Neolignan Glucosides From Phlomis Chimerae Boiss

Ersöz, Tayfun; Saraçoğlu, İclal; Taşdemir, Deniz; Kırmızıbekmez, Hasan; Dönmez, Alı A.; Ireland, Chris M.; Çalış, İhsan

doi:10.1515/znc-2002-3-404

Cited by 11 publications

(6 citation statements)

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“…(2), along with ten known compounds were isolated (Figure 1; Table ). The known compounds were identified as phlorin (3), 25,26 tadehaginoside (4), 27 28 apigenin (6), 29 apigenin 5-O -β -glucopyranoside (7), 30,31 isoschaftoside (8), 32 luteolin 7-O -β -glucuronide (9), 33,34 35,36 hispidulin (11), 37,38 and martynoside (12) 39 by comparison of their NMR spectral data with those in the literature. In addition to these isolated compounds, two more phenylethanoid glycosides, acteoside (13) and leucosceptoside A (14), were detected by HPLC-DAD analysis performed on the extract.…”

Section: Resultsmentioning

confidence: 99%

“…45 Although there are few phytochemical studies on this section, phenolic compounds such as flavonoids and phenylethanoid glycosides were isolated from the aerial parts of S. salviifolia and S. pontica. 22,26 In our study, we also isolated phenolic compounds and phenolic precursors such as phlorin derivatives and αpyrone glucosides. Phlorin (3) was isolated from only two Scutellaria species, S. baicalensis and S. pontica.…”

Section: Resultsmentioning

confidence: 99%

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Alpha-pyrone glycosides fromScutellaria salviifoliaBenth

Dogan¹,

Ishiuchi²,

Makino³

et al. 2019

Turk J Chem

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Scutellaria salviifolia Benth. is an endemic species growing in Turkey that belongs to the family Lamiaceae. As a result of a phytochemical study on the aerial parts of S. salviifolia Benth., two new and 10 known compounds were isolated from the aqueous fraction of methanolic extract. The new compounds are methylα-pyrone glucosides, 3,4-dihydroxy-6-methylpyran-2-one 3-Oβ-glucopyranoside (=scusalvioside A, 1), and 3,4-dihydroxy-6-methylpyran-2-one 3-Oβ-(6 ′-O-E-caffeoyl) glucopyranoside (=scusalvioside B, 2) with new skeletal structures. Along with them, 3 phloroglucinol glucosides [phlorin (3), tadehaginoside (4), and 6 ′′-O-Zp-coumaroyl phloroglucinol-1-Oβglucopyranoside (5)], 6 flavonoids [apigenin (6), apigenin 5-Oβ-glucopyranoside (7), isoschaftoside (8), luteolin 7-Oβ-glucuronide (9), luteolin 4 ′-Oβ-glucopyranoside (10), and hispidulin (11)], and one phenylethanoid glycoside [martynoside (12)] were also isolated as known compounds. Compounds 2 and 8 were isolated as a mixture. Structure elucidations of the isolated compounds were carried out using UV, 1 H NMR, 13 C NMR, 2D NMR, and HR-ESI-MS analyses. Moreover, the phenylethanoid glycosides acteoside (13) and leucosceptoside A (14) were also detected in the plant by HPLC-DAD study. Tadehaginoside, 6 ′′-O-Zp-coumaroyl phloroglucinol-1-Oβ-glucopyranoside, and luteolin 4 ′-Oβ-glucopyranoside were reported for the first time from a Scutellaria species with this study.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Alpha-pyrone glycosides fromScutellaria salviifoliaBenth

Dogan¹,

Ishiuchi²,

Makino³

et al. 2019

Turk J Chem

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“…The identication of the known compounds, des-p-hydroxybenzoyl kisasagenol B (4), 11 rehmaglutin C (5), 17 des-p-hydroxybenzoyl-3-deoxycatalpin (6), 18 6-O-(p-hydroxybenzoyl)-D-glucopyranose (7), 19 6-O-[(E)-feruloyl]-D-glucopyranose (8), 20 6-O-p-coumaroyl-D-glucopyranose (9), 21 ursolic acid (10), 22 rotundic acid (11), 23 arjunic acid (12), 24 2a,3a,19a-trihydroxy-12-oleanen-28-oic acid (13), 25 ursolic acid lactone (14), 26 martynoside (15), 27 verbascoside (kusaginin or acteoside, 16), 28 balanophonin (17), 29 9ahydroxysesamin (18), 30 D-pinoresinol (19), 31 9-methoxy-a-lapachone (20), 32 ladanein (21), 33 and p-hydroxybenzoic acid (22), 34 was conrmed by comparing their physical and spectroscopic data with those reported in the literature. The known compounds included various types of iridoids, triterpenoids, phenylethanoid glycosides, and lignans.…”

