Co-reporter:Qiu-Yan SongHai-Tao Yu, Xing-Xu Zhang, Zhi-Biao Nan, Kun Gao
Organic Letters 2017 Volume 19(Issue 1) pp:298-300
Publication Date(Web):December 28, 2016
DOI:10.1021/acs.orglett.6b03568
One novel hybrid peptide–polyketide, dahurelmusin A (1), was isolated from Elymus dahuricus infected by the Epichloë bromicola endophyte. Comprehensive spectroscopic analysis revealed that 1 is the first example of hybrid peptide–polyketide possessing an unprecedented 5-hydroxy-2,2,4,6-tetramethyl-3-oxooctanoic acid moiety. The single-crystal X-ray diffraction analyses allowed the absolute configuration assignment of this compound. Compound 1 also exhibited significant insecticidal activities against Rhopalosiphum padi and Brevicoryne brassicae with LC50 values of 0.092 and 0.251 mM, respectively.
Co-reporter:Wei-Yan Qi, Yu Shen, Yan Wu, Ying Leng, Kun Gao, Jian-Min Yue
Phytochemistry 2017 Volume 136(Volume 136) pp:
Publication Date(Web):1 April 2017
DOI:10.1016/j.phytochem.2017.01.009
•Twelve cembranoids were isolated from Macaranga deheiculata.•Deheiculatins C and G-L displayed moderate inhibitory activity against human and/or mouse11β-HSD1.•20-oxygenated cembranes are rare.Twelve cembranoids, deheiculatins A-L, were isolated from the leaves and twigs of Macaranga deheiculata. Their structures were elucidated on the basis of spectroscopic data. Five of these compounds displayed moderate inhibitory activity against human and/or mouse 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). 20-Oxygenated cembranes are rare.Cembranoids, deheiculatins A-L, were isolated from the leaves and twigs of Macaranga deheiculata. Dehiculatins C and G-J exhibited 11β-HSD1 inhibitory activity.Download high-res image (190KB)Download full-size image
Co-reporter:Quan LiuChenghui Wu, Aifeng Peng, Kun Gao, Jianjun ChenYa Li, Hua Fu
Journal of Agricultural and Food Chemistry 2017 Volume 65(Issue 7) pp:
Publication Date(Web):January 30, 2017
DOI:10.1021/acs.jafc.6b04162
Elymus natans, a perennial gramineous grass, plays an important role in animal husbandry and environmental sustenance in the Qinghai–Tibet plateau as a result of its high forage quality and good adaptability to the local environment. A bioassay showed that the extracts of green grasses of E. natans (GG) exhibited stronger phytotoxic activities than withered grasses (WG) against crops and grasses. In view of the secondary metabolites, which may be responsible for the resistance of the plant, the chemical components of GG were investigated. The flavone tricin, E1, and 10 flavonolignans, E2–E11, including three new flavonolignans, E2, E10, and E11, were isolated and identified. As far as we know, this is the first report on the chemical constitutions of the plant until now. The contents of compounds E1 and E4–E7 in GG were significantly higher than those in WG in high-performance liquid chromatography analysis, and they also showed observably phytotoxic activities against lettuce and Festuca arundinacea.Keywords: Elymus natans; flavonoids; flavonolignans; phytotoxic activities;
Co-reporter:Mei-Li Yang, Jian-Jun Chen, Hong-Bo Wei, Kun Gao
Phytochemistry Letters 2016 Volume 16() pp:236-240
Publication Date(Web):June 2016
DOI:10.1016/j.phytol.2016.04.017
•Two new highly oxygenated guaiane-type sesquiterpenoids were isolated from Senecio densiserratus.•The two new compounds inhibited HeLa cells with IC50 values of 9.5 and 10.4 μM.•The new compounds showed antifungal properties against Penicillium italicum and Rhizoctonia solani.Two new highly oxygenated guaiane-type sesquiterpenoids (1 and 2), along with nine known compounds (3–11) were isolated from the methanol extract of Senecio densiserratus Chang by cytotoxicity-guidance. Their structures were elucidated through spectroscopic analysis (IR, HRESIMS, 1D and 2D NMR) as well as by comparison with literature data. The two new compounds represent a rare type of guaiane sesquiterpenoid glucosides with angeloyloxy groups directly connected to the glycosyl moiety. Compounds 1–3, 8 and 10 displayed broad-spectrum inhibitory activity against the human leukemia cell (HL-60), human hepatoma cell (SMMC-7721) and human cervical carcinoma cell (HeLa), with IC50 values ranging from 9.5 to 28.3 μM in vitro. The new compounds also displayed moderate activity against plant pathogenic fungi of Penicillium italicum and Rhizoctonia solani with IC50 values from 19.4 to 33.1 μM.
Co-reporter:Yan-Yan Ma, Deng-Gao Zhao, Ya Li, Jian-Jun Chen, Jun Zeng, Qian-Qian Zhao, Kun Gao
Phytochemistry Letters 2016 Volume 15() pp:251-255
Publication Date(Web):March 2016
DOI:10.1016/j.phytol.2016.02.003
•11 triterpenes with diverse skeletons were isolated from A. tsangii.•New compounds 1 and 2 are rare examples of 29-nor-cycloartane triterpenes.•Mooratsanol A (1) showed the most potent cytotoxic activity.Two new 29-nor-cycloartane triterpenes, amooratsanols A and B (1, 2) along with nine known compounds including two 29-nor-cycloartane triterpenes (3, 9), two lupane triterpenes (4, 5), two cycloartane triterpenes (6, 10), two dammarane triterpenes (7, 8), as well as one dinorcycloartane triterpene (11) were isolated from the leaves and twigs of Amoora tsangii (Merr.) X. M. Their structures were established by spectroscopic methods (IR, HRESIMS, and NMR). The cytotoxicity of 1–11 was evaluated against the human fibro sarcoma HT1080, esophageal cancer TE, and non-small cell lung cancer A549 cell lines by the CCK8 assay. Cycloartanes (1–3, 6, and 9–11) displayed significant cytotoxic activity with IC50 values ranging from 2.56 to 19.05 μM. Among these triterpenes, mooratsanol A (1) showed the most potent cytotoxic activity, with IC50 values ranging from 2.56 to 5.10 μM.
Co-reporter:Qian-Qian Zhao, Qiu-Yan Song, Kan Jiang, Guang-Da Li, Wen-Jun Wei, Ya Li, and Kun Gao
Organic Letters 2015 Volume 17(Issue 11) pp:2760-2763
Publication Date(Web):May 19, 2015
DOI:10.1021/acs.orglett.5b01166
Two new triterpenoids, spirochensilides A (1) and B (2) were isolated from Abies chensiensis. Comprehensive spectroscopic analysis revealed that 1 and 2 are the first example of triterpenoids possessing a unique 8,10-cyclo-9,10-seco and methyl-rearranged carbon skeleton. The single crystal X-ray diffraction analyses and computational methods allowed the absolute configuration assignments of the two compounds. A plausible biogenetic pathway of spirochensilide A (1) is also proposed.
Co-reporter:Kan Jiang; Lu-Lin Chen; Shu-Fang Wang; Yi Wang; Ya Li
Journal of Natural Products 2015 Volume 78(Issue 5) pp:1037-1044
Publication Date(Web):May 6, 2015
DOI:10.1021/np5010196
Nine new terpenoids (1–3, 5–10), including three cyclolanostane triterpenoids (1–3) and six isopimarane diterpenoids (5–10), along with six known terpenoids (4, 11–15), were isolated from the leaves and twigs of Dysoxylum gotadhora. Compound 1 represents a class of rare natural 21,24-epoxy cyclolanostane-type triterpenoids, and compounds 2 and 3 are the first examples of 21,25-epoxy cyclolanostane-type triterpenoids. Compounds 1, 2, 4, 8, and 15 exhibited noteworthy inhibition of nitric oxide production induced by lipopolysaccharide in RAW 264.7 cells with IC50 values of 25.5, 41.5, 27.4, 14.5, and 45.2 μM, respectively.
