Co-reporter:Joseph Sakah Kaunda
Natural Products and Bioprospecting 2017 Volume 7( Issue 2) pp:181-199
Publication Date(Web):27 February 2017
DOI:10.1007/s13659-017-0123-0
Carissa L. is a genus of the family Apocynaceae, with about 36 species as evergreen shrubs or small trees native to tropical and subtropical regions of Africa, Asia and Oceania. Most of Carissa plants have been employed and utilized in traditional medicine for various ailments, such as headache, chest complains, rheumatism, oedema, gonorrhoea, syphilis, rabies. So far, only nine Carissa species have been phytochemically studied, which led to the identification of 123 compounds including terpenes, flavonoids, lignans, sterols, simple phenolic compounds, fatty acids and esters, and so on. Pharmacological studies on Carissa species have also indicated various bioactive potentials. This review covers the peer-reviewed articles between 1954 and 2016, retrieved from Pubmed, ScienceDirect, SciFinder, Wikipedia and Baidu, using “Carissa” as search term (“all fields”) and with no specific time frame set for search. Fifteen important medicinal or ornamental Carissa species were selected and summarized on their botanical characteristics, geographical distribution, traditional uses, phytochemistry, and pharmacological activities.
Co-reporter:Cheng-Zhen Gu, Jun-Jiang Lv, Xiao-Xia Zhang, Yi-Jun Qiao, Hui Yan, Yan Li, Dong Wang, Hong-Tao Zhu, Huai-Rong Luo, Chong-Ren Yang, Min Xu, and Ying-Jun Zhang
Journal of Natural Products 2015 Volume 78(Issue 8) pp:1829-1840
Publication Date(Web):July 22, 2015
DOI:10.1021/acs.jnatprod.5b00027
The roots of Panax notoginseng, an important Chinese medicinal plant, have been used traditionally in both the raw and processed forms, due to the different chemical constituents and bioactivities found. Thirty-eight dammarane-type triterpenoid saponins were isolated from the steam-processed roots of P. notoginseng, including 18 new substances, namely, notoginsenosides SP1–SP18 (1–18). The structures of 1–18 were determined on the basis of spectroscopic analysis and acidic hydrolysis. The absolute configuration of the hydroxy group at C-24 in 1–4, 19, and 20 was determined in each case by Mo2(AcO)4-induced circular dichroism. The new compounds were found to feature a diversity of highly oxygenated side chains, formed by hydrolysis of the C-20 sugar moiety followed by dehydration, dehydrogenation, epoxidation, hydroxylation, or methoxylation of the main saponins in the raw roots. The new saponins 1, 2, 6–8, 14, and 17 and the known compounds 20–27 showed promoting effects on the differentiation of PC12 cells, at a concentration of 10 μM.
Co-reporter:Jun-Jiang Lv, Shan Yu, Ying Xin, Hong-Tao Zhu, Dong Wang, Rong-Rong Cheng, Chong-Ren Yang, Min Xu and Ying-Jun Zhang
RSC Advances 2015 vol. 5(Issue 37) pp:29098-29107
Publication Date(Web):13 Mar 2015
DOI:10.1039/C4RA16624H
Time-dependent density functional theory (TDDFT) calculated electronic circular dichroism (ECD) and Mosher’s method were applied to establish the absolute configurations of six new highly oxygenated cleistanthane diterpenoid glucosides, phyllanembloids A–F (1–6), isolated from the roots of Phyllanthus emblica. Compounds 1–5 featured a carboxyl group at C-13 adjacent to the hydroxyl group at C-12, and are the first examples of cleistanthane diterpenoids with a salicylic acid fragment. The carboxyl group at C-13 can significantly affect the CD spectrum of cleistanthane diterpenoids, and make the excitations of phenylethylene dominate the Cotton effects (240 and 280 nm), rather than the benzene ring excitations dominating the Cotton effects at 220 and 240 nm as in the 13-methyl analogues. The characteristic Cotton effects of cleistanthane diterpenoids were summarized according to the experimental and calculated ECD curves, which can be applied as a common method to determine the absolute configurations of this type of diterpenoid.
Co-reporter:Jun-Jiang Lv, Shan Yu, Ying Xin, Rong-Rong Cheng, Hong-Tao Zhu, Dong Wang, Chong-Ren Yang, Min Xu, Ying-Jun Zhang
Phytochemistry 2015 Volume 117() pp:123-134
Publication Date(Web):September 2015
DOI:10.1016/j.phytochem.2015.06.001
•14 norbisabolane sesquiterpenoid glycosides were isolated from Phyllanthus emblica.•Their structures comprised of sesquiterpenoid aglycones and 14 saccharide moieties.•The absolute configurations of the aglycones were established by calculated ECD without hydrolysis.•The absolute configurations of saccharides were determined by chiral HPLC analysis.•Effects of anti CVB3, EV71, H3N2, HSV-1, and five cancer cell lines were evaluated.In an effort to identify anti-viral and cytotoxic compounds from Phyllanthus spp., 14 highly oxygenated norbisabolane sesquiterpenoids, phyllaemblicins H1–H14, were isolated from the roots of Phyllanthus emblica Linn, along with phyllaemblicins B and C and glochicoccinoside D. Their structures were determined on the basis of detailed spectroscopic analysis and chemical methods. Determination of absolute configurations of these compounds was facilitated by theoretical calculations of electronic circular dichroism (ECD) spectra using time-dependent density functional theory (TDDFT) for the aglycone components, and pre-column derivative/chiral HPLC analysis for the monosaccharides. The known glochicoccinoside D displayed potent activity against influenza A virus strain H3N2 and hand, foot and mouth virus EV71, with IC50 values of 4.5 ± 0.6 and 2.6 ± 0.7 μg/ml, respectively. Phyllaemblicin H1 showed moderate cytotoxicity against human cancer cell lines A-549 and SMMC-7721, with IC50 values of 4.7 ± 0.7 and 9.9 ± 1.3 μM, respectively.Pre-column derivative/chiral separation/DAD detection and theoretical calculations of ECD spectra using TDDFT were used to determine the absolute configurations of phyllaemblicins H1–H14, with antiviral activities, isolated from P. emblica.
Co-reporter:Jun-Jiang Lv, Ya-Feng Wang, Jing-Min Zhang, Shan Yu, Dong Wang, Hong-Tao Zhu, Rong-Rong Cheng, Chong-Ren Yang, Min Xu and Ying-Jun Zhang
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 43) pp:8764-8774
Publication Date(Web):12 Sep 2014
DOI:10.1039/C4OB01196A
During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1–G8 (1–8) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6–G8 (6–8) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory. The sesquiterpenoid glycoside dimers 6–9 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 ± 0.97 and 5.68 ± 1.75 μM towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively.
Co-reporter:Li-Wen Tian, Mu-Ke Tao, Min Xu, Jing Hu, Hong-Tao Zhu, Wen-Yong Xiong, Dong Wang, Chong-Ren Yang, and Ying-Jun Zhang
Journal of Agricultural and Food Chemistry 2014 Volume 62(Issue 50) pp:12229-12234
Publication Date(Web):November 19, 2014
DOI:10.1021/jf5036959
Ripe Pu-er tea, a special microbial postfermented tea originated from Yunnan Province, China, since ancient times, is made from green Pu-er tea prepared from the leaves of Camellia sinensis var. assamica (Theaceae). Chemical investigation on thearubigin (n-BuOH-soluble) fraction of the commercial ripe Pu-er tea, led to the identification of four new flavan-3-ol derivatives, 8-carboxymethyl-(+)-catechin (1), 8-carboxymethyl-(+)-catechin methyl ester (2), 6-carboxymethyl-(+)-catechin (3), and 6-carboxyl-(−)-gallocatechin (4), together with 18 known compounds, including other three flavan-3-ol derivatives (5–7), 10 flavonoid glycosides (8–17), two hydrolyzable tannins (18 and 19), two quinic acid derivatives (20–21), and a purine alkaloid (22). Flavonoid glycosides 8–11 are reported from tea plants for the first time. The thearubigin fraction of ripe Pu-er tea was qualitatively analyzed by HPLC, and gallic acid was found to be the major component. Compounds 4, 6–17, 21 and 22 were tested for their acute activities on insulin sensitivity in differentiated 3T3-L1 adipocytes, but none of them showed significant bioactivity at a concentration of 10 μM.
Co-reporter:Li-Wen Tian, Min Xu, Xing-Cong Li, Chong-Ren Yang, Hua-Jie Zhu and Ying-Jun Zhang
RSC Advances 2014 vol. 4(Issue 41) pp:21373-21378
Publication Date(Web):02 May 2014
DOI:10.1039/C4RA01078G
Two new phloroglucinol-coupled sesquiterpenoids, eucalmaidials A and B (1 and 2), were isolated from the juvenile leaves of Eucalyptus maideni, along with eight known macrocarpals (3–10), eucalyptone (11), and three known triterpenoids (12–14). Eucalmaidials A and B represent a new skeleton of phloroglucinol-coupled iphionane. Their structures were elucidated by extensive NMR spectroscopic analysis and theoretical calculation of the 13C NMR chemical shifts. The biosynthetic pathway of 1 and 2 was also postulated. Compounds 1, 3, 5, 7, 8, and 10–14 were evaluated for their antifungal and antibacterial activities. Compound 1 exhibited antifungal activity against Candida glabrata with an IC50 value of 0.75 μg mL−1.
