Co-reporter:Wen-qiong Wang, Li-jiang Xuan
Phytochemistry 2016 Volume 122() pp:119-125
Publication Date(Web):February 2016
DOI:10.1016/j.phytochem.2015.11.014
•Seven ent-6,7-secokaurane diterpenoids were isolated from Rabdosia serra.•The absolute configurations were determined by X-ray diffraction.•Weak to moderate cytotoxic activities of isolations were detected.Investigation of the hydrophobic extract of Rabdosia serra (Lamiaceae) led to the isolation of seven ent-6,7-secokaurane diterpenoids rabdosins E–K, along with twelve known ent-kaurane diterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of rabdosins E, F, H and I were determined by single-crystal X-ray diffraction, with rabdosin E having a 3,20-epoxy group. These diterpenoids could be divided into two types according to their skeletons: rabdosins E–J are ent-6,20-epoxy-6,7-secokaur-1,7-olides, and rabdosin K is an ent-6,7-secokaur-7,20-olide. Cytotoxicity evaluation showed that serrin B, serrin A, isodocarpin and lushanrubescensin J exhibited weak to moderate cytotoxic activities (IC50 < 10 μM) against two human cancer cell lines.Graphical abstractSeven enmein-type ent-kauranoids, named as rabdosins E–K, along with twelve known diterpenoids, were isolated from the hydrophobic extract of Rabdosia serra. Weak to moderate cytotoxic activities against two human cancer cell lines were detected.
Co-reporter:Yong Zheng, Wei-Bin Song and Li-Jiang Xuan
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 44) pp:10834-10843
Publication Date(Web):25 Aug 2015
DOI:10.1039/C5OB01465D
A directing-group-assisted copper-catalyzed oxidative esterification of phenols with aldehydes using TBHP as an oxidant was described. This methodology which showed the advantages of base, ligand free, short routes and functional group tolerance could be used as an alternative protocol for the classical esterification reactions.
Co-reporter:Yong Zheng, Wei-Bin Song, Shu-Wei Zhang and Li-Jiang Xuan
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 23) pp:6474-6478
Publication Date(Web):07 May 2015
DOI:10.1039/C5OB00601E
A ruthenium-catalyzed oxidative coupling of 2-aryl-quinazolinones with olefins via C–H bond activation followed by an intramolecular aza-Michael reaction is described. This strategy allows the direct and efficient construction of pyrrolo[2,1-b]quinazolin-9(1H)-one scaffolds.
Co-reporter:Wen-qiong Wang, Li-jiang Xuan
Phytochemistry Letters 2015 Volume 14() pp:23-26
Publication Date(Web):December 2015
DOI:10.1016/j.phytol.2015.08.013
•Chemical constituents of the hydrophilic extract of Dichondra repens are discussed.•A new acyclic sesquiterpenoid and its glucoside is reported.•A new pinene disaccharide is also discussed.•Cytotoxic activities of the three compounds against two human cancer cell lines are discussed.A new highly oxygenated acyclic sesquiterpenoid (2E, 6E)-8,10,11-trihydroxyl-7,11-dimethyl-3-hydroxymethyl-2,6-dodecadienoic acid (1) and its glucoside (2), together with a new pinane monoterpene disaccharide glucoside 6,6-dimethyl-2-methlenebicyclo [3.1.1]hept-3-O-(6-O-apiofuranosyl)-β-d-glucopyranoside (3) were isolated from hydrophilic extract of Dichondra repens. Their structures were elucidated on the basis of spectroscopic analyses and chemical methods. The three compounds did not show any cytotoxic activity (IC50 > 20 μM) against two human lung cancer cell lines (NCI-H661 and A549).
Co-reporter:Yong Zheng, Wei-Bin Song, Shu-Wei Zhang, Li-Jiang Xuan
Tetrahedron 2015 Volume 71(Issue 10) pp:1574-1580
Publication Date(Web):11 March 2015
DOI:10.1016/j.tet.2015.01.025
A palladium-catalyzed oxidative ortho-acylation of 2-arylbenzoxazoles and 2-arylbenzothiazoles using TBHP as oxidant was developed, in which readily available toluene derivatives were used as the in situ generated acyl sources. This reaction afforded the desired products in moderate to good yields, and exhibited excellent regioselectivity. The plausible mechanism was also proposed.