Co-reporter:Dong-Bo Zhang; Dao-Geng Yu; Meng Sun; Xu-Xin Zhu; Xiao-Jun Yao; Shuang-Yan Zhou; Jian-Jun Chen
Journal of Natural Products 2015 Volume 78(Issue 6) pp:1253-1261
Publication Date(Web):May 29, 2015
DOI:10.1021/acs.jnatprod.5b00051
Nine new monoterpenoid indole alkaloids, ervatamines A–I (1–9), and five known ones (10–14), were isolated from Ervatamia hainanensis. The new structures were elucidated by extensive spectroscopic analysis and comparison to known compounds. Their absolute configurations were determined by various methods including computational methods, X-ray diffraction analysis, and electronic circular dichroism spectroscopy, as well as chemical transformations. Ervatamine A (1) is a ring-C-contracted ibogan-type monoterpenoid indole alkaloid with an unusual 6/5/6/6/6 pentacyclic rearranged ring system. Ervatamines B–E (2–5) display a nitrogen-containing 9/6 ring system, which is rarely observed in nature. The epimeric ervatamines B (2) and C (3) possess a 22-nor-monoterpenoid indole alkaloid carbon skeleton, which was only found in deformylstemmadenine. Compounds 10 and 14 exhibited significant anti-inflammatory activities, with IC50 values of 25.5 and 41.5 μM, respectively, while the IC50 value of indomethacin as a positive control was found to be 42.6 μM. Additionally, compound 9 showed mild activity against 786-O and HL-60 cell lines.
Co-reporter:Yuanzhen Xu, Jianjun Chen, Ya Li, Shoujiao Peng, Xueyan Gu, Meng Sun, Kun Gao and Jianguo Fang
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 9) pp:2634-2639
Publication Date(Web):02 Jan 2015
DOI:10.1039/C4OB02462A
A novel anticancer prodrug compound 1, which was designed to be triggered by thiols and release the chemotherapeutic agent mechlorethamine, was successfully prepared and evaluated for the first time. The activation of compound 1 was determined by NMR analysis and denaturing alkaline agarose gel electrophoresis. A fluorescence image and comet assay indicated that the inducible reactivity of 1 could be accomplished in cell media. The anticancer activities are also discussed.
Co-reporter:Yuan-Zhen Xu, Xue-Yan Gu, Shou-Jiao Peng, Jian-Guo Fang, Ying-Mei Zhang, De-Jun Huang, Jian-Jun Chen, Kun Gao
European Journal of Medicinal Chemistry 2015 Volume 94() pp:284-297
Publication Date(Web):13 April 2015
DOI:10.1016/j.ejmech.2015.03.001
•27 new sesquiterpene mustards were designed and synthesized.•Their cytotoxic activities to human tumor cells in vitro have been screened.•The selectivity of compounds 2e and 2g was evaluated on human cancer and normal cells.•Compounds 2e and 2g could induce cell apoptosis and cell cycle arrest.•Compounds 2e and 2g could induce DNA cross-linking and the depletion of glutathione.Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive α-methylene-γ-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 μM. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design.
Co-reporter:Qiu-Yan Song, Zhi-Biao Nan, Kun Gao, Hui Song, Pei Tian, Xing-Xu Zhang, Chun-Jie Li, Wen-Bo Xu, and Xiu-Zhang Li
Journal of Agricultural and Food Chemistry 2015 Volume 63(Issue 40) pp:8787-8792
Publication Date(Web):September 22, 2015
DOI:10.1021/acs.jafc.5b04260
The development of high-quality herbage is an important aspect of animal husbandry. Inoculating beneficial fungi onto inferior grass is a feasible strategy for producing new varieties of high-quality herbage. Epichloë bromicola is a candidate fungus that is isolated from Elymus tangutorum. A total of 17 metabolites, 1–17, were obtained from E. bromicola, and their biological activities were assayed. Metabolite 1 exhibited antifungal activities against Alternaria alternata, Fusarium avenaceum, Bipolaris sorokiniana, and Curvularia lunata. EC50 values ranged from 0.7 to 5.3 μM, which were better than the positive control, chlorothalonil. Metabolite 8 displayed obvious phytotoxic effects toward Lolium perenne and Poa crymophila seedlings, and it was as active as glyphosate. None of these isolated metabolites displayed cytotoxicity against Madin-Darby bovine kidney cells. The IC50 values were greater than 100 μM, and the metabolites increased the growth of the cells at a concentration of 12.5 μM. The bioassay indicated that E. bromicola may be a beneficial fungus for producing new varieties of herbage with various resistances. Additionally, metabolite 7, 3-(2′-(4″-hydroxyphenyl)acetoxy)-2S-methylpropanoic acid, is a new natural product, and its stereochemistry was determined by means of optical rotation computation and chemical reactions.
Co-reporter:Cheng-Hui Wu, Li Zhang, Pan-Pan Zhou, Meng Sun, Kun Gao
Phytochemistry Letters 2015 Volume 14() pp:245-248
Publication Date(Web):December 2015
DOI:10.1016/j.phytol.2015.10.028
•Three new jacaranone derivatives from the aerial parts of the aerial parts of Senecio chrysanoides DC. were investigated.•Structures were elucidated on the basis of spectroscopic data, optical rotation calculations and CD analyses.•All the isolated compounds were evaluated for their cytotoxicity.•Compound 2 showed moderate cytotoxic activity against three human cancer cell linesThree new jacaranone derivatives, namely, (1R)-ethyl 1-hydroxy-4-oxo-2-cyclohexenylacetate (1), (1R, 6S)-ethyl 6-ethoxy-1-hydroxy-4-oxo-2-cyclohexenylacetate (2) and (1R, 6R)-ethyl 6-ethoxy-1-hydroxy-4-oxo-2-cyclohexenylacetate (3), along with a known jacaranone derivative, ethyl 1-hydroxy-4-oxocyclohexylacetate (4) were isolated from the aerial parts of Senecio chrysanoides DC.. Their structures were elucidated by spectroscopic methods, optical rotation calculations and CD analyses. All the isolated compounds were evaluated for their cytotoxicity against three human cancer cell lines in vitro. Compound 2 exhibited moderate inhibitory effects against these cancer cell lines.
Co-reporter:Yan-Jun Chen, Zheng-Ming Li, Kun Gao
Biochemical Systematics and Ecology 2015 Volume 59() pp:26-30
Publication Date(Web):April 2015
DOI:10.1016/j.bse.2014.12.022
•Sixteen compounds were isolated from the roots of Triosteum himalayanum Wall.•Two iridoid glucosides (1 and 2) are new compounds.•Compounds 9–16 were isolated from the genus Triosteum for the first time.The phytochemical investigation of the roots of Triosteum himalayanum Wall. led to the isolation of eleven iridoids (1–6 and 8–12), one monoterpene diglycoside (7), and four flavonoids (13–16), of which 4′,6′-di-O-isopropylidene sweroside (1) and secologanin diethylacetal (2) were new iridoid glucosides. The existence of iridoids and flavonoids provided further confirmation of the typical profile of the secondary metabolites found in the genus Triosteum, suggesting a close relationship among the species of Caprifoliaceae.
Co-reporter:Jian-Jun Chen ; Chao-Jun Chen ; Xiao-Jun Yao ; Xiao-Jie Jin
Journal of Natural Products 2014 Volume 77(Issue 6) pp:1329-1335
Publication Date(Web):June 10, 2014
DOI:10.1021/np5003302
Five new highly oxygenated eremophilane-type sesquiterpenoids, possessing C19 (1 and 2), C15 (3 and 4), and C14 (8) skeletons, along with eight known eremophilenolides were obtained from the aerial parts of Ligularia sagitta. The absolute configuration of 1 was assigned by X-ray diffraction analysis and that of 3 by ECD spectroscopy. Compounds 1–10 were evaluated for their antibacterial activities against Staphyloccocus aureus, Bacillus subtilis, Escherichia coli, Bacillus cereus, and Erwinia carotovora. Compounds 4 and 5 displayed broad-spectrum inhibitory activity against these bacteria with MIC values of approximately 7.25 μg/mL, followed by 3 and 6 with MIC values in the range of 23.0–125.0 μg/mL. Compounds 3 and 8 showed mild activity against three human tumor cell lines (IC50 ≈ 13 μM). Preliminary structure–activity relationships for these eremophilenolides are reported.
