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Phytochemical studies on the whole herb of Sphaerophysa salsula has resulted in the discovery of one new 8-isopentenyl isoflavone derivative, named sphaerosin s2 (3-(8-(2-hydroxypropan-2-yl)-3,4-dihydro-2H-furo[2,3-h]chromen-3-yl)-2,6-dimethoxyphenol) (1), along with four know 8-isopentenyl isoflavone derivatives (2-5). Compounds (2, 4 and 5) were isolated for the first time from this species. Their structures were elucidated on the basis of ESI-MS, UV, IR, 1D NMR and 2D NMR data.
Background: Dracocephalum heterophyllum was a traditional Tibetan medicine possesses various pharmacological effects involved in anti-inflammatory, antibacterial activities. However, its anti-hepatitis, antioxidant activity and bioactive compounds have not been reported, the objective of this research work was to investigate the pharmacological activity and bioactive compounds of D. heterophyllum extracts. Results: In the present study, the anti-hepatics and antioxidant activities of four D. heterophyllum extracts (i.e. petroleum ether extracts, ethyl acetate extracts, n-BuOH extracts, and water extracts) were conducted. The main chemical constituent of petroleum ether and ethyl acetate extracts were also isolated using chromatographic techniques and identified by NMR spectroscopic methods. The anti-hepatitis assay showed that the petroleum ether and ethyl acetate extracts of D. heterophyllum significantly prolonged the mean survival times and reduced the mortality of mouse hepatitis model induced by concanavalin A (ConA). The levels of alanine transaminase, aspartate transaminase in blood serum could be decreased obviously by ethyl acetate extracts compared with ConA group (P < 0.01). The histological analysis demonstrated that the ethyl acetate extracts could inhibit apoptosis and necrosis caused by ConA. In addition, the antioxidant activities of the four extracts of D. heterophyllum were measured by DPPH assay, ABTS assay, anti-lipidperoxidation assay, ferric reducing antioxidant power assay, ferrous metal ions chelating assay and determination of total phenolic contents. The results showed that the ethyl acetate extract had the highest antioxidant activities, followed by petroleum ether extract. Finally, nine mainly compounds were isolated from the Petroleum ether and ethyl acetate extracts, including four triterpenes: oleanolic acid ( 1), ursolic acid ( 2), pomolic acid ( 3), 2α- hydroxyl ursolic acid ( 4), three flavonoids: apigenin-7- O-rutinoside ( 5), luteolin ( 8), diosmetin ( 9) and two phenolic acids: rosmarinic acid ( 6), methyl rosmarinate ( 7). Conclusion: The Ethyl acetate extract of D. heterophyllum had the highest anti-hepatitis and antioxidants activities, followed by petroleum ether extract. The bioactive substances may be triterpenes, flavonoids and phenolic acids, the ethyl acetate extracts of D. heterophyllum may be possible candidates in developing anti-hepatitis medicine.
<br>Display Omitted<br> Two new phenolic acids (<b>1</b>⿿<b>2</b>) were isolated from the aerial parts of <b>Asterothamnus centrali-asiaticus</b>. Five knownphenolic acids (<b>3</b>⿿<b>7</b>) were also obtained from the title plant. <b>1</b>⿿<b>7</b> were evaluated for their anti-oxidant activity. <b>1</b>⿿<b>7</b> showed anti-oxidant activity with IC50 values ranging from 7.65 to 22.44 μg/mL.<br>Two new phenolic acids 2-hydroxy-5-[(6⿲-<b>O</b>-(<b>E</b>)-caffeoyl)-β-d-glucopyranosyl]-oxybenzoic acid (<b>1</b>) and 2-hydroxy-5-[(3⿲-<b>O</b>-(<b>E</b>)-caffeoyl)-β-d-glucopyranosyl]-oxybenzoic acid (<b>2</b>) were isolated from the aerial parts of <b>Asterothamnus centrali-asiaticus</b>, together with five known ones (<b>3</b>-<b>7</b>). Their structures were elucidated by extensive 1D and 2D NMR studies and HRESIMS investigations. The anti-oxidant activity of the isolates was evaluated through ABTS radical cation decolorization assay. The results showed that all of them exhibited anti-oxidant activity, and compound <b>7</b> was the most active compound with an IC50 value of 7.65 μg/mL.