Co-reporter:Ding-xiang Li, Yan-peng Yin, Jun Li, Li-jiang Xuan
Phytochemistry Letters 2015 11() pp: 220-223
Publication Date(Web):
DOI:10.1016/j.phytol.2015.01.003
Co-reporter:Wen-qiong Wang ; Wei-bin Song ; Xiao-jing Lan ; Min Huang
Journal of Natural Products 2014 Volume 77(Issue 10) pp:2234-2240
Publication Date(Web):October 13, 2014
DOI:10.1021/np500483d
Five new pentasaccharide resin glycosides, named merremins A–E (1–5), two new pentasaccharide resin glycoside methyl esters, named merremins F and G (6, 7), and four known resin glycosides, murucoidin IV, murucoidin V, stoloniferin IV, and murucoidin XVII, were obtained from the aerial parts of Merremia hederacea. This is the first report of resin glycosides obtained from M. hederacea. In addition, the new compounds can be divided into three types: those possessing an 18-membered ring (1–4), compound 5 with a 20-membered ring, and those with an acyclic core (6, 7). Furthermore, the different types of resin glycosides were evaluated for their multidrug resistance reversal activities. Compounds 1, 5, 6, and murucoidin V were noncytotoxic and enhanced the cytotoxicity of vinblastine by 2.3–142.5-fold at 25 μM. Compound 5 and murucoidin V, with 20-membered rings, were more active than compound 1, with an 18-membered ring.
Co-reporter:Yu-jie Huang ; Hui Lu ; Xue-li Yu ; Shu-wei Zhang ; Wen-qiong Wang ; Lin-yin Fen
Journal of Natural Products 2014 Volume 77(Issue 5) pp:1201-1209
Publication Date(Web):May 7, 2014
DOI:10.1021/np500077z
Thirteen new dammarane-type triterpenoids (1–13) and four known analogues, gentirigenic acid (14) and the gentirigeosides A, B, and E (15–17), were isolated from Gentianella azurea. Their structures were elucidated by detailed analysis of the NMR, MS, and X-ray crystallographic data. This is the first report of dammarane-type triterpenoids in the Gentianella genus. In addition, the known structures of gentirigenic acid (14) and the gentirigeosides A, B, and E (15–17) were revised based on the X-ray diffraction analysis. Gentirigeoside A (15) was found to inhibit nitric oxide production in RAW 264.7 macrophages with an IC50 value of 6.6 ± 2.1 μM.
Co-reporter:Yu-jie Huang, Hui Lu, Xue-li Yu, Wei-bing Song, Shu-wei Zhang, Lin-yin Fen, Li-jiang Xuan
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 22) pp:5260-5264
Publication Date(Web):15 November 2014
DOI:10.1016/j.bmcl.2014.09.055
A phytochemical investigation on crude extract of Gentianella azurea led to the isolation of ten new (1–10) and one known (11) secoiridoid glycosides. Their structures were unambiguously elucidated by analysis of 1D and 2D NMR. Compounds 2, 5 and 11 were found to inhibit nitric oxide (NO) production in RAW 264.7 macrophages with IC50 values of 52.78 ± 8.61, 0.69 ± 0.23 and 5.18 ± 1.33, respectively, while indomethacin, the positive control, showed an IC50 value of 1.25 ± 0.52 μM.
Co-reporter:Wei-bin Wei, Yu-jie Huang, Hai-jian Cong, Shu-wei Zhang, Da-ren Pan, Li-jiang Xuan
Phytochemistry Letters 2014 Volume 8() pp:101-104
Publication Date(Web):May 2014
DOI:10.1016/j.phytol.2014.02.011
•The water-soluble chemical constituents from Sarcopyramis nepalensis Wall were investigated for the first time.•Three new glycosides were isolated and their structures were elucidated.•This should be the first report on glycosides content of this plant.One new megastigmane glycoside 1 and two new terpenic glycosides 2 and 3, along with three known compounds, roseoside, pumilaside A, and terminolic acid were isolated from Sarcopyramis nepalensis Wall. The structures of these new compounds were elucidated on the basis of 1D, 2D NMR, MS spectroscopic analysis, and chemical methods.
