Dammarane triterpenoid saponins from Bacopa monnieri

2009 ◽  
Vol 87 (9) ◽  
pp. 1230-1234 ◽  
Author(s):  
Pamita Bhandari ◽  
Neeraj Kumar ◽  
Bikram Singh ◽  
Inderjeet Kaur
Keyword(s):  
Medicinal Plant ◽  
2D Nmr ◽  
Bacopa Monnieri ◽  
Spectroscopic Methods ◽  
Triterpenoid Saponins ◽  
Enhancing Effect ◽  
Indian Medicinal Plant ◽  
Aerial Parts ◽  
Memory Enhancer ◽  
Memory Enhancing

Bacopa monnieri is a well-known Ayurvedic Indian medicinal plant traditionally used as a memory enhancer. Its memory-enhancing effect is mainly attributed to dammarane triterpenoid saponins. In the present study, two new dammarane-type triterpenoid saponins, bacopaside-XI (1) and bacopaside-XII (2), together with known compounds, bacopaside IV, bacopaside V, and apigenin, were isolated from the aerial parts of the B. monnieri . The structures of the new saponins were elucidated as 3-O-[α-L-arabinofuranosyl(1→3)]-6-O-sulfonyl-β-D-glucopyranosyl pseudojujubogenin (1) and 3-O-{β-D-glucopyranosyl(1→3)[α-L-arabinofuranosyl(1→2)]-β-D-glucopyranosyl}-20-O-α-L-arabinopyranosyl pseudojujubogenin (2) on the basis of extensive investigations of 1D and 2D NMR (HMQC and HMBC), ESI-QTOF-MS/MS spectroscopic methods, and chemical evidences.

scholarly journals 30-Normedicagenic Acid Glycosides from Chenopodium Foliosum

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701
Author(s):  
Paraskev T. Nedialkov ◽  
Zlatina Kokanova-Nedialkova ◽  
Daniel Bücherl ◽  
Georgi Momekov ◽  
Jörg Heilmann ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Cell Lines ◽  
Interleukin 2 ◽  
Leukemic Cell ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Dioic Acid ◽  
Leukemic Cell Lines ◽  
Aerial Parts

Two new glycosides of 30-normedicagenic acid, namely 3- O-[ β-D-glucuronopyranosyl methyl ester]-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-D-glucopyranosyl ester, and 3- O-β-D-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid, together with the known 3- O-β-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester, and 3- O-β-glucuronopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR) and HRMS-ESI. The compounds were tested for cytotoxicity on three leukemic cell lines (BV-173, SKW-3, HL-60). In addition, the saponins showed moderate stimulatory effects on interleukin-2 production in PHA/PMA stimulated Jurkat E6.1 cells.

scholarly journals Phenolic Constituents of Knautia arvensis Aerial Parts

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Jaroslaw Moldoch ◽  
Barbara Szajwaj ◽  
Milena Masullo ◽  
Lukasz Pecio ◽  
Wieslaw Oleszek ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Flavone Glycoside ◽  
Aerial Parts ◽  
Dicaffeoylquinic Acid ◽  
Phenolic Constituents ◽  
First Time

A new C-6 flavone glycoside (6), together with seven known compounds, cryptochlorogenic acid (1), chlorogenic acid (2), 2- O- trans-caffeoylhydrocitric acid (3), isovitexin 7-β-D-glucopyranoside (4), 7,4′-dihydroxy-5-methoxyflavone-6- C-β-D-glucopyranoside (5), 3,5- O-dicaffeoylquinic acid (7) and 4,5- O-dicaffeoylquinic acid (8), were isolated from the aerial parts of Knautia arvensis. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis. Compounds 1, 3-5 and 8 are reported for the first time in Knautia arvensis.

Flavon- and Flavonolglycosides from Achillea pannonica Scheele

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Techniques ◽  
Chemotaxonomic Study ◽  
First Time ◽  
C Nmr

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly

scholarly journals Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1986394
Author(s):  
David Pertuit ◽  
Mpuza Kapundu ◽  
Anne-Claire Mitaine-Offer ◽  
Tomofumi Miyamoto ◽  
Chiaki Tanaka ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Triterpenoid Saponins

Two previously undescribed triterpenoid saponins together with 4 known ones were isolated from the stem bark of Pentaclethra eetveldeana De Wild. & Th. Dur. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments in combination with mass spectrometry as 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyloleanolic acid and 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosylhederagenin.

Flavonoids from Tephrosia major. A New Prenyl-β-hydroxychalcone

2002 ◽  
Vol 57 (7-8) ◽  
pp. 579-583 ◽  
Author(s):  
Federico Gómez-Garibay ◽  
Oswaldo Téllez-Valdez ◽  
Gregorio Moreno-Torres ◽  
José S. Calderón
Keyword(s):  
2D Nmr ◽  
Spectroscopic Methods ◽  
Prenylated Flavonoids ◽  
Aerial Parts

The roots and aerial parts of Tephrosia major Micheli, afforded a new prenylated-β-hydroxychalcone, characterized as 2′,6′-dihydroxy-3′-prenyl-4′-methoxy-β-hydroxychalcone. In addition, seven prenylated flavonoids, two rotenoids, β-sitosterol, stigmasterol, lupeol and quercetin were isolated. The structure of the new β-hydroxy chalcone was established by spectroscopic methods, including 2D NMR experiments.