The young leaves and shoots of Sibiraea laevigata, known as "Liucha", are used as tea by Tibetans to improve digestion after meals. Long-term consumption of "Liucha" will cause weight loss. In present work, we reported on the isolation and NMR and chemical analysis-based elucidation of seven new sorbitol O-caffeic acid ester derivatives named sorbitol esters A-G (1-7) and eighteen known phenolic compounds from S. laevigata. All of the isolates were evaluated for their antioxidant and α-glucosidase inhibitory activities. Among them sorbitol ester A (1), sorbitol ester D (4), sorbitol ester F (6), sorbitol ester G (7), isoferulic acid (15), methyl caffeate (18), trans-p-hydroxycinnamic acid (19), and kaempferol 3-O-β-d-(6″-E-p-coumaroyl)-glucopyranoside (25) showed more potent α-glucosidase inhibitory activity than the clinical drug acarbose.
The first phytochemical investigation on the roots of <b>Ligularia purdomii</b> led to the isolation and identification of 18 compounds, including two eremophilane sesquiterpenoids (<b>1</b> and <b>2</b>), three benzofuran derivatives (<b>3</b>-<b>5</b>), a triterpenoid (<b>6</b>), two steroids (<b>7</b> and <b>8</b>), nine phenolic components (<b>9</b>-<b>17</b>), and a monofatty glyceride (<b>18</b>). The structural elucidation of the isolated compounds was performed by spectroscopic data and comparison with the literature. Compounds (−)-syringaresinol (<b>11</b>), scopoletin (<b>13</b>), 3,5-dimethoxy-4-hydroxy-benzaldehyde (<b>14</b>), and glycerol monolinoleate (<b>18</b>) have not been recorded in <b>Ligularia</b> genus previously. The chemotaxonomic significance of these isolated compounds has been summarized.<br>• First phytochemical investigation on <b>L. purdomii.</b> • 18 compounds were identified from the acetone extract of <b>L. purdomii.</b> • Four compounds were reported from the genus <b>Ligularia</b> for the first time. • The results had important significance for chemotaxonomy of <b>L. purdomii.</b>
A phytochemical investigation of <b>Saxifraga tangutica</b> led to the isolation of 11 compounds, including eight diarylheptanoids (<b>1</b>-<b>6</b>, <b>10</b> and <b>11</b>) and three phenylpropanoids (<b>7</b>-<b>9</b>). The chemical structures were established by extensive analysis of their MS and NMR spectroscopic data or comparison with literature data. In the present research, we report the isolated compounds <b>1</b>-<b>11</b>, for the first time, in the species <b>S. tangutica</b>. Moreover, compounds <b>1</b>, <b>2</b> and <b>4</b>-<b>11</b> have not been reported from any species in Saxifragaceae family. Furthermore, we discuss the chemotaxonomic significance of the isolated compounds.<br>• Eight diarylheptanoids and three phenylpropanoids have been isolated from <b>Saxifraga tangutica.</b> • Compounds <b>1</b>-<b>11</b> are firstly reported in the species <b>Saxifraga tangutica.</b> • Compounds <b>1</b>, <b>2</b> and <b>4</b>-<b>11</b> are firstly isolated from genus <b>Saxifraga</b> or family Saxifragaceae.
Nitraria tangutorum Bor., having edible berries, is valued for reputed health benefits in Qinghai-Tibet plateau. The phytochemical research on the fruit juice of N. tangutorum led to the isolation of twenty-six compounds including five new compounds, tangutorids A-D (1, 2, 3a, and 3b), and (3E,5E)-7-O-β-glucosyl-4-(2-methoxy-2-oxoethyl)hepta-3,5-dienoic acid (15). The structures of these compounds were elucidated through comprehensive spectroscopic analyses. Tangutorids A-F were the first examples of glucose-derived β-carbolines from natural products. The biogenetic pathways of 1-8 were proposed to involve Pictet-Spengler reactions and described starting from the co-isolated tryptophan (10) and corresponding aldehydes. All isolates were evaluated for their antioxidant and α-glucosidase inhibitory activities. Compounds 21, 22, and 24 showed antioxidant activity with SC50 values ranging from 12.2±1.9 to 30.4±2.7μg/mL, and compound 1 showed strong α-glucosidase inhibitory effect with IC50 value of 63.3±4.6μg/mL.
