- Aqueous ionic liquids and deep eutectic solvents for cellulosic biomass pretreatment and saccharification
-
Ionic liquids (ILs) have proven effective solvents for pretreating lignocellulose, leading to the fast saccharification of cellulose and hemicellulose. However, the high cost of most ILs remains a major barrier to commercializing this recent approach at a practical scale. As a strategic detour, aqueous solutions of ILs are also being explored as less costly alternatives to neat ILs for cellulose pretreatment. However, limited studies on a few select IL systems are known and there remains no systematic survey of various ILs, eluding an in-depth understanding of pretreatment mechanisms afforded by aqueous IL systems. As a step toward filling this gap, this study presents results for Avicel cellulose pretreatment by neat and aqueous solutions (1.0 and 2.0 M) of 20 different ILs and three deep eutectic solvents, correlating enzymatic hydrolysis rates of pretreated cellulose with various IL properties such as hydrogen-bond basicity, polarity, Hofmeister ranking, and hydrophobicity. The pretreatment efficiencies of neat ILs may be loosely correlated to the hydrogen-bond basicity of the constituent anion and IL polarity; however, the pretreatment efficacies for aqueous ILs are more complicated and cannot be simply related to any single IL property. Several aqueous IL systems have been identified as effective alternatives to neat ILs in lignocellulose pretreatment. In particular, this study reveals that aqueous solutions of 1-butyl-3-methylimidazolium methanesulfonate ([BMIM][MeSO 3]) are effective for pretreating switchgrass (Panicum virgatum), resulting in fast saccharification of both cellulose and hemicellulose. An integrated analysis afforded by X-ray diffraction, scanning electron microscopy, thermogravimetric analysis and cellulase adsorption isotherm of lignocellulose samples is further used to deliver a more complete view of the structural changes attending aqueous IL pretreatment.
- Xia, Shuqian,Baker, Gary A.,Li, Hao,Ravula, Sudhir,Zhao, Hua
-
-
Read Online
- C30 and C31 Triterpenoids and Triterpene Sugar Esters with Cytotoxic Activities from Edible Mushroom Fomitopsis pinicola (Sw. Ex Fr.) Krast
-
Fomitopsis pinicola (Sw. Ex Fr.) Krast has been commonly used as a health food source and antitumor agent. To uncover bioactive key composition of F. pinicola, in our study, we investigated the chemical constituents of a methanol extract of F. pinicola and thirty-five lanostane-type tritetpenoids; 13 new compounds (1-13) and twenty-two known analogues (14-35) were isolated. Among them, compounds 1-9 were C30 lanostane triterpenoids and triterpene sugar esters, while compounds 10-13 were C31 triterpenoids and triterpene sugar esters. Their structures and absolute configurations were elucidated by extensive 1D, 2D NMR, MS, and IR spectra. Furthermore, cytotoxic activities of all isolates against five human tumor cell lines (HL-60, A549, SMMC-7721, MCF-7, and SW480) were evaluated. The results showed that compounds 12, 14, 17, 18, 22, and 23 displayed cytotoxic effects against five human tumor cell lines with IC50 values ranging from 3.92-28.51 μM. Meanwhile, compounds 9 and 35 exhibited selected inhibitory activities against HL-60, SMMC-7721, and MCF-7 with IC50 values in the range of 13.57-36.01 μM. Furthermore, the flow cytometry analysis revealed that compounds 17, 22, and 35 induced apoptosis in HL-60 cell lines. Their structure-activity relationships were preliminarily reported. These findings indicate the vital role of triterpenoids and their glycosides in explaining antitumor effects of F. pinicola and provide important evidence for further development and utilization of this fungus.
- Peng, Xing-Rong,Su, Hai-Guo,Liu, Jun-Hong,Huang, Yan-Jie,Yang, Xin-Zhi,Li, Zhong-Rong,Zhou, Lin,Qiu, Ming-Hua
-
-
Read Online
- Enzymatic Hydrolysis of Black Liquor Xylan by a Novel Xylose-Tolerant, Thermostable β-Xylosidase from a Tropical Strain of Aureobasidium pullulans CBS 135684
-
From three cell-associated β-xylosidases produced by Aureobasidium pullulans CBS 135684, the principal enzyme was enriched to apparent homogeneity and found to be active at high temperatures (60–70?°C) over a pH range of 5–9 with a specific activity of 163.3?units (U) mg?1. The enzyme was thermostable, retaining over 80% of its initial activity after a 12-h incubation at 60?°C, with half-lives of 38, 22, and 10?h at 60, 65, and 70?°C, respectively. Moreover, it was tolerant to xylose inhibition with a Ki value of 18?mM. The Km and Vmax values against p-nitrophenyl-β-d-xylopyranoside were 5.57?±?0.27?mM and 137.0?±?4.8?μmol?min?1?mg?1 protein, respectively. When combining this β-xylosidase with xylanase from the same A. pullulans strain, the rate of black liquor xylan hydrolysis was significantly improved by up to 1.6-fold. The maximum xylose yield (0.812?±?0.015?g?g?1 dry weight) was obtained from a reaction mixture containing 10% (w/v) black liquor xylan, 6?U?g?1 β-xylosidase and 16?U?g?1 xylanase after incubation for 4?h at 70?°C and pH 6.0.
- Bankeeree, Wichanee,Akada, Rinji,Lotrakul, Pongtharin,Punnapayak, Hunsa,Prasongsuk, Sehanat
-
-
Read Online
- Cycloartane triterpenoids from Actaea vaginata with anti-inflammatory effects in LPS-stimulated RAW264.7 macrophages
-
Five undescribed cycloartane triterpenoids, including two cycloartane trinor-triterpenoids, were isolated from a 70% ethanol extract of the whole plant of Actaea vaginata (Ranunculaceae), together with thirteen known cycloartane triterpenoids. Their structures were determined by spectroscopic techniques and quantum chemical calculations for intramolecular noncovalent interactions with reduced density gradient method. All compounds were evaluated for their anti-inflammatory effects by a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW264.7 macrophage cells, and some showed potent inhibitory effects with IC50 values ranging from 5.0 to 24.4 μM. Further mechanism studies showed that one compound dose-dependently suppressed LPS-induced NO production and pro-inflammatory cytokines secretion, and decreased the expression of iNOS, through inhibiting NF-κB activation.
- Fang, Zhu-Jun,Zhang, Tian,Chen, Shi-Xin,Wang, Yan-Lan,Zhou, Chang-Xin,Mo, Jian-Xia,Wu, Yong-Jiang,Xu, You-Kai,Lin, Li-Gen,Gan, Li-She
-
-
Read Online
- A new cycloartane triterpene glycoside from Souliea vaginata
-
A new cycloartane-type triterpene glycoside, namely soulieoside M (1), and one known compound, beesioside I (2), were isolated from the ethanolic extract of the rhizomes of Souliea vaginata. Their structures were determined spectroscopically and compared with previously reported spectral data. Compounds 1 and 2 were evaluated for their cytotoxic activities against three human cancer cell lines.
- Wu, Hai-Feng,Zhang, Gang,Wu, Mei-Chun,Yang, Wen-Ting,Ma, Guo-Xu,Chen, Di-Zhao,Xu, Xu-Dong,Zou, Qiong-Yu,Hu, Wei-Cheng
-
-
Read Online
- Three new cycloart-7-ene triterpenoid glycosides from Cimicifuga dahurica and their anti-inflammatory effects
-
Ten cycloart-7-ene triterpenoid glycosides, including three new compounds (1–3), were isolated from the roots of Cimicifuga dahurica. Their structures were elucidated on the basis of extensive spectroscopic analyses, chemical methods and comparison with literatures. In addition, the isolates were evaluated for their inhibitory effects on the production of NO, as well as the expressions of iNOS and COX-2 in LPS-stimulated RAW 264.7 macrophages. The results showed that compounds 3, 5, 6, 7 and 8 can reduce the release of NO in a dose-dependent manner. Mechanistically, Western blot analysis indicated that the NO inhibitory effects relied on down-regulating the expression of iNOS, and partially associated with lowering the expression of COX-2.
- Pang, Qian-Qian,Mei, Yu-Dan,Zhang, Yuan-Chu,Liu, Ling-Xian,Shi, Dan-Feng,Pan, Da-Bo,Yao, Xin-Sheng,Li, Hai-Bo,Yu, Yang
-
-
Read Online
- One new and seven known triterpene glycosides from the aerial parts of Cimicifuga dahurica
-
One new triterpene glycoside, asiaticoside I (1), along with seven known ones (2–8), were isolated from the aerial parts of Cimicifuga dahurica (Turcz.) Maxim. The structure of 1 was elucidated on the basis of extensive spectroscopic methods including 1D-NMR, 2D-NMR and MS data. The structures of known compounds were determined by comparison with the literature data. Compound 1 exhibited moderate cell growth inhibitory activities in vitro against HELF, non-small cell lung cancer A549, and pancreatic cancer PANC-1 cell lines, with IC50 values of 62.97, 43.19, and 60.40 μM, respectively.
