scholarly journals New Glycosides and Trypanocidal Metabolites from Vangueria edulis

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Shaymaa M. M. Mohamed ◽  
Khaled M. Elokely ◽  
Enaam Y. Bachkeet ◽  
Soad A. L. Bayoumi ◽  
Vincenzo Carnevale ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
Candida Glabrata ◽  
Iridoid Glycosides ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Brucei ◽  
Iridoid Glucoside ◽  
Iridoid Glucosides ◽  
Monoterpene Glycoside ◽  
First Time

A new iridoid glucoside, 10-methoxy apodanthoside (1), and a new monoterpene glycoside, (3S,6S)-cis linalool-3,7-oxide O-β-D-glucopyranosyl-(1′'→5′)-β-D-xylofuranoside (2), were isolated from V. edulis (Rubiaceae), along with eighteen known compounds (3–20), including monoterpenes, iridoid glycosides, and a lignin, which were encountered for the first time in the genus Vangueria,. The structural elucidation of the isolates was based on the analysis of spectroscopic (1D and 2D NMR) and HR-ESI-MS data. Detailed stereochemical studies of 1 and related iridoid glucosides (compounds 3, 4 and 8) were made by matching the calculated ECD peaks with the experimental ones. All isolates were tested for their antiprotozoal, antifungal, and antiplasmodial activities. Compounds 9, 15 and 16 showed good trypanocidal activities against Trypanosoma brucei brucei with IC50 values of 8.18, 9.02 and 7.80 μg/mL, respectively and IC90 values of >10, >10 and 9.76 μg/mL, respectively. Compound 16 showed a moderate activity against Candida glabrata with an IC50 value of 8.66 μg/mL. Compound 20 showed a weak antiplasmodial activity against chloroquine-sensitive (D6) and resistant (W2) Plasmodium falciparum with IC50 values of 3.29 (SI, >1.4) and 4.53 (SI, >1) μg/mL, respectively.

scholarly journals Unusual derivatives from Hypericum scabrum

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Sara Soroury ◽  
Mostafa Alilou ◽  
Thomas Gelbrich ◽  
Marzieh Tabefam ◽  
Ombeline Danton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Hypericum Scabrum ◽  
New Compounds ◽  
Absolute Structure

AbstractThree new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

scholarly journals Triterpenic Acids and Flavonoids from Satureja parvifolia. Evaluation of their Antiprotozoal Activity

2006 ◽  
Vol 61 (3-4) ◽  
pp. 189-192 ◽  
Author(s):  
Catalina van Baren ◽  
Ivie Anao ◽  
Paola Di Leo Lira ◽  
Silvia Debenedetti ◽  
Peter Houghton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
Moderate Activity ◽  
Antiprotozoal Activity ◽  
Active Components ◽  
Trypanosoma Brucei Rhodesiense ◽  
Meoh Extract ◽  
Triterpenic Acids ◽  
Bioassay Guided Fractionation ◽  
Low Cytotoxicity ◽  
First Time

Bioassay-guided fractionation of a Satureja parvifolia MeOH extract led to the isolation of eriodictyol, luteolin and ursolic and oleanolic acids as its active components against Plasmodium falciparum K1. This is the first time these compounds are reported as constituents of S. parvifolia. Ursolic acid showed an IC50 of 4.9 μg/ml, luteolin 6.4 μg/ml, oleanolic acid 9.3 μg/ml and eriodictyol 17.2 μg/ml. Antiplasmodial activity of eriodictyol and luteolin is reported here for the first time. Besides, the four compounds showed activity against P. falciparum 3D7 strain and Trypanosoma brucei rhodesiense. Eriodictyol showed moderate activity on all the parasites but was the most selective compound as a result of its rather low cytotoxicity (IC50 174.2 μg/ml) on the mammalian KB cell line.