A new diarylheptanoid, (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptan-3-one-5-O-β-D-6-Oacetylglucoside (<i>1</i>), together with two known diarylheptanoids, (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptan-3-one-5-O-β-D-glucopyranoside (<i>2</i>) and hirsutanonol (<i>3</i>), were isolated from Saxifraga tangutica. The structures of <i>1-3</i> were elucidated using 1D and 2D NMR spectral data, including high-resolution mass spectra (HR-ESI-MS). It was found that the new compound was acetyl-substituted (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptan-3-one-5-O-β-D-glucopyranoside.
A new isocoumarin, along with 10 known compounds, was isolated from the aerial parts of Aconitum gymnandrum. Their structures were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques. Among the known compounds, compound 11 was obtained as a natural product for the first time, which was previously reported as a synthetic product. In addition, compounds 1-5, 7 and 9 were tested for their cytotoxicity against four human cancer cell lines. The results showed that compounds 3, 4 and 7 displayed cytotoxicity against lung cancer A549 and gastric cancer MGC80, respectively, whereas 5 and 9 showed selective cytotoxicity against hepatocellular carcinoma HepG2.
<br>Display Omitted<br>• Two new monoterpenes named sibiscolactons A and B (<b>1</b> and <b>2</b>) were isolated from <b>Sibiraea laevigata</b>. • New compounds’ absolute configurations were established by electronic circular dichroism (ECD) calculations. • Eight known phenylpropanoids (<b>3</b>-<b>10</b>) were also obtained from the title plant. • <b>1</b>-<b>10</b> were evaluated for their cytotoxic activity. • Compound <b>3</b> displayed moderate cytotoxicity with IC50 values ranging from 10.8 to 49.2 μg mL−1.<br>Chemical investigation of the ethanol extract of the stalks and infructescence of <b>Sibiraea leavigata</b> led to the isolation of two new monoterpenes named (4<b>R</b>)-2-(2-hydroxy-4-methyl-3-pentenyl)furan-2(5<b>H</b>)-one (<b>1</b>) and (2<b>R</b>,4<b>R</b>)-2-(2-hydroxyethyl)-4-(2-methyl-1-propenyl)furan-5<b>H</b>-2-one (<b>2</b>) along with eight known phenylpropanoids (<b>3-10</b>). Their structures were established on the basis of the interpretation of spectroscopic data and electronic circular dichroism (ECD) calculations. In addition, all of these isolates were evaluated for their cytotoxic activity. The results showed that compound <b>3</b> displayed moderate cytotoxicity with IC50 values ranging from 10.8 to 49.2 μg mL−1 against five cell lines. While <b>1</b> showed selective promotion effects on proliferation of gastric cancer MGC803 and RSC96 cell lines.