Co-reporter:Wei-Yan Qi ; Wei-Yi Zhang ; Yu Shen ; Ying Leng ; Kun Gao ;Jian-Min Yue
Journal of Natural Products 2014 Volume 77(Issue 6) pp:1452-1458
Publication Date(Web):May 19, 2014
DOI:10.1021/np5002237
Eighteen new ingol-type diterpenes, euphorantins A–R (1–18), along with four known analogues (19–22), were isolated from the aerial parts of Euphorbia antiquorum. Compounds 1–3 are the first examples of C-17-oxygenated ingol-type diterpenes, and compounds 16–18 represent a rare class of 2,3-di-epimers of ingols. Diterpenes 1, 14, and 22 exhibited inhibitory activities against mouse 11β-HSD1 with IC50 values of 12.0, 6.4, and 0.41 μM, respectively.
Co-reporter:Li Zhang, Chun-Jiang Zhang, Dong-Bo Zhang, Juan Wen, Xiao-Wei Zhao, Ya Li, Kun Gao
Tetrahedron Letters 2014 Volume 55(Issue 10) pp:1815-1817
Publication Date(Web):5 March 2014
DOI:10.1016/j.tetlet.2014.01.122
A novel alkaloid, 17-nor-excelsinidine (1), possessing an unusual 1-azoniatricyclo [4.3.3.0] undecane moiety was isolated from the twigs and leaves of Alstonia scholaris alongside its biogenetically related strictamine (2). The structure and absolute stereochemistry of compound 1 were rigorously determined by a combination of NMR spectroscopy and X-ray crystallography. The 17-nor-excelsinidine (1) and strictamine (2) showed significant inhibitory activity against herpes simplex virus (HSV) and adenovirus (ADV).
Co-reporter:Weiyan Qi;Lei Hua
Chemistry & Biodiversity 2014 Volume 11( Issue 3) pp:364-395
Publication Date(Web):
DOI:10.1002/cbdv.201200244
Co-reporter:Jia Chen, Mei-Li Yang, Jun Zeng, Kun Gao
Phytochemistry Letters 2014 Volume 7() pp:156-160
Publication Date(Web):February 2014
DOI:10.1016/j.phytol.2013.11.016
•The alkaloidal fraction from Kopsia hainanensis showed antimicrobial activity.•Four new and eleven known alkaloids were isolated from the alkaloidal fraction.•Their structures were identified by spectroscopic data.•Compounds 2 and 8 exhibited broad-spectrum antibacterial and antifungal activities.Four new indole alkaloids, kopsininate (1), N1-decarbomethoxy chanofruticosinic acid (2), methyl N1-decarbomethoxy chanofruticosinate N(4)-oxide (3) and methyl chanofruticosinate N(4)-oxide (4), along with eleven known compounds were obtained from a Chinese medicinal plant, Kopsia hainanensis, with an activity-guided purification process. The structures of these compounds, 1–15, were established, mainly by spectroscopic analysis. These compounds were evaluated for antibacterial activities against five bacteria, in which compound 2 was the most active against Erwinia carotovora with MIC of 7.8 μg/ml. Moreover, compounds 2 and 8 were tested for antifungal activities against four plant pathogenic fungi, 2 exhibited potent inhibitory activities against Fusarium oxysporum f. sp. Cubense and F. oxysporum f. sp. Niveum, which was more active than the positive control (mildothane). These results provide promising baseline information for the potential use of this plant and its components in the control of food spoilage.
Co-reporter:Li Zhang, Yong-Liang Shao, Lei Hua, Ya Li, Syed Hamid Hussain, Mohammad Arfan, Kun Gao
Phytochemistry Letters 2014 Volume 7() pp:14-18
Publication Date(Web):February 2014
DOI:10.1016/j.phytol.2013.09.009
•Two new guaianolides and two known elemanolides were isolated from Vernonia anthelmintica Willd.•Their biosynthetic relationships were discussed.•Compounds 1–4 were evaluated for their cytotoxicity against HL-60 and SMMC-7721 cell lines.Two new guaianolides, (1R,4R,5S,6R,7R,8S)-8,15-dihydroxyguaia-10(14),11(13)-dien-12,6-olide (1) and (1R,4R,5S,6R,7R,8S,11S)-8,15-dihydroxyguaia-10(14)-en-6,12-olide (2), and two known elemanolides, (4S,5R,6R,7R,8S,10R,11S)-11,13-dihydrovernolepin (3) and (5R,6R,7R,8S,10R,11S)-melitensin (4) were isolated from the aerial parts of Vernonia anthelmintica Willd. The structures of these compounds were determined on the basis of IR, UV, MS, 1D-NMR and 2D-NMR, and their absolute configurations were deduced using the CD exciton chirality method and single-crystal X-ray diffraction. The possible biosynthetic relationships of compounds 1–4 are postulated. Compounds 1–4 were evaluated for their cytotoxicity against HL-60 and SMMC-7721 cell lines.
Co-reporter:Li Zhang, Chao-Jun Chen, Jia Chen, Qian-Qian Zhao, Ya Li, Kun Gao
Phytochemistry 2014 Volume 106() pp:134-140
Publication Date(Web):October 2014
DOI:10.1016/j.phytochem.2014.07.014
•Ten thiophene acetylenes were isolated from Xanthopappus subacaulis.•10,11-Threo-xanthopappin D exhibited strong antibacterial activity against Bacillus subtilis.•10,11-Erythro-xanthopappin D possessed broad-spectrum antibacterial activity against tested bacteria.In a search for naturally occurring antibacterial compounds in medicinal plants, six hitherto unknown thiophene acetylenes, named 10,11-threo-xanthopappin D, 10,11-erythro-xanthopappin D, 10,11-cis-xanthopappin B, 5-(but-4-chloro-3-hydroxy-1-ynyl)-2-(Z)-pent-3-ene-1-ynylthiophene, 5-(but-4-chloro-3-hydroxy-1-ynyl)-2-(E)-pent-3-ene-1-ynylthiophene, 5-(but-3,4-dihydroxy-1-ynyl)-2-(Z)-pent-3-ene-1-ynylthiophene and two furanosesquiterpenes, as well as fifteen known compounds, were isolated from Xanthopappus subacaulis, which has been used as a traditional Tibetan medicine in China. A biosynthetic pathway to thiophene acetylenes was proposed and, the isolated compounds were tested for their antibacterial activity against five bacteria. Within the series of thiophene acetylenes tested, 10,11-threo-xanthopappin D with a threo configuration exhibited strong activity against Bacillus subtilis, with a minimum inhibitory concentration (MIC) of 7.25 μg/mL, whereas 10,11-erythro-xanthopappin D with erythro configuration possessed broad-spectrum antibacterial activity against Escherichia coli, Bacillus cereus, Staphylococcus aureus and Erwinia carotovora, with MICs of 12.5, 15.5, 7.25 and 7.25 μg/mL, respectively. Meanwhile, the compounds 10,11-cis-xanthopappin B, xanthopappin B, 5-(but-4-chloro-3-hydroxy-1-ynyl)-2-(Z)-pent-3-ene-1-ynylthiophene and 5-(but-4-chloro-3-hydroxy-1-ynyl)-2-(E)-pent-3-ene-1-ynylthiophene substituted with a Cl atom at C-14 showed moderate inhibitory activity against E. coli, B. cereus, S. aureus, E. carotovora and B. subtilis, with MICs ranging from 31.25 to 62.5 μg/mL. The structures of these compounds were elucidated through the comprehensive analysis of spectroscopic data, including UV, IR, MS and NMR.Twenty-three compounds (six previously unknown) were identified from Xanthopappus subacaulis. Thiophene acetylenes showed significant antibacterial activity, in which 10,11-threo-xanthopappin D inhibited Bacillus subtilis with MIC of 7.25 μg/mL, 10,11-erythro-xanthopappin D inhibited Escherichia coli, Bacillus cereus, Staphylococcus aureus, and Erwinia carotovora, with MICs of 12.5, 15.5, 7.25, 7.25 μg/mL, respectively.
