Steroidal Glycosides from Veronica chamaedrys L. Part I. The Structures of Chamaedrosides C, C1, C2, E, E1 and E2

Marchenko, Alexandra; Kintya, P. K.; Wyrzykiewicz, Bożena; Gorincioi, Elena

doi:10.1177/1934578x1200700504

Cited by 5 publications

(7 citation statements)

References 15 publications

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“…As part of our efforts to complete the chemical profile of oat bran, five steroidal saponins 1 – 5 (Figure ) were isolated by means of chromatographic methods, including silica gel and Diaion HP-20 chromatography. Compounds 1 – 3 were identified as avenacosides A, B, and C, respectively, according to literature data. ,, Avenacoside A, 1, and avenacoside B, 2 , have been reported as the primary saponins in oat bran and analyzed by HPLC-TQ-MS and HPLC with UV detection. , Compound 3 was first discovered from fresh bulbs of Lilium brownii and subsequently isolated from oat bran and named avenacoside C by Lu et al…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 1−3 were identified as avenacosides A, B, and C, respectively, according to literature data. 22,32,33 Avenacoside A, 1, and avenacoside B, 2, have been reported as the primary saponins in oat bran and analyzed by HPLC-TQ-MS and HPLC with UV detection. 32,33 Compound 3 was first discovered from fresh bulbs of Lilium brownii 34 and subsequently isolated from oat bran and named avenacoside C by Lu et al 24 Compound 4 gave a deprotonated ion at m/z 915.7 [M − H] − in an HPLC-MS spectrum.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Steroidal Saponins in Oat Bran

Yang

Wang

et al. 2016

J. Agric. Food Chem.

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Saponins are one type of widespread defense compound in the plant kingdom and have been exploited for the production of lead compounds with diverse pharmacological properties in drug discovery. Oats contain two unique steroidal saponins, avenacoside A, 1, and avenacoside B, 2. However, the chemical composition, the levels of these saponins in commercial oat products, and their health effects are still largely unknown. In this study, we directly purified 5 steroidal saponins (1-5) from a methanol extract of oat bran, characterized their structures by analyzing their MS and NMR spectra, and also tentatively identified 11 steroidal saponins (6-16) on the basis of their tandem mass spectra (MS(n), n = 2-3). Among the five purified saponins, 5 is a new compound and 4 is purified from oats for the first time. Using HPLC-MS techniques, a complete profile of oat steroidal saponins was determined, and the contents of the two primary steroidal saponins, 1 and 2, were quantitated in 15 different commercial oat products. The total levels of these two saponins vary from 49.6 to 443.0 mg/kg, and oat bran or oatmeal has higher levels of these two saponins than cold oat cereal. Furthermore, our results on the inhibitory effects of 1 and 2 against the growth of human colon cancer cells HCT-116 and HT-29 showed that both had weak activity, with 2 being more active than 1.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Steroidal Saponins in Oat Bran

Yang

Wang

et al. 2016

J. Agric. Food Chem.

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“…The other known compounds were identified as protodioscin ( 2 ) [ 10 ], methyl protodioscin ( 3 ) [ 15 ], aspacochioside A ( 4 ) [ 16 ], aspacochioside C ( 5 ) [ 16 ], 15-hydroxypseudoprotodioscin ( 6 ) [ 17 ], and chamaedroside E ( 7 ) [ 18 ] by comparison of their NMR spectroscopic data with those previously reported data.…”

Section: Resultsmentioning

confidence: 99%

“…Although asapacochioside C ( 5 ) was cytotoxic against human lung adenocarcinoma A549 cells [ 21 ], it failed to show a significant cytotoxicity against human ovarian cancer cells in this study. Reportedly, chamaedroside E ( 7 ) was first isolated from Veronica chamaedrys [ 18 ]. However, the presence of 7 in A. cochinchinensis was found in this study, for the first time.…”

Section: Resultsmentioning

confidence: 99%

A Novel Cytotoxic Steroidal Saponin from the Roots of Asparagus cochinchinensis

Kim

Choi

Kim

et al. 2021

Plants

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A new steroidal saponin, 26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22α,26-triol 3-O-(1−4)-β-d-glucopyranosyl-α-l-rhamnopyranosyl-(1−2)-[α-l-rhamnopyranosyl-(1−4)]-β-d-glucopyranoside [asparacochioside A (1)] was isolated from a hot water extract of the roots of Asparagus cochinchinensis, together with the known steroidal saponins protodioscin (2), methyl protodioscin (3), aspacochioside A (4), aspacochioside C (5), 15−hydroxypseudoprotodioscin (6), and chamaedroside E (7). The structure of the new compound 1 was determined by interpretation of its spectroscopic data (1D- and 2D-NMR and HR−Q−TOF−MS) and sugar analysis. The isolated compounds 1−7 were tested for their in vitro cytotoxicity against human ovarian cancer cell lines (A2780 and SKOV3). Asparacochioside A (1) exhibited a significant cytotoxicity against both A2780 and SKOV3 cells with IC50 values of 5.25 ± 2.2 and 46.82 ± 9.43 μM, respectively. Furthermore, asparacochioside A (1) significantly increased the percentage of Annexin V-positive cells (apoptotic cells), suggesting that asparacochioside A induces ovarian cancer cell death via apoptosis.

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“…(Figure 17) [13]. A new phenylethanoid triglycoside, chionoside J (125), was isolated from Veronica beccabunga L. (brooklime) [54], while two new spirostane glycosides, chamaedrosides C (126) and C1 (127), two new furostane glycosides, chamaedrosides E (128) and E1 (129), and two new furospirostane glycosides were found in V. chamaedrys (Figure 18) [55]. Compounds in other species are detailed in Table 2, i.e., Veronica argute-serrata , Veronica biloba schreb.…”

Section: Phytochemical Characterization Of Veronica Plantsmentioning

confidence: 99%

Veronica Plants—Drifting from Farm to Traditional Healing, Food Application, and Phytopharmacology

Salehi

Shetty²,

et al. 2019

Molecules

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The Veronica genus, with more than 200 species, belongs to the Plantaginaceae family and is distributed over most of the Northern Hemisphere and in many parts of Southern Hemisphere. These plants are traditionally used in medicine for wound healing, in the treatment of rheumatism, and in different human diseases. This paper reviews the chemical composition of some valuable Veronica species, the possibilities Veronica extracts have in food preservation and as food ingredients, and their functional properties. Veronica species represent a valuable source of biological active secondary metabolites, including iridoid glycosides and phenolic compounds. In particular, due to presence of these phytochemicals, Veronica species exhibit a wide spectrum of biological activities, including antimicrobial and antioxidant. In fact, some studies suggest that some Veronica extracts can inhibit foodborne pathogens, such as Listeria monocytogenes, but only a few of them were performed in food systems. Moreover, anticancer, anti-inflammatory, and other bioactivities were reported in vitro and in vivo. The bioactivity of Veronica plants was demonstrated, but further studies in food systems and in humans are required.

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Steroidal Glycosides from Veronica chamaedrys L. Part I. The Structures of Chamaedrosides C, C₁, C₂, E, E₁ and E₂

Cited by 5 publications

References 15 publications

Steroidal Saponins in Oat Bran

Steroidal Saponins in Oat Bran

A Novel Cytotoxic Steroidal Saponin from the Roots of Asparagus cochinchinensis

Veronica Plants—Drifting from Farm to Traditional Healing, Food Application, and Phytopharmacology

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