Phytochemical investigation on <b>Asterothamnus centrali-asiaticus</b> afforded four new sesquiterpenes, asterothamnones A-D (<b>1</b>-<b>4</b>), and three new benzofuran derivatives (<b>5</b>-<b>7</b>) together with ten known compounds (<b>8</b>-<b>17</b>). Their structures were elucidated using 1D and 2D NMR and X-ray diffraction analyses. Compounds <b>1</b>-<b>4</b> were verified to be unusual eudesmane sesquiterpenes possessing 4,6-dien-3-one or 1,4,6-triene-3-one conjugated system. The absolute configurations of compounds <b>1</b>-<b>8</b> were established by means of calculated electronic circular dichroism (ECD). Furthermore, all isolates were evaluated for their cytotoxic and anti-oxidant activities. Results showed that <b>10</b>, <b>12</b> and, <b>14</b> exhibited cytotoxic activity against HepG2 cancer cells and <b>14</b> displayed cytotoxicity against MGC-803 cancer cells. Compounds <b>10</b> and <b>17</b> showed anti-oxidant effect.<br><br>Display Omitted
Four iridoid glucosides, shanzhiside methyl ester, phloyoside II, chlorotuberside, and penstemonoside, were isolated and purified from an herbal medicinal plant for the first time by high-speed counter-current chromatography (HSCCC) using a two-phase solvent system composed of ethyl acetate-n-butanol-water (5:14:12, v/v/v). A total of 37mg of shanzhiside methyl ester, 29mg of phloyoside II, 27mg of chlorotuberside, and 21mg of penstemonoside with the purity of 99.2%, 98.5%, 97.3%, and 99.3%, respectively, were obtained in one-step separation within 4h from 150mg of crude extract. To the best of our knowledge, this is the first report of separation and purification of iridoid glucosides from natural sources by HSCCC. The chemical structures of all the four compounds were identified by ESI-MS, (1)H NMR, and (13)C NMR.
A new flavonoid, along with 16 known ones, was separated from the aerial parts of Asterothamnus centrali-asiaticus. Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR techniques and HRESIMS. To confirm the structure of the new compound, computational prediction of its 13C chemical shifts was performed. All of the 17 flavonoids were reported from A. centrali-asiaticus for the first time. In addition, all flavonoids were evaluated for their antioxidant and α-glucosidase inhibitory activities. The results showed that 10 of them exhibited antioxidant activity. Meanwhile, four flavonoids displayed α-glucosidase inhibitory effect with IC50 values ranging from 38.9 to 299.7 μM.
<br>Display Omitted<br>• Three new monoterpene glycosides (<b>1</b>-<b>3</b>) were isolated from <b>Sibiraea laevigata</b> (L.) Maxim. • Fourteen known compounds (<b>4</b>-<b>17</b>) were also obtained from the title plant. • All of the isolated compounds were evaluated for their anti-oxidant and α-glucosidase inhibitory activities. • Compounds <b>7</b> and <b>17</b> exhibited α-glucosidase inhibitory effect with IC50 values of 220.0 and 113.0 μM, respectively.<br>Three new compounds, 3,7-dimethy-7-methoxy-3-octene-5-one-1-<b>O</b>-<b>β</b>-d-glucopyranoside (1), 3,7-dimethy-7-methoxy-3(<b>Z</b>)-octene-5-one-1-<b>O</b>-<b>β</b>-d-glucopyranoside (2) and 3,7-dimethy-3-hydroxy-6-octene-5-one-1-<b>O</b>-<b>β</b>-d-glucopyranoside (3), together with fourteen known compounds (4-17) were isolated from the leaves and shoots of <b>S. laevigata</b>. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including one- and two-dimensional NMR, as well as mass spectral data. All isolates were evaluated for their α-glucosidase inhibitory and antioxidant activities. The results demonstrated that 3,7-dimethyl-3(Z),6-ocatdien-5-one-1-<b>O</b>-<b>β</b>-d-glucoside (7) and sitosteryl <b>β</b>-d-glucoside (17) exhibited α-glucosidase inhibitory effects with IC50 values of 220.0 and 113.0 μM, respectively.
<br>Display Omitted<br>• Two new stilbenoid derivatives were isolated from <b>Sphaerophysa salsula</b>. • One compound were isolated for the first time from this species. • Eight known compounds were isolated from the plant. • These compounds enriched the structural types of natural products from <b>Sphaerophysa salsula</b>.<br>Two new compounds, gnetuhainins Fa (<b>1</b>) and cassigarols Ea (<b>2</b>), were isolated from the whole herb of <b>Sphaerophysa salsula</b> along with eight known compounds (<b>3</b>-<b>10</b>). The compounds (<b>4</b>) were isolated for the first time from this species. Their structures were elucidated by ESI-MS, UV, IR, 1D NMR and 2D NMR data.