- Hao, Yi-Meng,Luo, Wen,Jiang, Guan-Ze,Lv, Chong-Ning,Lu, Jin-Cai
-
-
Read Online
- Metabolic response of tomato leaves upon different plant-pathogen interactions
-
Introduction - Plants utilise vaious defence mechanisms against their potential biotic stressing agents such as viroids, viruses, bacteria or fungi and abiotic environmental challenges. Among them metabolic alteration is a common response in both compatible and incompatible plant-pathogen interactions. However, the identification of metabolic changes associated with defence response is not an easy task due to the complexity of the metabolome and the plant response. To address the problem of metabolic complexity, a metabolomics approach was employed in this study. Objective - To identify a wide range of pathogen (citrus exocortis viroid, CEVd, or Pseudomonas syringae pv. tomato)-induced metabolites of tomato using metabolomics. Methodology - Nuclear magnetic resonance (NMR) spectroscopy in combination with multivariate data analysis were performed to analyse the metabolic changes implicated in plant-pathogen interaction. Results - NMR-based metabolomics of crude extracts allowed the identification of different metabolites implicated in the systemic (viroid) and hypersensitive response (bacteria) in plant-pathogen interactions. While glycosylated gentisic acid was the most important induced metabolite in the viroid infection, phenylpropanoids and a flavonoid (rutin) were found to be associated with bacterial infection. Conclusions - NMR metabolomics is a potent platform to analyse the compounds involved in different plant infections. A broad response to different pathogenic infections was revealed at metabolomic levels in the plant. Also, metabolic specificity against each pathogen was observed. Copyright
- Lopez-Gresa, M. Pilar,Maltese, Federica,Belles, Jose Maria,Conejero, Vicente,Kim, Hye Kyong,Choi, Young Hae,Verpoorte, Robert
-
-
Read Online
- Hydrothermal production of furfural from xylose and xylan as model compounds for hemicelluloses
-
The uncatalyzed microwave-assisted hydrothermal conversion of xylose and xylan as hemicellulose model compounds to furfural at temperatures of 160-240 °C and reaction times of 5-240 min is investigated. With acceptable reaction rates at 200 °C the conversion of xylose provides furfural with a maximum yield of 49%. The conversion of xylan, however, requires lower temperatures (160-180 °C) in order to promote the hydrolysis of the polymer, yielding xylose as a furfural precursor. The Royal Society of Chemistry 2013.
- Moeller, Maria,Schroeder, Uwe
-
-
Read Online
- New phenolic compounds from Dendrobium capillipes and Dendrobium secundum
-
Phytochemical investigation of the stem of Dendrobium capillipes resulted in the isolation of a new flavonol glycoside namely quercetin-3-O-α-l- rhamnopyranosyl-(1 → 2)-β-d-xylopyranoside, along with seven known phenolic compounds which included two flavonol glycosides and five bibenzyls. From the stem of Dendrobium secundum, a new compound named 5-hydroxy-3,4,3,4,5- pentamethoxybibenzyl was characterized, together with two known bibenzyls and three glycosidic flavonoids. Some of the isolated bibenzyls showed cytotoxicity against KB, NCI-H187, and MCF-7 cancer cells, whereas all of the glycosidic flavonoids were devoid of activity.
- Phechrmeekha, Thanawuth,Sritularak, Boonchoo,Likhitwitayawuid, Kittisak
-
-
Read Online
- Evasteriosides A and B and other sulfated steroids from the Pacific starfish Evasterias retifera
-
Two new polar steroidal glycosides identified as sodium (20R,22E,24R,25S)-3-O-(β-d-xylopyranosyl)-24-methyl-5α-cholest-22- ene-3β,6β,8,15α,26-pentol 26-sulfate (evasterioside A) and sodium (20R,22E)-24-O-(β-d-xylopyranosyl)-5α-cholest-22-ene-3β, 6β,8,15α,24-pentol 3-sulfate (evasterioside B) were isolated from the Pacific starfish Evasterias retifera collected in the Sea of Japan. Five known compounds, viz., coscinasterioside B, aphelasterioside A, marthasterone 3-sulfate and (20R)-cholest-7-en-3β-ol and cholesterol sulfates, were identified. The structures of the new natural compounds were established using their 2D NMR and mass spectra and some chemical transformations.
- Levina,Kalinovskii,Andriyashchenko,Dmitrenok
-
-
Read Online
- Preparation and investigation of highly selective solid acid catalysts with sodium lignosulfonate for hydrolysis of hemicellulose in corncob
-
Saccharification of lignocellulose is a necessary procedure for deconstructing the complex structure for building a sugar platform that can be used for producing biofuel and high-value chemicals. In this study, a carbon-based solid acid catalyst derived f
- Li, Xun,Shu, Fengyao,He, Chao,Liu, Shuna,Leksawasdi, Noppol,Wang, Qiong,Qi, Wei,Alam, Md. Asraful,Yuan, Zhenhong,Gao, Yi
-
-
Read Online
- Soulieoside O, a new cyclolanostane triterpenoid glycoside from Souliea vaginata
-
A new cyclolanostane triterpenoid glycoside, soulieoside O (1), together with 25-O-acetylcimigenol-3-O-β-d-xylopyranoside (2) and cimigenol-3-O-β-d-xylopyranoside (3), was isolated from the rhizomes of Souliea vaginata. Their structures were characterized by spectroscopic analysis and chemical methods. The new compound showed moderate inhibitory activity against three human cancer cell lines with IC50 values of 9.3–22.5?μM.
- Wu, Hai-Feng,Li, Peng-Fei,Zhu, Yin-Di,Zhang, Xiao-Po,Ma, Guo-Xu,Xu, Xu-Dong,Liu, Yi-Lin,Luo, Zheng-Hong,Chen, Di-Zhao,Zou, Qiong-Yu,Zhao, Zi-Jian
-
-
Read Online
- A β-xylosidase from cell wall of maize: Purification, properties and its use in hydrolysis of plant cell wall
-
To study the potential of plant glycoside hydrolase for hemicelluloses hydrolysis, a β-xylosidase with molecular weight of 68.5kDa was purified from the maize during senescent stage. The optimal conditions for the β-xylosidase were 37°C and pH 4.5. In absence of substrate, the β-xylosidase was comparatively stable at 37°C and pH 4.5-5.5. At the optimum condition, the Km and kcat values of the β-xylosidase against p-nitrophenyl-xyloside were 2.5mM and 6.5s-1, respectively. The enzyme activity was promoted by LiCl, CaCl2, MnCl2, MgCl2, KCl, and NaCl, however severely inhibited by CuCl2, ZnCl2, AgNO3, HgCl2, and NiCl2. The purified β-xylosidase was active against xylobiose, xylotriose, xylotetraose, and xylopentaose. In hydrolysis of corn stover hemicellulose, the xylose production increased by 94.9% and 140% when Trichoderma reesei hemicellulase supplemented with purified β-xylosidase and crude cell wall proteins of corn stover, respectively. The biochemical characterization of the maize β-xylosidase makes it a promising candidate enzyme additive for hemicelluloses hydrolysis.
- Han, Yejun,Chen, Hongzhang
-
-
Read Online
- Triterpenoids and Flavonoids from the Leaves of Astragalus membranaceus and Their Inhibitory Effects on Nitric Oxide Production
-
Four new cycloartane triterpenes, named huangqiyegenins V and VI and huangqiyenins K and L (1-4, resp.), together with nine known triterpenoids, 5-13, and eight flavonoids, 14-21, were isolated from a 70%-EtOH extract of Astragalus membranaceus leaves. The structures of the new compounds were elucidated by detailed spectroscopic analyses, and the compounds were identified as (9β,11α,16β,20R,24S)-11,16,25-trihydroxy-20,24-epoxy-9,19-cyclolanostane-3,6-dione (1), (9β,16β,24S)-16,24,25-trihydroxy-9,19-cyclolanostane-3,6-dione (2), (3β,6α,9β,16β,20R,24R)-16,25-dihydroxy-3-(β-D-xylopyranosyloxy)-20,24-epoxy-9,19-cyclolanostan-6-yl acetate (3), and (3β,6α,9β,16β,24E)-26-(β-D-glucopyranosyloxy)-16-hydroxy-3-(β-D-xylopyranosyloxy)-9,19-cyclolanost-24-en-6-yl acetate (4). All isolated compounds were evaluated for their inhibitory activities against LPS-induced NO production in RAW264.7 macrophage cells. Compounds 1-3, 14, 15, and 18 exhibited strong inhibition on LPS-induced NO release by macrophages with IC50 values of 14.4-27.1μM.