scholarly journals A New Carbazole Alkaloid from Murraya koenigii Spreng (Rutaceae)

2008 ◽  
Vol 3 (10) ◽  
pp. 1934578X0800301 ◽  
Author(s):  
Suvra Mandal ◽  
Anupam Nayak ◽  
Samir K. Banerjee ◽  
Julie Banerji ◽  
Avijit Banerji
Keyword(s):  
Medicinal Plant ◽  
2D Nmr ◽  
Spectral Studies ◽  
Murraya Koenigii ◽  
Indian Medicinal Plant ◽  
Carbazole Alkaloids

A new carbazole alkaloid (kurryam) oxygenated at the 4-position, hitherto unknown among carbazole alkaloids, has been isolated from the seeds of an Indian medicinal plant, Murraya koenigii (Rutaceae). The structure has been established as 4-hydroxy-(2′,2′,3)-trimethyl-(6,7)-dimethoxy pyranocarbazole from extensive 2D NMR spectral studies. In addition, two known carbazole alkaloids, (2′,2′,3)-trimethyl 6-methoxy pyranocarbazole and (2′,2′,3)-trimethyl 6-hydroxy pyranocarbazole were isolated from the seeds of the same plant, of which (2′,2′,3)-trimethyl 6-methoxy pyranocarbazole exhibited significant antidiarrhoeal activity, as also did the new compound.

scholarly journals Triterpenoids from Aerial Parts of Glochidion eriocarpum

2010 ◽  
Vol 5 (3) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Vu Kim Thu ◽  
Phan Van Kiem ◽  
Pham Hai Yen ◽  
Nguyen Xuan Nhiem ◽  
Nguyen Huu Tung ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Chromatographic Separations ◽  
Triterpenoid Saponins ◽  
Fticr Ms ◽  
Aerial Parts ◽  
New Compounds

From the aerial parts of Glochidion eriocarpum, a new triterpene, glochieriol (1), three new triterpenoid saponins, glochieriosides C - E (2 - 4), together with four known triterpenes (glochidonol, glochidiol, lupeol, and 3- epi-lupeol) were isolated by using combined chromatographic separations. The structures of the new compounds were elucidated on the basis of spectroscopic data, including FTICR-MS, 1D and 2D NMR.

scholarly journals Flavonoids in Achillea collina

2001 ◽  
Vol 69 (1) ◽  
pp. 75-83 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Gottfried Reznicek ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
First Time

In a detailed study on the flavonoid pattern of Achillea collina BECKER ten flavonoids were isolated from a methanolic extract of aerial parts of the plant. Their structures were determined by UV, ESI-MS, GC-MS and NMR spectroscopic methods including 2D-NMR. Apigenin-7-O-rutinoside was proven for the first time in the genus Achillea.

Three new coumarin types from aerial parts of Ammi majus L. and their cytotoxic activity

2018 ◽  
Vol 73 (1-2) ◽  
pp. 1-7 ◽  
Author(s):  
Eman El-Sharkawy ◽  
Yasser Selim
Keyword(s):  
High Activity ◽  
Hct116 Cell ◽  
2D Nmr ◽  
In Vitro Cytotoxicity ◽  
Spectroscopic Methods ◽  
Aerial Parts ◽  
Western Asia ◽  
Ammi Majus ◽  
Diphenyl Tetrazolium Bromide

AbstractThree new coumarin types were isolated from the aerial parts of the wild medicinal plantAmmi majus, which was collected from western Asia (Saudi Arabia), including pyrano coumarin, namely, 5-isobutylcoumarin-6-C-glucoside(1); furanocoumarin, namely, 6,7,9-Trimethoxy-3-(8′-methoxy-2′-oxo-2H-chromen-3-yl)-2H-furo[3,2-g]chromen-2(3H)-one(2); and pyrone coumarin, namely, 6-hydroxy-3-(2-hydroxypropyl)-7-methoxy-4 methyl coumarin(3). The structures were determined by spectroscopic methods, mainly 1D- and 2D-NMR. In vitro cytotoxicity was evaluated by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) assay. The results of cytotoxicity depending on their structure features showed that compound3had high activity on different cell lines, while compound1showed no activity against HCT116. Compound2had high activity towards HCT116 cell line.

scholarly journals Triterpenoid Saponins from the Cultivar “Green Elf” of Pittosporum tenuifolium

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6805
Author(s):  
David Pertuit ◽  
Anne-Claire Mitaine-Offer ◽  
Tomofumi Miyamoto ◽  
Chiaki Tanaka ◽  
Christine Belloir ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
New Zealand ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Sweet Taste ◽  
Spectroscopic Methods ◽  
Triterpenoid Saponins ◽  
Crude Saponin ◽  
Aqueous Ethanolic Extract ◽  
Inhibitory Activities

Four oleanane-type glycosides were isolated from a horticultural cultivar “Green Elf” of the endemic Pittosporum tenuifolium (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, 3-O-β-d-galactopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and the known 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C (Eryngioside L). From the roots, the known 3-O-β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyloleanolic acid (Sandrosaponin X) was identified. Their structures were elucidated by spectroscopic methods including 1D- and 2D-NMR experiments and mass spectrometry (ESI-MS). According to their structural similarities with gymnemic acids, the inhibitory activities on the sweet taste TAS1R2/TAS1R3 receptor of an aqueous ethanolic extract of the leaves and roots, a crude saponin mixture, 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and Eryngioside L were evaluated.

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