Co-reporter:Jian-Qiang Zhao;Yan-Ming Wang;Hong-Tao Zhu
Natural Products and Bioprospecting 2014 Volume 4( Issue 4) pp:233-242
Publication Date(Web):2014 August
DOI:10.1007/s13659-014-0026-2
Two new highly oxygenated limonoids, flexuosoids A (1) and B (2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D–F (3–5), were isolated from the roots of Phyllanthus flexuosus, in addition to three known lignans, phyllanthusmin C, arabelline, and (+)-diasyringaresinol. Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1 and 2, two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1, C-2, C-3, C-7, C-11, C-17, and C-30, represent the second example of limonoids in the Euphorbiaceae family. Most of the isolates were tested for their antifeedant, anti-herpes simplex virus 1, and cytotoxic activities. The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm (Spodoptera exigua) with EC50 values of 25.1 and 17.3 μg/cm2, respectively. In addition, both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, along with the known lignan glycoside, phyllanthusmin C, with the IC50 values of 11.5 (1), 8.5 (2), and 7.8 (phyllanthusmin C) μM, respectively.
Co-reporter:Fang-Fang Liu;Yan-Ming Wang;Hong-Tao Zhu
Natural Products and Bioprospecting 2014 Volume 4( Issue 5) pp:297-308
Publication Date(Web):2014 October
DOI:10.1007/s13659-014-0039-x
“Long-Dan” and “Qin-Jiao” are two important TCM herbs since ancient times in China. In the Chinese Pharmacopoeia, the dried roots and rhizomes of four species from the genus Gentiana, e.g. Gentiana manshurica, G. scabra, G. triflora and G. rigescens, are recorded under the name of Gentianae Radix et Rhizoma (“Long-Dan” in Chinese), while the other four species from the same genus including G. macrophylla, G. crassicaulis, G. straminea and G. duhurica are recorded and used as the raw materials of Gentianae Macrophyllae Radix (“Qin-Jiao” in Chinese). On the basis of the establishment of a validated HPLC–UV method for quantifying simultaneously, five iridoid glycosides, e.g. loganic acid (1), swertiamarinin (2), gentiopicroside (3), sweroside (4) and 2′-(o,m-dihydroxybenzyl)sweroside (5) have been used successfully as chemical markers for the comparison of the species used as “Long-Dan”, “Qin-Jiao” and their adulterants in the present study. The results suggested that four iridoid glycosides 1–4 commonly existed in both “Long-Dan” and “Qin-Jiao”, while 2′-(o,m-dihydroxybenzyl)sweroside (5) also existed as one of the major components in “Dian-Long-Dan” species. Moreover, the contents of compounds 1–5 were various in different “Long-Dan” and “Qin-Jiao” species. Herein, we profiled and compared three “Long-Dan” species, four “Qin-Jiao” species and five adulterants by applying multivariate statistical techniques to their HPLC data sets to establish the differences and/or similarities.
Co-reporter:Jun-Jiang Lv, Shan Yu, Ya-Feng Wang, Dong Wang, Hong-Tao Zhu, Rong-Rong Cheng, Chong-Ren Yang, Min Xu, and Ying-Jun Zhang
The Journal of Organic Chemistry 2014 Volume 79(Issue 12) pp:5432-5447
Publication Date(Web):May 13, 2014
DOI:10.1021/jo5004604
Nineteen new highly oxygenated norbisabolane sesquiterpenoids, phyllanthacidoid acid methyl ester (1), and C-T (4–21), were isolated from Phyllanthus acidus Skeels, together with two known ones, phyllanthusols A (2) and B (3), whose sugar moiety was revised as glucosamine-N-acetate, rather than the previously assigned mannosamine-N-acetate. Compounds 2 and 3 were renamed respectively as phyllanthacidoids A (2) and B (3) to avoid confusion. All of the isolates except for 1 are glycosides, whose saccharide moieties possess a pentaoxy cyclohexane (scyllo quercitol) connecting with glucosamine-N-acetate or glucosyl moieties, which are first examples in natural products. Phyllanthacidoids N-R (15–19) with 8R configurations and/or 5,8-diketal skeleton, are unprecedented structures among norbisabolane sesquiterpenoids. Phyllanthacidoids S (20) and T (21) have the unusual tricyclo [3.1.1.1] oxygen bridge skeleton formed by a diketal system, of which the relative configurations of the aliphatic chain were assigned on the basis of heteronuclear coupling constants. The absolute configurations of compounds (1–21) were established by means of calculated electronic circular dichroism (ECD) and coupling constants. Compounds 1–5, 7–9, 10, and 14 displayed potential anti-hepatitis B virus (HBV) activities, with IC50 values of 0.8–36 μM against HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg), and the results indicated that the 5-ketal group and sugar moieties had contributions to the selectivity of HBsAg and HBeAg.
Co-reporter:Jian-Qiang Zhao, Yan-Ming Wang, Hong-Ping He, Sheng-Hong Li, Xiao-Nian Li, Chong-Ren Yang, Dong Wang, Hong-Tao Zhu, Min Xu, and Ying-Jun Zhang
Organic Letters 2013 Volume 15(Issue 10) pp:2414-2417
Publication Date(Web):May 2, 2013
DOI:10.1021/ol400875n
A new 6/6/5/6-fused limonoid, phyllanthoid A (1), possessing both 19/30 and 19/29 oxygen bridges was isolated from Phyllanthus cochinchinensis (Euphorbiaceae), together with a new related limonoid, phyllanthoid B (2). Their structures were determined by spectroscopic analysis and single-crystal X-ray diffraction in the case of 1. Compound 1 displayed moderate antifeedant against the generalist plant-feeding insect Spodoptera exigua and cytotoxicity against the MCF-7 cell line.
Co-reporter:Jun-Jiang Lv ; Min Xu ; Dong Wang ; Hong-Tao Zhu ; Chong-Ren Yang ; Yi-Fei Wang ; Yan Li
Journal of Natural Products 2013 Volume 76(Issue 5) pp:926-932
Publication Date(Web):April 26, 2013
DOI:10.1021/np400084t
Six new bisbenzylisoquinoline alkaloids (1–6) and seven known compounds (8–14) were isolated from the tubers of Stephania epigaea, in addition to the major alkaloid, cepharanthine (7). The structures of 1–6 were elucidated by combined spectroscopic data analysis and chemical methods, with their configurations determined from their optical rotation values and confirmed using circular dichroism. Compounds 1–6 belong to the oxyacanthine type of bisbenzylisoquinoline alkaloids and have a rare methylenedioxy substituent. Compound 1, a dimer composed of benzylisoquinoline and seco-aristolactam units, represents a new type of bisbenzylisoquinoline alkaloid, while compounds 3–6 are bisbenzylisoquinoline N-oxides. These compounds were evaluated for their in vitro cytotoxicities against six human cancer cell lines (A-549, ECA109, HL-60, MCF-7, SMMC-7721, and SW480). Cepharanthine (7), the major component of S. epigaea, exhibited cytotoxicity against all of these cancer cell lines except ECA109, while its known analogue, 10, displayed cytotoxicity against all six cancer cell lines.
Co-reporter:Jian-Qiang Zhao, Jun-Jiang Lv, Yan-Ming Wang, Min Xu, Hong-Tao Zhu, Dong Wang, Chong-Ren Yang, Yi-Fei Wang, Ying-Jun Zhang
Tetrahedron Letters 2013 Volume 54(Issue 35) pp:4670-4674
Publication Date(Web):28 August 2013
DOI:10.1016/j.tetlet.2013.06.082
Three structurally interesting new diterpenoids, phyllanflexoids A–C (1–3), together with cleistanthol (4) were isolated from the roots of Phyllanthus flexuosus. Their structures with the absolute stereochemistry were elucidated on the basis of comprehensive spectroscopic analysis, computational method, and acidic hydrolysis in the case of 3. Compounds 1–3 were phenylacetylene-bearing tricyclic diterpenes and 3 was the first example of phenylacetylene-bearing 18-nor-diterpenoid glycoside. Compounds 1, 2, and 4 exhibited weak cytotoxicity against human esophagus cancer cell ECA109 with IC50 of 42.7, 21.4, and 24.5 μM, respectively.
Co-reporter:Gai-Mei She;Chong-Ren Yang
Chemistry & Biodiversity 2013 Volume 10( Issue 6) pp:1081-1087
Publication Date(Web):
DOI:10.1002/cbdv.201200103
Abstract
Balanophora involucrata Hook.f. & Thomson (Balanophoraceae) is a parasite plant often growing on the roots of leguminous plants. The whole herb has been used medicinally for the treatment of irregular menstruation, cough, hemoptysis, traumatic injury and bleeding, dizziness and gastralgia in Yunnan Province, China. The 2,2-diphenyl-2-picrylhydrazyl (DPPH) assay on the 60% aq. acetone extract of the fresh whole plant of B. involucrata showed considerable radical-scavenging activity (SC50 15.3 μg/ml). Further purification on the extract led to the isolation of one new phenolic glycoside, sieboldin-3′-ketocarboxylic acid (1), and one new cyanogenic glycoside, proacacipetalin 6′-O-β-D-glucopyranoside (2), together with 26 known compounds including three 4″-O-galloyl and 2″,3″-O-(S)-hexahydroxydiphenoyl (HHDP) derivatives of dihydrochalcone glucosides, seven hydrolyzable tannins, and alkane glycosides. The cyanogenic compound isolated from the Balanophoraceae family for the first time might be a signal molecule between B. involucrata and its hosts. The free-radical-scavenging activity of the isolated compounds was also examined by DPPH assay.
Co-reporter:Ying Zhang;Chong-Ren Yang
Helvetica Chimica Acta 2013 Volume 96( Issue 9) pp:1807-1813
Publication Date(Web):
DOI:10.1002/hlca.201200586
Abstract
Two new spirostanol saponins, namely elephanosides G and H (1 and 2, resp.) were isolated from the leaves of Yucca elephantipes (Agavaceae), together with the two known furostanol saponins 3 and 4 and the six known flavonoid O- and C-glycosides 5–10. The new structures were elucidated as (3β,25S)-spirost-5-en-3-yl O-β-D-glucopyranosyl-(13)-O-β-D-glucopyranosyl-(14)-β-D-galactopyranoside (1) and (3β,5β,25R)-3-[(2-O-β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]spirostan-12-one (2) on the basis of detailed spectroscopic analysis and acidic hydrolysis.
