Flavonol and iridoid glycosides of Ajuga remota aerial parts

A new flavone glycoside, 6-hydroxyluteolin 7-O-[6m-benzoyl-β -D-glucopyranosyl-(1 → 2)]-β - D-glucopyranoside (aphyllanthoside, 1) was isolated from the MeOH extract of the aerial parts of Globularia aphyllanthes. Besides this new compound, two flavonoid glycosides (6-hydroxyluteolin 7-O-[6m-(E)-caffeoyl-β -D-glucopyranosyl-(1 → 2)]-β -D-glucopyranoside and isoquercitrin), three phenylethanoid glycosides (verbascoside, rossicaside A, and trichosanthoside A), and 11 iridoid glycosides (aucubin, catalpol, 10-O-benzoylcatalpol, globularin, asperuloside, besperuloside, asperulosidic acid, daphylloside, scandoside, alpinoside and baldaccioside) were also obtained and characterized. Identification of the isolated compounds was carried out by spectroscopic analysis including 1D and 2D NMR experiments as well as HRMS

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Two New Acylated Iridoid Glycosides from Verbascum undulatum

Zeitschrift für Naturforschung C ◽

10.1515/znc-2000-7-829 ◽

2000 ◽

Vol 55 (7-8) ◽

pp. 667-670 ◽

Cited By ~ 5

Author(s):

Prokopios Magiatis ◽

Eleni Melliou ◽

Eugenia Tsitsa ◽

Catherine Charvala ◽

Sofia Mitaku

Keyword(s):

Nmr Spectroscopy ◽

Spectral Methods ◽

Iridoid Glycosides ◽

2D Nmr ◽

2D Nmr Spectroscopy ◽

Aerial Parts ◽

Phytochemical Investigation

Abstract On further phytochemical investigation of the aerial parts of Verbascum undulatum, two new acylated iridoid glycosides, 6-O-[3-O-(trans-3,4-dim ethoxycinnamoyl)-α- ʟ-rhamnopyranosyl] aucubin (1) and 6-O -[3-O-(trans-p-methoxycinnamoyl)-α-ʟ-rhamnopyranosyl]aucubin (2) were isolated. These structures were determined by spectral methods, mainly by 1D and 2D NMR spectroscopy.

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A New Iridoid from the Aerial Parts of Hedyotis Pilulifera

Natural Product Communications ◽

10.1177/1934578x1601100311 ◽

2016 ◽

Vol 11 (3) ◽

pp. 1934578X1601100

Author(s):

Nguyen Thi Hoai ◽

Ho Viet Duc ◽

Nguyen Dinh Quynh Phu ◽

Takeshi Kodama ◽

Takuya Ito ◽

...

Keyword(s):

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Iridoid Glycosides ◽

Bacterial Species ◽

2D Nmr ◽

Spectral Analyses ◽

Esi Ms ◽

Aerial Parts ◽

Nmr Data ◽

Mic Value

A new iridoid, 10-acetylborreriagenin (1), and five known iridoid glycosides (2–6), were isolated from the aerial parts of Hedyotis pilulifera. Their structures were elucidated by spectral analyses, including 1D- and 2D-NMR, and HR-ESI-MS, and comparisons with the NMR data reported in the literature. The isolated compounds 1–6 were tested against six bacterial species. Among them, 10-acetylborreriagenin (1) showed antibacterial activity against Staphylococcus aureus, with an MIC value of 100 μg/mL.

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Bioassay-Guided Isolation of Anti-Alzheimer Active Components from the Aerial Parts of Hedyotis diffusa and Simultaneous Analysis for Marker Compounds

Molecules ◽

10.3390/molecules25245867 ◽

2020 ◽

Vol 25 (24) ◽

pp. 5867

Author(s):

Jun Hee Park ◽

Wan Kyunn Whang

Keyword(s):

Inhibitory Activity ◽

Short Term Memory ◽

Biological Activities ◽

Iridoid Glycosides ◽

Positive Control ◽

Active Components ◽

Aerial Parts ◽

Natural Medicine ◽

Hedyotis Diffusa ◽

Marker Compounds

Previous studies have reported that Hedyotis diffusa Willdenow extract shows various biological activities on cerebropathia, such as neuroprotection and short-term memory enhancement. However, there has been a lack of studies on the inhibitory activity on neurodegenerative diseases such as Alzheimer’s disease (AD) through enzyme assays of H. diffusa. Therefore, H. diffusa extract and fractions were evaluated for their inhibitory effects through assays of enzymes related to AD, including acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and β-site amyloid precursor protein cleaving enzyme 1 (BACE1), and on the formation of advanced glycation end-product (AGE). In this study, ten bioactive compounds, including nine iridoid glycosides 1–9 and one flavonol glycoside 10, were isolated from the ethyl acetate and n-butanol fractions of H. diffusa using a bioassay-guided approach. Compound 10 was the strongest inhibitor of cholinesterase, BACE1, and the formation of AGEs of all isolated compounds, while compound 5 had the lowest inhibitory activity. Compounds 3, 6, and 9 exhibited better inhibitory activity than other compounds on AChE, and two pairs of diastereomeric iridoid glycoside structures (compounds 4, 8, and 6, 7) showed higher inhibitory activity than others on BChE. In the BACE1 inhibitory assay, compounds 1–3 were good inhibitors, and compound 10 showed higher inhibitory activity than quercetin, the positive control. Moreover, compounds 1 and 3 were stronger inhibitors of the formation of AGE than aminoguanidine (AMG), the positive control. In conclusion, this study is significant since it demonstrated that the potential inhibitory activity of H. diffusa on enzymes related to AD and showed the potential use for further study as a natural medicine for AD treatment on the basis of the bioactive components isolated from H. diffusa.