Co-reporter:Dong-Bo Zhang, Jian-Jun Chen, Li Zhang, Qiu-Yan Song, Kun Gao
Phytochemistry Letters 2014 10() pp: 76-79
Publication Date(Web):
DOI:10.1016/j.phytol.2014.08.008
Co-reporter:Deng-Gao Zhao ; JianJun Chen ; Ya-Rong Du ; Yan-Yan Ma ; Ya-Xiong Chen ; Kun Gao ;Bu-Rong Hu
Journal of Medicinal Chemistry 2013 Volume 56(Issue 4) pp:1467-1477
Publication Date(Web):January 29, 2013
DOI:10.1021/jm3014663
Several new series of 5,6,7-trimethoxyindole derivatives were synthesized and their structure–activity relationships (SARs) were studied. Some of these compounds exhibited strong antiproliferative activities in the submicromolar range. N-Methyl-5,6,7-trimethoxylindoles 21 and 31 displayed the highest antiproliferative activities, with IC50 values ranging from 22 to 125 nM in four human cancer cell lines and activated human umbilical vein endothelial cells (HUVECs). In addition to vascular disrupting activity verified by in vitro assays, compounds 21 and 31 displayed much higher selectivity for activated HUVECs versus quiescent HUVECs than those of colchicine and combretastatinA-4. The polymerization of cancer cell tubulin was inhibited and the cell cycle was arrested in the G2/M phase after treatment with 21 and 31. It was showed that 21 disrupted tumor vasculature by use of in vivo assay. Our results suggest that these two new compounds we synthesized may become the promising leads for the development of vascular disrupting agents.
Co-reporter:Yan-Yan Ma, Deng-Gao Zhao, and Kun Gao
Journal of Natural Products 2013 Volume 76(Issue 4) pp:564-570
Publication Date(Web):March 1, 2013
DOI:10.1021/np300742d
Five new sesquiterpene lactones, racemosalactones A–E (1–5), along with 19 known sesquiterpene latones (6–24), were isolated from the roots of Inula racemosa. Their structures were elucidated by extensive spectroscopic analysis, and the absolute configuration of 2 was deduced from X-ray diffraction analysis. Compounds 1, 6, 8, 10, 12, 14, and 17 exhibited antiproliferative activities with IC50 values ranging from 0.38 to 4.19 μg/mL against human non-small-cell lung cancer A549, hepatocellular carcinoma HepG2, and human fibrosarcoma HT1080 cells. Compounds 6 and 8 exhibited antiproliferative activities against endothelial cells with IC50 values of 2.4 and 2.5 μg/mL, respectively. Furthermore, compounds 6 and 8 both inhibited endothelial cell tube formation at 1.0 μg/mL. A method for the rapid and straightforward preparative-scale isolation of compound 6 from alantolides is described.
Co-reporter:Qiu-Yan Song, Kan Jiang, Qian-Qian Zhao, Kun Gao, Xiao-Jie Jin and Xiao-Jun Yao
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 7) pp:1251-1258
Publication Date(Web):17 Dec 2012
DOI:10.1039/C2OB27115J
Eleven new triterpenoids, schinchinenins A–H (1–8) and schinchinenlactones A–C (9–11) together with three known triterpenoids, henrischinins A–C (12–14), were isolated from the leaves and stems of Schisandra chinensis by bioassay-guided fractionation. Schinchinenin A (1) is the first example of a highly oxygenated triterpenoid characterized by a 5/5/7/6/5-fused pentacyclic ring and a 3-one-2-oxabicyclo[3.2.1]-octane moiety. Schinchinenins E and F (5 and 6) are highly oxygenated triterpenoids that contain a hydroperoxyl moiety, which is rare in compounds from the Schisandra genus. The structures and stereochemistry of 1–11 were elucidated using spectroscopic analysis, single-crystal X-ray diffraction, computational optical rotation, chemical transformation, and CD exciton chirality methods. The activities of compounds 1, 2, 7, and 12–14 against HSV-2 and adenovirus were evaluated for the first time, and of these compounds, 13 was the most active inhibitor of HSV-2, with a selectivity index value as high as 29.95.
Co-reporter:Weiqing Xie, Hexiang Wang, Feng Fan, Junshan Tian, Zhiwei Zuo, Weiwei Zi, Kun Gao, Dawei Ma
Tetrahedron Letters 2013 Volume 54(Issue 33) pp:4392-4396
Publication Date(Web):14 August 2013
DOI:10.1016/j.tetlet.2013.05.146
Construction of continuous all-carbon quaternary centers via intramolecular oxidative coupling was described. Intramolecular oxidative coupling of bisoxindole linked by diol derived from d-tartaric acid diastereoselectively produced C1 or C2 isomers of the annulation product. The selectivity was realized by judiciously choosing base and solvent employed in the reaction. As key intermediates for the synthesis of cyclotryptamine alkaloids, the resulting bisoxindole should be applicable to the total syntheses of complex indole alkaloids with continuous all-carbon quaternary centers.
Co-reporter:Qiu-Yan Song, Chun-Jiang Zhang, Ya Li, Juan Wen, Xiao-Wei Zhao, Zhen-Ling Liu, Kun Gao
Phytochemistry Letters 2013 Volume 6(Issue 2) pp:174-178
Publication Date(Web):May 2013
DOI:10.1016/j.phytol.2012.12.008
The systematic isolation of the EtOAc extract from Schisandra sphenanthera fruit was performed during a search for HSV-2 and adenovirus inhibitors. Sixteen lignans were obtained, with compound 1 representing a new and rare type of lignan in the genus Schisandra. Their structures were elucidated by spectroscopy and comparison with literature data. Among all the lignans tested for their antiviral activities, compound 14 was the most active against HSV-2 with a selectivity index value up to 29.83. Moreover, the new compound 1, and the known ones (4, 6, 7, 10 and 14) also exhibited moderate inhibition of HSV-2 and adenovirus. To the best of our knowledge, this is the first report that these lignans from Schisandra genus were shown to have modest activity against HSV-2 and adenovirus. Meanwhile, structure–activity relationships of some lignans for the inhibitory activity against HSV-2 and adenovirus were discussed in this study.Graphical abstractHighlights► Sixteen lignans were obtained by bioactivity-guided isolation of the EtOAc extract. ► Compound 14 was the most active against HSV-2 with selectivity index value of 29.83. ► Compound 1 was a new and rare type of lignan in the Schisandra genus. ► Compound 1 showed moderate inhibitory activities against HSV-2 and adenovirus. ► These isolated lignans first exhibited inhibition of HSV-2 and adenovirus.
Co-reporter:Yan-Yan Ma, Deng-Gao Zhao, Ying Zhai, Ya Li, Kun Gao
Phytochemistry Letters 2013 Volume 6(Issue 4) pp:645-648
Publication Date(Web):November 2013
DOI:10.1016/j.phytol.2013.08.004
•Compounds 1–4 were rarely reported trinorsesquiterpenoids.•The structure of a previously reported trinorsesquiterpenoid was revised to compound 2.•The absolute configuration of compounds 1–3 was determined.•Compound 2 showed significant antiproliferative activities.Four trinorsesquiterpenoids (1–4) were isolated from the roots of Inula racemosa and the structures of two new compounds, (4R,5S,10S)-5-hydroxy-11,12,13-trinoreudesm-6-en-8-one (1) and (4R,5R,10R)-4,15-epoxy-11,12,13-trinoreudesman-8-one (3), were elucidated by extensive spectroscopic analysis. Furthermore, the structure of compound 2a should be revised as (4R,5R,10S)-5-hydroxy-11,12,13-trinoreudesm-6-en-8-one (2) and compound 2 showed antiproliferative activity against A549, HepG2, and HT1080 cell lines with IC50 values of 3.71, 5.94, and 3.95 μg/mL, respectively.