Co-reporter:Bin Wang;Hong-Tao Zhu;Dong Wang;Chong-Ren Yang
Natural Products and Bioprospecting 2013 Volume 3( Issue 3) pp:93-98
Publication Date(Web):2013 June
DOI:10.1007/s13659-013-0028-5
Co-reporter:Jian-Qiang Zhao;Yan-Ming Wang;Dong Wang
Natural Products and Bioprospecting 2013 Volume 3( Issue 2) pp:61-65
Publication Date(Web):2013 April
DOI:10.1007/s13659-013-0026-7
Co-reporter:Dong Wang, Peng-Ying Liao, Hong-Tao Zhu, Ke-Ke Chen, Min Xu, Ying-Jun Zhang, Chong-Ren Yang
Food Chemistry 2012 Volume 132(Issue 4) pp:1808-1813
Publication Date(Web):15 June 2012
DOI:10.1016/j.foodchem.2011.12.010
Notoginseng, the root of Panax notoginseng (Burk.) F. H. Chen (Araliaceae), a famous traditional Chinese medicine, has been used in both raw and processed forms due to their different therapeutic functions. In this study, HPLC analyses on saponin composition of processed notoginseng were conducted, which revealed that, during the steaming process, the five main saponin constituents (ginsenosides Rg1, Rb1, Rd, and Re, and notoginsenoside R1) in raw notoginseng decreased gradually and some other new saponins were formed. Among these, eight newly converted ginsenosides were identified as 20(S)-Rh1, 20(R)-Rh1, Rk3, Rh4, 20(S)-Rg3, 20(R)-Rg3, Rk1 and Rg5. Different processing methods, including steaming and baking, were studied, along with the correlative dynamic curves of the transformation of saponins. The results indicated that the moisture content and temperature were the determinant effecting factors in the preparing process, and water content was necessary and high temperature was helpful for saponin transformation.Highlights► Processed Panax notoginseng is one important form of this medical plant. ► Saponin composition differs in raw and steamed notoginseng. ► Eight modified saponins were identified in steamed notoginseng. ► Water content is necessary for saponin transformation. ► High temperature is helpful for saponin transformation.
Co-reporter:Li-Fang Zhu, Min Xu, Hong-Tao Zhu, Dong Wang, Shi-Xiong Yang, Chong-Ren Yang, and Ying-Jun Zhang
Journal of Agricultural and Food Chemistry 2012 Volume 60(Issue 49) pp:12170-12176
Publication Date(Web):November 21, 2012
DOI:10.1021/jf302726t
Camellia taliensis (W. W. Smith) Melchior, belonging to the genus Camellia sect. Thea (Theaceae), is an endemic species distributed from the west and southwest of Yunnan province, China, to the north of Myanmar. Known as a wild tea tree, its leaves have been used commonly for producing tea beverages by the local people of its growing area. One new flavan-3-ol dimer, talienbisflavan A (1), was isolated from green tea prepared from the leaves of C. taliensis collected from the east side of the Ai-Lao mountains, Yuanjiang county of Yunnan province, China. In addition, five hydrolyzable tannins (2–6), five flavonols and flavonol glycosides (9–13), three flavan-3-ols (14–16), nine simple phenolic compounds and glycosides (7, 8, and 17–23), and caffeine (24) were identified. Their structures were determined by detailed spectroscopic analysis. All of the isolated phenolic compounds were tested for their antioxidant activities by DPPH and ABTS+ radical scavenging assays. The contents of its main chemical compositions were also compared with those collected from the Lincang area of Yunnan province by high-performance liquid chromatography analysis.
Co-reporter:Li-Wen Tian;Min Xu;Yan Li;Xing-Yao Li;Dong Wang;Hong-Tao Zhu;Chong-Ren Yang
Chemistry & Biodiversity 2012 Volume 9( Issue 1) pp:123-130
Publication Date(Web):
DOI:10.1002/cbdv.201100021
Abstract
Three new phenolic compounds, eucalmaidin F (1), (3S)-5-guaiacyl-3-hydroxypentanoic acid (2), and 8-β-C-glucopyranosyl-5,7-dihydroxy-2-isobutylchromone (3), were isolated from the branches of E. maideni, together with 30 known compounds, including four phenylpropanoids, three lignans, four phloroglucinol glucosides, five dihydroflavonoids, seven simple phenolic compounds, six terpenoids, and glycerol. The new structures were established by spectroscopic studies (MS, and 1D- and 2D-NMR), chemical degradation, and modified Mosher's method. Compounds 3, guaiacylglycerol, 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one, caffeic acid, (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid, (7′S,8R,8′R)-lyoniresinol, (+)-lyoresinol 3α-O-α-L-rhamnopyranoside, garcimangosone, phlorocetophenone 2′-glucopyranoside, (+)-taxifolin 3α-O-α-L-rhamnopyranoside, (+)-aromadendrin, (+)-taxifolin, resveratrol, piceatannol, 3,4,5-trihydroxyphenol. Tachiaside, gallic acid, macrocapals A und G, and oleuropeic acid were evaluated for their cytotoxicities against five human cancer cell lines. Resveratrol, piceatannol, gallic acid, and macrocapal G exhibited moderate inhibitory effects on human myeloid heukemia HL-60 cell, with IC50 values of 22.05, 22.05, 7.75, and 31.93 μM, respectively; and only macrocapal G showed inhibitory effect on hepatocellular carcinoma SMMC-7721 cell, with an IC50 value of 26.75 μM.
Co-reporter:Qing-An Zheng;Min Xu;Chong-Ren Yang;Dong Wang
Natural Products and Bioprospecting 2012 Volume 2( Issue 3) pp:111-116
Publication Date(Web):2012 June
DOI:10.1007/s13659-012-0020-5
Co-reporter:Tao Lv;Min Xu;Dong Wang;Hong-Tao Zhu
Natural Products and Bioprospecting 2012 Volume 2( Issue 5) pp:217-221
Publication Date(Web):2012 October
DOI:10.1007/s13659-012-0067-3
Chemical study on the roots of Gentiana crassicaulis Duthie ex Burk (Gentianaceae) afforded 15 compounds, including two new iridoid glycosides, qinjiaosides B (1) and C (2). Their structures were elucidated by spectroscopic methods and chemical evidence. The isolated iridoid glycosides 1, 4–6 and 8–11 were tested for their anti-inflammatory activity by the inhibitory effects on LPS-induced NO and TNF-α production in macrophage RAW264.7 cells. All of them showed inhibitory effects on inflammatory mediators NO at a concentration of 15 µM, while 5 and 9 displayed the most potential inhibitory effects on TNF-α with IC50 of 0.06 and 0.05 µM, respectively. The structure-activity relationships (SARs) of these iridoid derivatives were discussed.
Co-reporter:Yan-Ming Wang;Min Xu;Dong Wang;Hong-Tao Zhu
Natural Products and Bioprospecting 2012 Volume 2( Issue 1) pp:1-10
Publication Date(Web):2012 February
DOI:10.1007/s13659-011-0043-3
“Long-Dan” is an important traditional Chinese medicinal (TCM) herb used widely for the treatment of inflammation, hepatitis, rheumatism, cholecystitis, and tuberculosis. In the Chinese Pharmacopoeia, the roots and rhizomes of four species from the genus Gentiana (Gentianaceae) are recorded as the original materials of “Long-Dan”, called Gentianae Radix et Rhizoma. The species included G. manshurica, G. scabra, G. triflora and G. rigescens, which are distributed in different areas of China. Though iridoid and secoiridoid glucosides were reported as the main constituents in “Long-Dan”, these four different species also resulted in different minor components, which may related to their pharmacological activities. Herein, we summarized the herbal textual study, distribution, chemical constituents, biological investigation and quality control of the recorded “Long-Dan” origins in Chinese Pharmacopoeia during the period 1960 to 2011.
Co-reporter:Xian-You Wang, Min Xu, Chong-Ren Yang, Ying-Jun Zhang
Food Chemistry 2011 Volume 126(Issue 3) pp:1039-1043
Publication Date(Web):1 June 2011
DOI:10.1016/j.foodchem.2010.11.116
The seed of Michelia hedyosperma Law (Magnoliaceae) is a commonly used spice by the local people living in the south of Yunnan province, China. From which, six new phenylpropanoid glycosides, michehedyosides A–F (1–6) were obtained, in addition to six known compounds, eugenol, eugenol 4-O-β-d-glucopyranoside, martynoside, alaschanioside C, 3,4-methylenedioxycinnamyl alcohol, and (+)-pinoresinol 4-O-β-d-glucoside. Their structures were elucidated on the basis of detailed spectroscopic analyses and chemical methods.Research highlights► The seed of Michelia hedyosperma is a commonly used spice in the southern China. ► Six new phenylpropanoid glycosides were identified, together with six known ones. ► The new compounds were named michehedyosides A–F.
Co-reporter:Da-Fang Gao, Min Xu, Ping Zhao, Xiao-Yuan Zhang, Yi-Fei Wang, Chong-Ren Yang, Ying-Jun Zhang
Food Chemistry 2011 Volume 124(Issue 2) pp:432-436
Publication Date(Web):15 January 2011
DOI:10.1016/j.foodchem.2010.06.048
The seed cake is a big by-product after crushing cooking oil from the seeds of Camellia oleifera Abel. Chemical investigation on the seed cake of C. oleifera led to the isolation of two new kaempferol acetylated glycosides (1 and 2). In addition, five kaempferol glycosides (3–7) and their aglycone, kaempferol (8), were also obtained, in addition to gallic acid (9). Their structures were determined by the detailed spectroscopic analysis and acidic hydrolysis. The new compounds were characterised as kaempferol-3-O-[4′′′′-O-acetyl-α-l-rhamnopyranosyl-(1→6)]-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (1) and kaempferol-3-O-[4′′′′-O-acetyl-α-l-rhamnopyranosyl-(1→6)]-[β-d-xylopyranosyl-(1→2)]-β-d-gluco-pyranoside (2), respectively. The DPPH radical scavenging activity of all the isolated compounds was described.
