Triterpenoid saponins and iridoid glycosides from the aerial parts of Cephalaria pastricensis

Gođevac, Dejan; Mandić, Boris; Vajs, Vlatka; Tešević, Vele; Menković, Nebojša; Janaćković, Pedja; Milosavljević, Slobodan

doi:10.1016/j.bse.2006.05.015

Cited by 16 publications

(9 citation statements)

References 18 publications

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“…It was found that, these results demonstrate heavy crude oil was appropriately modified to J Surfact Deterg (2016) 19:1251-1261 1255 Fig. 4 13 C-NMR of the extracted saponin from this study (a) and commercial saponin (b) [32] light oil. Our results have been summarized in Table 1.…”

Section: Investigation Of Viscosity and Api Gravity Changesmentioning

confidence: 63%

“…Oligosaccharide linkage absorptions to sapogenins, that is C-O-C, were evident between 1072 cm -1 in the standard, and 1057 cm -1 in the produced saponin. After all the aforementioned infrared spectra have been referred by researchers owing to the oleanolic acid/ ester, these oleane-type triterpenoid saponins are characterized by the C-O infrared absorbance [30][31][32]. Broad bond at 3413.47 cm -1 indicate its glycoside nature.…”

Section: Resultsmentioning

confidence: 99%

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Production of Saponin Biosurfactant from Glycyrrhiza glabra as an Agent for Upgrading Heavy Crude Oil

Hajimohammadi

Hosseini

Amani

et al. 2016

J Surfact & Detergents

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Saponins are the main group of phytogenic biosurfactants extracted from plants. One of the significant applications of these compounds is upgrading and viscosity reduction of heavy crude oil water in oil (W/O) emulsions. In this research, use of saponin extracted from Glycyrrhiza glabra was investigated for viscosity reduction of heavy crude oil and upgrading its API properties. The extracted saponin was characterized using Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy. Phase behavior analysis demonstrated a reduction in initial viscosity and improved API gravity of the heavy oil from 2350 mPa·s and 19 to 900 mPa·s and 27, respectively. In addition, the emulsification index (E24) was found to be 98 % at a saponin concentration of 8 % w/v. It was observed that the emulsions were stable in the pH range of 5.5–13, temperature from 30 to 80 °C and salinity up to 6 % w/v of NaCl solution. Average diameter of W/O droplets evaluated by dynamic light scattering (DLS) were in the range of 10–15 µm. The results obtained from the present research revealed that the extracted saponin improved the physical characteristics of heavy crude oil. We propose the use of saponin as a potential alternative to conventional emulsifiers for upgrading heavy crude oil in petroleum industry.

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Section: Investigation Of Viscosity and Api Gravity Changesmentioning

confidence: 63%

Section: Resultsmentioning

confidence: 99%

Production of Saponin Biosurfactant from Glycyrrhiza glabra as an Agent for Upgrading Heavy Crude Oil

Hajimohammadi

Hosseini

Amani

et al. 2016

J Surfact & Detergents

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“…Comparison of the resulting spectra with those reported in the literature identified the isolated compounds as loganin (1) and gentiopicrin (2) [2][3][4].…”

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confidence: 83%

Iridoid glycosides from Cephalaria kotschyi roots

Mustafaeva

Élias²,

Balansard³

et al. 2008

Chem Nat Compd

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“…The iridoid glycosides loganin, loganic acid, and cantleyoside of Cephalaria and other genus of the Dipsacaceae family [16][17][18][19][20] have been previously reported. These compounds are used as chemosystematic markers for plants of the Dipsacaceae family.…”

Section: Cephalaria Kotschyimentioning

confidence: 95%

Chemical constituents from the roots of Cephalaria kotschyi

et al. 2011

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Cephalaria kotschyi Boiss. et Hoh. (Dipsacaceae) is an endemic plant of the Caucasus region growing in Azerbaijan. Earlier phytochemical studies reported the isolation of triterpene saponins, flavonoids, and gentianine type alkaloids from the roots and flowers of C. kotschyi [1][2][3][4][5][6][7]. In our previous study we described the isolation of the iridoid glycosides loganin and gentiopicroside from the roots of this plant [8].Herein we report, together with the gentiopicroside and loganin described previously, the isolation of three iridoid and secoiridoid glycosides: loganic acid [9], swertiamarin [10], and cantleyoside [11]; two furofuranic lignans: prinsepiol glycoside [12] and 8-hydroxypinoresinol-4c-O-E-D-glucoside [13]; and two triterpene saponins: giganteoside Jc [14] and dipsacoside B [15], from an investigation of the chemical constituents of the roots of C. kotschyi. The plant was collected in the Lerik region of Azerbaijan in September 2005. A voucher specimen (C 8131005) was deposited at the herbarium of the Botanical Institute, Academy of Science, Azerbaijan.Air-dried roots (100 g) were extracted by percolation at room temperature with MeOH (1 L for 24 h), and the obtained solution was concentrated under vacuum. The MeOH extract (5 g) was submitted to flash column chromatography on polyamide MN SC 6 Macherey Nagel® (70 Pm), using a step gradient of H 2 O-MeOH of 90:10, 50:50, and 0:100, to give 3 main fractions (F1-F3). Fraction F1 was further purified by low-pressure liquid chromatography on Prepamatic Chromatospac 10 (Jobin Yvon) with Lichroprep RP18 Merck® (25-40 Pm). A step gradient of H 2 O-MeOH and 0:100, 1 L for each) allowed us to obtain 20 fractions, Sp1-Sp20. Fractions Sp2, Sp5, Sp7, Sp9, and Sp16 afforded respectively loganic acid (18 mg), swertiamarin (73 mg), gentiopicroside (250 mg), loganin (75 mg), and cantleyoside (230 mg). Purification of fractions Sp12 and Sp13 by means of preparative high-performance liquid chromatography on a Symmetry C18 column (5 Pm, 250 u 4.6, waters®), using H 2 O-MeOH (75:25), yielded prinsepiol glycoside (20 mg) and 8-hydroxypinoresinol glycoside (18 mg) respectively. Fraction F2 (1 g) was fractionated by silica gel CC using CH 2 Cl 2 -MeOH-H 2 O (50:16:3) and (30:13:3) successively as eluent to give dipsacoside B (30 mg) and giganteoside Jc (30 mg). The structural elucidations of the obtained compounds were performed by spectroscopic analysis, including 2D NMR data, and confirmed by comparison with the previously reported data. NMR spectra were recorded in CD 3 OD (G ppm) on a Bruker DRX 500 spectrometer operating at 500.13 MHz and 125.13 MHz.All the isolated compounds, except loganin and gentiopicroside, have been reported for the first time from C. kotschyi. The iridoid glycosides loganin, loganic acid, and cantleyoside of Cephalaria and other genus of the Dipsacaceae family [16][17][18][19][20] have been previously reported. These compounds are used as chemosystematic markers for plants of the Dipsacaceae family. The secoiridoid swertiamarin has b...

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Triterpenoid saponins and iridoid glycosides from the aerial parts of Cephalaria pastricensis

Cited by 16 publications

References 18 publications

Production of Saponin Biosurfactant from Glycyrrhiza glabra as an Agent for Upgrading Heavy Crude Oil

Production of Saponin Biosurfactant from Glycyrrhiza glabra as an Agent for Upgrading Heavy Crude Oil

Iridoid glycosides from Cephalaria kotschyi roots

Chemical constituents from the roots of Cephalaria kotschyi

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