Bioactive Saponins and Glycosides. XXVIII. New Triterpene Saponins, Foliatheasaponins I, II, III, IV, and V, from Tencha (the Leaves of Camellia sinensis) (original) (raw)
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A Review on Saponins from Medicinal Plants: Chemistry, Isolation, and Determination
Journal of Nanomedicine Research, 2019
Saponin isolated from medicinal plants is a naturally occurring bioorganic molecule with high molecular weight and its aglycone (water non-soluble part) nucleus having 27 to 30 carbon atoms besides one or two sugar moieties (water soluble part) containing at least 6 or 12 carbon atoms respectively. The complexity of saponin chemistry maybe considered as a gap for many scientists and researchers to understand the relationship between the chemical structure and its medical or pharmaceutical behavior. Recently, the increase in demand of saponin applications was observed due to various biological, medicinal, and pharmaceutical actions. Therefore, this present review article provides detailed information about the chemistry of saponin, especially triterpenoid saponin. Classifications, chemical structure, the possible traditional isolation ways, qualitative, and quantitative determination of saponins were included exclusively. Examples of mono and bidesmosidic structure of oleanolic acid and hederagenin also outlined. Structural differences between triterpenoid, steroid, and alkaloid glycosides were summarized according to their atoms, rings, and functional groups.
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005
The seeds of the tea plant [Camellia sinensis (L.) O. KUNTZE (Theaceae)] are known to contain saponin constituents with an insectifuge activity and its crude saponin fraction has been used as a surface-active agent. 2) Previously, we reported the structure elucidation and anti-sweet activity of two acylated polyhydroxyoleane-12-ene oligoglycosides, theasaponins E 1 (6) and E 2 (7), from the seeds of C. sinensis cultivated in Japan. 2) In addition, from the seeds and leaves of C. sinensis var. assamica PIERRE cultivated in Sri Lanka, we isolated assamsaponins A (8), B (9), C (10), D (11), E, F (12), G, H, and I (13) with gastric emptying activity and an accelerating effect on gastrointestinal transit. 3,4) Recently, we characterized floratheasaponins A (14), B, and C with antihyperlipidemic activity from the flowers of C. sinensis. 1) As a continuing study on the bioactivity of saponin constituents from the tea plant, we found that the saponin fraction of the methanolic extract from the seeds of C. sinensis showed protective effects on ethanol-and indomethacin-induced gastric
Chemosystematically valuable triterpenoid saponins from Glandularia x hybrida
Phytochemistry, 2020
Phytochemical investigation of the ethanolic extract of Glandularia x hybrida roots resulted in the isolation and identification of five previously undescribed saponins, 3-O-β-ᴅ-xylopyranosyl-hederagenin-28-O-β-ᴅ-glucopyranosyl (1→2)-O-β-ᴅ-glucopyranosyl ester, 3-O-β-ᴅ-xylopyranosyl-hederagenin-28-O-β-ᴅ-glucopyranosyl (1→2)-[β-ᴅ-glucopyranosyl (1→6)]-β-ᴅ-glucopyranosyl ester, hederagenin-28-O-β-ᴅ-glucopyranosyl (1→2)-[β-ᴅ-glucopyranosyl (1→6)]-β-ᴅ-glucopyranosyl ester, 23-O-acetyl-3-O-β-ᴅ-xylopyranosyl-pomolic acid-28-O-β-ᴅ-glucopyranosyl ester, and 23-O-acetyl-pomolic acid-3-O-β-ᴅ-xylopyranoside, along with eleven structurally diverse compounds. The structural characterizations of the isolated compounds were determined using physical data, comprehensive 1D and 2D NMR spectral analysis, and HRESIMS. All isolated saponins are hederagenin or pomolic acid glycosides conjugated with differentiable sugar units bound to C-3 and/or C-28 of the aglycone through ether and/or ester glycosidic linkages, respectively. Structural diversity of these isolated secondary metabolites would have a great impact on the future chemosystematic studies of this plant. Four saponins, obtained in good yield were evaluated for their anti-inflammatory activities in a rat model using the carrageenan-induced paw edema protocol. Two of these exhibited significant anti-inflammatory activities demonstrated through inhibition of the paw edema by 64 and 60%.