Co-reporter:Li-Wen Tian, Min Xu, Dong Wang, Hong-Tao Zhu, Chong-Ren Yang, Ying-Jun Zhang
Biochemical Systematics and Ecology 2011 Volume 39(Issue 2) pp:156-158
Publication Date(Web):April 2011
DOI:10.1016/j.bse.2011.01.014
Eighteen phenolic compounds, including eight flavonoids, five hydrolysable tannins, two lignans and three simple phenolic compounds were isolated on the leaves of Syzygium forrestii (Myrtaceae). Of them, nine compounds are new for the genus Syzygium, while three are new for the family Myrtaceae. The existence of acetylated glycosidic flavonoids in the genus Syzygium is firstly reported. Several flavonoid glycosides and hydrolysable tannins could be served as the chemotaxonomic markers of the genus Syzygium.Highlights► Eighteen phenolic compounds were isolated from Syzygium forrestii Merr. and Perry. ► Nine compounds are new for the genus Syzygium. ► Myricitrin and hydrolysable tannis can serve as the chemosystematic markers.
Co-reporter:Ping Zhao;Da-Fang Gao;Min Xu;Zhuo-Gong Shi;Dong Wang;Chong-Ren Yang
Chemistry & Biodiversity 2011 Volume 8( Issue 11) pp:1931-1942
Publication Date(Web):
DOI:10.1002/cbdv.201000265
Co-reporter:Min Xu;Ming Zhang;Dong Wang;Chong-Ren Yang
Chemistry & Biodiversity 2011 Volume 8( Issue 10) pp:1891-1900
Publication Date(Web):
DOI:10.1002/cbdv.201000220
Abstract
Gentiana rhodanthaFranch. ex Hemsl. (Gentianaceae), an annual herb widely distributed in the southwest of China, has been medicinally used for the treatment of inflammation, cholecystitis, and tuberculosis by the local people of its growing areas. Chemical investigation on the whole plants led to the identification of eight new phenolic compounds, rhodanthenones A–D (1–4, resp.), apigenin 7-O-glucopyranosyl-(13)-glucopyranosyl-(13)-glucopyranoside (5), 1,2-dihydroxy-4-methoxybenzene 1-O-α-L-rhamnopyranosyl-(16)-β-D-glucopyranoside (6), 1,2-dihydroxy-4,6-dimethoxybenzene 1-O-α-L-rhamnopyranosyl-(16)-β-D-glucopyranoside (7), and methyl 2-O-β-D-glucopyranosyl-2,4,6-trihydroxybenzoate (8), together with eleven known compounds, 9–19. Their structures were determined on the basis of detailed spectroscopic analyses and chemical methods. Acetylcholinesterase (AChE) inhibition and cytotoxicity tests against five human cancer cell lines showed that only rhodanthenone D (4) and mangiferin (12) exhibited 18.4 and 13.4% of AChE inhibitory effects at a concentration of 10−4M, respectively, while compounds 1–5 and the known xanthones lancerin (11), mangiferin (12), and neomangiferin (13) displayed no cytotoxicity at a concentration of 40 μM.
Co-reporter:Lei Zhou;Min Xu;Chong-Ren Yang;Yi-Fei Wang
Helvetica Chimica Acta 2011 Volume 94( Issue 2) pp:218-223
Publication Date(Web):
DOI:10.1002/hlca.201000151
Abstract
Four new patchoulol derivatives, 8α,9α-dihydroxypatchoulol (1), 3α,8α-dihydroxypatchoulol (2), 6α-hydroxypatchoulol (3), and 2β,12-dihydroxypatchoulol (4), were isolated from the aerial part of Pogostemon cablin (Labiatae), together with nine known compounds, sesquiterpenoids 5–8 and flavonoids 9–13. Their structures were elucidated by detailed spectroscopic analysis, using 1D- and 2D-NMR techniques.
Co-reporter:Min Zhou;Min Xu;Dong Wang;Hong-Tao Zhu;Chong-Ren Yang
Helvetica Chimica Acta 2011 Volume 94( Issue 11) pp:2010-2019
Publication Date(Web):
DOI:10.1002/hlca.201100085
Abstract
Phytochemical investigation of the rhizomes of Panax japonicus C. A. Meyer (Araliaceae) resulted in the isolation of two new dammarane-type triterpenoid saponins, yesanchinoside R1 (1) and yesanchinoside R2 (2), together with one new natural product, 6′′′-O-acetylginsenoside Re (3). In addition, 25 known compounds, including 23 triterpenoid saponins, 4–26, β-sitosterol 3-O-β-D-glucopyranoside (27), and ecdysterone (28), were also identified. The known saponins 12, 15, and 18–22 were reported for the first time from the title plant. Their structures were elucidated on the basis of detailed spectroscopic analyses, including 1D- and 2D-NMR techniques, as well as acidic hydrolysis.
Co-reporter:Qing Liu;Jun-Jiang Lv;Min Xu;Dong Wang
Natural Products and Bioprospecting 2011 Volume 1( Issue 3) pp:124-128
Publication Date(Web):2011 December
DOI:10.1007/s13659-011-0036-2
Co-reporter:Li-Wen Tian, Ying-Jun Zhang, Chang Qu, Yi-Fei Wang and Chong-Ren Yang
Journal of Natural Products 2010 Volume 73(Issue 2) pp:160-163
Publication Date(Web):January 21, 2010
DOI:10.1021/np900530n
Five new phloroglucinol glycosides, eucalmainosides A−E (1−5), were isolated from the fresh fruits of Eucalyptus maideni, along with 15 flavonoids (6−20), seven (+)-oleuropeic acid derivatives (15, 16, and 22−26), three hydrolyzable tannins (32−34), and six simple phenolic compounds (21, 27−31). Their structures were determined on the basis of spectroscopic analyses, including HSQC, HMBC, and acidic hydrolysis. The in vitro anti-herpes simplex virus 1 (HSV-1) assay indicated that the flavonols, myricetin (6) and quercetin (7), and the ellagitannin isocoriariin F (33) showed weak anti-HSV-1 activity with TIC values of 0.31, 0.33, and 0.12 mM, respectively.
Co-reporter:Min Xu, Ying-Jun Zhang, Xing-Cong Li, Melissa R. Jacob, and Chong-Ren Yang
Journal of Natural Products 2010 Volume 73(Issue 9) pp:1524-1528
Publication Date(Web):August 18, 2010
DOI:10.1021/np100351p
Six new steroidal saponins (1−6), angudracanosides A−F, were isolated from fresh stems of Dracaena angustifolia, together with eight known compounds. The structures of compounds 1−6 were determined by detailed spectroscopic analyses and chemical methods. Antifungal testing of all compounds showed that 6 and 7 were active against Cryptococcus neoformans with IC50s of 9.5 and 20.0 μg/mL, respectively.
Co-reporter:Da-Fang Gao, Min Xu, Chong-Ren Yang, Mei Xu and Ying-Jun Zhang
Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 15) pp:8820-8824
Publication Date(Web):July 13, 2010
DOI:10.1021/jf101490r
Camellia pachyandra Hu. is a species in Camellia sect. Heterogenea (Theaceae), whose leaves have been used for making tea and consumed by the local people living in Yunnan province, China. This is the first investigation of the chemical constituents in the leaves of C. pachyandra, from which 22 phenolic compounds including nine hydrolyzable tannins (1−9), 11 flavonol glycosides (10−20), and two simple phenolics (21, 22) were isolated. It was noted that the leaves of the title plant contained no caffeine and no catechin, whereas hydrolyzable tannins were found to be the major constituents, of which the content of ellagitannin 5 reached to 3.7%. All the isolates were evaluated for their antioxidant activities by DPPH radical scavenging and tyrosinase inhibitory assays. Though the secondary metabolites without caffeine and catechins are different from the commonly consumed tea plants, the results suggested that the leaves of C. pachyandra, rich in hydrolyzable tannins as potent antioxidants, could be developed as an ideal resource for a natural beverage without caffeine.
Co-reporter:Li-Wen Tian;Chong-Ren Yang
Helvetica Chimica Acta 2010 Volume 93( Issue 11) pp:2194-2202
Publication Date(Web):
DOI:10.1002/hlca.201000067
Abstract
Four new phenolic compounds, 7-O-methylcatechin 5-O-β-D-glucopyranoside (1), 6-O-feruloyl-D-glucopyranose (2), demethylpiperitol 4-O-β-D-glucopyranoside (3), and 2-episesaminol 2-O-β-D-glucopyranoside (4) were isolated from the fresh leaves of Eucalyptus maideni, together with six hydrolyzable tannins, 5–10, a flavonol glycoside, 11, three simple phenolics, 12–14, a monoterpene glucoside, 15, and a rosenoside, 16. Their structures were determined on the basis of detailed spectroscopic analysis, acidic hydrolysis, and enzymatic hydrolysis. The known compounds 10 and 13 were obtained from the genus Eucalyptus for the first time.
Co-reporter:Min Xu;Chong-Ren Yang
Helvetica Chimica Acta 2010 Volume 93( Issue 2) pp:302-308
Publication Date(Web):
DOI:10.1002/hlca.200900157
Abstract
Two new steroidal bisdesmosides, cambodracanosides A and B (1 and 2, resp.), were isolated from the fresh stems of Dracaena cambodiana, together with seven known glycosides. The structures of the new saponins were elucidated on the basis of detailed spectroscopic analyses, including 1D- and 2D-NMR techniques, and acidic hydrolysis.