Section: Resultsmentioning

confidence: 99%

Chemical components from the seeds of Catalpa bungei and their inhibitions of soluble epoxide hydrolase, cholinesterase and nuclear factor kappa B activities

et al. 2016

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Two new chlorinated iridoids, named bungosides A (1) and B (2), were isolated from the seeds of Catalpa bungei (family Bignoniaceae). Their structures were elucidated on the basis of NMR analysis. Twenty known compounds (3-22) were also characterized, including in one case (6-O-phydroxybenzoylglutinoside, 3) the assignment of the absolute configuration by employing electronic circular dichroism (CD) and time-dependent density functional theory (TDDFT) calculations. Compounds 1-3 were unusual cage-like iridoids with an oxygen bridge between C-3 and C-10. Among the isolates, ursolic acid lactone (14) was the most active soluble epoxide hydrolase (sEH) inhibitor with an IC 50 19.1 AE 0.8 mM. In addition, D-pinoresinol (19) and ladanein (21) displayed selectively inhibitory effects on butyrylcholinesterase (BChE) with IC 50 of 31.5 AE 0.4 mM and 33.0 AE 2.3 mM, respectively, but not acetylcholinesterase (AChE) activity, and only compound 18 suppressed NF-kB activity in HepG2 cells (IC 50 21.53 AE 2.37 mM).

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“…Phlomis species contain a diverse range of compounds, including iridoid glucosides [14][15][16], phenylpropanoid glycosides [17], flavonoid glycosides [18], lignans [19], neolignan glycosides [20], monoterpene glycosides [21], megastigmanes [22], diterpene glycosyl esters [23,24], nortriterpenes [25,26] and essential oils [5], which were reported to be responsible for various biological and pharmacological properties. Among them are the antinociceptive, anti-inflammatory [27][28][29], antioxidant [30][31][32][33][34], antimicrobial [35,36], wound-healing, antidiabetic [37,38] and antihemoroidal activity [39], as well as the antiplasmodial and anticancer activities [12,38,[40][41][42][43].…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents and Anticancer Activities of the Extracts from Phlomis × commixta Rech. f. (P. cretica × P. lanata)

Stefanakis,

Tsiftsoglou,

Mašković

et al. 2024

IJMS

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The present work is the first report on the ingredients of the P. × commixta hybrid, a plant of the genus Phlomis. So far, thirty substances have been isolated by various chromatographic techniques and identified by spectroscopic methods, such as UV/Vis, NMR, GC-MS and LC-MS. The compounds are classified as flavonoids: naringenin, eriodyctiol, eriodyctiol-7-O-β-D-glucoside, luteolin, luteolin-7-O-β-D-glucoside, apigenin, apigenin-7-O-β-D-glucoside, diosmetin-7-O-β-D-glucoside, quercetin, hesperetin and quercetin-3-O-β-D-glucoside; phenylpropanoids: martynoside, verbascoside, forsythoside B, echinacoside and allysonoside; chromene: 5,7-dihydroxychromone; phenolic acids: caffeic acid, p-hydroxybenzoic acid, chlorogenic acid, chlorogenic acid methyl ester, gallic acid, p-coumaric acid and vanillic acid; aliphatic hydrocarbon: docos-1-ene; steroids: brassicasterol and stigmasterol; a glucoside of allylic alcohol, 3-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranosyl-oct-1-ene-3-ol, was fully characterized as a natural product for the first time. Two tyrosol esters were also isolated: tyrosol lignocerate and tyrosol methyl ether palmitate, the latter one being isolated as a natural product for the first time. Moreover, the biological activities of the extracts from the different polarities of the roots, leaves and flowers were estimated for their cytotoxic potency. All root extracts tested showed a high cytotoxic activity against the Hep2c and RD cell lines.

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Neolignan Glucosides From Phlomis Chimerae Boiss

Cited by 11 publications

References 1 publication

Alpha-pyrone glycosides fromScutellaria salviifoliaBenth

Alpha-pyrone glycosides fromScutellaria salviifoliaBenth

Chemical components from the seeds of Catalpa bungei and their inhibitions of soluble epoxide hydrolase, cholinesterase and nuclear factor kappa B activities

Chemical Constituents and Anticancer Activities of the Extracts from Phlomis × commixta Rech. f. (P. cretica × P. lanata)

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