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 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 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 New Neuritogenic Steroid Glycosides from the Vietnamese Starfish Linckia Laevigata

2007 ◽  
Vol 2 (1) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Alla A. Kicha ◽  
Natalia V. Ivanchina ◽  
Anatoly I. Kalinovsky ◽  
Pavel S. Dmitrenok ◽  
Natalia V. Palyanova ◽  
...  
Keyword(s):  
Neuronal Differentiation ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Chemical Transformations ◽  
Steroid Glycosides ◽  
New Compounds ◽  
Neuritogenic Activity ◽  
Linckia Laevigata

Two new steroid glycosides, linckosides L1 (1) and L2 (2), were isolated, along with the previously known echinasteroside C (3) from the ethanolic extract of the Vietnamese blue starfish, Linckia laevigata. The structures of the new compounds were elucidated by spectroscopic methods (mainly 2D NMR) and chemical transformations. Lifetime observations and analyses of silver impregnated preparations on the culture of neuroblastoma C-1300 cells showed that glycosides 1, 2, and 3 are capable of inducing neuronal differentiation similar to that of neurotrophins and of enhancing substantially the neuritogenic activity of NGF.

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 Gas Chromatography-Mass Spectrometry Analysis ofUlva fasciata(Green Seaweed) Extract and Evaluation of Its Cytoprotective and Antigenotoxic Effects

2015 ◽  
Vol 2015 ◽  
pp. 1-11 ◽  
Author(s):  
Idania Rodeiro ◽  
Sitlali Olguín ◽  
Rebeca Santes ◽  
José A. Herrera ◽  
Carlos L. Pérez ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Gas Chromatography ◽  
Antioxidant Properties ◽  
Ethanolic Extract ◽  
Mass Spectrometry Analysis ◽  
Gas Chromatography Mass Spectrometry ◽  
Rat Liver Microsomes ◽  
Ulva Fasciata ◽  
Chromatography Mass Spectrometry ◽  
Aqueous Ethanolic Extract

The chemical composition and biological properties ofUlva fasciataaqueous-ethanolic extract were examined. Five components were identified in one fraction prepared from the extract by gas chromatography-mass spectrometry, and palmitic acid and its ethyl ester accounted for 76% of the total identified components. Furthermore, we assessed the extract’s antioxidant properties by using the DPPH, ABTS, and lipid peroxidation assays and found that the extract had a moderate scavenging effect. In an experiment involving preexposition and coexposition of the extract (1–500 µg/mL) and benzo[a]pyrene (BP), the extract was found to be nontoxic to C9 cells in culture and to inhibit the cytotoxicity induced by BP. As BP is biotransformed by CYP1A and CYP2B subfamilies, we explored the possible interaction of the extract with these enzymes. The extract (25–50 µg/mL) inhibited CYP1A1 activity in rat liver microsomes. Analysis of the inhibition kinetics revealed a mixed-type inhibitory effect on CYP1A1 supersome. The effects of the extract on BP-induced DNA damage and hepatic CYP activity in mice were also investigated. Micronuclei induction by BP and liver CYP1A1/2 activities significantly decreased in animals treated with the extract. The results suggest thatUlva fasciataaqueous-ethanolic extract inhibits BP bioactivation and it may be a potential chemopreventive agent.

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.

scholarly journals Charantoside L, A New Cucurbitane-Type Glycoside from Momordica charantia L. with α-Glucosidase Inhibitory Activities

2022 ◽  
Vol 17 (1) ◽  
pp. 1934578X2110689
Author(s):  
Duong Thi Hai Yen ◽  
Pham Hai Yen ◽  
Nguyen Quang Hop ◽  
Nguyen Anh Hung ◽  
Ha Thi Thu Tran ◽  
...  
Keyword(s):  
Ethanol Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Momordica Charantia ◽  
Spectroscopic Methods ◽  
Inhibitory Effects ◽  
Chemical Structures ◽  
Glucosidase Activity ◽  
Inhibitory Activities ◽  
Reported Data

A new cucurbitane-type glycoside (1) and two known compounds (2-3) were isolated from the ethanol extract of the fruits of Momordica charantia L. Their chemical structures were determined as (19 S,23 E)-5 β­,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol 3 -O-β-D-allopyranoside (1), goyaglycoside d (2), and (19 S,23 E)-5 β,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol (3) on the basis of the extensive spectroscopic methods, including 1D, 2D NMR, HRESIMS, and in comparison with the reported data. Compounds 1 to 3 were evaluated for α-glucosidase inhibitory effects. Compounds 1 and 2 showed anti α-glucosidase activity with IC50 values of 134.12 ± 11.20 and 163.17 ± 13.71 µM, respectively, compared with the positive control, acarbose, IC50 160.99 ± 14.30 μM. Compounds 2 and 3 were first isolated from plant M. charantia growing in Vietnam.

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.

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