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1.
《化学与生物多样性》2018,15(2)
The defatted fractions of the Faramea hyacinthina and F. truncata (Rubiaceae) leaf MeOH extracts showed in vitro non‐cytotoxic and anti‐dengue virus serotype 2 (DENV2) activity in human hepatocarcinoma cell lineage (HepG2). Submitting these fractions to the developed RP‐SPE method allowed isolating the antiviral flavanone (2S)‐isosakuranetin‐7‐O‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 1 ) from both species and yielded less active sub‐fractions. The new diastereoisomeric epimer pair (2S) + (2R) of 5,3′,5′‐trihydroxyflavanone‐7‐O‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 2a / 2b ) from F. hyacinthina; the known narigenin‐7‐O‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 3 ) from both species; rutin ( 4 ) and quercetin‐4′‐β‐d ‐O‐glucopyranosyl‐3‐O‐rutinoside ( 5 ) from F. hyacinthina, and kaempferol‐3‐O‐rutinoside ( 6 ), erythroxyloside A ( 7 ) and asperuloside ( 8 ) from F. truncata have been isolated from these sub‐fractions. Compounds 4 – 8 are reported for the first time in Faramea spp. 相似文献
2.
Si‐Yuan Ma Ling‐Gao Shi Zheng‐Bing Gu Yu‐Lan Wu Liu‐Bin Wei Qi‐Qiu Wei Xing‐Ling Gao Na Liao 《化学与生物多样性》2018,15(9)
Five chromone glycosides were isolated from the water‐soluble portions of 70% EtOH extract of the roots of Saposhnikovia divaricata, including two new chromone glycosides 1 and 2 . The structures of the chromone glycosides were identified as (3′S)‐3′‐O‐β‐d ‐apiofuranosyl‐(1 → 6)‐β‐d ‐glucopyranosylhamaudol ( 1 ), (2′S)‐4′‐O‐β‐d ‐apiofuranosyl‐(1 → 6)‐β‐d ‐glucopyranosylvisamminol ( 2 ), 3′‐O‐glucopyranosylhamaudol ( 3 ), 4′‐O‐β‐d ‐glucopyranosylvisamminol ( 4 ), and 4′‐O‐β‐d ‐glucopyranosyl‐5‐O‐methylvisamminol ( 5 ) on the basis of extensive spectroscopic methods, and the absolute configurations of the new compounds were elucidated by the electronic circular dichroism (ECD) calculation and acid hydrolysis. The cytotoxic activities of the glycosides 1 – 5 against three human cancer cell lines (PC‐3, SK‐OV‐3, and H460) were evaluated. The result showed that compounds 1 – 5 had weak cytotoxic activities against the human cancer cell lines with IC50 values in the range of 48.54 ± 0.80 – 94.25 ± 1.45 μm . 相似文献
3.
Gentiana rhodantha Franch. ex Hemsl. (Gentianaceae), an annual herb widely distributed in the southwest of China, has been medicinally used for the treatment of inflammation, cholecystitis, and tuberculosis by the local people of its growing areas. Chemical investigation on the whole plants led to the identification of eight new phenolic compounds, rhodanthenones A–D ( 1 – 4 , resp.), apigenin 7‐O‐glucopyranosyl‐(1→3)‐glucopyranosyl‐(1→3)‐glucopyranoside ( 5 ), 1,2‐dihydroxy‐4‐methoxybenzene 1‐O‐α‐L ‐rhamnopyranosyl‐(1→6)‐β‐D ‐glucopyranoside ( 6 ), 1,2‐dihydroxy‐4,6‐dimethoxybenzene 1‐O‐α‐L ‐rhamnopyranosyl‐(1→6)‐β‐D ‐glucopyranoside ( 7 ), and methyl 2‐O‐β‐D ‐glucopyranosyl‐2,4,6‐trihydroxybenzoate ( 8 ), together with eleven known compounds, 9 – 19 . Their structures were determined on the basis of detailed spectroscopic analyses and chemical methods. Acetylcholinesterase (AChE) inhibition and cytotoxicity tests against five human cancer cell lines showed that only rhodanthenone D ( 4 ) and mangiferin ( 12 ) exhibited 18.4 and 13.4% of AChE inhibitory effects at a concentration of 10−4 M , respectively, while compounds 1 – 5 and the known xanthones lancerin ( 11 ), mangiferin ( 12 ), and neomangiferin ( 13 ) displayed no cytotoxicity at a concentration of 40 μM . 相似文献
4.