scholarly journals Secondary Metabolites from Eremostachys Laciniata

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
İhsan Çalış ◽  
Ayşegül Güvenç ◽  
Metin Armağan ◽  
Mehmet Koyuncu ◽  
Charlotte H. Gotfredsen ◽  
...  
Keyword(s):  
Methyl Ester ◽  
2D Nmr ◽  
Phenylethanoid Glycosides ◽  
Iridoid Glucoside ◽  
Aerial Parts ◽  
Iridoid Glucosides ◽  
Close Relationship ◽  
Flavone Derivatives ◽  
Optical Rotations ◽  
Relationship Of

From the aerial parts of Eremostachys laciniata (Lamiaceae), a new acidic iridoid glucoside, 5-desoxysesamosidic acid (1) was isolated in addition to thirteen known iridoid glucosides, 5-desoxysesamoside (2), sesamoside (3), 6β-hydroxy-7- epi-loganin (4), chlorotuberoside (5), 5-deoxypulchelloside I (6), lamalbide (7), lamalbidic acid (8), phloyosides I (7- epi-phlomiol) (9), and II (10), phlomiol (11), shanzhiside (12), shanzhiside methyl ester (13), and barlerin (8- O-acetylshanzhiside methyl ester) (14), four phenylethanoid glycosides, verbascoside (15), leucosceptoside A (16), martynoside (17), and forsythoside B (18), and five flavone derivatives, luteolin (19), luteolin 7- O-β-D-glucopyranoside (20), luteolin 7- O-(6″- O-β-D-apiofuranosyl)-β-D-glucopyranoside (21), apigenin 7- O-β-D-glucopyranoside (22), and apigenin 7- O-(6″- O-p-coumaroyl)-β-D-glucopyranoside (23). The structures of the metabolites were elucidated from spectroscopic (UV, IR, 1D- and 2D-NMR) and ESI-MS evidence, as well as from their specific optical rotations. The presence of these metabolites of three different classes strongly supports the close relationship of the genera Eremostachys and Phlomis.

Phenylpropanoid and Iridoid Glucosides from the Whole Plant of Hemiphragma heterophyllum and Their alpha-Glucosidase Inhibitory Activities

Planta Medica ◽  
2020 ◽  
Vol 86 (03) ◽  
pp. 205-211
Author(s):  
Yan-Hong Li ◽  
Jia-Meng Dai ◽  
Cui Yang ◽  
Meng-Yuan Jiang ◽  
Yong Xiong ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Iridoid Glucoside ◽  
2D Nmr Spectroscopy ◽  
Whole Plant ◽  
Ic50 Value ◽  
Iridoid Glucosides ◽  
Alpha Glucosidase

AbstractThree phenylpropanoid glucosides (1 – 3) and one iridoid glucoside (11), together with eleven known glucosides, were isolated from the ethanol extract of the whole plant of Hemiphragma heterophyllum. Their structures were elucidated by means of 1D and 2D NMR spectroscopy, HRMS, and chemical methods. All compounds except 11 and 13 – 15 showed varying degrees of α-glucosidase inhibitory activity. Compounds 5, 9, and 12 were marginally active in the bioassay, while compounds 1 – 4, 6 – 8, and 10 exhibited appreciable inhibitory activity with an IC50 value of 33.6 ~ 83.1 µM, which was much lower than that of the positive control acarbose (IC50 = 310.8 µM).

scholarly journals Separation of Five Iridoid Glycosides from Lonicerae Japonicae Flos Using High-Speed Counter-Current Chromatography and Their Anti-Inflammatory and Antibacterial Activities

Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 197 ◽  
Author(s):  
Ran Yang ◽  
Lei Fang ◽  
Jia Li ◽  
Zhenhua Zhao ◽  
Hua Zhang ◽  
...  
Keyword(s):  
High Speed ◽  
Iridoid Glycosides ◽  
Platelet Activating Factor ◽  
2D Nmr ◽  
Solvent System ◽  
Antibacterial Activities ◽  
Two Phase ◽  
Iridoid Glucosides ◽  
Anti Inflammatory ◽  
Counter Current