- Wang, Zhi-Bin,Zhai, Ya-Dong,Ma, Zhen-Ping,Yang, Chun-Juan,Pan, Rong,Yu, Jia-Li,Wang, Qiu-Hong,Yang, Bing-You,Kuang, Hai-Xue
-
-
Read Online
- A new triterpene and phenolic compounds from the roots of Pteroxygonum giraldii
-
A chemical investigation of the roots of Pteroxygonum giraldii led to the isolation of a new arborane-type triterpene, pteroxygonumnol A (1), a new myricetin glycoside, myricetin 3-O-β-D-galactopyranoside 3′-O-β-D-xylopyranoside (2), and a group of phenolic lipids, 3-6, along with four known phenolic compounds, (-)-epigallocatechin, (-)-epigallocatechin gallate, gallic acid, and 2-(4-hydroxyphenyl)acetic acid. Their structures were elucidated on the basis of extensive spectroscopic analyses. Copyright
- Chai, Xin,Su, Yan-Fang,Zhang, Jun,Yan, Shi-Lun,Gao, Yan-Hong,Gao, Xiu-Mei
-
-
Read Online
- Neolignans and flavonoids from the root bark of Illicium henryi
-
Two new neolignans (1 and 2) were isolated from the root bark of Illicium henryi, along with four known neolignans and seven known flavonoids (3-13). Their structures were elucidated on the basis of spectroscopic and chemical methods. The absolute configurations of compounds 1 and 2 were determined by the CD spectrum.
- Xiang, Wen-Juan,Ma, Lei,Hu, Li-Hong
-
-
Read Online
- Cimicifugadine from Cimicifuga foetida, a new class of triterpene alklaoids with novel reactivity
-
An unprecedented triterpene alkaloid glycoside, designated cimicifugadine (1), with a pyridine ring incorporated to a cycloartane triterpenoid nucleus, was isolated from the roots of Cimicifuga foetida. Its structure was established on the basis of extensive spectroscopic measurements and chemical transformation with the absolute configuration at C-24 determined to be S by a modified Mosher method. It demonstrated a novel reactivity in mild acidic media whereby the cyclopropane ring is opened followed by the formation of two isomeric conjugated trienes.
- Dan, Chun,Zhou, Van,Ye, Deng,Peng, Shulin,Ding, Lisheng,Gross, Michael L.,Qiu, Samuel X.
-
-
Read Online
- New flavonoids from punica granatum flowers
-
Two new flavonoids were isolated from the flowers of Punica granatum Linn. (Punicaceae) along with the known compounds ellagic acid, gallic acid, sucrose, and gallic acid glycoside. The structures of the new flavonoids have been characterized as 5,6,7,8,2
- Bagri, Priyanka,Ali,Sultana, Shahnaz,Aeri, Vidhu
-
-
Read Online
- A New Diarylheptanoid from the Twigs of Quercus Acutissima and their Neuroprotective Activity
-
A new diarylheptanoid glycoside, acutissioside A (4), along with five known diarylheptanoids (1–3, 5, 6) was isolated from the twigs of Quercus acutissima Carruth. The structure of the new compound was determined via spectral analysis, including NMR spectra (1H and 13C NMR, 1H–1H COSY, HSQC, HMBC) and HR-ESI-MS, acid hydrolysis, and specific optical rotation data. The neuroprotective effect of all the diarylheptanoid compounds (1–6) was evaluated. Compound 1 exhibited NGF secretion to 154.60 ± 2.87%, which was stronger than that of the positive control 6-shogaol (140.45 ± 2.18%).
- Cha, Joon Min,Subedi, Lalita,Khan, Zahra,Kim, Sun Yeou,Lee, Kang Ro
-
-
Read Online
- Two novel lignans from Gaultheria yunnanensis
-
Two new lignans, 9-salicyl-(+)-isolariciresinol (1) and gaultheroside G (2), together with seven known compounds, were isolated from the ethanolic extract of the whole plant of Gaultheria yunnanensis. Their structures were determined by extensive NMR and MS analyses. Gaultheroside G (2) was found to have an unusual ether linkage between the 2 and 9′ positions of aryl-tetralin lignan skeleton. All nine compounds were assayed for inhibitory effects against nitric oxide and pro-inflammatory cytokines TNF- and IL-6 release in LPS-induced RAW 246.7 macrophages, while no significant activities were observed for the evaluated compounds. 2014
- Gao, Yan-Ping,Shen, Yun-Heng,Xu, Xi-Ke,Tian, Jun-Mian,Zeng, Hua-Wu,Lin, Sheng,Liu, Chun-Mei,Zhang, Wei-Dong
-
-
Read Online
- Lignan glucosides from sinomenium acutum rhizomes
-
The new lignan glucoside, acutumoside (1), was isolated from Sinomenium acutum rhizomes together with nine known compounds (2-10). The structure of 1 was elucidated on the basis of extensive spectroscopic analyses, including two-dimensional nuclear magnet
- Kim, Ki Hyun,Moon, Sae Rom,Kim, Chung Sub,Woo, Kyeong Wan,Choi, Sang Un,Lee, Kang Ro
-
-
Read Online
- Cycloartane-type triterpenes from the leaves of Homonoia riparia with VEGF-induced angiogenesis inhibitory activity
-
Six new cycloartane-type triterpenes (1-6), 24-methylenecycloartane- 3β,6β,7β-triol (1), 24-methylenecycloartane-3β,6β, 7β,16β-tetraol (2), 24-methylenecycloartane-3β,6β,16β- triol (3), 24-methylenecycloartane-3β,7β,16β-triol 3-O-β-d-xylopyranoside (4), 2
- Lee, Iksoo,Kim, Junghyun,Kim, Young Sook,Yoo, Nam Hee,Kim, Chan-Sik,Jo, Kyuhyung,Kim, Joo-Hwan,Bach, Tran The,Kim, Jin Sook
-
-
Read Online
- A new diarylheptanoid and a new diarylheptanoid glycoside isolated from the roots of Juglans mandshurica and their anti-inflammatory activities
-
A new diarylheptanoid, (2S,3S,5S)-2,3,5-trihydroxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane (1), and a new diarylheptanoid glycoside, (2S,3S,5S)-2,3-dihydroxy-5-O-β-d-xylopyranosyl-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane (2), together with three known compounds, rhoiptelol C (3), rhoiptelol B (4) and 3′,4″-epoxy-2-O-β-d-glucopyanosyl-1-(4-hydroxyphenyl)- 7-(3-methoxyphenyl)heptan-3-one (5) were isolated from the roots of Juglans mandshurica (Juglandaceae). The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Compounds 1–5 were assayed for their inhibitory effects on the production of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells.
- Diao, Shengbao,Jin, Mei,Sun, Jinfeng,Zhou, Yi,Ye, Chao,Jin, Yong,Zhou, Wei,Li, Gao
-
-
Read Online
- Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions
-
Sargassum fusiforme polysaccharides (SFPs), including SFP-3-40, SFP-3-60, SFP-3-80, SFP-7-40, SFP-7-60, SFP-7-80, SFP-10-40, SFP-10-60, and SFP-10-80, were extracted at different pH (3, 7, and 10), and then precipitated with graded precipitation of 40%, 60% and 80% (v/v) ethanol solution, respectively. Their physicochemical properties and α-glucosidase inhibitory activity were determined. Results showed that SFPs significantly differed in the contents of total sugar, protein, uronic acid, sulfate, the zeta potential, and molecular weight distribution. SFPs, including SFP-10-40, SFP-10-60, and SFP-10-80, had bigger absolute zeta potential value and higher respective average molecular weight in the same ethanol concentration precipitate. All samples were mainly composed of fucose, glucuronic acid, and mannose with different molar ratios. The extraction pH and precipitation ethanol solution concentration caused little changes in functional groups, but significantly altered surface morphology of SFPs. Congo red test revealed that all polysaccharides were not helical polysaccharides. Rheological measurements indicated that SFPs were pseudoplastic fluids and showed elastic behavior of the gel. Except SFP-3-40 and SFP-3-60, all other samples had a stronger α-glucosidase inhibitory activity than that of acarbose. The inhibition type of SFPs against α-glucosidase varied owing to different extraction pH and precipitation ethyl concentration. This study shows that extraction pH can significantly affect the structure and hypoglycemic activity of SFPs and provide a data support for the scientific use of Sargassum fusiforme in industrial production.
- Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen
-
p. 602 - 610
(2021/11/30)
-
- Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells
-
The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of s
- Fukaya, Haruhiko,Kuroda, Minpei,Matsuo, Yukiko,Mimaki, Yoshihiro,Takatori, Kazuhiro,Tsuchihashi, Hiroko
-
-
- Triterpene glycosides and phenylpropane derivatives from Staurogyne concinnula possessing anti-angiogenic activity
-
After anti-angiogenic activity screening, the potential n-butanol layer partitioned from the ethanol extract of Staurogyne concinnula was conducted. Further purification by Diaion HP20 column and preparative HPLC chromatography, four undescribed triterpen
- Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Pan, Wen-Pin,Cheng, Jing-Jy,Lee, Ching-Kuo,Kuo, Yao-Haur
-
-
- New triterpene glycosides from the far eastern starfish solaster pacificus and their biological activity
-
Three new triterpene glycosides, pacificusosides A–C (1–3), and three previously known triterpene glycosides, cucumariosides C1 (4), C2 (5), and A10 (6), were isolated from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The structures of 1–3 were elucidated by extensive NMR and ESIMS techniques and chemical transformations. Compound 1 has a novel, unique structure, containing an aldehyde group of side chains in its triterpene aglycon. This structural fragment has not previously been found in the sea cucumber triterpene glycosides or starfish steroidal glycosides. Probably, pacificusoside A (1) is a product of the metabolism of the glycoside obtained through dietary means from a sea cucumber in the starfish. Another two new triterpene glycosides (2, 3) have closely related characteristics to sea cucumber glycosides. The cytotoxicity of compounds 1–6 was tested against human embryonic kidney HEK 293 cells, colorectal carcinoma HT-29 cells, melanoma RPMI-7951 cells, and breast cancer MDA-MB-231 cells using MTS assay. Compounds 4–6 revealed the highest cytotoxic activity against the tested cell lines, while the other investigated compounds had moderate or slight cytotoxicity. The cytotoxic effects of 2–6 were reduced by cholesterol like the similar effects of the previously investigated individual triterpene glycosides. Compounds 3, 4, and 5 almost completely suppressed the colony formation of the HT-29, RPMI-7951, and MDA-MB-231 cells at a nontoxic concentration of 0.5 μM.
- Malyarenko, Timofey V.,Kicha, Alla A.,Kalinovsky, Anatoly I.,Dmitrenok, Pavel S.,Malyarenko, Olesya S.,Kuzmich, Alexandra S.,Stonik, Valentin A.,Ivanchina, Natalia V.
-
-
- New dammarane-type glycosides from Gynostemma pentaphyllum and their lipid-lowering activity
-
Gynostemma pentaphyllum (Thunb.) Makino has a long history as food and diary supplement in China. At present, there are some products for hyperlipidemia in the market, including G. pentaphyllum tea, healthy wine and healthy food. In order to discover proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibitors, fourteen new triterpenoid saponins named gypenoside LXXXVIII-CI (1–14) along with six known compounds (15–20) were isolated from G. pentaphyllum. Their structures were elucidated by means of various spectroscopic techniques. Eight isolates were evaluated the inhibitory effect on PCSK9 in HepG2 cells. The results showed that three dammarane-type glycosides (2, 3, 15) remarkably reduced PCSK9 expression at 10 μM concentration. These findings suggested that G. pentaphyllum was worthy of further investigation to find small molecule PCSK9 inhibitors and facilitate their utilization as functional food ingredients.
- Weng, Xin,Lou, Yun-Yun,Wang, Yun-Shan,Huang, Ya-Ping,Zhang, Jian,Yin, Zhi-Qi,Pan, Ke
-
-
- Two new iridoid glycosides from Gardeniae Fructus
-
Two new iridoid glycosides, genipin 1,10-di-O-α-L-rhamnoside (1) and genipin 1,10-di-O-β-D-xylopyranoside (2), along with thirteen known compounds (3–15) were isolated from Gardeniae Fructus. Their structures were elucidated by physical data analyses such as NMR, UV, IR, HR-ESI-MS, as well as chemical hydrolysis. All compounds were tested for their tyrosinase inhibitory and antioxidant activities. At a concentration of 25 μM, compound 13 showed obvious mushroom tyrosinase inhibition activity with % inhibition value of 36.52 ± 1.98%, with kojic acid used as the positive control (46.09 ± 1.29%). At a concentration of 1 mM, compounds 8 and 9 exhibited considerable DPPH radical scavenging activities, with radical scavenging rates of 48.54 ± 0.47%, 58.59 ± 0.39%, respectively, with L-ascorbic acid used as the positive control (59.02 ± 0.77%).
- Shu, Penghua,Yu, Mengzhu,Zhu, Huiqing,Luo, Yuehui,Li, Yamin,Li, Nianci,Zhang, Hui,Zhang, Jialong,Liu, Guangwei,Wei, Xialan,Yi, Wenhan
-
-
- New Phenylpropanoid Glycosides from Illicium majus and Their Radical Scavenging Activities
-
Chemical investigation of the ethanol extract of the branch and leaves of Illicium majus resulted in the isolation of four new phenylpropanoid glycosides (1–4) and one new phenolic glycoside (9), along with 13 known ones. Spectroscopic techniques were use
- Li, Fang,Yan, Ting-Ting,Fu, Ying-Ying,Zhang, Nen-Ling,Wang, Lei,Zhang, Yan-Bing,Du, Juan,Liu, Ji-Feng
-
-
- A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities
-
Our continuing search for marine bioactive secondary metabolites led to the screening of crude extracts of sea cucumbers by the model of Pyricularia oryzae. A new sulfated triterpene glycoside, coloquadranoside A (1), together with four known triterpene glycosides, philinopside A, B, E and pentactaside B (2–5) were isolated from the sea cucumber Colochirus quadrangularis, and their structures were elucidated using extensive spectroscope analysis (ESI-MS, 1D and 2D NMR) and chemical methods. Coloquadranoside A possesses a 16-acetyloxy group in the holostane-type triterpene aglycone with a 7(8)–double bond, a double bond (25,26) at its side chain, and two β-D-xylose in the carbohydrate chain. Coloquadranoside A exhibits in vitro some antifungus, considerable cytotoxicity (IC50 of 0.46–2.03 μM) against eight human tumor cell lines, in vivo antitumor, and immunomodulatory activity.
- Han, Hua,Qi, Xin-Rui,Shen, Li,Tang, Hai-Feng,Xu, Qiang-Zhi,Yang, Wen-Sheng,Yi, Yang-Hua,Yuan, Chun-Hong
-
-
- Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn
-
In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides A─C (1─3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (1), 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (2), and 3-O-{α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-[α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.
- Le Doux Kamto, Eutrophe,Noté, Olivier Placide,Kinyok, Mc Jesus,Wilhelm, Anke,Mbing, Joséphine Ngo,Antheaume, Cyril,de Théodore Atchadé, Alex,Pegnyemb, Dieudonné Emmanuel,Ndinteh, Derek Tantoh,Haddad, Mohamed,Bonnet, Susan L.
-
-
- Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens
-
Arylnaphthalene lignans (ANLs) were known to have axial chirality due to the biphenyl skeleton with hindered rotation at the single bond. However, the stable ANL atropisomers have not been isolated from nature until the present study. Phytochemical separation of the methanol extract of the stems and barks of Justicia procumbens led to the isolation of 11 ANL glycosides including four pairs of new atropisomers with stable confirmations at room temperature. Their structures were deduced from elucidation of the extensive spectral data, and their absolute configurations were determined by the circular dichroism, electronic circular dichroism, and X-ray methods as well as the total synthesis of one pair of the atropisomers. The ANL compounds were evaluated for their antiviral potential, and it was found that they displayed great antiviral activity discrepancy between a pair of atropisomers due to the geometric orientation. The 1′P-oriented atropisomers showed much more significant antiviral potency than their corresponding 1′M-oriented counterparts. The biological activity discrepancy caused by the axial chirality will not only inspire synthetic design of novel ANL atropisomers to enrich the structural diversity, but also provide important hints to direct the synthetic approaches toward the antiviral drug development of ANL compounds.