Yang Gao Jie Mi Chang‐Long Zhang Xiao‐Qing Zhang Ya‐Jie Peng He Bao Hai‐Long Zhang 《化学与生物多样性》2019,16(1)
Continually phytochemical study of the roots of Heracleum dissectum had led to the isolation of three previously undescribed polyacetylene glycosides ( 1 – 3 ), together with seven known compounds, including one polyacetylene ( 8 ) and six coumarins ( 4 – 7 and 9 – 10 ) using diverse chromatographic methods. The structures of these three new compounds were characterized and identified as deca‐4,6‐diyn‐1‐yl β‐d ‐glucopyranosyl‐(1→6)‐β‐d ‐glucopyranosyl‐(1→2)‐β‐d ‐glucopyranoside ( 1 ), (8Z)‐dec‐8‐ene‐4,6‐diyn‐1‐yl β‐d ‐glucopyranosyl‐(1→6)‐β‐d ‐glucopyranosyl‐(1→2)‐β‐d ‐glucopyranoside ( 2 ), and (8E)‐dec‐8‐ene‐4,6‐diyn‐1‐yl β‐d ‐glucopyranosyl‐(1→6)‐β‐d ‐glucopyranosyl‐(1→2)‐β‐d ‐glucopyranoside ( 3 ) based on their physicochemical properties and extensive analyses of various spectroscopic data. Their triglycerides accumulating activities were assayed and the results showed that the three new polyacetylene glycosides ( 1 – 3 ) exhibited triglyceride accumulating activities in 3T3‐L1 adipocytes. 相似文献
5.
Inhibition of NO Production by Grindelia argentina and Isolation of Three New Cytotoxic Saponins
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Natalia P. Alza Eva‐Maria Pferschy‐Wenzig Sabine Ortmann Nadine Kretschmer Olaf Kunert Gerald N. Rechberger Rudolf Bauer Ana P. Murray 《化学与生物多样性》2014,11(2):311-322
A bioassay‐guided phytochemical analysis of the ethanolic extract of Grindelia argentina Deble & Oliveira ‐Deble (Asteraceae) allowed the isolation of a known flavone, hispidulin, and three new oleanane‐type saponins, 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 2 ), 3‐O‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester, ( 3 ) and 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 4 ), named grindeliosides A–C, respectively. Their structures were determined by extensive 1D‐ and 2D‐NMR experiments along with mass spectrometry and chemical evidence. The isolated compounds were evaluated for their inhibitory activities against LPS/IFN‐γ‐induced NO production in RAW 264.7 macrophages and for their cytotoxic activities against the human leukemic cell line CCRF‐CEM and MRC‐5 lung fibroblasts. Hispidulin markedly reduced LPS/IFN‐γ‐induced NO production (IC50 51.4 μM ), while grindeliosides A–C were found to be cytotoxic, with grindelioside C being the most active against both CCRF‐CEM (IC50 4.2±0.1 μM ) and MRC‐5 (IC50 4.5±0.1 μM ) cell lines. 相似文献
6.
Two novel flavanone glycosides, homoeriodictyol 7‐O‐β‐D ‐[6‐(3‐hydroxybutanoyl)glucopyranoside] (viscumneoside IX; 1 ) and homoeriodictyol 7‐O‐β‐D ‐[6‐(3‐hydroxybutanoyl)glucopyranosyl](1→2)‐β‐D ‐glucopyranoside (viscumneoside X; 2 ), together with four known flavanoids, 2‐homoeriodictyol 7‐O‐β‐D ‐glucopyranoside ( 3 ), viscumneoside I ( 4 ), viscumneoside III ( 5 ), and 4′,5‐dihydroxy‐3′‐methoxy‐7‐(2‐O‐α‐L ‐rhamnopyranosyl‐β‐D ‐glucopyranosyloxy)flavanone ( 6 ) were isolated from stems and leaves of Viscum coloratum. Their structures were elucidated on the basis of their NMR spectra, HR‐FAB‐MS data, and acid hydrolysis. Inhibitory effects of the four compounds 1 – 4 on the formation of osteoclast‐like multinucleated cells were investigated. As a result, all the four flavanoids showed significant inhibitory effects on the formation of osteoclast‐like multinuclear cells even at a low concentration of 2 μg/ml. The activities of 1 – 4 at such a concentration exceeded or approximated to that of elcitonin, the positive control drug at a concentration of 2 U/ml, suggesting that they may be of interest for the development of new anti‐osteoporosis drugs. 相似文献
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9.