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Metabolic Profile of and Antimicrobial Activity in the Aerial Part of Leonurus turkestanicus V.I. Krecz. et Kuprian. from Kazakhstan

Journal of AOAC International ◽

10.5740/jaoacint.17-0236 ◽

2017 ◽

Vol 100 (6) ◽

pp. 1700-1705 ◽

Cited By ~ 4

Author(s):

Olga Sermukhamedova ◽

Krzysztof Kamil Wojtanowski ◽

Jarosław Widelski ◽

Izabela Korona-Głowniak ◽

Hosam O Elansary ◽

...

Keyword(s):

Antimicrobial Activity ◽

Inhibitory Concentration ◽

Iridoid Glycosides ◽

Chloroform Extract ◽

Bacillus Species ◽

Alcoholic Extract ◽

Aerial Parts ◽

Nitrogen Containing Compounds ◽

First Time ◽

Tof Ms

Abstract An HPLC quadrupole time-of-flight (Q-TOF) MS method was developed for the identification of secondary metabolites in Leonurus turkestanicus V.I. Krecz. et Kuprian. Ethanolic and chloroform extracts from the plant’s aerial parts were tested. A total of 16 compounds (iridoid glycosides, phenylpropanoids, flavonoids, and nitrogen-containing compounds, as well as diterpene acetate derivatives) were identified and tentatively characterized based on (or using) their retention times and UV and Q-TOF-MS data. Previously reported aucubin (1),6-deoxy-8-acetylharpagid(2), and stachydrine(13, 15)and homostachydrine isomers(14, 16)were identified, along with a lavandulifolioside isomer(3),verbascoside(4),rutin(5),3-O-kaempferol rutinoside (6), and an unknown diterpene acetate(8).Compounds3–6were detected for the first time in this plant. Additionally. antimicrobial activity was evaluated. No significant differences were found between ethanolic and chloroform extracts of L. turkestanicus; however, the alcoholic extract showed stronger antifungal activity [minimal inhibitory concentration (MIC) of 2.5–5 mg/mL], whereas the chloroform extract showed stronger activity against the tested spore-forming Bacillus species (MIC 1.25–2.5 mg/mL).

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Phenylethanoid and Iridoid Glycosides from Veronica Chamaedrys L.

Chemistry Journal of Moldova ◽

10.19261/cjm.2008.03(2).08 ◽

2008 ◽

Vol 3 (2) ◽

pp. 101-104

Author(s):

Alexandra Marchenko ◽

Pavel Kintia ◽

Natalia Mashcenco ◽

Carla Bassarello ◽

Sonia Piacente ◽

...

Keyword(s):

Spectral Analysis ◽

Iridoid Glycosides ◽

Iridoid Glycoside ◽

Phenylethanoid Glycosides ◽

Aerial Parts ◽

First Time

Three phenylethanoid glycosides (1, 2, 3) and one iridoid glycoside (4) were isolated from aerial parts of Veronica chamaedrys L. (Scrophulariaceae) for the first time. On the basis of spectral analysis, the structures of these compounds were determined to be acteoside (3,4-dihydroxy-β-phenylethoxy-O-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D-glucopyranoside) (1), ehrenoside (3,4-dihydroxy-β-phenylethoxy-O-α-L-arabinopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D-glucopyranoside) (2), chamaedroside (3,4-dihydroxy-β-phenylethoxy-O-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-α-L-arabinopyranoside) (3) and aucuboside (4).

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Iridoid Glycosides and Phenolic Glycosides from Buddleja asiatica with Anti-inflammatory and Cytoprotective Activities

Natural Product Communications ◽

10.1177/1934578x1801300102 ◽

2018 ◽

Vol 13 (1) ◽

pp. 1934578X1801300 ◽

Cited By ~ 2

Author(s):

Truong Thi Thu Hien ◽

Tran Hong Quang ◽

Bui Huu Tai ◽

Nguyen Xuan Nhiem ◽

Pham Hai Yen ◽

...

Keyword(s):

Cell Death ◽

Methanol Extract ◽

Iridoid Glycosides ◽

Iridoid Glycoside ◽

Inhibitory Effects ◽

Chemical Structures ◽

Aerial Parts ◽

Spectroscopic Analyses ◽

Nitrite Production ◽

Bv2 Microglia

Chemical investigation of the methanol extract of the aerial parts of Buddleja asiatica resulted in the isolation of a new iridoid glycoside, buddlejasiaside A (1) and 11 known compounds: 6- O -[α-L-(4-isoferuloyl)-rhamnopyranosylcatalpol (2), specioside (3), verminoside (4), minecoside (5), 6- O -( p -hydroxybenzoyl)-ajugol (6), 6- O -caffeoyl ajugol (7), litanthosalin 8), eurostoside (9), 10- O -caffeoylaucubin (10), phlorizin (11), and garashangin (12). Their chemical structures were identified based on the MS and NMR spectroscopic analyses and comparing with the data reported in the literature. Compounds 1, 2, and 8-10 showed the modest inhibitory effects against nitrite production in LPS-stimulated BV2 microglia, with IC50 values ranging from 43.5-79.6 μM. Compounds 6, 7, and 11 protected HT22 hippocampal cells from glutamate-induced cell death, with EC50 values of 38.9, 14.8, and 27.1 μM, respectively.

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