Co-reporter:Qing Liu;Ping Zhao;Xing-Cong Li;MelissaR. Jacob;Chong-Ren Yang
Helvetica Chimica Acta 2010 Volume 93( Issue 2) pp:265-271
Publication Date(Web):
DOI:10.1002/hlca.200900177
Abstract
Three new α-tetralone galloylglucosides, 1–3, were isolated from the fresh pericarps of Juglans sigillata (Juglandaceae), together with six known compounds. The structures of the new compounds were determined as 1,2,3,4-tetrahydro-7-hydroxy-4-oxonaphthalen-1-yl 6-O-[(3,4,5-trihydroxyphenyl)carbonyl]-β-D-glucopyranoside (1), (1S)-1,2,3,4-tetrahydro-8-hydroxy-4-oxonaphthalen-1-yl 6-O-[(3,4,5-trihydroxyphenyl)carbonyl]-β-D-glucopyranoside (2), and 1,2,3,4-tetrahydro-7,8-dihydroxy-4-oxonaphthalen-1-yl 6-O-[(3,4,5-trihydroxyphenyl)carbonyl]-β-D-glucopyranoside (3), respectively, on the basis of detailed spectroscopic analyses, and acidic and enzymatic hydrolysis. The antimicrobial activities of the isolated compounds 2, 4, and 7–9 were evaluated.
Co-reporter:Li-Wen Tian, Ying Pei, Ying-Jun Zhang, Yi-Fei Wang and Chong-Ren Yang
Journal of Natural Products 2009 Volume 72(Issue 6) pp:1057-1060
Publication Date(Web):May 7, 2009
DOI:10.1021/np800760p
Five new 7-O-methylkaempferol and -quercetin glycosides, namely, nervilifordins A−E (1−5), were isolated from the whole plant of Nervilia fordii, together with seven known flavonoids (6, 7, and 9−13) and one known coumarin (8). Their structures were elucidated on the basis of extensive spectroscopic analyses, including HSQC, HMBC, ROESY, and chemical methods. Compounds 1−3 and 6−13 were evaluated for their anti-herpes simplex virus 1 (HSV-1) activity and cytotoxicity on African green monkey kidney cells (Vero cells) in vitro. Of the tested compounds, only esculetin (8) exhibited antiviral activity against HSV-1, while the aglycones (11−13) showed stronger cytotoxicity on Vero cells than their glycosides (1−3, 6, and 7).
Co-reporter:Li-Wen Tian, Ying-Jun Zhang, Yi-Fei Wang, Chi-Choi Lai and Chong-Ren Yang
Journal of Natural Products 2009 Volume 72(Issue 9) pp:1608-1611
Publication Date(Web):September 9, 2009
DOI:10.1021/np900290s
Five new (+)-oleuropeic acid derivatives, eucalmaidins A−E (1−5), together with 12 known compounds (6−17), were isolated from the fresh leaves of Eucalyptus maideni. Structures of the new compounds were determined on the basis of spectroscopic analyses (HSQC, HMBC, and 1H−1H COSY), chemical degradation, and enzymatic hydrolysis. Of the tested compounds, only quercetin showed slight anti-herpes simplex virus 1 (HSV-1) activity in vitro.
Co-reporter:Qing Liu, Ya-Feng Wang, Rong-Jie Chen, Mei-Ying Zhang, Yi-Fei Wang, Chong-Ren Yang and Ying-Jun Zhang
Journal of Natural Products 2009 Volume 72(Issue 5) pp:969-972
Publication Date(Web):April 17, 2009
DOI:10.1021/np800792d
Three new norsesquiterpenoid glycosides, 4′-hydroxyphyllaemblicin B (1) and phyllaemblicins E (2) and F (3), were isolated from the roots of Phyllanthus emblica, together with three known compounds, phyllaemblic acid (4), phyllaemblicin B (5), and phyllaemblicin C (6). Of these, 3 is a new norsesquiterpenoid dimer. The structures of 1−3 were established by spectroscopic data information and by acidic hydrolysis. The isolated compounds, together with two other known analogues, phyllaemblic acid methyl ester (7) and phyllaemblicin A (8), were evaluated for their antiviral activity toward coxsackie virus B3 (CVB3) by an in vitro cytopathic effect inhibitory assay. Compounds 5−7 exhibited strong anti-CVB3 activity.
Co-reporter:Qing Liu, Ying-Jun Zhang, Chong-Ren Yang and Mei Xu
Journal of Agricultural and Food Chemistry 2009 Volume 57(Issue 2) pp:586-590
Publication Date(Web):January 7, 2009
DOI:10.1021/jf802974m
Camellia crassicolumna var. multiplex (Chang et Tan) Ming belonging to Camellia sect. Thea (Theaceae), is endemic to the southeastern area of Yunnan province, China, where the leaves have been commonly used for making tea and beverages consumed widely. HPLC analysis showed that there was no caffeine or theophylline contained in the leaves; however, thin layer chromatography (TLC) analysis suggested the abundant existence of phenolic compounds. Further detailed chemical investigation of the green tea produced from the leaves of the plant led to the identification of 18 phenolic compounds, including four flavan-3-ols (1−4), six flavonol glycosides (5−10), three hydrolyzable tannins (11−13), two chlorogenic acid derivatives (14, 15), and three simple phenolic compounds (16−18). The isolated compounds were evaluated for their antioxidant activities by 1,1′-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and tyrosinase inhibitory assays. Most of them exhibited significant DPPH radical scavenging activities, whereas flavan-3-ols and hydrolyzable tannins showed stronger inhibitory activities on tyrosinase. The results suggest that C. crassicolumna could be an ideal plant resource for a noncaffeine beverage.
Co-reporter:Min Xu, Chong Ren Yang, Ying Jun Zhang
Chinese Chemical Letters 2009 Volume 20(Issue 10) pp:1215-1217
Publication Date(Web):October 2009
DOI:10.1016/j.cclet.2009.05.006
Two new phenolic glycosides, 2,3-dihydroxybenzoic acid methyl ester 3-O-β-d-glucopyranosyl-(1-6)-β-d-glucopyranoside (1) and 2,5-dihydroxylbenzofuran 5-O-β-d-xylopyranosyl-(1-6)-O-β-d-glucopyranoside (2), were isolated as the minor chemical constituents from the roots of Gentiana rigescens, along with 15 known compounds. Their structures were elucidated by detailed spectroscopic analysis, including 1D, 2D NMR and chemical method. All of these compounds were isolated for the first time from the title plant. Moreover, compounds 1 and 2 were tested for the antifungal activities on three plant pathogens Peronophythora litchi, Glomerella cingulata, and Glorosprium musarum.
Co-reporter:Min Xu;Ming Zhang, ;Chong-Ren Yang
Helvetica Chimica Acta 2009 Volume 92( Issue 6) pp:
Publication Date(Web):
DOI:10.1002/hlca.200990006
No abstract is available for this article.
Co-reporter:Gai-Mei She;Chong-Ren Yang
Chemistry & Biodiversity 2009 Volume 6( Issue 6) pp:875-880
Publication Date(Web):
DOI:10.1002/cbdv.200800139
Co-reporter:Min Xu;Ming Zhang, ;Chong-Ren Yang
Helvetica Chimica Acta 2009 Volume 92( Issue 2) pp:321-327
Publication Date(Web):
DOI:10.1002/hlca.200800258
Co-reporter:Wei Wang;Shu-Fen Zeng;Chong-Ren Yang
Helvetica Chimica Acta 2009 Volume 92( Issue 9) pp:1817-1822
Publication Date(Web):
DOI:10.1002/hlca.200900036
Abstract
One new hydrolyzable tannin, 1-O-[(E)-p-coumaroyl]-3-O-galloyl-β-D-glucopyranose (1), was isolated from the rhizome of Balanophora harlandii, together with 18 known phenolic compounds. Their structures were determined by detailed spectroscopic analysis. Of the known compounds, 3-O-caffeoyl-D-glucopyranose (6) was obtained as a natural product for the first time, and compounds 2–6 and 8–19 were identified for the first time from this plant. The radical-scavenging activity of the isolated compounds was tested by a DPPH assay.
Co-reporter:Da-Fang Gao, Ying-Jun Zhang, Chong-Ren Yang, Ke-Ke Chen and Hong-Jian Jiang
Journal of Agricultural and Food Chemistry 2008 Volume 56(Issue 16) pp:7517-7521
Publication Date(Web):July 16, 2008
DOI:10.1021/jf800878m
The chemical constituents of green tea prepared from the leaves of Camellia taliensis (W. W. Smith) Melchior (Theaceae) were investigated for the first time. Of these, 19 phenolic compounds including 8 hydrolyzable tannins (1−8), 6 catechin derivatives (9−14), 3 quinic acid aromatic esters (15−17), and 2 simple phenolics (18, 19) were identified, along with caffeine (20). Their antioxidant activities were evaluated by DPPH radical scavenging and tyrosinase inhibitory assays. Moreover, the chemical composition was compared with that in the cultivated tea plant, C. sinensis var. assamica, by HPLC analysis. It was noted that C. taliensis has similar chemical features with the cultivated tea plant; that is, both of them contain rich flavan-3-ols and caffeine. In addition, there are abundant hydrolyzable tannins as specific characteristic constituents contained in the leaves of C. taliensis. Therein, 1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-β-d-glucopyranose (8), as a major compound in C. taliensis, showed remarkable antioxidant activity. The results suggested that C. taliensis could be a valuable plant resource for the production of tea.
Co-reporter:Peng-Ying Liao, Dong Wang, Ying-Jun Zhang and Chong-Ren Yang
Journal of Agricultural and Food Chemistry 2008 Volume 56(Issue 5) pp:1751-1756
Publication Date(Web):February 7, 2008
DOI:10.1021/jf073000s
Notoginseng, the root of Panax notoginseng (Burk.) F. H. Chen (Araliaceae), is a Chinese traditional medicine, which is used in both raw and processed forms due to their different pharmacological activities. Detailed chemical investigation on steamed notoginseng led to the isolation of 27 dammarane-type triterpenoids (1–27), including 4 new glycosides, namely, notoginsenosides ST-1−ST-3 and ST-5 (1–4), in addition to 3 other known compounds. Of the new compounds, 1–3 possess new aglycones. Their structures were elucidated on the basis of detailed analyses of their 1D and 2D NMR spectra and chemical reactions. The known compounds, koryoginsenoside-R1 (19), yesanchinoside D (20), 6′′-O-acetylginsenoside Rg3 (24), and 3β,6α,12β-trihydroxydammar-20(21),24-diene (25), were isolated from notoginseng for the first time.