Htay Htay Shwe Mye Aye Myint Myint Sein Khin Than Htay Peter Kreitmeier Jürg Gertsch Oliver Reiser Jörg Heilmann 《化学与生物多样性》2010,7(3):610-622
Three new steroid saponins (3β,25R)‐spirost‐5‐en‐3‐yl 6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→4)‐6‐deoxy‐α‐L ‐mannopyranosyl‐(1→3)]‐β‐D ‐glucopyranoside ( 1 ), (3β,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐hydroxyfurost‐5‐en‐3‐yl 6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L ‐mannopyranosyl‐(1→3)]‐β‐D ‐glucopyranoside ( 3 ), and (3β,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐hydroxyfurost‐5‐en‐3‐yl 6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→4)‐6‐deoxy‐α‐L ‐mannopyranosyl‐(1→3)]‐β‐D ‐glucopyranoside ( 5 ), as well as the new pregnane glycoside (3β,16β)‐3‐{[6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L ‐mannopyranosyl‐(1→3)]‐β‐D ‐glucopyranosyl]oxy}‐20‐oxopregn‐5‐en‐16‐yl (4R)‐5‐(β‐D ‐glucopyranosyloxy)‐4‐methylpentanoate ( 6 ), were isolated from the rhizomes of Tacca integrifolia together with two known (25R) configurated steroid saponins (3β,25R)‐spirost‐5‐en‐3‐yl 6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L ‐mannopyranosyl‐(1→3)]‐β‐D ‐glucopyranoside ( 2 ) and (3β,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurost‐5‐en‐3‐yl 6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L ‐mannopyranosyl‐(1→3)]‐β‐D ‐glucopyranoside ( 4 ). The cytotoxic activity of the isolated compounds was evaluated in HeLa cells and showed the highest cytotoxicity value for compound 2 with an IC50 of 1.2±0.4 μM . Intriguingly, while compounds 1 – 5 exhibited similar cytotoxic properties between 1.2±0.4 ( 2 ) and 4.0±0.6 μM ( 5 ), only compound 2 showed a significant microtubule‐stabilizing activity in vitro. 相似文献
10.
Four New Steroidal Glycosides,Protolinckiosides A – D,from the Starfish Protoreaster lincki
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Timofey V. Malyarenko Alla A. Kicha Anatoly I. Kalinovsky Natalia V. Ivanchina Roman S. Popov Evgeny A. Pislyagin Ekaterina S. Menchinskaya Krishna Pillai Padmakumar Valentin A. Stonik 《化学与生物多样性》2016,13(8):998-1007
Four new steroidal glycosides, protolinckiosides A – D ( 1 – 4 , resp.), were isolated along with four previously known glycosides, 5 – 8 , from the MeOH/EtOH extract of the starfish Protoreaster lincki. The structures of 1 – 4 were elucidated by extensive NMR and ESI‐MS techniques as (3β,4β,5α,6β,7α,15α,16β,25S)‐4,6,7,8,15,16,26‐heptahydroxycholestan‐3‐yl 2‐O‐methyl‐β‐d ‐xylopyranoside ( 1 ), (3β,5α,6β,15α,24S)‐3,5,6,8,15‐pentahydroxycholestan‐24‐yl α‐l ‐arabinofuranoside ( 2 ), sodium (3β,6β,15α,16β,24R)‐29‐(β‐d ‐galactofuranosyloxy)‐6,8,16‐trihydroxy‐3‐[(2‐O‐methyl‐β‐d ‐xylopyranosyl)oxy]stigmast‐4‐en‐15‐yl sulfate ( 3 ), and sodium (3β,6β,15α,16β,22E,24R)‐28‐(β‐d ‐galactofuranosyloxy)‐6,8,16‐trihydroxy‐3‐[(2‐O‐methyl‐β‐d ‐xylopyranosyl)oxy]ergosta‐4,22‐dien‐15‐yl sulfate ( 4 ). The unsubstituted β‐d ‐galactofuranose residue at C(28) or C(29) of the side chains was found in starfish steroidal glycosides for the first time. Compounds 1 – 4 significantly decreased the intracellular reactive oxygen species (ROS) content in RAW 264.7 murine macrophages at induction by proinflammatory endotoxic lipopolysaccharide (LPS) from E. coli. 相似文献
11.