Co-reporter:Hai-Jian Cong, Qing Zhao, Shu-Wei Zhang, Jiao-Jiao Wei, Wen-Qiong Wang, Li-Jiang Xuan
Phytochemistry 2014 100() pp: 76-85
Publication Date(Web):April 2014
DOI:10.1016/j.phytochem.2014.01.004
Co-reporter:Hai-Jian Cong, Shu-Wei Zhang, Yu Shen, Yong Zheng, Yu-Jie Huang, Wen-Qiong Wang, Ying Leng, and Li-Jiang Xuan
Journal of Natural Products 2013 Volume 76(Issue 7) pp:1351-1357
Publication Date(Web):July 12, 2013
DOI:10.1021/np400235s
Eleven new guanidine alkaloids, plumbagines A–G (2–8) and plumbagosides A–D (9–12), as well as two known analogues (1, 13), were isolated from the aerial parts of Plumbago zeylanica. Their structures were elucidated by spectroscopic analyses including 1D and 2D NMR, MS, IR, and CD methods. The absolute configuration of 1 was determined by single-crystal X-ray diffraction of its derivative (1a).
Co-reporter:Yong Zheng, Shu-Wei Zhang, Hai-Jian Cong, Yu-Jie Huang, and Li-Jiang Xuan
Journal of Natural Products 2013 Volume 76(Issue 12) pp:2210-2218
Publication Date(Web):December 4, 2013
DOI:10.1021/np400545v
Fourteen new cassane diterpenoids, caesalminaxins A–L (1–14), and three known compounds were isolated from the seeds of Caesalpinia minax. Among the new diterpenoids, compounds 3 and 4 possess a rare spiro C/D ring system. The C-16 epimeric mixture 1/2 has an unprecedented carbon skeleton, presumably derived from 3 by cleavage of the C-13–C-14 bond. Compound 5 is the first example of a cassane diterpenoid with a spiro A/B ring system. The structures of the compounds were elucidated on the basis of 1D and 2D NMR analysis, and the absolute configurations of 3, 4, 9, and 11 were determined by single-crystal X-ray crystallography. Biosynthesis pathways for 1/2, 3, and 5 are postulated. Compounds 4, 8, and the known bonducellpin D exhibited moderate activity against four tested human cancer cell lines, HepG-2, K562, HeLa, and Du145.
Co-reporter:Hai Jian Cong, Shu Wei Zhang, Chong Zhang, Yu Jie Huang, Li Jiang Xuan
Chinese Chemical Letters 2012 Volume 23(Issue 7) pp:820-822
Publication Date(Web):July 2012
DOI:10.1016/j.cclet.2012.04.021
A novel dimeric procyanidin glucoside, catechin 3-O-acetate-(4α→8)-catechin 3-O-acetate-3′-O-β-d-glucopyranoside (1), along with five flavonoids and one lignan were isolated from the aerial parts of Polygonum aviculare. Their structures were elucidated by spectroscopic analyses including 1D, 2D NMR, MS and CD methods.
Co-reporter:Chong Yao, Shu Jie Zhang, Zheng Zhong Bai, Tong Zhou, Li Jiang Xuan
Chinese Chemical Letters 2011 Volume 22(Issue 2) pp:175-177
Publication Date(Web):February 2011
DOI:10.1016/j.cclet.2010.09.028
Two new benzopyran derivatives, 1-[(rel 2S,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]ethanone (1), and 1-[(rel 2S,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]ethanone (2), along with four known flavonoids, prodelphinidin C, prodelphinidin B3, (−)-epi-gallocatechin and (+)-gallocatechin, were isolated from the stems of Gouania leptostachya DC. var. tonkinensis Pitard. Their structures were determined on the basis of spectroscopic methods including HR-ESI-MS, 1D and 2D NMR. Prodelphinidin C exhibited significant inhibitory activity for α-glucosidase.