Co-reporter:Dong-Ling Niu, Li-Song Wang, Ying-Jun Zhang, Chong-Ren Yang
Biochemical Systematics and Ecology 2008 Volume 36(5–6) pp:423-429
Publication Date(Web):May–June 2008
DOI:10.1016/j.bse.2008.01.009
The chemical variability of Acroscyphus sphaerophoroides, a lichenized Ascomycota commonly found in the Hengduanshan Mountains, has been investigated by high performance liquid chromatography (HPLC) and thin layer chromatography (TLC). Gyrophoric acid (GA) is shown to be the constant major component, together with skyrin, graciliformin and rugulosin. Two chemical races are recognized, which show some correlations with substrates. The obtained data indicated that the chemistry of A. sphaerophoroides distributed in Hengduanshan Mountains is different from that growing in the other areas of the world according to previous reports. Meanwhile, a detailed morphological study has also been carried out, and the taxonomy, distribution, as well as ecology of this species are discussed.
Co-reporter:Xian-You Wang;Dong Wang;Xiao-Xia Ma;Chong-Ren Yang
Helvetica Chimica Acta 2008 Volume 91( Issue 1) pp:60-66
Publication Date(Web):
DOI:10.1002/hlca.200890013
Abstract
Two new dammarane-type triterpenoidal saponins, notoginsenosides FP1 (1) and FP2 (2), were isolated from the fruit pedicels of Panax notoginseng, along with 22 known compounds. Their structures were elucidated on the basis of spectroscopic evidences and chemical methods. The known compounds were identified as ginsenosides Rg1 (3), Re (4), Rb3 (5), Rc (6), Rd (7), Rb2 (8), Rb1 (9), F2 (10), and F1 (11); as notoginsenosides R1 (12), Fa (13), and Fc (14); as vina-ginsenoside R7 (15); as gypenosides IX (16), XVII (17), and XIII (18), and as chikusetsusaponin-L5 (19), quercetin 3-O-β-D-glucopyranosyl-(12)-β-D-galactopyranoside (20), kaempferol 3-O-β-D-glucopyranosyl-(12)-β-D-galactopyranoside (21), benzyl-β-primeveroside (22), (S)-tryptophan (23), and icariside B6 (24). Compounds 15, 19 and 22–24 are reported for the first time from the title plant.
Co-reporter:Xi-Feng Teng;Jia-Yue Yang;Chong-Ren Yang
Helvetica Chimica Acta 2008 Volume 91( Issue 7) pp:1305-1312
Publication Date(Web):
DOI:10.1002/hlca.200890142
Abstract
Thirty-one phenolic constituents, including 13 flavonol glycosides, 3 dihydroflavonols, 5 flavan-3-ols, 4 hydrolyzable tannins, and 6 phenylpropanoids, were isolated from the fresh flowers of Camellia reticulata for the first time. Five of them are new flavonol glycosides. Their structures were elucidated by detailed spectroscopic analyses.
Co-reporter:Xiaoxia Ma;Chongren Yang;Yingjun Zhang
Magnetic Resonance in Chemistry 2008 Volume 46( Issue 6) pp:571-575
Publication Date(Web):
DOI:10.1002/mrc.2212
Abstract
The complete assignments of all the 1H and 13C NMR signals of three polyhydroxylated 12-ursen-type triterpenes, 6β,19α,22α-trihydroxyurs-12-en-3-oxo-28-oic acid (1), 3β,6α,19α,23-tetrahydroxyurs-12-en-28- oic acid (2) and 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic acid (3), were carried out by means of homo- and hetero-nuclear two-dimensional NMR experiments. Compounds 1–3 were isolated from the aerial parts of Dischidia esquirolii. Of them, 1 and 2 were identified as new polyhydroxylated ursolic acid derivatives. Compound 2 is the C-6 hydroxyl epimer of 3, which was isolated first from Adina rubella, and its structure is revised in this paper. Copyright © 2008 John Wiley & Sons, Ltd.
Co-reporter:Ying Zhang, Ying-Jun Zhang, Melissa R. Jacob, Xing-Cong Li, Chong-Ren Yang
Phytochemistry 2008 Volume 69(Issue 1) pp:264-270
Publication Date(Web):January 2008
DOI:10.1016/j.phytochem.2007.06.015
Ten steroidal saponins with cis-fused A/B ring, including a smilagenin glycoside, elephanoside A (4), and the five furostanol bisdesmosides, elephanosides B–F (6–10), were isolated from the stems of Yucca elephantipes Regel. (Agavaceae). Their structures were determined by detailed chemical and spectroscopic analysis. All the isolated compounds were tested for their in vitro antifungal and antibacterial activities. Only the two known spirostanol glycosides Ys-II (1) and Ys-IV (2) showed moderate inhibitory activity against the growth of Candida albicans and Cryptococcus neoformans.Ten steroidal saponins with cis-fused A/B ring, including a smilagenin glycoside, elephanoside A (4), and the five furostanol bisdesmosides, elephanosides B–F (6–10), were isolated from the stems of Yucca elephantipes Regel. (Agavaceae). Of these, two known smilagenin glycosides, Ys-II (1) and Ys-IV (2), showed moderate antifungal activity against Candida albicans and Cryptococcus neoformans.
Co-reporter:Kai-Jin Wang, Chong-Ren Yang, Ying-Jun Zhang
Food Chemistry 2007 Volume 101(Issue 1) pp:365-371
Publication Date(Web):2007
DOI:10.1016/j.foodchem.2006.01.044
Chinese toon (the fresh young leaves and shoots of Toona sinensis), known as a tree vegetable, belongs to the family of Meliaceae. It is one of the most popular vegetables in China. The 80% acetone extract of Chinese toon exhibited considerable antioxidant activity in the 1,1-diphenyl-2-picryldydrazyl (DPPH) radical-scavenging assay. Bioassay-guided purification of the extract led to the isolation of 12 phenolic compounds (1–12), whose structures were determined by detailed spectroscopic analyses, including UV, IR, MS, 1D and 2D NMR techniques. Of them, compounds 3–8 and 11 were isolated from T. sinensis for the first time. All of the isolated compounds were examined for their antioxidant activities by the DPPH method, and the results showed that gallic acid and its derivatives, gallotannins and flavonoids were the main constituents contributing to the antioxidant activity of Chinese toon. From the health point of view, Chinese toon is an ideal dietary vegetable with natural antioxidants.
Co-reporter:Zhong-Jun Zha;Min Xu;Xiang-Lan Zhang;Chong-Ren Yang;Xue-Ling Qin
Chemistry & Biodiversity 2007 Volume 4(Issue 9) pp:2246-2252
Publication Date(Web):21 SEP 2007
DOI:10.1002/cbdv.200790183
The 1,1-diphenyl-2-picrydydrazyl (DPPH) assay on the extract of Phyllanthus urinaria L. (Euphorbiaceae) displayed considerable radical-scavenging activity (SC50=14.3 μg/ml). Further bioassay-guided purification of the extract led to the isolation of a series of 15 phenolic compounds, including the ellagitannins 1–7, the flavonoids 8–10, and the simple hydroxylated (or glycosylated) aromatic acids 11–15. Their structures were identified by spectroscopic analyses and comparison with authentic samples or literature data. The structure of repandinin B (1) was for the first time fully assigned by 1D- and 2D-NMR experiments. The phenolic compounds 1, 3, 4, 6, 9, 11, and 15 have not been isolated before from the title plant. The antioxidant activities and mushroom-tyrosinase-inhibitory activities of all compounds were determined by DPPH-radical-scavenging and mushroom-tyrosinase-inhibitory assays (Table 2).
Co-reporter:Kai-Jin Wang;Chong-Ren Yang
Chemistry & Biodiversity 2006 Volume 3(Issue 12) pp:1317-1324
Publication Date(Web):18 DEC 2006
DOI:10.1002/cbdv.200690135
The 80% acetone extract of Balanophora polyandraGriff. (Balanophoraceae) was found to exhibit high radical-scavenging activity (SC50=14.48 μg/ml) towards 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Further chemical investigation led the isolation of two new hydrolysable tannins, balapolyphorins A (1) and B (2), together with 20 known phenolic compounds (3–22). Their structures were established by detailed spectroscopic analysis, and the radical-scavenging properties of all isolated compounds were determined by DPPH assay.
Co-reporter:Jiang-Tao Chen;Hai-Zhou Li;Dong Wang;Chong-Ren Yang
Helvetica Chimica Acta 2006 Volume 89(Issue 7) pp:1442-1448
Publication Date(Web):26 JUL 2006
DOI:10.1002/hlca.200690144
Three new dammarane monodesmosides, named notoginsenosides Ft1 (1), Ft2 (2), and Ft3 (3), together with three known ginsenosides, were obtained from a mild acidic hydrolysis of the saponins from notoginseng (Panax notoginseng (Burk.) F. H. Chen) leaves. Their structures were elucidated to be (3β,12β,20R)-12,20-dihydroxydammar-24-en-3-yl O-β-D-xylopyranosyl-(1 2)-O-β-D-glucopyranosyl-(1 2)-β-D-glucopyranoside (1), (3β,12β)-12,20,25-trihydroxydammaran-3-yl O-β-D-xylopyranosyl-(1 2)-O-β-D-glucopyranosyl-(1 2)-β-D-glucopyranoside (2), and (3β,12β,24ξ)-12,20,24-trihydroxydammar-25-en-3-yl O-β-D-xylopyranosyl-(1 2)-O-β-D-glucopyranosyl-(1 2)-β-D-glucopyranoside (3), by means of spectroscopic evidences. The known ginsenosides Rh2 and Rg34–6 were obtained as the major products from this acidic deglycosylation.