Piptadenin,a Novel 3,4‐Secooleanane Triterpene and Piptadenamide,a New Ceramide from the Stem Bark of Piptadeniastrum africanum (Hook.f.) Brenan
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Amadou Dawé Marius Mbiantcha Yannick Fongang William Yosseu Nana Fawai Yakai Gilbert Ateufack Muhammad Ali Shaiq Iqbal Lubna Mehreen Lateef Bonaventure Tchaleu Ngadjui 《化学与生物多样性》2017,14(2)
Piptadenin ( 1 ), a new triterpene along with piptadenamide ( 10 ), a new ceramide, have been isolated from the AcOEt‐soluble fraction of the MeOH extract of the stem bark of Piptadeniastrum africanum along with nine known compounds, 1‐O‐[(3β,22β)‐3,22‐dihydroxy‐28‐oxoolean‐12‐en‐28‐yl]‐β‐d ‐glucopyranose ( 2 ), 22β‐hydroxyoleanic acid ( 3 ), oleanic acid ( 4 ), lupeol ( 5 ), betulinic acid ( 6 ), 5α‐stigmasta‐7,22‐dien‐3β‐ol ( 7 ), 5α‐stigmasta‐7,22‐dien‐3‐one ( 8 ), (3β)‐stigmast‐5‐en‐3‐yl β‐d ‐glucopyranoside ( 9 ) and 2,3‐dihydroxypropyl hexacosanoate ( 11 ). Except for compound 11 , all the isolated compounds are reported for the first time from this plant. The structures of the isolated compounds were elucidated by spectroscopic data including 1D and 2D NMR. The pure compounds 1 – 11 were subjected to the pharmacological screening and compounds 2 , 5 – 7 and 9 exhibited potent urease inhibitory activity with IC50 value of 25.8, 28.9, 30.1, 31.8 and 32.7 μm , respectively, whereas compound 1 showed moderate activity (IC50 = 98.7 μm ). The potent urease inhibitory activity supplemented the previous literature reports and medicinal uses of this plant. 相似文献
12.
Eman Al‐Sayed Omayma A. Eldahshan Dina M. Bahgat Abdel Nasser B. Singab 《化学与生物多样性》2016,13(12):1666-1673
Two new oleanane‐type saponins: β‐d ‐xylopyranosyl‐(1 → 4)‐6‐deoxy‐α‐l ‐mannopyranosyl‐(1 → 2)‐1‐O‐{(3β)‐28‐oxo‐3‐[(2‐O‐β‐d ‐xylopyranosyl‐β‐d ‐glucopyranosyl)oxy]olean‐12‐en‐28‐yl}‐β‐d ‐glucopyranose ( 1 ) and 1‐O‐[(3β)‐28‐oxo‐3‐{[β‐d ‐xylopyranosyl‐(1 → 2)‐α‐l ‐arabinopyranosyl‐(1 → 6)‐2‐acetamido‐2‐deoxy‐β‐d ‐glucopyranosyl]oxy}olean‐12‐en‐28‐yl]β‐d ‐glucopyranose ( 2 ), along with two known saponins: (3β)‐3‐[(β‐d ‐Glucopyranosyl‐(1 → 2)‐β‐d ‐glucopyranosyl)oxy]olean‐12‐en‐28‐oic acid ( 3 ) and (3β)‐3‐{[α‐l ‐arabinopyranosyl‐(1 → 6)‐[β‐d ‐glucopyranosyl‐(1 → 2)]‐β‐d ‐glucopyranosyl]oxy}olean‐12‐en‐28‐oic acid ( 4 ) were isolated from the acetone‐insoluble fraction obtained from the 80% aqueous MeOH extract of Albizia anthelmintica Brongn . leaves. Their structures were identified using different NMR experiments including: 1H‐ and 13C‐NMR, HSQC, HMBC and 1H,1H‐COSY, together with HR‐ESI‐MS/MS, as well as by acid hydrolysis. The four isolated saponins and the fractions of the extract exhibited cytotoxic activity against HepG‐2 and HCT‐116 cell lines. Compound 2 showed the most potent cytotoxic activity among the other tested compounds against the HepG2 cell line with an IC50 value of 3.60μm . Whereas, compound 1 showed the most potent cytotoxic effect with an IC50 value of 4.75μm on HCT‐116 cells. 相似文献
13.