Co-reporter:Jia Chen, Mei Li Yang, Jun Zeng, Kun Gao
Phytochemistry Letters 2013 Volume 6(Issue 1) pp:41-45
Publication Date(Web):February 2013
DOI:10.1016/j.phytol.2012.10.013
The present study was aimed at the identification of antimicrobial components from Araucaria cunninghamii with an activity-guided purification process. Eight compounds were obtained from the most active n-BuOH fraction and identified as the new compound 4-n-butoxyl-phenylpropanetriol (1), together with seven known compounds (2–8). These compounds were tested for antimicrobial activities against five bacteria and four plant pathogenic fungi. Within the series of compounds tested, compound 2 was the most active, particularly displaying moderate antibacterial activities against Erwinia carotovora and Bacillus subtilis with MICs 7.8 and 15.5 μg/ml. Moreover, this compound exhibited inhibitory activities against four plant pathogenic fungi: Helminthosporium sativum, Rhizoctonia solani, Fusarium oxysporum f. sp. Niveum and Fusarium oxysporum f. sp. Cubense, with EC50 values of 42.3, 90.0, 62.7 and 100.2 μg/ml. To our knowledge, this is the first report that the n-BuOH fraction and compound 2 from A. cunninghamii showed inhibitory activity against plant pathogenic fungi.Graphical abstractHighlights► n-BuOH fraction from Araucaria cunninghamii showed antimicrobial activity. ► Compound 2 possesses broad-spectrum antifungal activity. ► Compound 2 displayed moderate antibacterial activity. ► Compound 1 was found to be a new propanetriol derivative.
Co-reporter:Jian-Jun Chen, Hong-Bo Wei, Yuan-Zhen Xu, Shu-Chen Hu, Kun Gao
Tetrahedron 2013 69(49) pp: 10598-10603
Publication Date(Web):
DOI:10.1016/j.tet.2013.10.047
Co-reporter:Jian-Jun Chen ; Wen-Xian Li ; Kun Gao ; Xiao-Jie Jin ;Xiao-Jun Yao
Journal of Natural Products 2012 Volume 75(Issue 6) pp:1184-1188
Publication Date(Web):May 29, 2012
DOI:10.1021/np200693z
Bioactivity-directed fractionation of a methanol extract of Ligularia hodgsonii afforded two new monoterpenoids, liguhodgcins A (1) and B (2), with an unusual δ-lactone-containing skeleton. Moreover, liguhodgcin A (1) contained a chlorine atom. The structures and absolute configurations of the two compounds were elucidated using NMR spectroscopy, X-ray crystallography, ECD data, and computational approaches. A probable biosynthesis pathway to 1 and 2 was also proposed and discussed. The cytotoxicity of compounds 1 and 2 was evaluated against the human leukemia (HL-60), human hepatoma (SMMC-7721), and human cervical carcinoma (HeLa) cell lines.
Co-reporter:Ya Li, Tong-Tong Wang, Jie Zhao, Xiang Shi, Shu-Chen Hu, Kun Gao
Food Chemistry 2012 Volume 131(Issue 3) pp:972-976
Publication Date(Web):1 April 2012
DOI:10.1016/j.foodchem.2011.09.089
Three new norditerpenoids, (4S,5R,9S,10R)-methyl 19-hydroxy-15,16-dinorlabda-8(17),11E-dien-13-oxo-18-oate (1), (4R,5R,9R,10R,13S/R)-13-hydroxypodocarp-8(14)-en-19-oic acid (2/3) were isolated from Agathis macrophylla, together with 11 known diterpenoids. The structures of these compounds, 1–14, were established, mainly by spectroscopic analysis. The inactivation of protein tyrosine phosphatase 1B (PTP1B) by compounds 5–9 and 11–13 was tested and the cytotoxicity of compounds 1–14 against HL60 cell and SMMC-7721 cell were evaluated. Biological screening studies indicated that compounds 5, 7/8 and 9 were mild inactivators of PTP1B, whilst compounds 1, 4, 6, 7/8, and 10–12 exhibited moderate activity against both of the tested cell lines.Highlights► Three new norditerpenoids were isolated from Agathis macrophylla. ► Four compounds displayed inhibitory activities against PTP1B. ► Eight compounds exhibited moderate activity against the tested cell lines.
Co-reporter:Jia Chen, Ya Li, Li-Qiong Yang, Yan-Zhong Li, Zhi-Biao Nan, Kun Gao
Food Chemistry 2012 Volume 131(Issue 2) pp:546-551
Publication Date(Web):15 March 2012
DOI:10.1016/j.foodchem.2011.09.021
The present study was aimed at the identification of biological components from pathogenic-infected Astragalus adsurgens with an activity-guided purification process. Fifteen flavonoids were obtained from the most active ethyl acetate fraction and identified as astradsurnin (1), a new chalcone derivative, together with fourteen known flavonoids (2–15). These compounds were tested for antibacterial activities against five bacteria and cytotoxic activities against two selected cancer cells. Within the series of flavonoids tested, compounds 4 and 15 were the most active against Escherichia coli, Bacillus cereus, Staphylococcus aureus, Erwinia carotovora and Bacillus subtilis with MICs ranging from 7.8 to 31.3 μg/ml. Moreover, compounds 4 and 5 exhibited moderate activity against HL-60 and SMMC-7721 cells with IC50 values between 5 and 10 μg/ml. To our knowledge, this is the first time that it has been reported on the biological and chemical study of A. adsurgens infected by Embellisia astragali.Highlights► EtOAc extract from infected Astragalus adsurgens showed antibacterial activity. ► Four compounds displayed inhibitory activities against tested bacteria. ► Nine compounds exhibited moderate activities against tested cancer cells. ► Compound 1 was found to be a new chalone derivative.
Co-reporter:Xuejian Zhang, Jianjun Chen, Kun Gao
Biochemical Systematics and Ecology 2012 Volume 45() pp:7-11
Publication Date(Web):December 2012
DOI:10.1016/j.bse.2012.07.013
Phytochemical investigation of the leaves and stems of Glochidion wrightii Benth. led to the isolation of one new triterpenoid ester, 3β-tetradecanoyloxy-1β-hydroxylup-20(29)-ene (1), and twenty-nine known compounds (2–30), including (3β,16β)-lup-20(30)-ene-3,16,29-triol (8) reported as a natural product for the first time. Their structures were identified by spectroscopic analysis and by comparison of their spectral data with those reported in the literature. The chemotaxonomic analysis is concordant with the newest molecular phylogenetic and morphological classifications that the genus Glochidion is deeply embedded within the large Phyllanthus.Graphical abstractHighlights► One new triterpenoid ester 1 was yielded from Glochidion wrightii. ► Compound 8 was reported as a natural product for the first time. ► Twenty-one compounds were obtained from the genus Glochidion for the first time. ► The genus Glochidion is embedded within Phyllanthus from a chemotaxonomic view.
Co-reporter:Lei Hua, Jia Chen, Kun Gao
Phytochemistry Letters 2012 Volume 5(Issue 3) pp:541-544
Publication Date(Web):September 2012
DOI:10.1016/j.phytol.2012.05.009
Ligularia achyrotricha (Diels) Ling has been used as a traditional Tibetan herbal medicine. Ligulachyroine A (1), a new twelve-membered macrocyclic pyrrolizidine alkaloid with a ketonic group located at C-3 and an hydroxy group linked at C-8, was isolated from the roots of L. achyrotricha. It is particularly noteworthy that the structure of 1 rarely appears in any other naturally occurring twelve-membered macrocyclic pyrrolizidine alkaloid reported to date. Three known lignans (2–4) and eight known coniferyl and sinapyl alcohol derivatives (5–12) were also obtained in this species. Their structures were elucidated through a careful analysis of their IR, MS, and NMR spectra. Compound 1 exhibited moderate activity against HL-60 and SMMC-7721 cells.Graphical abstractHighlights► Ligularia achyrotricha is a traditional Tibetan medicine. ► Ligulachyroine A, a new alkaloid was isolated from the roots of L. achyrotricha. ► Eleven known compounds were also isolated from this species. ► Ligulachyroine A exhibited moderate activity against HL-60 and SMMC-7721 cells.