- Zhao, Yang,Ku, Chuen-Fai,Xu, Xin-Ya,Tsang, Nga-Yi,Zhu, Yu,Zhao, Chen-Liang,Liu, Kang-Lun,Li, Chuang-Chuang,Rong, Lijun,Zhang, Hong-Jie
-
p. 5568 - 5583
(2021/05/07)
-
- Neuroprotective and anti-inflammatory phenylethanoid glycosides from the fruits of Forsythia suspensa
-
Neuroinflammation is emerging as a crucial reason of major neurodegenerative diseases in recent years. Increasingly evidences have supported that bioactive natural products from traditional Chinese medicines have efficiency for neuroinflammation. Forsythia suspensa, a typical medicinal herb, showed potential neuroprotective and anti-inflammatory properties in previous pharmacological studies. In our research to obtain neuroprotective and anti-inflammatory natural products, three unprecedented C6–C7′/C6–C16′ linked phenylethanoid glycoside dimers (1–3), three new phenylethanoid glycosides (4–6), and six known compounds (7–12) were isolated from the fruits of Forsythia suspensa. Their structures were determined by comprehensive spectroscopic data and comparison to the literature data. All isolated compounds were evaluated their neuroprotective and anti-inflammatory activities. Compounds 1 and 10 exhibited significant neuroprotective activities with the cell viability values of 75.24 ± 8.05% and 93.65 ± 10.17%, respectively, for the serum-deprivation and rotenone induced pheochromocytoma (PC12) cell injury. Meanwhile, compound 1 exhibited excellent anti-inflammatory activity against tumor necrosis factor (TNF)-α expression in LPS induced RAW264.7 cells with the IC50 value of 1.30 μM. This study revealed that the bioactive phenylethanoid glycosides may attenuate neuroinflammation through their neuroprotective and anti-inflammatory activities.
- Feng, Zi-Meng,Jiang, Jian-Shuang,Shao, Si-Yuan,Yang, Ya-Nan,Zhang, Fan,Zhang, Pei-Cheng
-
-
- Isolation, identification, and quantification of triterpene saponins in the fresh fruits of Panax notoginseng
-
This study is to develop a method for isolation, identification, and quantitative determination of dammarane-type triterpene saponins in the Panax notoginseng fruits (PNF). The saponins were isolated by a serious of chromatographic methods, and their structures were elucidated on the basis of spectroscopic evidence and comparison with those of literature reports. Quantitative assay was performed on an ultra-performance liquid chromatography-UV (UPLC-UV) method. As a result, 22 saponins were isolated from the extract of PNF, among them, compound 1 was a new saponin, named as malonylgypenoside IX, compounds 3–10, and 14–18 were isolated from the PNF for the first time. As to quantitative analysis, the calibration curves showed good linearity (r > 0.998) within the concentration range, and the method validation provided good reproducibility and sensitivity for the quantification of eight major saponins with precision and accuracy of less than 3.0%.
- Jin, Yin-ping,Li, Ya-li,Qu, Zheng-yi,Wang, He-cheng,Wang, Ying-ping
-
-
- Cytotoxic triterpenoid saponins from Thalictrum atriplex
-
Two new cycloartane glycosides, cycloatriosides A and B (1–2), and a new oleanolic acid glycoside, thaliatrioside A (3), along with 7 known triterpenoids (4–10) were isolated from Thalictrum atriplex. The structures of the new compounds were established as 3-O-β-D-galactopyranosyl (20S, 24 R)-3β,16β,25,29-tetrahydroxy-20,24-epoxycycloartane-29-O-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl-(1→2)-α-arabinopyranosyl-3β,22ξ,30-trihydroxycycloart-24-en-21-oic acid α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (2) and 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-oleanolic acid 28-O-β-D-glucopyranosyl ester (3) on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis. Their cytotoxic activities against human lung cancer cells A549 and human breast cancer cells MDA-MB-231 were evaluated using MTT method. Compound 9 showed cytotoxicity against MDA-MB-231 cell line with the IC50 value of 72.53 ± 1.08 μM.
- Meng, FanCheng,Wei, XiaoDong,Sun, Yan,Zeng, QingHong,Wang, Guowei,Lan, XiaoZhong,Liao, ZhiHua,Chen, Min
-
p. 5757 - 5764
(2020/10/20)
-
- A new isoflavone glycoside from flowers of Pueraria Montana var. lobata (Willd.) Sanjappa & Pradeep
-
A new isoflavone glycoside, named 3’-hydroxytectorigenin-7-O-β-D-xylosyl-(1→6)-β-D-glucopyranoside (1) was isolated from the flowers of Pueraria montana var. lobata (Willd.) Sanjappa & Pradeep. The structure of compound 1 was characterised by HR-ESI-MS and NMR spectroscopic methods. In radical scavenging activity test using 2, 2-diphenyl-1-picrylhydrazyl (DPPH), compound 1 showed moderate activity with IC50 value of 42 ± 4.2 μg/mL.
- Ma, Yilong,Shang, Yafang,Zhong, Zhifeng,Zhang, Yingshuo,Yang, Yang,Feng, Jun,Wei, Zhaojun
-
p. 1459 - 1464
(2019/08/26)
-
- Two new 3-hexenol glycosides from the calyces of Physalis alkekengi var. franchetii
-
Two new hexenol glycosides, (Z)-hex-3-en-1-ol O-β-d-xylcopyranosyl-(1-6)-β -d-glucopyranosyl-(1-2)-β-d-glucopyranoside (1) and (E)-hex-3-en-1-ol O-β-d-xylcopyranosyl-(1-6)-β-d-glucopyranosyl-(1-2)-β-d-glucopyranoside (2), were isolated from the 50% ethanol elution of macroporous resin of Physalis alkekengi var. franchetii. Their structures were established by detailed spectroscopic analysis, including extensive 2D-NMR data. This is the first time to report the (Z) and (E) 3-hexenol glycosides from Physalis alkekengi var. franchetii.
- Shu, Zunpeng,Tang, Yun,Yang, Yanni,Ding, Zihe,Zhong, Renxing,Xia, Tianyi,Li, Xinjia,Zheng, Cuiying,Wen, Zhixiong,Li, Wei,Wang, Yi
-
p. 1274 - 1280
(2019/08/07)
-
- Cytotoxic steroidal saponins from the roots and rhizomes of Maianthemum henryi
-
Henryiosides F and G (1 and 2), two new steroidal saponins along with two known analogues (3 and 4) were obtained from the roots and rhizomes of Maianthemum henryi. Their structures were determined by physicochemical properties and spectroscopic methods including 1D, 2D-NMR, IR and HR-ESI-MS data analysis. Cytotoxic activity in human HepG2 and SW620 tumour cells were evaluated by the MTT method and all of the saponins exhibited cytotoxicity with IC50 values ranging from 15.33 μM to 57.85 μM.
- Zhang, Xin,Sun, Jing,Zhang, Xiaofei,Zhang, Shuo,Zhang, Xuan,Xue, Xuanji,Guo, Zengjun
-
p. 1808 - 1815
(2019/08/07)
-
- Anti-inflammatory glycosides from the roots of Paeonia intermedia C. A. Meyer
-
Three new phenolic glycosides, intermedia A–C (1–3), one new acyclic alcohol glycoside, intermedia D (4), together with 3 known glycosides (5–7), were isolated from the dried roots of Paeonia intermedia C. A. Meyer. Their structures were established by means of extensive spectroscopic analysis (HRESIMS, NMR). Compound 1 have a rare benzo[1,5]dioxepine skeleton. The bioassay results showed that compound 3 exhibited inhibitory activity against proinflammatory cytokines nitric oxide (NO) secretion in LPS-activated RAW264.7 cells with an IC50 value of 85.76 ± 1.36 μM.
- Yu, Liang,Zhu, Ling-Juan,Wang, An-Hua,Qin, Yu,Zhang, Xue,Jia, Jing-Ming,Yao, Xin-Sheng
-
p. 1452 - 1458
(2019/08/30)
-
- Neuroprotective triterpene saponins from the leaves of Panax notoginseng
-
Two new triterpene saponins, namely notoginsenoside Ng5 (1) and notoginsenoside Ng6 (2) were isolated from the leaves of Panax notoginseng, along with five known ones. Their structures were determined by chemical methods, NMR and X-ray experiments. The absolute configuration of compound 3 with four sugar units was confirmed by single crystal X-ray analysis. Compounds 2–4 and 6 inhibited PC12 cell damage induced by serum deprivation, and increased cell viability from 58.7 ± 6.7% to 66.7 ± 4.5%, 76.1 ± 6.1%, 64.7 ± 5.2% and 67.2 ± 5.0% at 10 μM, respectively.
- Huang, Ji-Wu,Du, Yi-Qian,Li, Chuang-Jun,Yang, Jing-Zhi,Ma, Jie,Zang, Ying-Da,Chen, Nai-Hong,Zhang, Dong-Ming
-
supporting information
p. 2388 - 2394
(2019/11/13)
-
- Isolation and structure elucidation of a new flavonol glycoside from Sabia Parviflora
-
A new flavonol glycoside named Sabiapside A (1), along with four known compounds, quercetin-3-O-gentiobioside (2), camellianoside (3), isobariclisin-3-O- rutinoside (4), tsubakioside A (5), was isolated from Sabia parviflora. Their structures were elucidated by extensive spectroscopic analysis including MS, UV, IR and NMR data. The antioxidant activities of these glycosides evaluated by ABTS+ and DPPH radical scavenging reaction was higher than that of vitamin C used as the reference antioxidant.