Co-reporter:Qing-Xiong Yang;Min Xu;Chong-Ren Yang;Hai-Zhou Li
Helvetica Chimica Acta 2004 Volume 87(Issue 5) pp:1248-1253
Publication Date(Web):25 MAY 2004
DOI:10.1002/hlca.200490114
Four new steroidal saponins, named disporosides A–D (1–4), corresponding to (3β,25R)-3-[(β-D-glucopyranosyl-(12)-[β-D-glucopyranosyl-(16)]-β-D-glucopyranosyl)oxy]-5β-spirostan (1), (3β,25R)-3-[(β-D-glucopyranosyl-(12)-[6-O-hexadecanoyl-β-D-glucopyranosyl-(16)]-β-D-glucopyranosyl)oxy]-5β-spirostan (2), (3β,22R,25R)-26-[(β-D-glucopyranosyl)oxy]-3-[(β-D-glucopyranosyl-(12)-β-D-glucopyranosyl)oxy]-5β-furostan (3), and (3β,22R,25R)-26-[(β-D-glucopyranosyl)oxy]-3-[(β-D-glucopyranosyl-(12)-[β-D-glucopyranosyl-(16)]-β-D-glucopyranosyl)oxy]-5β-furostan (4), have been isolated from the fresh rhizomes of Disporopsis pernyi, together with the three known compounds Ys-I, agavoside B, and (3β,25R)-3-[(β-D-xylopyranosyl-(13)-β-D-glucopyranosyl-(14)-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one. Their structures were elucidated by spectroscopic analyses, chemical transformations (acid hydrolysis), and comparison with literature data.
Co-reporter:Xiao-Xia Ma, Dong Wang, Ying-Jun Zhang, Chong-Ren Yang
Steroids (September–October 2011) Volume 76(Issues 10–11) pp:1003-1009
Publication Date(Web):1 September 2011
DOI:10.1016/j.steroids.2011.03.019
HPLC analysis of the roots of Cynanchum otophyllum Scheind (Asclepiadaceae) led to the isolation of six new pregnane glycosides, specifically otophyllosides N-P (2–4) and otophyllosides Q-S (7–9), in addition to the identification of three known C-21 steroidal glycosides, otophylloside A (1), otophylloside B (5) and caudatin 3-O-β-d-glucopyranosyl-(1→4)-β-d-oleandropyranosyl-(1→4)-β-d-cymaropyranosyl-(1→4)-β-d-cymaropyranoside (6). The structure of each glycoside was determined by detailed spectroscopic analysis and chemical methods. All compounds contain qingyangshengenin or caudatin aglycones and a straight sugar chain consisting of 4-7 hexosyl moieties with the mode of 1→4 linkage. The optically isomeric monosaccharides, d- and l-cymarose, coexisted in both otophyllosides R (8) and S (9).Highlights► In this study, the compositions of Cynanchum otophyllum were further studied. ► Six new pregnane glycosides, otophyllosides N-S, were isolated by prep. HPLC. ► The compounds possess qingyangshengenin or caudatin as aglycones. ► A straight sugar chain consists of 4-7 hexosyl moieties with 1→4 linkage. ► The optically isomeric d- and l-cymarose coexisted in otophyllosides R and S.
Co-reporter:Xiao-Xia Ma, Fang-Ting Jiang, Qing-Xiong Yang, Xiu-Hua Liu, Ying-Jun Zhang, Chong-Ren Yang
Steroids (October 2007) Volume 72(Issues 11–12) pp:778-786
Publication Date(Web):1 October 2007
DOI:10.1016/j.steroids.2007.06.001
Six new pregnane glycosides with an acyl at C-12 and a straight sugar chain at C-3, namely otophyllosides H–M (1–6), were isolated from the roots of Cynanchum otophyllum (Asclepiadaceae) collected from Eryuan County in Yunnan province of China. Their structures were characterized to be qingyangshengenin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-digitoxopyranoside (1), qingyangshengenin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (2), qingyangshengenin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (3), qingyangshengenin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-thevetopyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (4), caudatin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranoside (5), caudatin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-cymaropyranoside (6), respectively, on the basis of detailed spectroscopic analysis and chemical method.
Co-reporter:Ying Pei, Yang-Fei Xiang, Jia-Nan Chen, Chun-Hua Lu, Jing Hao, Qian Du, Chi-choi lai, Chang Qu, Shen Li, Huai-Qiang Ju, Zhe Ren, Qiu-Ying Liu, Sheng Xiong, Chui-Wen Qian, Fan-Li Zeng, Pei-Zhuo Zhang, Chong-Ren Yang, Ying-Jun Zhang, Jun Xu, Kaio Kitazato, Yi-Fei Wang, et al.
Antiviral Research (January 2011) Volume 89(Issue 1) pp:98-108
Publication Date(Web):January 2011
DOI:10.1016/j.antiviral.2010.11.012
Co-reporter:Ying Zhang, Haizhou Li, Chongren Yang, Yingjun Zhang
Acta Pharmaceutica Sinica B (February 2013) Volume 3(Issue 1) pp:
Publication Date(Web):1 February 2013
DOI:10.1016/j.apsb.2012.12.002
Smilacina atropurpurea (family Convallariaceae) is a perennial herb used medicinally for the treatment of lung ailments, rheumatism, menstrual disorders, and cuts and bruises, by the local people of its growing areas in southwest China. The tender aerial part has also been used as a wild vegetable by Lisu, Naxi and Tibetan people. Chemical analysis of the rhizomes of this plant has allowed us to isolate two new minor steroidal tetraglycosides, specifically atropurosides H (1) and I (2), by repeated column chromatography over silica gel and reversed phase silica. The structures were determined to be (25R,S)-12β-hydroxy-spirost-5-ene-3β-yl-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1) and (25S)-5α-spirost-17α-hydroxy-3β-yl-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galacto pyranoside (2), respectively, on the basis of detailed spectroscopic analysis including 1D and 2D NMR techniques.Graphical abstractTwo new minor steroidal tetraglycosides, specifically atropurosides H (1) and I (2), were isolated by repeated column chromatography over silica gel and reversed phase silica.Download full-size image
Co-reporter:Jun-Jiang Lv, Ya-Feng Wang, Jing-Min Zhang, Shan Yu, Dong Wang, Hong-Tao Zhu, Rong-Rong Cheng, Chong-Ren Yang, Min Xu and Ying-Jun Zhang
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 43) pp:NaN8774-8774
Publication Date(Web):2014/09/12
DOI:10.1039/C4OB01196A
During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1–G8 (1–8) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6–G8 (6–8) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory. The sesquiterpenoid glycoside dimers 6–9 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 ± 0.97 and 5.68 ± 1.75 μM towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively.
![Spirost-5-en-12-one,3-[(6-deoxy-4-O-b-D-glucopyranosyl-b-D-galactopyranosyl)oxy]-, (3b,25R)-](http://img.cochemist.com/ccimg/145900/145867-18-1.png)
![Spirost-5-en-12-one,3-[(6-deoxy-4-O-b-D-glucopyranosyl-b-D-galactopyranosyl)oxy]-, (3b,25R)-](http://img.cochemist.com/ccimg/145900/145867-18-1_b.png)
![Furost-5-en-12-one,3-[(4-O-b-D-glucopyranosyl-b-D-galactopyranosyl)oxy]-26-(b-D-glucopyranosyloxy)-22-hydroxy-,(3b,25R)-](http://img.cochemist.com/ccimg/145900/145854-04-2.png)
![Furost-5-en-12-one,3-[(4-O-b-D-glucopyranosyl-b-D-galactopyranosyl)oxy]-26-(b-D-glucopyranosyloxy)-22-hydroxy-,(3b,25R)-](http://img.cochemist.com/ccimg/145900/145854-04-2_b.png)
![ETHANONE, 1-[2-[1,2-DIHYDROXY-1-(HYDROXYMETHYL)ETHYL]-5-HYDROXY-6-BENZOFURANYL]-](http://img.cochemist.com/ccimg/850500/850452-17-4.png)
![ETHANONE, 1-[2-[1,2-DIHYDROXY-1-(HYDROXYMETHYL)ETHYL]-5-HYDROXY-6-BENZOFURANYL]-](http://img.cochemist.com/ccimg/850500/850452-17-4_b.png)
![Spirosta-5,25(27)-dien-12-one,3-[(O-b-D-glucopyranosyl-(1®2)-O-[b-D-glucopyranosyl-(1®3)]-O-b-D-glucopyranosyl-(1®4)-b-D-galactopyranosyl)oxy]-, (3b)-](http://img.cochemist.com/ccimg/139400/139390-87-7.png)
![Spirosta-5,25(27)-dien-12-one,3-[(O-b-D-glucopyranosyl-(1®2)-O-[b-D-glucopyranosyl-(1®3)]-O-b-D-glucopyranosyl-(1®4)-b-D-galactopyranosyl)oxy]-, (3b)-](http://img.cochemist.com/ccimg/139400/139390-87-7_b.png)
![b-D-Galactopyranoside, (3b)-spirosta-5,25(27)-dien-3-yl O-b-D-glucopyranosyl-(1®2)-O-[b-D-xylopyranosyl-(1®3)]-O-b-D-glucopyranosyl-(1®4)-](http://img.cochemist.com/ccimg/139400/139367-82-1.png)
![b-D-Galactopyranoside, (3b)-spirosta-5,25(27)-dien-3-yl O-b-D-glucopyranosyl-(1®2)-O-[b-D-xylopyranosyl-(1®3)]-O-b-D-glucopyranosyl-(1®4)-](http://img.cochemist.com/ccimg/139400/139367-82-1_b.png)
![b-D-Glucopyranoside,4-[(2S,3R)-2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2-benzofuranyl]-2-methoxyphenyl](http://img.cochemist.com/ccimg/131800/131723-83-6.png)
![b-D-Glucopyranoside,4-[(2S,3R)-2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2-benzofuranyl]-2-methoxyphenyl](http://img.cochemist.com/ccimg/131800/131723-83-6_b.png)