Chemical Constituents of the Rare Cliff Plant Oresitrophe rupifraga and Their Antineuroinflammatory Activity
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Four new ( 1 – 4 ) and thirteen known ( 5 – 17 ) compounds were isolated from a rare cliff plant, Oresitrophe rupifraga. Based on spectroscopic evidence, the new structures were established to be [(2S,3R,4R)‐4‐(4‐methoxybenzyl)‐2‐(4‐methoxyphenyl)‐tetrahydrofuran‐3‐yl]methanol ( 1 ), (3α)‐23‐(acetyloxy)‐3‐hydroxyolean‐12‐en‐29‐oic acid ( 2 ), 3α,23‐(isopropylidenedioxy)olean‐12‐en‐29‐oic acid ( 3 , artifact of isolation), and (3β,15β)‐3‐hydroxycholest‐5‐en‐15‐yl β‐d ‐glucopyranoside ( 4 ), respectively. Among the isolates, compounds 1 , 4 , epieudesmin ( 7 ), and 1‐O‐(9Z,12Z,15Z‐octadecatrienoyl)glycerol ( 17 ) were found to show significant antineuroinflammatory effects by inhibiting the NO production in lipopolysaccharide (LPS)‐stimulated murine BV‐2 microglial cells, with IC50 values of 7.21, 9.39, 4.96, and 8.51 μm , respectively. 相似文献
14.
Basile‐Jimmy Djimtombaye Özgen Alankuş‐Çalışkan Derya Gülcemal Ikhlas A. Khan Hüseyin Anıl Erdal Bedir 《化学与生物多样性》2013,10(7):1328-1334
From the whole plant of Astragalus halicacabus (Sect. Halicacabus), a new cycloartane‐type glycoside, (20R,24S)‐3‐O‐[α‐L ‐arabinopyranosyl‐(1→2)‐β‐D ‐xylopyranosyl]‐20,24‐epoxy‐16‐O‐β‐D ‐glucopyranosyl‐3β,6α,16β,25‐tetrahydroxycycloartane, and a new glycoside, 3‐O‐[β‐D ‐apiofuranosyl‐(1→2)‐β‐D ‐glucopyranosyl]maltol were isolated together with seven known cycloartane‐type glycosides, i.e., cyclocanthoside D, askendosides D, F, and G, cyclosieversioside G, cyclostipuloside A, elongatoside, and a known maltol glucoside, 3‐O‐β‐D ‐glucopyranosylmaltol. The structures were elucidated by means of high‐resolution mass spectrometry, and extensive 1D‐ and 2D‐NMR spectroscopic analysis. This is the first phytochemical work on A. halicacabus, and a maltol glycoside was encountered for the first time in the Leguminosae family. 相似文献
15.
Anti‐HSV‐1 and HSV‐2 Flavonoids and a New Kaempferol Triglycoside from the Medicinal Plant Kalanchoe daigremontiana
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Fernanda Gouvêa Gomes Ürményi Georgia do Nascimento Saraiva Livia Marques Casanova Amanda dos Santos Matos Luiza Maria de Magalhães Camargo Maria Teresa Villela Romanos Sônia Soares Costa 《化学与生物多样性》2016,13(12):1707-1714
Kalanchoe daigremontiana (Crassulaceae) is a medicinal plant native to Madagascar. The aim of this study was to investigate the flavonoid content of an aqueous leaf extract from K. daigremontiana (Kd), and assess its antiherpetic potential. The major flavonoid, kaempferol 3‐O‐β‐d ‐xylopyranosyl‐(1 → 2)‐α‐l ‐rhamnopyranoside ( 1 ), was isolated from the AcOEt fraction (Kd‐AC). The BuOH‐soluble fraction afforded quercetin 3‐O‐β‐d ‐xylopyranosyl‐(1 → 2)‐α‐l ‐rhamnopyranoside ( 2 ) and the new kaempferol 3‐O‐β‐d ‐xylopyranosyl‐(1 → 2)‐α‐l ‐rhamnopyranoside‐7‐O‐β‐d ‐glucopyranoside ( 3 ), named daigremontrioside. The crude extract, Kd‐AC fraction, flavonoids 1 and 2 were evaluated using acyclovir‐sensitive strains of HSV‐1 and HSV‐2. Kd‐AC was highly active against HSV‐1 (EC50 = 0.97 μg/ml, SI > 206.1) and HSV‐2 (EC50 = 0.72 μg/ml, SI > 277.7). Flavonoids 1 and 2 showed anti‐HSV‐1 (EC50 = 7.4 μg/ml; SI > 27 and EC50 = 5.8 μg/ml; SI > 8.6, respectively) and anti‐HSV‐2 (EC50 = 9.0 μg/ml; SI > 22.2 and EC50 = 36.2 μg/ml; SI > 5.5, respectively) activities, suggesting the contribution of additional substances to the antiviral activity. 相似文献
16.