Co-reporter:Jia Chen, Jian-Jun Chen, Xiaojun Yao and Kun Gao
Organic & Biomolecular Chemistry 2011 vol. 9(Issue 15) pp:5334-5336
Publication Date(Web):02 Jun 2011
DOI:10.1039/C1OB05724C
Kopsihainanine A (1), an unprecedented skeleton with a 6/5/6/6/6 pentacyclic rearranged ring system, together with a new biogenetically related compound, kopsihainanine B (2), were isolated from Kopsia hainanensis. Their structures were elucidated by means of spectroscopic methods. The absolute configuration of 1 was determined by ECD calculation.
Co-reporter:Qiu-Yan Song, Wei-Yan Qi, Zheng-Ming Li, Jie Zhao, Jian-Jun Chen, Kun Gao
Food Chemistry 2011 Volume 128(Issue 2) pp:495-499
Publication Date(Web):15 September 2011
DOI:10.1016/j.foodchem.2011.03.059
During a search for plant extracts that possess activity against the fungi that cause diseases in plants, a 95% ethanol extract from the roots of Astilbe myriantha Diels showed inhibitory activity against Colletotrichum gloeosporioides. Bioassay-guided fractionation of the 95% ethanol extract led to the isolation of seven triterpenoids (1–7). Their structures were elucidated by spectroscopy and by a comparison with literature data. Among these compounds, 3β,6β,24-trihydroxyurs-12-en-27-oic acid (7) was the most active inhibitor of C. gloeosporioides, with >68.0% inhibition at 100 mg/ml after 72 h. Moreover, compound 7 displayed broad-spectrum inhibitory activity against Rhizoctonia solani, Fusarium oxysporum f. sp. Niveum, Fusarium oxysporum f. sp. Cubens, C. gloeosporioides, Penicillium citrinum, Colletotrichum lagenarium, and Penicillium digitatum, with EC50 values ranging from 13.9 to 34.0 μg/ml. The potential of compound 7 as a fungicide is therefore promising. In addition, compound 1 was found to be a new triterpenoid, 3β,6β-dihydroxyurs-12-en-7α,27α-olide, which possesses six rings.Highlights► 95% ethanol extract from Astilbe myriantha Diels showed inhibitory activity. ► Compound 7 was the main active ingredient against Colletotrichum gloeosporioides. ► Compound 7 displayed broad-spectrum inhibitory activities against tested fungi. ► Compound 1 was found to be a new triterpenoid, which possesses six rings.
Co-reporter:Yin Qiang;Baoshi Zhou
Chemistry & Biodiversity 2011 Volume 8( Issue 5) pp:792-815
Publication Date(Web):
DOI:10.1002/cbdv.201000046
Co-reporter:Jie Zhao;Huan-Xing Ding;Qiu-Yan Song
Chemistry & Biodiversity 2011 Volume 8( Issue 11) pp:1943-1957
Publication Date(Web):
DOI:10.1002/cbdv.201000267
Co-reporter:Yin Qiang;Dao-Lin Du;Yan-Jun Chen
Helvetica Chimica Acta 2011 Volume 94( Issue 5) pp:817-823
Publication Date(Web):
DOI:10.1002/hlca.201000301
Abstract
Two new ent-kaurane diterpenes, wedelidins A (8) and B (9), together with eighteen other constituents, including the sesquiterpenoids 1 and 2, ent-kaurane diterpenes 3–7, triterpenoids 10 and 11, steroids 12–14, and flavonoids 15–17 as well as benzene derivatives 18–20, were isolated from the aerial parts of Wedelia trilobata. The structures of wedelidins A (8) and B (9) were elucidated by extensive spectroscopic analyses (including UV, IR, NMR, and MS). Furthermore, the structures of compounds 2 and 3 were confirmed by X-ray single-crystal diffraction analyses.
Co-reporter:Quan Liu, Ling Shen, Tong-Tong Wang, Chao-Jun Chen, Wei-Yan Qi, Kun Gao
Food Chemistry 2010 Volume 122(Issue 1) pp:55-59
Publication Date(Web):1 September 2010
DOI:10.1016/j.foodchem.2010.01.069
Three new compounds, 2-acetyl-5-isopentenyl-6-methylbenzofuran (1), 1,3-dimethoxy-4,6-dimethylnaphthofuran (2), and 3,4,5-trimethoxycinnamyl angelic acid ester (3), along with 13 known compounds were isolated from the roots of Ligularia veitchiana, which are commonly used as a folk medicine and food supplement in China. Their structures were elucidated by spectroscopic techniques. Biological screening studies indicated that compound 2 displayed a moderate activity against Staphylococcus aureus, which may be due to the existence of a modified eremophilane skeleton, whilst compounds 11, 12 and 15 exhibited potent activity against HL-60 and HeLa cell lines.
Co-reporter:Jie Zhao, Ya Li, Quan Liu, Kun Gao
Food Chemistry 2010 Volume 120(Issue 2) pp:512-516
Publication Date(Web):15 May 2010
DOI:10.1016/j.foodchem.2009.10.045
In a search for some naturally occurring antimicrobial compounds found in medicinal plants, herbs and spice extracts, four thymol derivatives were isolated from the roots of Inula hupehensis (a medicinal plant) and identified as the new compound 9-O-β-d-glucopyranosyl-9-hydroxythymol (1), together with 8,9-epoxy-10-isobutyryloxythymyl isobutyrate (2), 8-hydroxy-9, 10-diisobutyloxythymol (3) and 8,9,10-trihydroxythymol (4). These thymol derivatives, with a semi-synthetic compound 9,10-dihydroxy-8-methoxythymol (5), were tested for their antimicrobial activities against three bacteria and six plant pathogenic fungi. Within the series of thymol derivatives tested, compound 3 was the most active, particularly displaying moderate antibacterial activities against Staphylococcusaureus, Methicillin-resistant S. aureus and Escherichia coli with MICs of 62.3, 62.8, and 250 μg/ml. Moreover, this compound exhibited inhibitory activities against three plant pathogenic fungi: Rhizoctonia solani, Phytophthora melonis and Peronophythora litchi, with EC50 values of 157, 180 and 141 μg/ml. To our knowledge, this is the first report that these five thymol derivatives show inhibitory activity against plant pathogenic fungi.
Co-reporter:Jian-Jun Chen, Zheng-Ming Li, Kun Gao, Jin Chang and Xiao-Jun Yao
Journal of Natural Products 2009 Volume 72(Issue 6) pp:1128-1132
Publication Date(Web):May 8, 2009
DOI:10.1021/np900120q
Two new steroids, vladimuliecins A (1) and B (2), were isolated by bioassay-guided fractionation from the rhizome of Vladimiria muliensis. Compounds 1 and 2 are the first examples possessing a pentacyclic 3α,5α-cyclopregnane-type framework. The structures of vladimuliecins A (1) and B (2) and their deacetylated derivative (3) were determined on the basis of IR, MS, 1D NMR, 2D NMR, and X-ray data analyses. The absolute configuration of the 10 stereogenic centers of compounds 1 and 2 was determined to be 3R,5R,6R,8S,9R,10R,13R,14R,17S,20R by means of auxiliary chiral MTPA derivatives and optical rotation calculation. A probable biosynthesis pathway to 1 and 2 is also proposed and discussed. In addition, the cytotoxicity of compounds 1, 2, and 3 was evaluated against selected cancer cell lines, including human leukemia cell (HL-60), human hepatoma cell (SMMC-7721), and human cervical carcinoma cell (HeLa) lines.
Co-reporter:Zheng-Ming Li, Jian-Jun Chen, Ya Li, Kun Gao, Jin Chang, Xiao-Jun Yao
Tetrahedron Letters 2009 50(28) pp: 4132-4134
Publication Date(Web):
DOI:10.1016/j.tetlet.2009.04.111
Co-reporter:Jian-Jun Chen, Dong-Qing Fei, Sheng-Gao Chen and Kun Gao
Journal of Natural Products 2008 Volume 71(Issue 4) pp:547-550
Publication Date(Web):February 23, 2008
DOI:10.1021/np070483l
A new triterpenoid with a rearranged ursane skeleton, 3β-acetoxyl-11α-methoxybauer-8-en-7α-ol (1), two new ursane triterpenoids, 1α,5α-dioxy-11α-hydroxyurs-12-en-3-one (2) and urs-3β,13α,18β-triol (3), together with three known ursane triterpenoids (4–6) were isolated from the rhizome of Vladimiria muliensis. Their structures were elucidated on the basis of spectroscopic methods (IR, EIMS, HRESIMS, 1D and 2D NMR, and X-ray crystallography diffraction). Compounds 2 and 4 exhibited modest antimicrobial activity against Escherichia coli, Candida albicans, Pseudomonas aeruginosa, Enterococcus faecalis, Bacillus cereus, and Staphylococcus aureus.