Co-reporter:Xiao-Ping Hu;Shu-Wei Zhang;Shan-Shan Liu
Helvetica Chimica Acta 2011 Volume 94( Issue 4) pp:675-685
Publication Date(Web):
DOI:10.1002/hlca.201000270
Abstract
Five new anthraquinone glycosides, hedanthrosides A–E (1–5, resp.) and two new iridoid glycosides, hediridosides A and B (6 and 7, resp.), along with two known anthraquinones and four known iridoids, were isolated from the stems of Hedyotis hedyotidea (DC.) Merr. The structures of the new compounds were elucidated on the basis of 1D- and 2D-NMR, and HR-MS analysis and chemical methods.
Co-reporter:Tong Zhou, Shu-wei Zhang, Shan-shan Liu, Hai-jian Cong, Li-jiang Xuan
Phytochemistry Letters 2010 Volume 3(Issue 4) pp:242-247
Publication Date(Web):17 December 2010
DOI:10.1016/j.phytol.2010.10.001
Four daphnodorin dimers named herein as edgechrins A–D (1–4) were isolated from the stems and twigs of Edgeworthia chrysantha Lindl. along with four known compounds identified as daphnodorin A (5), B (6), C (7) and I (8). Their structures were established by spectroscopic methods, including IR, HR-MS, and 1D- and 2D NMR. All of these compounds showed potent in vitro α-glucosidase inhibitory activity with IC50 values in the range of 0.4–20 μM.Graphical abstractFour daphnodorin dimers, named edgechrins A–D, were isolated from the stems and twigs of Edgeworthia chrysantha along with four daphnodorin monomers, daphnodorin A, B, C and I. Their inhibitory activities of α-glucosidase were evaluated.Research highlights▶ Four daphnodorin dimers were isolated from Edgeworthia chrysantha. ▶ Structures of them were established by spectroscopic methods. ▶ Daphnodorin dimers showed α-glucosidase inhibitory activities.
Co-reporter:Shan-Shan Liu;Tong Zhou;Shu-Wei Zhang
Helvetica Chimica Acta 2009 Volume 92( Issue 6) pp:1070-1079
Publication Date(Web):
DOI:10.1002/hlca.200800392
Co-reporter:Juan Yu;Hao-Hao Zhang;Qiang Yu
Helvetica Chimica Acta 2009 Volume 92( Issue 9) pp:1880-1888
Publication Date(Web):
DOI:10.1002/hlca.200900081
Abstract
Six prenylated phenols, sabphenols A and B (1 and 2, resp.), and sabphenosides A–D (3–6, resp.), along with eight known constituents, were isolated from the rhizomes of Sabia japonicaMax. Their structures were established on the basis of 1D- and 2D-NMR spectral analysis.
Co-reporter:Shanshan Liu, Huilin Zhu, Shuwei Zhang, Xiaohui Zhang, Qiang Yu and Lijiang Xuan
Journal of Natural Products 2008 Volume 71(Issue 5) pp:755-759
Publication Date(Web):March 19, 2008
DOI:10.1021/np0703489
Five new naturally occurring abietane diterpenoids (1–5) along with three known diterpenoids (6–8) were isolated from an acetone-soluble extract of the roots of Clerodendrum bungei. The structures of the new compounds were elucidated on the basis of spectroscopic analysis and chemical methods. In addition, all compounds were evaluated for cytotoxic activity against the cultured B16 (murine melanoma), HGC-27 (human gastric), and HEK-293 (human epithelial kidney) cell lines. Uncinatone (7) exhibited moderate cytotoxicity, inhibited cell proliferation, and induced cell-cycle G2/M phase arrest.