Nguyen Van Thang Vu Kim Thu Nguyen Xuan Nhiem Duong Thi Dung Tran Hong Quang Bui Huu Tai Hoang Le Tuan Anh Pham Hai Yen Nguyen Thi Thanh Ngan Nguyen Huy Hoang Phan Van Kiem 《化学与生物多样性》2017,14(5)
Five new oleanane‐type saponins, hirsutosides A – E, were isolated from the leaves of Glochidion hirsutum (Roxb .) Voigt . Their structures were elucidated as 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranoside ( 1 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐β‐d ‐glucopyranoside ( 2 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐6‐acetyl‐[β‐d ‐glucopyranosyl‐(1 → 3)]‐β‐d ‐glucopyranoside ( 3 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐〈‐l ‐arabinopyranoside ( 4 ), and 21β‐benzoyloxy‐3β,16β,23‐trihydroxyolean‐12‐ene‐28‐al 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐α‐l ‐arabinopyranoside ( 5 ). All isolated compounds were evaluated for cytotoxic activities on four human cancer cell lines, HepG‐2, A‐549, MCF‐7, and SW‐626 using the SRB assay. Compounds 1 , 2 , 4 , and 5 showed significant cytotoxic activities against all human cancer cell lines with IC50 values ranging from 3.4 to 10.2 μm . Compound 3 containing acetyl group at glc C(6″) exhibited weak cytotoxic activity with IC50 values ranging from 47.0 to 54.4 μm . 相似文献
17.
Gökhan Şenel Derya Gülcemal Milena Masullo Sonia Piacente Tamer Karayıldırım 《化学与生物多样性》2014,11(3):408-418
Three new oleanane‐type glycosides, 1 – 3 , were isolated from the whole plant of Tremastelma palaestinum (L.) Janchen, along with eight known triterpene glycosides. The structures of the new compounds were established as 3‐O‐[β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→3)‐β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→2)‐α‐l‐ arabinopyranosyl]hederagenin ( 1 ), 3‐O‐[β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→3)‐β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→2)‐α‐l‐ arabinopyranosyl]hederagenin 28‐O‐β‐d‐ glucopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl ester ( 2 ), and 3‐O‐[α‐l‐ rhamnopyranosyl‐(1→3)‐β‐d‐ glucopyranosyl‐(1→3)‐α‐l‐ rhamnopyranosyl‐(1→2)‐α‐l‐ arabinopyranosyl]oleanolic acid 28‐O‐β‐d‐ glucopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl ester ( 3 ) by using 1D‐ and 2D‐NMR techniques and mass spectrometry. This is the first report on the phytochemical investigation of a species belonging to Tremastelma genus. 相似文献
18.
Hai‐Long Zhang Xin‐Yuan Wu Jie Mi Ya‐Jie Peng Zhi‐Gang Wang Ying Liu Xiu‐Li Wu Yang Gao 《化学与生物多样性》2017,14(9)
Using various chromatographic methods, a new piperidinone alkaloid, (3S)‐3‐{4‐[(1E)‐3‐hydroxyprop‐1‐en‐1‐yl]‐2‐methoxyphenoxy}piperidin‐2‐one ( 1 ), together with 10 known compounds, bergapten ( 2 ), xanthotoxol ( 3 ), isopimpinellin ( 4 ), isobergapten ( 5 ), heratomol‐6‐O‐β‐d ‐glucopyranoside ( 6 ), scopoletin ( 7 ), apterin ( 8 ), 3‐methoxy‐4‐β‐d ‐glucopyranosyloxypropiophenone, (praeroside; 9 ), tachioside ( 10 ) and coniferin ( 11 ), were isolated from roots of Heracleum dissectum Ledeb . Their structures were elucidated on the basis of physicochemical properties and the detailed interpretation of various spectroscopic data. All the isolated compounds were screened for anti‐inflammatory activity in vitro. As the results, compound 1 and 8 showed significantly inhibitory activity on nitric oxide production in RAW264.7 cells. 相似文献
19.