- Sun, Qingwen,Pan, Guoji,Xu, Wenfen,Lu, Xian,Bai, Caihong,Liu, Mengge,Chen, Yinrui
-
p. 2408 - 2413
(2019/11/14)
-
- New lupane-type and ursane-type triterpene saponins from the leaves of Trevesia palmata
-
Three new triterpene saponins including two lupane-types and an ursane-type were isolated from the leaves of Trevesia palmata. Their structures were determined as 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-α-L-arabinopyranoside (1), 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl] ester (2), and 2α,3β,23-trihydroxyurs-12-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl] ester (3) by analysis of their HR-ESI-MS, 1D and 2D NMR spectra. The 2α,3β,23-trioxygenated pentacyclic triterpenes were uncommonly found in the nature. At concentration of 100 μM, compounds 1–3 inhibited NO production in LPS activated BV2 cells with inhibitory rates of 17.4 ± 1.8%, 33.1 ± 1.2%, and 11.7 ± 2.2%, respectively. But, they did not significantly inhibit yeast α-glucosidase activity.
- Yen, Pham Hai,Doan, Vu Van,Lien, Giang Thi Kim,Chuong, Nguyen Th? Hong,Thanh, Nguyen Thi Viet,Trang, Do Thi,Dung, Duong Thi,Nhiem, Nguyen Xuan,Tai, Bui Huu,Minh, Chau Van,Kiem, Phan Van
-
supporting information
p. 3285 - 3292
(2019/12/11)
-
- Two new dammarane-type triterpenoids from the stems and leaves of Panax notoginseng
-
Two new dammarane-type triterpenoids, notoginsenoside SY1 (1) and notoginsenoside SY2 (2), were isolated from the stems and leaves of Panax notoginseng. Their structures were elucidated to be 3β, 12β-dihydroxy-22, 23, 24, 25, 26, 27-hexanordammarane-20-on
- Yang, Chong-Kang,Xiong, Jiao,Shen, Yong
-
p. 341 - 347
(2020/03/11)
-
- Two new triterpenoid-chromone hybrids from the rhizomes of Actaea cimicifuga L. (syn. Cimicifuga foetida L.) and their cytotoxic activities
-
Two new triterpenoid-chromone hybrids, cimitriteromones H (1) and I (2), along with two known analogues (3, 4) were isolated from the phytochemical research on the n-butyl alcohol extracts of Actaea cimicifuga rhizomes. The new compounds were elucidated by spectroscopic experiments and chemical method. The cytotoxic activities of the isolated compounds were tested on A-549/Taxol cell line. Cimitriteromone I (2) showed cytotoxicity with IC50 value of 27.14 ± 1.38 μM comparable to positive control group cisplatin (IC50 value of 25.80 ± 1.15 μM).
- Shi, Qiang-Qiang,Gao, Ya,Lu, Jing,Zhou, Lin,Qiu, Ming-Hua
-
p. 193 - 199
(2020/07/03)
-
- New steroidal glycosides from the roots of Asparagus cochinchinensis
-
Steroidal saponins were the main active constituents of the traditional medicinal herb Asparagus cochinchinensis. A phytochemical investigation of A. cochinchinensis roots led to the isolation of nine new steroidal glycosides (1–9) and seven known analogues (10–16). Their structures were established by spectroscopic analyses as well as necessary chemical evidence.
- Pang, Xu,Gao, Lin,Wang, Bei,Chen, Xiao-Juan,Zhang, Jie,Guo, Bao-Lin,Ma, Bai-Ping
-
p. 205 - 216
(2021/02/03)
-
- Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities
-
Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A?C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A?C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16β-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16β-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A?C, (22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol3-O-β-D-xylopyranosyl-(1→3)-β-D-glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC50 = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC50 value of 37.32 ± 0.793 μM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.
- Kaunda, Joseph Sakah,Qin, Xu-Jie,Zhu, Hong-Tao,Wang, Dong,Yang, Chong-Ren,Zhang, Ying-Jun
-
-
- Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk
-
In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosi
- Moffi Biang, Armand Emmanuel,Messi, Lin Marcellin,Le Doux Kamto, Eutrophe,Simo, Line Made,Lavedan, Pierre,Vedrenne, Marc,Mbing, Josephine Ngo,Pegnyemb, Dieudonné Emmanuel,Haddad, Mohamed,Noté, Olivier Placide
-
-
- Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities
-
Three undescribed oleanane type triterpenoid saponins (1–3), along with one known saponin (4) were isolated from the whole herb of Hylomecon japonica. Their structures were elucidated by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HR-ESI-MS) and chromatographic date (GC and LC) as 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl ester (3), 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl ester (4). All saponins possess a partial sequence β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl at C-3 of the aglycon. Compound 1 has cytotoxic activity against human colon cancer cell lines HT29, 3 against human gastric cancer cell lines AGS, and 4 against human lung cancer cell lines A549, AGS and HT29. Among them, compounds 3 and 4 showed significant inhibitory effect against AGS with IC50 value of 6.01 ± 1.4 μM, 3.66 ± 1.8 μM, respectively. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon japonica and their bioactivities.
- Li, Fei,Wu, Si-Tong,Qu, Ming-Hui,Wang, Yi-Xiao,Ma, Chun-Liu,Yu, Bai-Hong,Wang, Guang-Shu
-
-
- New dammarane-type triterpenoid saponins from Gynostemma pentaphyllum and their Sirt1 agonist activity
-
Gynostemma pentaphyllum (Thunb.) Makino (Cucurbitaceae family) is a perennial creeping plant with a common Chinese name of “south ginseng”. To date, more than 250 individual saponins with dammarane-type skeleton have been isolated from G. pentaphyllum. The purpose of this study was the isolation and structural characterization of novel, minor gypenosides from G. pentaphyllum and evaluation of their Sirt1 agonist activity. Individual saponins from G. pentaphyllum were isolated and purified by a variety of chromatography techniques, and their structures were elucidated by means of various spectroscopic analysis and comparision with the reported data. Sirt1 enzyme activity detection kit was used to preliminarily evaluate the Sirt1 agonist activity of thirty three individual saponins purified from G. pentaphyllum. Fourteen new triterpenoid saponins named gypenoside CII-CXV (1–14) along with twenty six known compounds (15–40) were isolated from G. pentaphyllum. Thirty three of all the isolates were screened for Sirt1 agonist activity, and the results showed that three dammarane-type saponins (2, 18, 37) and one cucurbitane-type saponin 33 exhibited satisfactory Sirt1 agonist activity. These findings suggested that G. pentaphyllum was worthy of further investigation to find small molecule Sirt1 agonist and facilitate their utilization as “south ginseng”.
- Lou, Yun-Yun,Zheng, Xian,Huang, Ya-Ping,Mu, Long,Zhang, Xiao-Gai,Zhao, Zhi-Wei,Song, Zhe,Zhang, Jian,Yin, Zhi-Qi,Pan, Ke
-
-
- Cytotoxic steroidal glycosides from Polygonatum odoratum (Mill.) Druce
-
Twenty-five steroidal glycosides including eight undescribed compounds which were named as polygonatumosides H–O, were isolated from the 70 % EtOH extract of rhizomes of Polygonatum odoratum (Mill.) Druce (Asparagaceae). Their structures were elucidated b
- Chen, Gang,Feng, Yuan,Koike, Kazuo,Li, Ning,Li, Wei,Liu, Bo,Liu, Xin,Sun, Lu,Zhou, Di
-
-
- Triterpenoid saponins from the leaves and stems of Pericampylus glaucus and their insulin mimetic activities
-
During an attempt to discover insulin mimetics, thirteen new triterpenoid saponins (1–13), including three phytolaccagenic acids (1, 2, and 12) and ten serjanic acids (3–11 and 13), as aglycones were isolated from a 70% ethanol extract of leaves and stems from Pericampylus glaucus. The chemical structures of compounds 1–13 were determined through spectroscopic data analysis, including NMR, IR, and HRESIMS. All isolated compounds (1–13) were evaluated using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) as a fluorescent-tagged glucose probe to determine their stimulatory effects on glucose uptake in differentiated 3 T3-L1 adipocyte cells. Consequently, four compounds (4, 7, 11, and 12) exhibited stimulatory effects on glucose uptake.