Co-reporter:Chun-Mei Liu, He-Xiang Wang, Shi-Lei Wei and Kun Gao
Journal of Natural Products 2008 Volume 71(Issue 5) pp:789-792
Publication Date(Web):April 18, 2008
DOI:10.1021/np070618n
Six new oleanane-type triterpenes (1−6), along with five known compounds, were isolated from the flowers and roots of Saussurea muliensis. On the basis of spectroscopic methods, with special emphasis on 1D and 2D NMR techniques, the structures of the new compounds were characterized as 3β,22α-dihydroxyolean-12-en-30-oic acid (1), 3α-(E)-caffeoyloxyolean-12-en-30-oic acid (2), 3α-(E)-coumaroyloxyolean-12-en-30-oic acid (3), 3α,22α-diacetoxy-20β,21α,29-trihydroxy-30-norolean-12-ene (4), 3α,22α-diacetoxy-21α,29-dihydroxy-20β-methoxy-30-norolean-12-ene (5), and 3α,22α-diacetoxy-20β,21α-dihydroxy-29-palmityloxy-30-norolean-12-ene (6). The isolated compounds (1−6) were not active against Staphylococcus aureus, Escherichia coli, Bacillus cereus, and Candida albicans.
Co-reporter:Sheng-Gao CHEN;Ya LI;Jie ZHAO
Chinese Journal of Chemistry 2008 Volume 26( Issue 3) pp:531-535
Publication Date(Web):
DOI:10.1002/cjoc.200890100
Abstract
Three new prenylfuranoisoflavonoids, namely, 5-hydroxy-7-(2-hydroxyisopropyl)-4′-methoxy-9-prenylfurano [3,2-g]isoflavone (1), 5-hydroxy-4′-methoxy-9-prenylfurano[3,2-g]isoflavone (2), 5-hydroxy-4′-methoxy-7-prenyl-furano[2,3-h]isoflavone (3) were isolated from the roots of Hedysarum scopariu and structurally established by means of detailed spectroscopic analyses (IR, EI- or HR-ESI-MS as well as 1D- and 2D-NMR), and by comparison of their spectroscopic data with those reported for structurally related compounds.
Co-reporter:Chun-Mei Liu;He-Xiang Wang;Shi-Lei Wei
Helvetica Chimica Acta 2008 Volume 91( Issue 2) pp:308-316
Publication Date(Web):
DOI:10.1002/hlca.200890036
Abstract
The new pyrrolizidine alkaloid glycoside 1, and the three new highly oxygenated bisabolane sesquiterpenes 4–6, together with the two known pyrrolizidine alkaloids 2 and 3, were isolated from the roots of Ligularia cymbulifera (W. W. Smith) Hand.-Mazz. Their structures were established on the basis of spectroscopic analysis, especially 1D- and 2D-NMR data. The cytotoxic activities of compounds 1, 2, and 4–6 were evaluated against hepatoma (BEL-7402), human leukemia (HL-60), human ovarian carcinoma (HO-8910), and nasopharyngeal carcinoma (KB) cell lines (Tables 1–3). Compound 6 showed weak cell-growth inhibition of BEL-7402 cell.
Co-reporter:He-Xiang Wang, Chun-Mei Liu, Quan Liu, Kun Gao
Phytochemistry 2008 Volume 69(Issue 10) pp:2088-2094
Publication Date(Web):July 2008
DOI:10.1016/j.phytochem.2008.04.008
Eight sesquiterpenes, including four guaiane-types containing an interesting epoxy unit (1–4), a rare tricyclic carbon skeleton-type (5) and three eudesmane-types (6–8), along with five known compounds, were isolated from rhizomes of Atractylodes lancea. The structures and relative configurations of 1–8 were determined by analysis of spectroscopic data, and the absolute configuration of 8 was assigned by application of the CD technique. Compounds 1, 2 and 4 were evaluated for their cytotoxic effects against P388 and A549 cells, but all were inactive. Possible biosynthetic pathways for sesquiterpenes (1–8) were discussed.A rare tricyclic carbon skeleton-type. three eudesmane-type and four guaiane-type sesquiterpenes were isolated from the rhizomes of Atractylodes lancea. Compounds 1, 2 and 4 were evaluated for their cytotoxic effects against P388 and A549 cells but all were inactive.
Co-reporter:Yan-Jun Chen;Ya Li;Jian-Jun Chen
Helvetica Chimica Acta 2007 Volume 90(Issue 1) pp:176-182
Publication Date(Web):26 JAN 2007
DOI:10.1002/hlca.200790013
Three new substituted 2,3-dihydro-1-benzofuran derivatives, compounds 1–3, were isolated from two extracts of Gerbera saxatilis, together with twelve known constituents. The structures of the new compounds were established by means of detailed spectroscopic analysis and by comparison of analytical data with those reported for structurally related compounds.
Co-reporter:Er-Wei Li;Zhong-Jian Jia;Xue Gao
Chemistry & Biodiversity 2007 Volume 4(Issue 3) pp:531-538
Publication Date(Web):19 MAR 2007
DOI:10.1002/cbdv.200790046
Four new labdane-type rhamnopyranosides derived from 13-epimanool, compounds 1–4, with differently acetylated sugar moieties, were isolated from A. veitchianus. Their structures and absolute configurations were elucidated by chemical transformation, spectroscopic and mass-spectrometric analyses (IR, 1D- and 2D-NMR, HR-ESI-MS), as well as by single-crystal X-ray diffraction (compound 1). The isolates 2–4 were investigated for their cytotoxic properties against cultured human hepatoma (SMMC-7721), ovarian neoplasm (HO-8910), and leukemia (HL-60) cells, and for their antibacterial activities against Escherichia coli, Bacillus subtilis, and Staphylococcus aureus.
Co-reporter:Chun-Mei Liu;Yan-Jun Chen;Qiu-Hong Wu
Helvetica Chimica Acta 2006 Volume 89(Issue 5) pp:915-922
Publication Date(Web):24 MAY 2006
DOI:10.1002/hlca.200690094
Three new eremophilane-type sesquiterpenes, (6β,8α)-6-(acetyloxy)-8-hydroxyeremophil-7(11)-en-12,8-olide (1), (6α,8α)-6-hydroxyeremophil-7(11)-en-12,8-olide (2), and (6α,8α)-6-(acetyloxy)eremophil-7(11)-en-12,8-olide (3) ((8α)-eremophil-7(11)-en-12,8-olide = (4aR,5S,8aR,9aS)-4a,5,6,7,8,8a,9,9a-octahydro-3,4a,5-trimethylnaphtho[2,3-b]furan-2(4H)-one), besides the recently elucidated eremoligularin (4) and bieremoligularolide (5), as well as a new highly oxygenated monoterpene, rel-(1R,2R,3R,4S,5S)-p-menthane-1,2,3,5-tetrol (12), together with six known constituents, i.e., the sesquiterpenes 6 and 7, the norsesquiterpenes 8–10, and the monoterpene 13, were isolated from the roots of Ligularia muliensis. In addition, an attempt to dimerize 1 to a bieremophilenolide (Scheme) resulted in the generation of the new derivative (6β,8β)-6-(acetyloxy)-8-chloroeremophil-7(11)-en-12,8-olide (11). The new structures were established by means of detailed spectroscopic analysis (IR, FAB-, EI-, or HR-ESI-MS as well as 1D- and 2D-NMR experiments). Compounds 4 and 5 were evaluated for their antitumor effects in vitro (Table 3).