A high-speed counter-current chromatography (HSCCC) method, using a two-phase solvent system composed of ethyl acetate/n-butanol/methanol/water (5:1:1:5, v/v/v/v), was successfully established to separate the five iridoid glucosides 7-O-ethyl sweroside (1), secologanin dimethylacetal (2), adinoside F (3), (7R)-secologain n-butyl methyl acetal (4) and adinoside G (5) from Lonicerae Japonicae Flos. Their purities were 96.8%, 98.5%, 93.3%, 98.0% and 99.9%, respectively. All the iridoid glucosides were identified by HR-ESI-MS, 1D and 2D NMR. Compounds 3 and 5 are new iridoid glucosides. The anti-inflammatory tests showed that compounds 1–5 all expressed moderate inhibitory effects on β-glucuronidase release in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF) with IC50 values ranging from 4.52 to 6.50 µM, while the antibacterial assays demonstrated that all the compounds displayed mild inhibitory activities against Staphylococcus aureus ATCC 25923 with MIC values ranging from 13.7 to 26.0 µg/mL.

scholarly journals Two New Naphthoquinone Derivatives from the Stem Bark of Callicarpa Maingayi

2012 ◽  
Vol 7 (10) ◽  
pp. 1934578X1200701
Author(s):  
Sumayah Mohammed Asiri ◽  
Khozirah Shaari ◽  
Faridah Abas ◽  
Nabil Ali Al-Mekhlafi ◽  
Nordin H. Lajis
Keyword(s):  
Cytotoxic Activity ◽  
Human Breast Cancer ◽  
2D Nmr ◽  
Stem Bark ◽  
Chloroform Fraction ◽  
Moderate Activity ◽  
Human Breast ◽  
Spectroscopic Analyses ◽  
First Time

Two new naphthoquinones designated as 3α-hydroxy-2-(2-hydroxypropan-2-yl)-9α-methoxy-2,3,3α,9α-tetra-hydronaphtho[2,3-b]furan-4,9-dione (callicarpa-quinone A, 1) and 5-hydroxy-2-(2-hydroxypropan-2-yl)naphtho[2,3-b]furan-4,9-dione (callicarpaquinone B, 2) were isolated from the chloroform fraction of Callicarpa maingayi. Three other known compounds, identified as avicequinone-C (3), wodeshiol (4) and paulownin (5), were reported for the first time from this species. The structure elucidation of compounds was established by comprehensive 1D and 2D NMR spectroscopic analyses as well as EIMS, UV and IR spectral data. Compounds 1 and 2 were tested in vitro for their cytotoxic activity against human breast cancer MCF-7cells. Compound 2 exhibited strong cytotoxic activity with an IC50 value of 1.9 ± 0.2 μM, while 1 showed moderate activity with an IC50 value of 25.0 ± 4.3 μM.

Chemical Constituents from Pedicularis rex C. B. Clarke

2007 ◽  
Vol 62 (11) ◽  
pp. 1465-1470 ◽  
Author(s):  
Hong-Biao Chu ◽  
Ning-Hua Tan ◽  
Yu-Mei Zhanga
Keyword(s):  
Chemical Constituents ◽  
Iridoid Glycosides ◽  
2D Nmr ◽  
Chemical Methods ◽  
Phenylpropanoid Glycoside ◽  
Nmr Techniques ◽  
First Time