Jie Zhang Ryosuke Koike Ayako Yamamoto Motohiko Ukiya Makoto Fukatsu Norihiro Banno Motofumi Miura Shigeyasu Motohashi Harukuni Tokuda Toshihiro Akihisa 《化学与生物多样性》2013,10(10):1851-1865
A new flavonoid glycoside, chrysin 6‐C‐β‐rutinoside (chrysin α‐L ‐rhamnopyranosyl‐(1→6)‐C‐β‐glucopyranoside; 2 ), and two new triterpene glycosides, (31R)‐31‐O‐methylpassiflorine ( 7 ) and (31S)‐31‐O‐methylpassiflorine ( 8 ), along with 14 known glycosides, including three flavonoid glycosides, 1, 3 , and 4 , six triterpene glycosides, 5, 6 , and 9 – 12 , three cyano glycosides, 13 – 15 , and two other glycosides, 16 and 17 , were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1 – 17 against the melanogenesis in the B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), three compounds, isoorientin ( 1 ), 2 , and (6S,9R)‐roseoside ( 17 ), exhibited inhibitory effects with 37.3–47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8–100.2% cell viability) at 100 μM . Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP‐1, and tyrosinase, in a concentration‐dependent manner while exerted almost no influence on the level of TRP‐2, suggesting that this compound inhibits melanogenesis on the α‐MSH‐stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP‐1 and tyrosinase. In addition, compounds 1 – 17 were evaluated for their inhibitory effects against the Epstein? Barr virus early antigen (EBV‐EA) activation induced by 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells. 相似文献
20.
Insecticidal Metabolites from the Rhizomes of Veratrum album against Adults of Colorado Potato Beetle,Leptinotarsa decemlineata
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Tuba Aydin Ahmet Cakir Cavit Kazaz Neslihan Bayrak Yasin Bayir Yavuz Taşkesenligil 《化学与生物多样性》2014,11(8):1192-1204
The dried rhizomes of Veratrum album were individually extracted with CHCl3, acetone, and NH4OH/benzene to test the toxic effects against the Colorado potato beetle, Leptinotarsa decemlineata, which is an important agricultural pest. Fifteen compounds in various amounts were isolated from the extracts using column and thin‐layer chromatography. The chemical structures of 14 compounds were characterized as octacosan‐1‐ol ( 1 ), β‐sitosterol ( 2 ), stearic acid ( 3 ), diosgenin ( 4 ), resveratrol ( 5 ), wittifuran X ( 6 ), oxyresveratrol ( 7 ), β‐sitosterol 3‐O‐β‐D ‐glucopyranoside ( 8 ), diosgenin 3‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyronoside ( 9 ), oxyresveratrol 3‐O‐β‐D ‐glucopyranoside ( 10 ), jervine ( 11 ), pseudojervine ( 13 ), 5,6‐dihydro‐1‐hydroxyjervine ( 14 ), and saccharose ( 15 ) using UV, IR, MS, 1H‐ and 13C‐NMR, and 2D‐NMR spectroscopic methods. However, the chemical structure of 12 , an oligosaccharide, has not fully been elucidated. Compounds 4, 6, 9 , and 10 were isolated from V. album rhizomes for the first time in the current study. The toxic effects of three extracts (acetone, CHCl3, and NH4OH/benzene) and six metabolites, 2, 2 + 4, 5, 7, 8 , and 11 , were evaluated against the Colorado potato beetle. The assay revealed that all three extracts, and compounds 7, 8 , and 11 exhibited potent toxic effects against this pest. This is the first report on the evaluation of the toxic effects of the extracts and secondary metabolites of V. album rhizomes against L. decemlineata. Based on these results, it can be concluded that the extracts can be used as natural insecticides. 相似文献