Co-reporter:Jun Wu;Xiao-Hui Zhang;Shu-Wei Zhang
Helvetica Chimica Acta 2008 Volume 91( Issue 1) pp:136-143
Publication Date(Web):
DOI:10.1002/hlca.200890004
Abstract
Two unusual 9′-norneolignans, bombasin (1) and bombasin 4-O-β-glucoside (2), and a novel D-gulono-γ-lactone derivative, bombalin (3), were isolated from the flowers of Bombax malabaricum, together with the three known compounds dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (4), trans-3-(p-coumaroyl)quinic acid (5), and neochlorogenic acid (6). Their structures were elucidated by extensive spectroscopic methods as well as chemical transformation. Compounds 1–3 were evaluated against the HGC-27 gastrointestinal and Hela cervical human cancer cell lines, but all were inactive in both lines (IC50>50 μM).
Co-reporter:Shu-Wei Zhang and Li-Jiang Xuan
The Journal of Antibiotics 2008 61(1) pp:43-45
Publication Date(Web):2008-01-01
DOI:10.1038/ja.2008.109
A new cyclopentenone derivative, named as 2-(3-carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone, and a new furan derivative, named as 5-(2-hydroxyethyl)-2-furanacetic acid, were isolated from the cultivated Cordyceps cicadae mycelia. Their structures were determined by spectroscopic methods, including 2D NMR analyses.
Co-reporter:Xiaohui Zhang, Huilin Zhu, Shuwei Zhang, Qiang Yu and Lijiang Xuan
Journal of Natural Products 2007 Volume 70(Issue 9) pp:1526-1528
Publication Date(Web):September 1, 2007
DOI:10.1021/np070256j
Phytochemical investigation of the chemical constituents of the roots of Bombax malabaricum afforded nine cadinane sesquiterpenoids, including five new compounds (bombamalones A–D, 1–4; bombamaloside, 5), and four known compounds (isohemigossypol-1-methyl ester, 6; 2-O-methylisohemigossylic acid lactone, 7; bombaxquinone B, 8; and lacinilene C, 9). The structures of 1–5 were identified by spectroscopic methods and comparison with literature values. Compounds 1–9 were evaluated against the HGC-27 human gastrointestinal cancer cell line, but all were inactive (IC50 >10 µM).
Co-reporter:Li-Jiang Xuan;Shu-Wei Zhang
Helvetica Chimica Acta 2007 Volume 90(Issue 2) pp:404-410
Publication Date(Web):20 FEB 2007
DOI:10.1002/hlca.200790047
Five new aromatics bearing a 4-O-methylglucose unit, namely 3-methoxy-1,4-hydroquinone 1-(4′-O-methyl-β-glucopyranoside) (=4-hydroxy-3-methoxyphenyl 4-O-methyl-β-glucopyranoside; 1), 3-methoxy-1,4-hydroquinone 4-(4′-O-methyl-β-glucopyranoside) (=4-hydroxy-2-methoxyphenyl 4-O-methyl-β-glucopyranoside; 2), vanillic acid 4-(4′-O-methyl-β-glucopyranoside) (=3-methoxy-4-[(O-methyl-β-glucopyranosyl)oxy]benzoic acid; 3), 5-methoxycinnamic acid 3-O-(4′-O-methyl-β-glucopyranoside) (=(2E)-3-{3-methoxy-5-[(4-O-methyl-β-glucopyranosyl)oxy]phenyl}prop-2-enoic acid; 4), and naphthalene-1,8-diol 1,8-bis(4′-O-methyl-β-glucopyranoside) (=naphthalene-1,8-diyl bis(4-O-methyl-β-glucopyranoside; 5), were isolated from the cultivated Cordyceps cicadae mycelia, together with thirteen known compounds. Their structures were determined by spectroscopic methods. The absolute configurations of the sugar units were not determined.
Co-reporter:Qiang Yu;Hui-Lin Zhu;Xiao-Hui Zhang
Chemistry & Biodiversity 2007 Volume 4(Issue 5) pp:998-1002
Publication Date(Web):18 MAY 2007
DOI:10.1002/cbdv.200790091
A new cardenolide, 3-O-(β-glucopyranosyl)acovenosigenin A (1), was isolated from the roots of Streptocaulon griffithii, together with eight known cardenolides, compounds 2–9. All compounds showed significant in vitro inhibition of the proliferation of the human gastrointestinal cancer cell line HGC-27, with IC50 values in the range of ca. 20–564 nM, taxol being used as positive control. Compound 1 was also found to be strongly cytotoxic against other human tumor cell lines, including A549, MCF-7, and Hela cells.