One new ionone glycoside, pedicurexoside (1), one new flavonoid, 5, 4′-dihydroxy-3′-methoxyflavone- 7-O-6″-n-butyryl-β -D-glucopyranoside (2), two new iridoid glycosides, 6-O-ethyl-aucubin (7), 6-O-ethyl-epiaucubin (8), and one new phenylpropanoid glycoside, 4-hydroxy-phenylpropenyl- α-L-rhamnopyranosyl-(1→3)-4-O- feruloyl-β -D-glucopyranoside (13), together with eleven known compounds, apigenin (3), luteolin (4), chrysoeriol (5), luteolin-7-O-β -D-glucopyranoside (6), aucubin (9), yuheinoside (10), euphroside (11), mussaenoside (12), verbascoside (14), martynoside (15) and isomartynoside (16), were isolated from Pedicularis rex. The structures of 1 - 16 were elucidated mainly by 1D and 2D NMR techniques, MS evidence and chemical methods. The ionone derivative with thirteen carbon atoms was found in Pedicularis plants for the first time.

scholarly journals Iridoid Glucosides from Veronica pectinata var. glandulosa

2003 ◽  
Vol 58 (7-8) ◽  
pp. 481-484 ◽  
Author(s):  
U. Sebnem Harput ◽  
Akito Nagatsu ◽  
Yukio Ogihara ◽  
Iclal Saracoglu
Keyword(s):  
Nmr Spectroscopy ◽  
2D Nmr ◽  
Iridoid Glucoside ◽  
2D Nmr Spectroscopy ◽  
Iridoid Glucosides

Abstract A new highly oxygenated iridoid glucoside, urphoside B (1) was isolated from the Veronica pectinata var. glandulosa together with seven known iridoid glucosides, aucubin, catalpol, veronicoside, catalposide, verproside, amphicoside and 6-O-veratroyl catalpol. The planar as well as the stereo structures of the isolated compounds were determined by means of extensive 1D- and 2D-NMR spectroscopy and confirmed by HR-Mass.

scholarly journals Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2862
Author(s):  
Christine C. Waleguele ◽  
Brice M. Mba’ning ◽  
Angelbert F. Awantu ◽  
Jean J. K. Bankeu ◽  
Yannick S. F. Fongang ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
Trypanosoma Brucei Brucei ◽  
Preliminary Screening ◽  
Nmr Data ◽  
Antitrypanosomal Activity ◽  
Phytochemical Investigation ◽  
Ic50 Value ◽  
New Compounds ◽  
First Time

The MeOH/CH2Cl2 (1:1) extracts of the roots and leaves of Beilschmiedia louisii and B. obscura showed potent antitrypanosomal activity during preliminary screening on Trypanosoma brucei brucei. Phytochemical investigation of these extracts led to the isolation of a mixture of two new endiandric acid derivatives beilschmiedol B (1) and beilschmiedol C (2), and one new phenylalkene obscurene A (3) together with twelve known compounds (4–15). In addition, four new derivatives (11a–11d) were synthesized from compound 11. Their structures were elucidated based on their NMR and MS data. Compounds 5, 6, and 7 were isolated for the first time from the Beilschmiedia genus. Additionally, the NMR data of compound 4 are given here for the first time. The isolates were evaluated for their antitrypanosomal and antimalarial activities against Tb brucei and the Plasmodium falciparum chloroquine-resistant strain Pf3D7 in vitro, respectively. From the tested compounds, the mixture of new compounds 1 and 2 exhibited the most potent antitrypanosomal activity in vitro with IC50 value of 4.91 μM.

scholarly journals Iridoid Glucosides from Wendlandia Tinctoria roots

2011 ◽  
Vol 6 (6) ◽  
pp. 1934578X1100600
Author(s):  
Biswanath Dinda ◽  
Sudhan Debnath ◽  
Rajarshi Banik ◽  
Noriko Sato ◽  
Yoshihiro Harigaya
Keyword(s):  
Chemical Analysis ◽  
2D Nmr ◽  
Iridoid Glucoside ◽  
Iridoid Glucosides

A new iridoid glucoside, 8- O-( E)-caffeoylmussaenosidic acid (1), together with ixoside (2), was isolated from the roots of Wendlandia tinctoria. The structure of the new compound was established on the basis of detailed spectroscopic (2D NMR) and chemical analysis.

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