Oleanane-type triterpene saponins from Calendula stellata

Lehbili, Meryem; Magid, Abdulmagid Alabdul; Kabouche, Ahmed; Voutquenne-Nazabadioko, Laurence; Abedini, Amin; Morjani, Hamid; Sarazin, Thomas; Gangloff, Sophie C.; Kabouche, Zahia

doi:10.1016/j.phytochem.2017.08.015

Cited by 28 publications

(22 citation statements)

References 29 publications

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“…The HMBC spectrum revealed proper correlations for this methyl group with C-4 (δC 38.8), C-5 (δC 55.7), C-3 (δC 89.6), as well as C-24 (δC 15.6). The chemical shifts values for all protons and carbons of the aglycone moiety (Table 1) were in accordance with the literature data of echinocystic acid (3β,16αdihydroxyolean-12-en-28-oic acid) (Lehbili et al, 2017), which was further confirmed by COSY, HSQC, HMBC and ROESY experiments on 5. Consequently, the structure of 5 was concluded to be…”

Section: Resultssupporting

confidence: 89%

“…Through an extensive 2D-NMR study, the aglycone was identified as 3β,16α,23trihydroxyolean-12-en-28-oic acid, commonly named caulophyllogenin, which is in good agreement with literature data (Table 1) (Matsuo et al, 2009). The chemical shift values of C-3 (δC 82.0) and C-28 (δC 175.7) suggested that the saponin was a bisdesmosidic glycoside with saccharide units attached to these positions (Lehbili et al, 2017 and2018). The HMBC spectrum showed cross-peaks between H-16 signal with C-14, C-15, C-17, C-18 and C-22, thus unambiguously locating the hydroxyl group at C-16 (δC 72.7).…”

Section: Resultssupporting

confidence: 83%

“…The HMBC spectrum showed cross-peaks between H-16 signal with C-14, C-15, C-17, C-18 and C-22, thus unambiguously locating the hydroxyl group at C-16 (δC 72.7). The 16α-configuration of hydroxyl group was evident from the small J values of , characteristic of an equatorial proton (Lehbili et al, 2017). Moreover, ROESY correlation was observed between Me-26 (δH 0.79) and H-16 β-oriented while no one was observed between Me-27 (δH 1.37) an H-16 confirming that H-16 had β-configuration.…”

Section: Resultsmentioning

confidence: 90%

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Triterpene saponins from Silene gallica collected in North-Eastern Algeria

et al. 2020

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Eleven previously undescribed triterpene saponins, named silenegallisaponin A-K (1-11), were isolated from the aerial parts of Silene gallica L. Their structures were elucidated by analysis of 1Dand 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). The saponins comprised caulophyllogenin, echinocystic acid, or quillaic acid substituted at C-3 by a β-D-glucuronic acid or β-D-galactopyranosyl-(13)-β-D-glucuronopyranoside and at C-28 by a β-D-fucopyranose substituted at C-2 by β-D-glucose and at C-3 by a β-D-glucose or a β-D-quinovose.

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Section: Resultssupporting

confidence: 89%

Section: Resultssupporting

confidence: 83%

Section: Resultsmentioning

confidence: 90%

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Triterpene saponins from Silene gallica collected in North-Eastern Algeria

et al. 2020

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“…Summing up, the obtained results confirmed that micelle-mediated extracts from marigold flowers, regardless of the surfactants used, showed higher antioxidant activity than the water extract (Table 3). The higher antioxidant activity of ethanol marigold extracts is probably linked to the content of triterpene saponins (Lehbili et al, 2017).…”

Section: Resultsmentioning

confidence: 99%

Application of Polyethylene/Polypropylene Glycol Ethers of Fatty Alcohols for Micelle‐Mediated Extraction of Calendula anthodium

Śliwa

Sikora

et al. 2018

J Surfact & Detergents

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Classical extraction methods used for the isolation of active substances from the plant materials are expensive, complicated, and often environmentally unfriendly. The ultrasonic assisted micelle‐mediated extraction (UAMME) method seems to be an interesting alternative. In this study, Calendula anthodium UAMME extract composition and antioxidant properties were examined. Several nonionic surfactants, from the group of ethoxy/propoxylated fatty alcohols, were applied in the extraction process. The results were compared with water and water‐ethanoic extracts of marigold flowers. Bioflavonoid compositions of the extracts were determined using ultra‐performance liquid chromatography–diode‐array detector–mass spectrometry (UPLC‐DAD‐MS). Their antioxidant properties were evaluated using free radical‐scavenging activity (2,2‐Diphenyl‐1‐picrylhydrazyl, DPPH) measurement and Follin's method. Additionally, the structure of the selected flavonoids solubilized in the micelle solution was theoretically simulated using molecular dynamics (MD). The results confirmed that the UAMME method might be an alternative method for the sourcing of the plant extracts rich in natural antioxidants. The results indicated that UAMME extracts showed 19–37% higher DPPH radical inhibition than aqueous extracts. Furthermore, the selection of a suitable surfactant may thus provide the expected composition of the extract. Due to the use as eluents in UAMME, safe raw materials, the obtained marigold flower extracts can be applied as components in the cosmetic and pharmaceutical products.

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“…Oleanane-type triterpenes such as oleanolic acid are one of pentacyclic triterpenes and have been isolated from many food and medicinal plants. These oleanane-type triterpenes including saponins have been reported to possess many biological effects such as anti-inflammatory, anti-obesity, anti-cancer, and anti-oxidant effects [1][2][3][4][5]. However, chemical and pharmacological studies on oleanane-type triterpenes with highly-substituted oxygen functional groups and without glycoside moieties have not been investigated sufficiently yet.…”

mentioning

confidence: 99%

Oleanane-type Triterpenes with Highly-Substituted Oxygen Functional Groups from the Flower Buds of Camellia sinensis and Their Inhibitory Effects against NO Production and HSV-1

Yoneda

Nakamura

Ogawa

et al. 2018

Natural Product Communications

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Acylated oleanane-type triterpenes named chakasapogenins I (1), II (2), and III (3) were isolated from the hydrolysis product of the extract obtained from the flower buds of Camellia sinensis. The chemical structures of new triterpenes were elucidated on the basis of chemical and physicochemical evidence. chakasapogenin III (3) inhibited nitric oxide (NO) production in lipopolysaccharide-(LPS) activated RAW264.7 macrophages. In addition, R 1-barrigenol (7) showed antiviral effect at 10M against herpes simplex virus type-1 (HSV-1).

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Oleanane-type triterpene saponins from Calendula stellata

Cited by 28 publications

References 29 publications

Triterpene saponins from Silene gallica collected in North-Eastern Algeria

Triterpene saponins from Silene gallica collected in North-Eastern Algeria

Application of Polyethylene/Polypropylene Glycol Ethers of Fatty Alcohols for Micelle‐Mediated Extraction of Calendula anthodium

Oleanane-type Triterpenes with Highly-Substituted Oxygen Functional Groups from the Flower Buds of Camellia sinensis and Their Inhibitory Effects against NO Production and HSV-1

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