples and the aglycone 1a. The UV spectral data of 1a with diagnostic shift reagents [5] indicated a flavone, absence of a free ortho-dihydroxyl pattern, occupation at positions-3′ and -4′, and a free hydroxyl group at position-7. The UV spectral data of 1 indicated a flavone with occupation at positions-7,3′ and -4′ [5].The EI-MS spectrum of permethylated [6] 1 gave a molecular ion peak at m/z 546 (66%) in accordance with fully methylated luteolin glucoside. A fragment at m/z 328 was due to the aglycone luteolin bearing three methoxyl groups. The identity of the glucose moiety was confirmed by the fragment at m/z 218 due to the ion [glucose-H] + and the fragment at m/z 187 for the ion [glucose-MeOH] + .The 1 H NMR spectrum of 1 showed that it is a monoglucoside of luteolin dimethylether on the basis of the signal H-1 glucose (δ 5.1), and the coupling constant (J = 7.5 Hz) is characterized for a β-linked glucose. Furthermore, the chemical shift (δ 5.1) confirmed that the glucose is directly attached to the aglycone [7]. The spectrum also showed signals at δ 7.4 and δ 6.9 (m; d, J = 8.0 Hz) assigned for H-2′,6′ and H-5′, confirming the disubstituted pattern at ring-B. Two doublets (J = 2.5 Hz) at

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“…To date, only two diglucosylfl avonoids containing truxinic acid moieties have been identifi ed in the plant kingdom, namely stachysetin and monochaetin from Stachys aegyptiaca (El-Ansari et al, 1995) and Monochaetum multifl orum (Isaza et al, 2001), respectively.…”

Section: Resultsmentioning

confidence: 99%

Flavonoids from Pseudotsuga menziesii

Krauze-Baranowska

Sowiński

Kawiak

et al. 2013

Zeitschrift Für Naturforschung C

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1 Four O-acylated flavonol glycosides, new in the plant kingdom, were isolated from the needles of Pseudotsuga menziesii. Their structures were established by 1D and 2D NMR and MS data as: daglesioside I [kaempferol 3-O-[2’’,5’’-O-(4’’’,4IV-dihydroxy)-β- truxinoyl]-α-L-arabinofuranoside] (), daglesioside II [kaempferol 3-O-[2’’,5’’-O-(4’’’- hydroxy)-β-truxinoyl]-α-L-arabinofuranoside] (2), daglesioside III [kaempferol 3-O-[2’’,5’’- di-O-(E)-p-coumaroyl]-α-L-arabinofuranoside] (3), and daglesioside IV [kaempferol 3-O-[3’’,6’’-di-O-(E)-cinnamoyl]-β-D-glucopyranoside] (4). In addition, the known fl avonoids (E)-tiliroside, (E)-ditiliroside, astragalin (kaempferol 3-O-β-D-glucopyranoside), isorhamnetin, kaempferol, and quercetin were identifi ed. The cytotoxic activity of compounds 1 and 3 was evaluated towards the HL-60, HeLa, and MDA-MB468 cell lines.

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Stachysetin, a diapigenin-7-glucoside-p,p′-dihydroxy-truxinate from Stachys aegyptiaca

Cited by 61 publications

References 9 publications

Double directional adjusting estrogenic effect of naringin from Rhizoma drynariae (Gusuibu)

Double directional adjusting estrogenic effect of naringin from Rhizoma drynariae (Gusuibu)

A new flavone glucoside from Stachys aegyptiaca

Flavonoids from Pseudotsuga menziesii

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