Co-reporter:Hai-Xia Jiang;Ya Li;Jing Pan
Helvetica Chimica Acta 2006 Volume 89(Issue 3) pp:558-566
Publication Date(Web):24 MAR 2006
DOI:10.1002/hlca.200690059
Four new terpenoids, namely, rel-(1R,2S,3R,4R,6S)-p-menthane-1,2,3,6-tetrol (1), rel-(1R,2R,3R,4S,6S)-p-menthane-1,2,3,6-tetrol (2), 9-hydroxythymol 3-O-angelate (3), and (3β,20R)-20-hydroxylanost-25-en-3-yl palmitate (4), together with fourteen known compounds, were isolated from the AcOEt part of the MeOH extracts of Eupatorium fortunei. In addition, two other monoterpenoids, ‘acetone thymol-8,9-diyl ketal’ (19) and 8-methoxy-9-hydroxythymol 3-O-angelate (20) were also obtained which were probably artifacts but have never been reported in the literature. The structures of the new compounds, including their relative configurations, were established by an extensive study of their spectral data, especially 1D- and 2D-NMR. The cytotoxic activity of the new compounds against human hepatoma (SMMC-7721), human leukemia (HL-60), and human hepatocyte (LO2) cells was investigated.
Co-reporter:Qian-Qian Zhao, Shu-Fang Wang, Ya Li, Qiu-Yan Song, Kun Gao
Fitoterapia (June 2016) Volume 111() pp:87-94
Publication Date(Web):1 June 2016
DOI:10.1016/j.fitote.2016.04.002
The phytochemical investigation of Abies chensiensis led to the isolation and identification of nine new compounds including eight triterpenoids (1–8) and a new abietane-type diterpene (9), along with three known compounds (10 − 12). The absolute configuration of 9 was assigned by X-ray diffraction analysis. Compounds 1–11 were evaluated for the anti-inflammatory activity. Among the tested compounds, 1, 2, 5 and 6 exhibited potent inhibitory activity with IC50 values of 15.97, 18.73, 20.18 and 10.97 μM, respectively.Download high-res image (270KB)Download full-size image
Co-reporter:Junmin Zhang, Ya Li, Dongzhu Duan, Juan Yao, Kun Gao, Jianguo Fang
Biochemical Pharmacology (15 February 2016) Volume 102() pp:
Publication Date(Web):15 February 2016
DOI:10.1016/j.bcp.2015.12.004
•Alantolactone (ATL) inhibits thioredoxin reductase (TrxR).•ATL induces generation of reactive oxygen species in HeLa cells.•ATL causes accumulation of the oxidized thioredoxin in cells.•Knockdown of TrxR sensitizes cells to ATL treatment.•ATL elicits oxidative stress-mediated apoptosis in HeLa cells.The mammalian thioredoxin reductase (TrxR) isoenzymes, TrxR1 in cytosol or nucleus, TrxR2 in mitochondria, and TrxR3 in testis, are essential seleno-flavoenzymes with a conserved penultimate selenocysteine (Sec) residue at the C-terminus, and have attracted increasing interests as potential targets for development of cancer chemotherapeutic agents. The sesquiterpene lactone alantolactone (ATL), an active component from the traditional folk medicine Inula helenium, has been documented possessing multiple pharmacological functions, especially the anticancer activity. However, the underlying mechanism has not been well defined. We reported that ATL inhibits both the recombinant TrxR and the enzyme in the cellular environment. The alpha-methylene-gamma-lactone moiety in ATL and the Sec residue in TrxR are critical for targeting TrxR by ATL. By employing our newly developed pull down assay, we demonstrated the remarkable elevation of the oxidized thioredoxin in HeLa cells after ATL treatment. In addition, ATL elicits accumulation of reactive oxygen species, and eventually induces apoptosis of HeLa cells. Importantly, overexpression of the functional TrxR attenuates the cytotoxicity of ATL, while knockdown of the enzyme sensitizes the cells to ATL treatment. Targeting TrxR thus discloses a novel molecular mechanism underlying the cellular action of ATL, and sheds light in considering the usage of ATL as a potential cancer chemotherapeutic agent.
Co-reporter:Meili Yang, Junmin Zhang, Ya Li, Xiao Han, Kun Gao, Jianguo Fang
Archives of Biochemistry and Biophysics (1 October 2016) Volume 607() pp:20-26
Publication Date(Web):1 October 2016
DOI:10.1016/j.abb.2016.08.008
•DHC inhibited thioredoxin reductase (TrxR1).•DHC treatment elicited accumulation of ROS.•DHC induced oxidative stress-mediated apoptosis in HeLa cells.In a screen for mammalian thioredoxin reductases inhibitors, an MeOH extract from the roots of Saussurea lappa C.B. Clarke (Compositae) inhibited the activity of cytosolic thioredoxin reductase (TrxR1). Bioassay-guided separation of the extract led to the isolation of a new TrxR1 inhibitor, dehydrocostus lactone (DHC), a guaiane-type sesquiterpene. The content of DHC in the extract was determined to be 0.4%. DHC inhibited human cervical carcinoma HeLa cells with an IC50 of ∼12.00 μM but displayed less cytotoxicity to human immortalized normal liver cells L02. We observed that DHC killed HeLa cells through induction of apoptosis. DHC inhibited the activity of TrxR1 in HeLa cells, which elicited an accumulation of reactive oxygen species (ROS) in cells and a collapse of the intracellular redox equilibrium and eventually induced apoptosis of HeLa cells.Download high-res image (188KB)Download full-size image
Co-reporter:Yuanzhen Xu, Jianjun Chen, Ya Li, Shoujiao Peng, Xueyan Gu, Meng Sun, Kun Gao and Jianguo Fang
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 9) pp:NaN2639-2639
Publication Date(Web):2015/01/02
DOI:10.1039/C4OB02462A
A novel anticancer prodrug compound 1, which was designed to be triggered by thiols and release the chemotherapeutic agent mechlorethamine, was successfully prepared and evaluated for the first time. The activation of compound 1 was determined by NMR analysis and denaturing alkaline agarose gel electrophoresis. A fluorescence image and comet assay indicated that the inducible reactivity of 1 could be accomplished in cell media. The anticancer activities are also discussed.
Co-reporter:Jia Chen, Jian-Jun Chen, Xiaojun Yao and Kun Gao
Organic & Biomolecular Chemistry 2011 - vol. 9(Issue 15) pp:NaN5336-5336
Publication Date(Web):2011/06/02
DOI:10.1039/C1OB05724C
Kopsihainanine A (1), an unprecedented skeleton with a 6/5/6/6/6 pentacyclic rearranged ring system, together with a new biogenetically related compound, kopsihainanine B (2), were isolated from Kopsia hainanensis. Their structures were elucidated by means of spectroscopic methods. The absolute configuration of 1 was determined by ECD calculation.
Co-reporter:Qiu-Yan Song, Kan Jiang, Qian-Qian Zhao, Kun Gao, Xiao-Jie Jin and Xiao-Jun Yao
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 7) pp:NaN1258-1258
Publication Date(Web):2012/12/17
DOI:10.1039/C2OB27115J
Eleven new triterpenoids, schinchinenins A–H (1–8) and schinchinenlactones A–C (9–11) together with three known triterpenoids, henrischinins A–C (12–14), were isolated from the leaves and stems of Schisandra chinensis by bioassay-guided fractionation. Schinchinenin A (1) is the first example of a highly oxygenated triterpenoid characterized by a 5/5/7/6/5-fused pentacyclic ring and a 3-one-2-oxabicyclo[3.2.1]-octane moiety. Schinchinenins E and F (5 and 6) are highly oxygenated triterpenoids that contain a hydroperoxyl moiety, which is rare in compounds from the Schisandra genus. The structures and stereochemistry of 1–11 were elucidated using spectroscopic analysis, single-crystal X-ray diffraction, computational optical rotation, chemical transformation, and CD exciton chirality methods. The activities of compounds 1, 2, 7, and 12–14 against HSV-2 and adenovirus were evaluated for the first time, and of these compounds, 13 was the most active inhibitor of HSV-2, with a selectivity index value as high as 29.95.
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