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.

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.

scholarly journals New Triterpenoid Saponins from the Roots of Saponaria officinalis

2013 ◽  
Vol 8 (12) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Barbara Moniuszko-Szajwaj ◽  
Łukasz Pecio ◽  
Mariusz Kowalczyk ◽  
Ana M. Simonet ◽  
Francisco A. Macias ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Electrospray Ionization ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Methods ◽  
Triterpenoid Saponins ◽  
Esi Ms ◽  
Gypsogenic Acid ◽  
Saponaria Officinalis

Three new triterpenoid saponins (1–3), along with nine known saponins, were isolated from the roots of Saponaria officinalis L. Two of them: vaccaroside D (4) and dianchinenoside B (5) are known, but not previously reported for S. officinalis, and seven others: saponarioside C (6), D (7), F (8), G (9), I (10), K (11), and L (12) have been previously isolated from this plant. The structures of the new saponins were established as 3- O-β-D-xylopyranosyl-16α-hydroxygypsogenic acid-28- O-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (1), 3- O-β-D-xylopyranosyl-16α-hydroxygypsogenic acid-28- O-[β-D-glucopyranosyl-(1→3)]-[α-D-galactopyranosyl-(1→6)-α-D-galactopyranosyl-(1→6)-β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (2) and 3- O-β-D-xylopyranosyl-gypsogenic acid-28- O-[β-D-glucopyranosyl-(1→3)]-[6- O-(3-hydroxy-3-methylglutaryl)-β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (3). Their structures were elucidated by extensive spectroscopic methods, including 1D- (1H, 13C) and 2D-NMR (D QF-COSY, TOCSY, ROESY, HSQC and HMBC) experiments, as well as high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), ESI-MS/MS and acid hydrolysis.

scholarly journals Lanostane-Type Saponins from Vitaliana primuliflora

Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1606 ◽  
Author(s):  
Włodarczyk ◽  
Szumny ◽  
Gleńsk
Keyword(s):  
Mass Spectrometry ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Resonance Spectroscopy ◽  
Tandem Mass ◽  
Triterpenoid Saponins ◽  
The Family ◽  
Chemotaxonomic Markers ◽  
First Time

The phytochemistry of the genera Androsace, Cortusa, Soldanella, and Vitaliana, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana. These two nor-triterpenoid saponins were characterized as (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-β-d-glucopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one and (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-nor-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae.

Glycosides from Cephalaria Species

2010 ◽  
Vol 65 (11) ◽  
pp. 1384-1392 ◽  
Author(s):  
Erkan Halay ◽  
Süheyla Kırmızıgül
Keyword(s):  
Mass Spectrometry ◽  
Oleanolic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Nmr Techniques ◽  
Basic Hydrolysis ◽  
Hydrolysis Of ◽  
Chemical Evidence

Three novel triterpene glycosides (1 - 3), namely lycicoside I, II and cilicicoside I, were isolated from two different Cephalaria (Dipsacaceae) species along with one known oleanane- and one iridoit- type of glycoside. The structures of these compounds were established as 3-O-[β -D-glucopyranosyl( 1→3)-α-L-rhamnopyranosyl(1→4)-β -D-xylopyranosyl(1→4)-β -D-xylopyranosyl]-28-O-[β -Dglucopyranosyl( 1→6)-β -D-glucopyranosyl]-oleanolic acid (1), 3-O-[β -D-xylopyranosyl(1→3)-α- L-rhamnopyranosyl(1→4)-β -D-xylopyranosyl]-28-O-[β -D-glucopyranosyl]-oleanolic acid (2) from Cephalaria lycica Matthew and 3-O-{β -D-glucopyranosyl(1→4)-β -D-xylopyranosyl(1→3)-α-Lrhamnopyranosyl( 1→2)-[β -D-glucopyranosyl(1→3)]-α -L-rhamnopyranosyl}-28-O-[β -D-glucopyranosyl( 1→6)-β -D-glucopyranosyl]-hederagenin (3) from Cephalaria cilicica Boiss. & Kotschy, on the basis of spectroscopic methods (1D and 2D NMR techniques, mass spectrometry) and chemical evidence. In addition, three new prosapogenins, 1B - 3B, were obtained from the basic hydrolysis of 1 - 3. The antimicrobial activity of 1 - 3 was tested against some Gram-positive and Gram-negative bacteria strains.

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 Four Flavan-3-ol Compounds From The Stembark of Chisocheton balansae C.DC. (MELIACEAE)

Molekul ◽  
2021 ◽  
Vol 16 (1) ◽  
pp. 9
Author(s):  
Unang Supratman ◽  
Mohamad Fajar ◽  
Supriatno Salam ◽  
Rani Maharani ◽  
Desi Harneti ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
13C Nmr ◽  
Chemical Structure ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Endemic Plants ◽  
North Sulawesi ◽  
First Time

Chisocheton balansae C.DC., is one of the Meliaceae family plants which is the endemic plants from Soputan Mountain, North Sulawesi, Indonesia. This study was aimed to determine the chemical structure of flavan-3-ol compounds from ethyl acetate extract of C. balansae C.DC stembark. Dried powder of C. balansae C.DC stem bark was extracted consecutively with n-hexane, ethyl acetate, and methanol solvents. Four flavan-3-ol compounds, named catechin (1), epicatechin (2), epigallocatechin-3-O-gallate (3), and epicatechin-3-O-gallate (4) were successfully isolated from ethyl acetate extract. The chemical structure of these isolates was determined by spectroscopic methods (1H-NMR, 13C-NMR, DEPT, and 2D-NMR) and comparison with previous reported spectral data. These compounds are first time reported from this plant.