Triterpenoid saponins from the roots of tea plant ( Camellia sinensis var. assamica
Phytochemistry, 2000
Three olean-12-ene type triterpenoid saponins, named TR-saponins A, B and C, were isolated as methyl esters from tea roots (Camellia sinensis var. assamica ) after treatment with diazomethane. Their structures were established as the methyl esters of 3-O-a-L-arabinopyranosyl (1 4 3)-b-D-glucuronopyranosyl-21, 22-di-O-angeloyl-R 1 -barrigenol-23-oic acid, 3-O-a-Larabinopyranosyl (1 4 3)-b-D-glucuronopyranosyl-21-O-angeloyl-22-O-2-methylbutanoyl-R 1 -barrigenol-23-oic acid and 3-O-a-Larabinopyranosyl (1 4 3)-b-D-glucuronopyranosyl-16a-O-acetyl-21-O-angeloyl-22-O-2-methylbutanoyl-R 1 -barrigenol-23-oic acid, 2 by extensive 1D and 2D-NMR as well as FABMS and HR-MS analyses. 7
Medicinal Aspect of Saponins shows their wide range of Pharmacological/Biological activities
2010
Saponins (saponosides) belong to a group of secondary metabolites, widely distributed mainly, but not exclusively, among plants. The saponins are naturally occurring surfaceactive glycosides. They are reported to occur in over 500 species from over 90 families of both edible and nonedible plants. Chemically, saponins are glycosides consisting of a sugar moiety and non-sugar aglycone, called also sapogenin. Depending on the number of sugar chains attached to the aglycone, mono-, biand tridesmosides are distinguished. According to the structure of aglycone, saponins are classified into steroidal and triterpenoid. Saponins have a high ability to bind to cell membrane sterols, which is responsible at least in part for their biological activities. They reveal also strong haemolytic properties, which differ depending on the saponin type and its aglycone structure. Saponins exhibit a wide range of biological properties and are believed to be one of the key biologically active constituents ...
New triterpenoid saponins from the roots of Saponaria officinalis
Natural product communications, 2013
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-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-[beta-D-glucopyranosyl-(1 -->6)-beta-D-glucopyranoside (1), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-[beta-D-glucopyranosyl-(1-->3)]-[alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (2) and 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-[beta-D-glucopyranosyl-(1-->3)]-[6-O-(3-hydroxy-3-methylglutaryl)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3). Their structures were elucida...
Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel
Beilstein Journal of Organic Chemistry, 2012
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 pentasac-Beilstein J. Org. Chem. 2012, 8, 763-775. 764 charide 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.
Direct Detection Of Triterpenoid Saponins In Medicinal Plants
African Journal of Traditional, Complementary and Alternative Medicines, 2008
Direct detection of saponins in medicinal plants using Fourier Transform Infrared (FTIR) spectroscopy is reported in this paper. Crude dry plant powders were mixed with potassium bromide (KBr) powder and compressed to a thin pellet for infrared examination. FTIR spectra of the test samples showed-OH,-C=O, C-H, and C=C absorptions characteristic of oleanane triterpenoid saponins. The CO -C absorptions indicated glycoside linkages to the sapogenins. Phytochemical analysis confirmed the presence of saponins in the tested specimens. Entada leptostachya was used as a reference sample. Dry plant powder was extracted sequentially with hexane, dichloromethane, ethyl acetate and methanol. FTIR spectra of the reference sample powder and its organic solvent extracts showed characteristic saponin absorption peaks. These results indicated that direct detection of saponins in medicinal plants was possible by infrared analysis. Lengthy exhaustive chemical analyses necessary for detection of saponins could be avoided.
A New Triterpene Saponin from Chenopodium ficifolium
The new triterpene saponin 3-O--d-glucopyranoside, 28--d-glucopyranosyl-(1 5 2)--d-glucopyranosiduronic acid oleanolate was isolated from the roots of Chenopodium ficifolium. The known compounds stigmasterol-3-O-glucoside and 3-O--d-glucopyranosiduronic acid, 28--d-glucopyranosyl oleanolate were also isolated. The latter compound, oleanolic acid, -sitosterol and its glucoside were isolated from the aerial parts. The identity of these compounds was verified through different chemical and physico-chemical evidences including different 1D and 2D NMR experiments.