- Lee, Hee-Ju,Cho, Hyo-Moon,Park, Eun-Jin,Lee, Ba-Wool,Nghiem, Duc-Trong,Pham, Ha-Thanh-Tung,Pan, Cheol-Ho,Oh, Won-Keun
-
-
- Four New Triterpenoid Saponins from the Root of Ilex centrochinensis
-
One new siaresinolic acid saponin (1) and three new rotundic acid saponins (2–4) were isolated from the roots of Ilex centrochinensis. Their structures were confirmed by detailed analysis of standard spectroscopic data (IR, MS, 1D and 2D NMR). Compounds 1–4 exhibited anti-inflammatory activity by inhibiting nitric oxide production in a lipopolysaccharide-induced RAW264.7 cell inflammatory model. However, they showed no significant lipid-lowering activity against the production of triglycerides in the lipid-accumulation model of HepG2 cells induced by oleic acid.
- Deng, Xue-Ying,Hu, Ze-Hua,Li, Lu-Jun,Lu, Yan-Xia,Shi, Yu,Yang, Hang,Yi, Ying-Tao
-
-
- Cloning and characterization of the β-xylosidase from Dictyoglomus turgidum for high efficient biotransformation of 10-deacetyl-7-xylosltaxol
-
With the aim of finding an extracellular biocatalyst that can efficiently remove the C-7 xylose group from 10-deacetyl-7-xylosltaxol, a Dictyoglomus turgidum β-xylosidase was cloned and expressed in Escherichia coli BL21 (DE3). The molecular mass of purified Dt-Xyl3 was approximately 84 kDa. The recombinant Dt-Xyl3 was most active at pH 5.0 and 75 °C, retaining 88% activity at 65 °C for 1 h, and displaying excellent stability over pH 4.0–7.5 for 24 h. In terms of kinetic parameters, the Km and Vmax values for pNPX were 0.8316 mM and 5.0178 μmol/mL·min, respectively. Moreover, Dt-Xyl3 was activated by Mn2+ and Ba2+ and inhibited by Cu2+, Ni+ and Al3+. In particular, it displayed high tolerance to salts with 60.8% activity in 20% (w/v) NaCl. Ethanol and methanol at 5–15% showed little effect on the enzymatic activity. Dt-Xyl3 demonstrated multifunctional activities followed by pNPX, pNPAraf and pNPG and had a high selectivity for cleaving the outer xylose moieties of 10-deacetyl-7-xylosltaxol with Kcat/Km 110.87 s?1/mM, which produced 10-deacetyl-taxol to semi-synthesize paclitaxel. Under the optimized conditions (60 °C, pH 4.5, enzyme dosage of 0.5 U/mL), 1 g of 10-deacetyl-7-xylosltaxol was transformed to its corresponding aglycone 10-deacetyl-taxol within 30 min, with a molar conversion of 98%. This is the first report that Dictyoglomus turgidum can produce extracellular GH3 β-xylosidase with highly specific activity for 10-deacetyl-7-xylosltaxol biotransformation, thus leading to the application of β-xylosidase Dt-Xyl3 as a biocatalyst in biopharmaceutics.
- Li, Qi,Jiang, Yujie,Tong, Xinyi,Pei, Jianjun,Xiao, Wei,Wang, Zhenzhong,Zhao, Linguo
-
-
- Novel steroidal glycosides from the whole plants of helleborus foetidus
-
Phytochemical analysis of the whole Helleborus foetidus plants identified 28 steroidal glycosides (1-28), including 20 novel spirostanol glycosides (1-20) and a novel furostanol glycoside (21). The structures of the newly identified compounds were elucidated by two-dimensional NMR spectroscopy and hydrolytic cleavage. Compounds 12, 13, and 15 were determined to be spirostanol trisdesmosides bearing sugar moieties at the C-1, -21, and -24 hydroxy groups of the aglycone unit. The isolated compounds were subsequently evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung carcinoma cells. In particular, 7 showed cytotoxic activity against the HL-60 and A549 cells, with IC50 values of 5.9 and 6.6μM, respectively, whereas 19 was selectively cytotoxic to A549 cells with an IC50 value of 5.5μM.
- Iguchi, Tomoki,Uchida, Yuka,Takano, Shingo,Yokosuka, Akihito,Mimaki, Yoshihiro
-
p. 273 - 287
(2020/11/26)
-
- New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.
-
Five new triterpenoid saponin glycosides, trichocucumerisides A-E (1-5), together with eleven known compounds (6-16) were isolated from Trichosanthes cucumerina fruit fibers. The structures of the new compounds were elucidated by detailed analysis of NMR and mass spectroscopic data as well as chemical reactions. The anti-inflammatory study against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells shows that compounds 7 and 9 exhibited stronger NO inhibitory activity, with IC50 values of 3.0 and 2.7 μM, respectively, with comparison to positive references Celecoxib and aminoguanidine (IC50 values 75.7 and 75.0 μM, respectively). Compounds 7 and 9 also possessed a greater selectivity index (SI) of approximately 3-4-fold activity than that of the positive references.
- Chulrik, Wanatsanan,Chunglok, Warangkana,Li, Jian-Xin,Suebsakwong, Parichat,Suksamrarn, Apichart,Yao, Zhu-Jun
-
p. 10461 - 10470
(2020/03/27)
-
- Novel dammarane-type saponins from Gynostemma pentaphyllum and their neuroprotective effect
-
Three novel dammarane-type saponins, 2α,3β,12β,20(S),24(S)-pentahydroxydammar-25-ene-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-β-D-glucopyranoside (1, namely gypenoside J1), 2α,3β,12β,20(S),25-pentahydroxydammar-23-ene-3-O-β-D-glucopyranosyl-(1
- Chang, Tuo,Cui, Wei-Ye,Lin, Man,Piao, Xiang-Lan,Wang, Yu-Rong,Xing, Shao-Fang
-
p. 651 - 658
(2018/10/24)
-
- Structural investigation and comparative cytotoxic activity of water-soluble polysaccharides from fruit bodies of the medicinal fungus quinine conk
-
The structures and cytotoxic activities of water-soluble polysaccharides were investigated to search for biologically active polysaccharides from the fruit bodies of quinine conks (Fomitopsis officinalis). The decoctions of this medical fungus are actively used in folk medicine in many countries and traditional Chinese medicine. From the fungal extract we prepared, only branched β-glucan had cytotoxic activity among all the water-soluble polysaccharides. This glucan is characterized by a regular structure. Its backbone is formed by 1,3-linked β-D-Glcp residues, of which every third residue is substituted at O-6 by a single β-D-Glcp residue. It has a triple helix conformation according to the data obtained from a colorimetric assay with Congo red dye and is characterized by a high-weight average molar mass (Mw > 800 kDa). β-Glucan possessed cytotoxic activity against HeLa cells (IC50 = 318 ± 47 μg/mL) and induced the formation of apoptotic bodies around most cancer cells at a concentration of 200 μg/mL. It should be noted that extraction with boiling water, which is usually used to obtain extracts and decoctions, is unable to isolate active β-glucan. Active β-glucan can be obtained in an individual state by cold alkali extraction after dehydration of the fruit bodies and removal of the components extractable by boiling water.
- Golovchenko, Victoria V.,Naranmandakh, Shinen,Ganbaatar, Jamsranjav,Prilepskii, Artur Yu.,Burygin, Gennady L.,Chizhov, Alexander O.,Shashkov, Alexander S.
-
-
- Cycloartane-type triterpenoids from the root of Astragalus membranaceus var. mongholicus
-
Three new (1–3) and 11 known (4–14) cycloartane-type triterpenoids were isolated from the root of Astragalus membranaceus var. mongholicus. Their structures were determined by spectroscopic analyses and chemical methods. Cycloartane-type triterpenoids are a class of major bioactive constituents in the root of A. membranaceus var. mongholicus, and the discovery of compounds 1–3 added new members of this kind of natural product.
- Bao, Xue-Feng,Cao, Pei-Hong,Gao, Hao,Li, Shuang,Luo, Zhi-Hui,Xiao, Luo-Min,Zhao, Sen-Sen,Zheng, Jun-Xia,Zhi, Hui,Zhou, Zheng-Qun
-
-
- New benzoic acid glycosides from Sophora flavescens
-
Two new benzoic acid derivatives, sophophenoside A (1) and sophophenoside B (2), were isolated from Sophora flavescens. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. Compounds 1 and 2 were assayed for their hepatoprotective activity on the cytotoxic effect of D-galactosamine on HL-7702 cells, and compound 1 exhibited a moderate hepatoprotective activity at a concentration of 10 μM.