scholarly journals Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

2012 ◽  
Vol 8 ◽  
pp. 763-775 ◽  
Author(s):  
Elena A Khatuntseva ◽  
Vladimir M Men’shov ◽  
Alexander S Shashkov ◽  
Yury E Tsvetkov ◽  
Rodion N Stepanenko ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antifungal Activity ◽  
Methanol Extract ◽  
Keyhole Limpet Hemocyanin ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Triterpenoid Saponins ◽  
Pure Compounds ◽  
Ester Linkage ◽  
Quillaic Acid

Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the obtained saponins were elucidated by a combination of mass spectrometry and 2D NMR spectroscopy. A study of acute toxicity, hemolytic, anti-inflammatory, immunoadjuvant and antifungal activity was carried out. Both saponins 1 and 2 were shown to exhibit immunoadjuvant properties within the vaccine composition with keyhole limpet hemocyanin-based immunogen. The availability of saponins 1 and 2 as individual pure compounds from the extract of the roots of A. gypsophiloides makes it a prospective source of immunoactive agents.

New Constituents from Gymnocarpos decander

Planta Medica ◽  
2017 ◽  
Vol 83 (14/15) ◽  
pp. 1200-1206 ◽  
Author(s):  
Houria Bechlem ◽  
Teresa Mencherini ◽  
Mohamed Bouheroum ◽  
Samir Benayache ◽  
Roberta Cotugno ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Antiproliferative Activity ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Nmr Analysis ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Resolution Mass

AbstractThe phytochemical investigation of Gymnocarpos decander aerial parts extract afforded two new saponins, 3-O-β-D-glucuronopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-O-β-D-apiofuranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester (1), 3-O-β-D-glucuronopyranosyl-2β,3β,16α-trihydroxyolean-12-en-28-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester (2), and three new flavonol glycosides, isorhamnetin 3-O-2′′′′-O-acetyl−β-D-xylopyranosyl-(1 → 6)-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (3), isorhamnetin 3-O-2‴-O-acetyl−β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside (4), and quercetin 3-O-2‴-O-acetyl−β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside (5), together with three known compounds. Their structures were determined by spectroscopic methods including 1D and 2D NMR analysis and high-resolution mass spectrometry. The new isolates were investigated for their potential cytotoxic activity on three cancer cell lines. Compounds 1 and 2 showed moderate antiproliferative activity.

Chlorosphaerolactylates A-D: The Natural Chlorinated Lactylates Isolated from the Portuguese Cyanobacterium Sphaerospermopsis Sp. LEGE 00249

2020 ◽  
Author(s):  
Ignacio Gutiérrez-del-Río ◽  
Nelly B. de Fraissinette ◽  
Raquel Castelo-Branco ◽  
Flavio Oliveira ◽  
João Morais ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Biofilm Formation ◽  
Candida Parapsilosis ◽  
Methanolic Extract ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Minor Components ◽  
Staphylococcus Hominis ◽  
Resolution Mass

The unprecedented natural chlorinated lactylates, chlorosphaerolactylates A-D (<b>1</b>-<b>4</b>), were isolated from the methanolic extract of the cyanobacterium <i>Sphaerospermopsis</i> sp. LEGE 00249 through a combination of bioassay-guided and MS-guided approaches. Compounds <b>1</b>-<b>4</b> are esters of (mono-, di- or tri-)chlorinated lauric acid and lactic acid, whose structures were assigned on the basis of spectrometric and spectroscopic methods inclusive of 1D and 2D NMR experiments. High-resolution mass-spectrometry datasets also demonstrated the existence of other minor components that were identified as chlorosphaero(bis)lactylate analogues. The chlorosphaerolactylates were tested for potential antibacterial, antifungal and antibiofilm properties using bacterial and fungal clinical isolates. Compounds <b>1-4</b> inhibited the growth of <i>Staphylococcus aureus </i>S54F9 and <i>Candida parapsilosis </i>SMI416, as well as, affected the biofilm formation of coagulase-negative <i>Staphylococcus hominis </i>FI31.

scholarly journals An isoflavan and saponins from Astragalus depressus L.

2015 ◽  
Vol 80 (2) ◽  
pp. 137-142 ◽  
Author(s):  
Leyla Maamria ◽  
Hamada Haba ◽  
Catherine Lavaud ◽  
Dominique Harakat ◽  
Mohammed Benkhaled
Keyword(s):  
Mass Spectrometry ◽  
Secondary Metabolites ◽  
Ethyl Acetate ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Esi Mass Spectrometry

In this study, nine known secondary metabolites were isolated from ethyl acetate and n-butanol extracts of Astragalus depressus L. (Fabaceae family), including one isoflavan, namely pendulone (1) and eight saponins, namely cyclogaleginoside A (2), astrasieversianin II (3), astrasieversianin IV (4), astrasieversianin VII (5), astrasieversianin VI (6), astrasieversianin XIV (7), dehydrosoyasaponin I (8) and soyasaponin I (9). The structures of compounds 1-9 were elucidated by using spectroscopic methods, including 1D and 2D NMR, ESI mass spectrometry and comparison with literature data.

Sign in / Sign up

Export Citation Format

Share Document