Co-reporter:Lili Jiang, Shuwei Zhang, Lijiang Xuan
Phytochemistry 2007 Volume 68(Issue 19) pp:2444-2449
Publication Date(Web):October 2007
DOI:10.1016/j.phytochem.2007.05.032
Five oxanthrone C-glycosides, namely rumejaposide A–E, and an epoxynaphthoquinol, together with eight known compounds, 2,6-dihydroxy benzoic acid, 4-hydroxy benzoic acid, epicatechin, 4-hydroxy-3-methoxy benzoic acid, 2,6-dimethoxy-4-hydroxyl benzoic acid, rutin, emodin and 2-acetyl-1,8-dihydroxy-3-methyl-6-methoxynaphthalene, were isolated from the roots of Rumex japonicus. The structures of the oxanthrone C-glycosides were elucidated by application of spectroscopic methods as (10R)10-C-β-glucopyranosyl-1,8,10-trihydroxy-2-carboxyl-3-methyl-9(10H)-anthracenone, (10S)10-C-β-glucopyranosyl-1,8,10-trihydroxy-2-carboxyl-3-methyl-9(10H)-anthracenone, (10R)10-C-β-glucopyranosyl-1,6,8,10-tetrahydroxy-2-carboxyl-3-methyl-9(10H)-anthracenone, (10R)10-C-β-glucopyranosyl-1,6,8,10-tetrahydroxy-3-hydroxymethyl-9(10H)-anthracenone, and (10R)10-C-β-glucopyranosyl-1,6,8,10-tetrahydroxy-3-methyl-9(10H)-anthracenone. Absolute configurations for each compound were deduced by analyses of CD spectra and comparison with those known similar compounds. The structure of epoxynaphthoquinol was elucidated by spectroscopic methods as 3-acetyl-2-methyl-1,4,5-trihydroxy-2,3-epoxynaphthoquinol, and its relative configuration was determined by a 2D-ROESY experiment.Five oxanthrone C-glycosides, namely rumejaposide A–E, and an epoxynaphthoquinol were isolated from roots of Rumex japonicus, along with eight known compounds. Their structures were established by spectroscopic methods.
Co-reporter:Lijiang Xuan;Shuwei Zhang
Helvetica Chimica Acta 2006 Volume 89(Issue 6) pp:1241-1245
Publication Date(Web):27 JUN 2006
DOI:10.1002/hlca.200690121
Three new phenolic compounds, 5-O-(β-apiosyl-(1 2)-O-β-xylopyranosyl)gentisic acid (1), 1-O-(β-apiosyl-(1 6)-O-β-glucopyranosyl)-3-O-methylphloroglucinol (2), and 15-O-(α-rhamnopyranosyl)aloe-emodin (3), together with the known compound aloe emodin (4), were isolated from the stems of Spatholobus suberectus. Their structures were characterized by chemical and spectroscopic methods. The absolute configurations of the sugar units were not determined.
Co-reporter:Yong Zheng, Wei-Bin Song, Shu-Wei Zhang and Li-Jiang Xuan
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 23) pp:NaN6478-6478
Publication Date(Web):2015/05/07
DOI:10.1039/C5OB00601E
A ruthenium-catalyzed oxidative coupling of 2-aryl-quinazolinones with olefins via C–H bond activation followed by an intramolecular aza-Michael reaction is described. This strategy allows the direct and efficient construction of pyrrolo[2,1-b]quinazolin-9(1H)-one scaffolds.
Co-reporter:Yong Zheng, Wei-Bin Song and Li-Jiang Xuan
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 44) pp:NaN10843-10843
Publication Date(Web):2015/08/25
DOI:10.1039/C5OB01465D
A directing-group-assisted copper-catalyzed oxidative esterification of phenols with aldehydes using TBHP as an oxidant was described. This methodology which showed the advantages of base, ligand free, short routes and functional group tolerance could be used as an alternative protocol for the classical esterification reactions.