- Jiang, Jian-Shuang,Shen, Yi,Feng, Zi-Ming,Yang, Ya-Nan,Zhang, Xu,Yuan, Xiang,Zhang, Pei-Cheng
-
p. 1145 - 1151
(2020/09/01)
-
- Cytotoxic steroidal glycosides from the underground parts of Hosta ventricosa
-
A phytochemical study on the underground parts of Hosta ventricosa yielded one new spirostanol saponin (1), two new furostanol saponins (2 and 3), and one new pregnane glycoside (4), along with three known compounds (5?7). Their structures were elucidated on the basis of chemical and spectroscopic analysis. All isolated compounds were evaluated for their cytotoxic effects against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480). Compounds 1, 2, and 5?7 showed cytotoxic activities with IC50 values of 3.21-17.06 μM.
- Chu, Hong-Biao,Dan, Zeng-Lamu,Gao, Yan,Li, Dan,Li, Rui,Zhang, Jia-Ping
-
-
- New 20(S)-protopanaxadiol type saponins from the leaves of Panax notoginseng and their potential anti-inflammatory activities
-
Through the combination of various chromatographies, 11 new 20(S)-protopanaxadiol (PPD) type saponins, named as notoginsenosides NL-E1 ? NL-E4 (1–4), NL-F1 (5), NL-F2 (6), NL-G1 (7), NL-G2 (8), NL-H1 ? NL-H3 (9–11) were obtained from the leaves of Panax notoginseng. Their structures were ascertained based on the extensive spectroscopic methods and chemical reactions. Meanwhile, the 20(S)-PPD type saponins with aglycone, (20S,24ζ)-3β,12β,20,24,25-pentahydroxy dammarane, was only found from the leaves of P. notoginseng. The characteristic could be used to distinguish the extracts of P. notoginseng leaves from its other medicinal parts such as roots, rhizomes, flowers or seeds. Furthermore, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As a result, compounds 2–7, 10 could exert NO inhibitory activity at 25 μM without cytotoxicity. Moreover, the inhibitory activities of them were in dose-dependent manner at 1, 10, and 25 μM. Especially, notoginsenoside NL-F2 (6) still possessed strong biological activity at 1 μM.
- Ruan, Jingya,Sun, Fan,Wang, Tao,Xiang, Guilin,Zhang, Yi,Zhang, Ying,Zhao, Wei,Zheng, Dandan
-
-
- Isolation of chemical constituents with anti-inflammatory activity from Reineckia carnea herbs
-
Three new saponins (1–3), a new natural product (4) and six other known compounds (5–10) were isolated from the whole Reineckia carnea plant. Their structures were established by comparison of their NMR spectra and MS data with literature data. In addition, all the isolated compounds were evaluated in vitro for anti-inflammatory activities against LPS-stimulated nitric oxide (NO) production in RAW 264.7 macrophages. Compounds 1–4 exhibited anti-inflammatory activities with IC50 values of 37.5 μM, 31.4 μM, 34.6 μM, and 56.1 μM, respectively. Furthermore, compounds 5–10 showed anti-inflammatory activities with IC50 values ranging from 20.3 to 42.9 μM.
- Xu, Xu,Tan, Ting,Zhang, Jing,Li, Zhi-Feng,Yang, Shi-Lin,Wen, Quan,Feng, Yu-Lin
-
p. 303 - 315
(2019/03/14)
-
- New C,O-Glycosylflavones from the Genus Silene
-
Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s
- Olennikov,Kashchenko
-
p. 1026 - 1034
(2020/11/05)
-
- Two novel non-holostane type glycosides from the viscera of sea cucumber Apostichopus japonicus
-
Two novel glycosides, apostichoposide A1 (1) and B1 (2), were isolated from the viscera of Chinese sea cucumbers (Apostichopus japonicus, Selenka) collected in the Bohai sea. Both the isolated glycosides were characterized by non-holostane type aglycones having 18(16)-lactone and 7(8)-double bond. Cytotoxic activities of the two compounds were evaluated against three human cancer cell lines. Compound 1 had adequate cytotoxic activity against MGC-803 and PC-3M cell lines. Our results indicated that glycosides present in A. japonicus viscera are an important high value resource for biotechnological applications.
- Zhang, Xuan-Ming,Han, Li-Wen,Sheng, Wen-Long,Li, Xiao-Bin,Zhang, Shan-Shan,Guo, Jing-Lan,Lin, Hou-Wen,Liu, Ke-Chun
-
p. 329 - 337
(2019/06/27)
-
- Characterization of a recombinant β-xylosidase of GH43 family from Bacteroides ovatus strain ATCC 8483
-
A novel β-1,4-xylosidase was identified from the genome of Bacteroides ovatus strain ATCC 8483 and overexpressed in Escherichia coli BL21 (DE3) cells. The molecular weight of recombinant enzyme named BoXyl43A was calculated to be 37.1 kDa. Using p-nitrophenyl-β-D-xylopyranoside (pNPβXyl) as substrate, BoXyl43A was most active at pH 7.0 and 35 °C. The enzyme could be activated by Mg2+ and Mn2+. The Km and Vmax of BoXyl43A against pNPβXyl were 1.71 ± 0.21 mM, 7.41 ± 0.81 μmol/min/mg, respectively. BoXyl43A hydrolyzed xylooligosaccharide to produce D-xylose as main product, indicating that BoXyl43A acted as an exo-β-1,4-xylosidase. The mixture of BoXyl43A and PoAbf62A (α-L-arabinofuranosidase) exhibited significant synergistic effects on the degradation of arabinoxylan. Therefore, BoXyl43A would be a useful tool to degrade hemicellulose.
- Zhou, Andong,Hu, Yanbo,Li, Jingjing,Wang, Weiyang,Zhang, Mengshan,Guan, Shuwen
-
-
- Hypoglycemic triterpenoid glycosides from Cyclocarya paliurus (Sweet Tea Tree)
-
Four new rarely occurred seco-dammarane triterpenoid glycosides (1–4) and four new dammarane triterpenoid glycosides (5–8), along with four known triterpenoids (9–12), were isolated from the 70% ethanol extract of the leaves of Cyclocarya paliurus (family Juglandaceae). Their structures were elucidated by extensive spectroscopic methods, including 1D/2D NMR and HRESIMS data, together with chemical analysis and DFT GIAO 13C NMR calculation. In bioassay, compounds 5–8 significantly increased glucose consumption in 3T3-L1 adipocytes, which could be the bioactive constituents for the anti-diabetes effect of the traditional usage of C. paliurus.
- Chen, Zuhui,Li, Jing,Lv, Wenyan,Sun, Huihui,Tan, Jie,Wang, Wenxuan,Wu, Jianping,Xu, Jialing,Xu, Kangping,Xuan, Tongyao,Yang, Zhichun,Ye, Zijun,Zhu, Hui,Zou, Zhenxing
-
-
- Three new spirostanol glycosides from Helleborus thibetanus
-
An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1 D, 2 D NMR spectra, together with IR and MS met
- Li, Zhang-Peng,Su, Yan-Fang,Wei, Zi-Ye,Yang, Feng-Ying,Zhang, Hui
-
p. 975 - 980
(2019/01/09)
-
- Triterpene glycosides from Silene odontopetala
-
Silene species are known for their use in traditional medicine in treating several diseases. To the authors’ knowledge there is no report on the chemical composition of S. odontopetala. Therefore, the phytochemical investigation of the methanol extract of S. odontopetala was carried out, leading to the isolation of six undescribed oleanane-type glycosides along with the known saponin azukisaponin IV. Their structures were elucidated by the analysis of 1D and 2D-NMR experiments, along with mass spectrometry analysis. The cytotoxic activity of oleanane-type saponins was evaluated against a small panel of cancer cell lines, including PC-3 (prostate carcinoma cells), MCF-7 (breast cancer cells), A549 (alveolar basal carcinoma cells), and HeLa (cervical carcinoma cells). Furthermore, the activity of isolated compounds against a normal cell line HEK-293, used for assessing their cytotoxicity, was evaluated.
- ün, Rabia Nur,Alankus, Ozgen,Karayildirim, Tamer,Masullo, Milena,Nalbantsoy, Ay?e,Piacente, Sonia
-
-
- Three new acylphloroglucinol glucosides from the roots of Lysidice rhodostegia and their antioxidant activities
-
Three new acylphloroglucinol glucosides, rhodosides A-C (1–3), and three known ones (4–6) were isolated from the roots of Lysidice rhodostegia. The new structures were identified by MS, NMR, and acid hydrolysis. In addition, the antioxidant capacities of the isolated compounds were evaluated using DPPH radical-scavenging assay, and compounds 1–6 exhibited obvious antioxidant activities with IC50 values of 24.65 ± 1.27 to 38.11 ± 1.35 μM.
- Li, Yaolan,Li, Yingying,Wang, Guocai,Wu, Chun,Xu, Yaping,Yi, Xue,Zhang, Yubo
-
-