![[4,8':4',8''-Ter-2H-1-benzopyran]-3,3',3'',5,5',5'',7,7',7''-nonol,2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-,(2R,2'R,2''R,3R,3'R,3''R,4R,4'S)-](http://img.cochemist.com/ccimg/37100/37064-30-5.png)
![[4,8':4',8''-Ter-2H-1-benzopyran]-3,3',3'',5,5',5'',7,7',7''-nonol,2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-,(2R,2'R,2''R,3R,3'R,3''R,4R,4'S)-](http://img.cochemist.com/ccimg/37100/37064-30-5_b.png)
![Oleanan-29-al,13,28-epoxy-3-[(O-b-D-glucopyranosyl-(1®2)-O-[O-b-D-xylopyranosyl-(1®2)-b-D-glucopyranosyl-(1®4)]-a-L-arabinopyranosyl)oxy]-16-hydroxy-, (3b,16a,20b)-](http://img.cochemist.com/ccimg/23700/23643-61-0.png)
![Oleanan-29-al,13,28-epoxy-3-[(O-b-D-glucopyranosyl-(1®2)-O-[O-b-D-xylopyranosyl-(1®2)-b-D-glucopyranosyl-(1®4)]-a-L-arabinopyranosyl)oxy]-16-hydroxy-, (3b,16a,20b)-](http://img.cochemist.com/ccimg/23700/23643-61-0_b.png)
![1-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-hydroxy-5-(4-hydroxyphenyl)-4-[(7-methoxy-1-benzofuran-2-yl)carbonyl]-1,5-dihydro-2H-pyrrol-2-one](http://img.cochemist.com/ccimg/7100/7050-40-0.png)
![1-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-hydroxy-5-(4-hydroxyphenyl)-4-[(7-methoxy-1-benzofuran-2-yl)carbonyl]-1,5-dihydro-2H-pyrrol-2-one](http://img.cochemist.com/ccimg/7100/7050-40-0_b.png)
![[(2R,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate](http://img.cochemist.com/ccimg/5200/5127-64-0.png)
![[(2R,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate](http://img.cochemist.com/ccimg/5200/5127-64-0_b.png)
![POTASSIUM TRIFLUORO(1-{[(2-METHYL-2-PROPANYL)OXY]CARBONYL}-3-AZET<WBR />IDINYL)BORATE(1-)](http://img.cochemist.com/ccimg/3200/3175-89-1.png)
![POTASSIUM TRIFLUORO(1-{[(2-METHYL-2-PROPANYL)OXY]CARBONYL}-3-AZET<WBR />IDINYL)BORATE(1-)](http://img.cochemist.com/ccimg/3200/3175-89-1_b.png)
![4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-,(2R,3R)-](http://img.cochemist.com/ccimg/600/572-31-6.png)
![4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-,(2R,3R)-](http://img.cochemist.com/ccimg/600/572-31-6_b.png)
![(2S,3aR,4S,4'S,5'R,6S,7aR)-3a,4-Dihydroxy-4'-[(4-hydroxybenzoyl)o xy]-5'-methyl-3-oxodecahydro-3H-spiro[1-benzofuran-2,2'-pyran]-6- carboxylic acid](http://img.cochemist.com/ccimg/927900/927812-23-5.png)
![(2S,3aR,4S,4'S,5'R,6S,7aR)-3a,4-Dihydroxy-4'-[(4-hydroxybenzoyl)o xy]-5'-methyl-3-oxodecahydro-3H-spiro[1-benzofuran-2,2'-pyran]-6- carboxylic acid](http://img.cochemist.com/ccimg/927900/927812-23-5_b.png)
![[1,1'-BIPHENYL]-4,4'-DIOL, 3,5-DIMETHOXY-](http://img.cochemist.com/ccimg/916300/916206-05-8.png)
![[1,1'-BIPHENYL]-4,4'-DIOL, 3,5-DIMETHOXY-](http://img.cochemist.com/ccimg/916300/916206-05-8_b.png)
![(5alpha,8xi,9xi,12alpha,13xi,14beta)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,5,10,14-pentamethylgonan-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/194900/194861-70-6.png)
![(5alpha,8xi,9xi,12alpha,13xi,14beta)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,5,10,14-pentamethylgonan-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/194900/194861-70-6_b.png)
![b-D-Glucopyranose,1-(3,4,5-trihydroxybenzoate), cyclic 2®2:4®1-ester with (2S)-2-[(3S,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioicacid](http://img.cochemist.com/ccimg/166900/166833-80-3.png)
![b-D-Glucopyranose,1-(3,4,5-trihydroxybenzoate), cyclic 2®2:4®1-ester with (2S)-2-[(3S,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioicacid](http://img.cochemist.com/ccimg/166900/166833-80-3_b.png)
![2,4,6-trihydroxy-5-{1-[6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde](http://img.cochemist.com/ccimg/142700/142628-54-4.png)
![2,4,6-trihydroxy-5-{1-[6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde](http://img.cochemist.com/ccimg/142700/142628-54-4_b.png)
![1,3-Benzenedicarboxaldehyde,5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxy-](http://img.cochemist.com/ccimg/142700/142628-53-3.png)
![1,3-Benzenedicarboxaldehyde,5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxy-](http://img.cochemist.com/ccimg/142700/142628-53-3_b.png)
![2(1H)-Pyridinone,1-[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]-5,6-dihydro-, (E)- (9CI)](http://img.cochemist.com/ccimg/130300/130263-10-4.png)
![2(1H)-Pyridinone,1-[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]-5,6-dihydro-, (E)- (9CI)](http://img.cochemist.com/ccimg/130300/130263-10-4_b.png)
![Pyrrolidine,1-[(2E,8E)-9-(1,3-benzodioxol-5-yl)-1-oxo-2,8-nonadienyl]- (9CI)](http://img.cochemist.com/ccimg/117200/117137-67-4.png)
![Pyrrolidine,1-[(2E,8E)-9-(1,3-benzodioxol-5-yl)-1-oxo-2,8-nonadienyl]- (9CI)](http://img.cochemist.com/ccimg/117200/117137-67-4_b.png)
![(2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-[[(8r,10r,12s,13r,14s,17s)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2z)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol](http://img.cochemist.com/ccimg/105600/105558-26-7.png)
![(2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-[[(8r,10r,12s,13r,14s,17s)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2z)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol](http://img.cochemist.com/ccimg/105600/105558-26-7_b.png)
![Benzoic acid,2-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo[1]benzopyrano[5,4,3-cde][1]benzopyran-1-yl)-3,4,5-trihydroxy-](http://img.cochemist.com/ccimg/103800/103744-88-3.png)
![Benzoic acid,2-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo[1]benzopyrano[5,4,3-cde][1]benzopyran-1-yl)-3,4,5-trihydroxy-](http://img.cochemist.com/ccimg/103800/103744-88-3_b.png)
![1,3-Propanediol, 2-[2,6-dimethoxy-4-[tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3,5-](/data/chemimg/2078400/97465-75-3.png)
![1,3-Propanediol, 2-[2,6-dimethoxy-4-[tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3,5-](/data/chemimg/2078400/97465-75-3_b.png)
![2(3H)-Furanone,dihydro-3,4-bis[(3-hydroxy-4-methoxyphenyl)methyl]-, (3R,4R)-](http://img.cochemist.com/ccimg/93400/93376-04-6.png)
![2(3H)-Furanone,dihydro-3,4-bis[(3-hydroxy-4-methoxyphenyl)methyl]-, (3R,4R)-](http://img.cochemist.com/ccimg/93400/93376-04-6_b.png)
![3,3,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one](http://img.cochemist.com/ccimg/91500/91485-02-8.png)
![3,3,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one](http://img.cochemist.com/ccimg/91500/91485-02-8_b.png)
![3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-,(2R,3S,4S)-](http://img.cochemist.com/ccimg/83400/83327-19-9.png)
![3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-,(2R,3S,4S)-](http://img.cochemist.com/ccimg/83400/83327-19-9_b.png)
![4-[3-(HYDROXYMETHYL)PHENOXY]PHENOL](http://img.cochemist.com/ccimg/79000/78910-33-5.png)
![4-[3-(HYDROXYMETHYL)PHENOXY]PHENOL](http://img.cochemist.com/ccimg/79000/78910-33-5_b.png)
![(R)-1-O-(beta-D-glucopyranosyl)-2-[2-methoxy-4-(omega-hydroxypropyl)phenoxy]-propan-3-ol](http://img.cochemist.com/ccimg/68400/68340-35-2.png)
![(R)-1-O-(beta-D-glucopyranosyl)-2-[2-methoxy-4-(omega-hydroxypropyl)phenoxy]-propan-3-ol](http://img.cochemist.com/ccimg/68400/68340-35-2_b.png)
![8-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one](http://img.cochemist.com/ccimg/61400/61360-94-9.png)
![8-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one](http://img.cochemist.com/ccimg/61400/61360-94-9_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one](http://img.cochemist.com/ccimg/52000/51938-32-0.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one](http://img.cochemist.com/ccimg/52000/51938-32-0_b.png)
![Phenol, 2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]-](/data/chemimg/53300/40957-99-1.png)
![Phenol, 2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]-](/data/chemimg/53300/40957-99-1_b.png)
![SODIUM (2S)-2-[(2,2-DICHLOROACETYL)AMINO]-3-HYDROXY-PROPANOATE](http://img.cochemist.com/ccimg/34500/34425-25-7.png)
![SODIUM (2S)-2-[(2,2-DICHLOROACETYL)AMINO]-3-HYDROXY-PROPANOATE](http://img.cochemist.com/ccimg/34500/34425-25-7_b.png)
![β-D-Glucopyranose, cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 4-[4-hydrogen (3-carboxy-3,4-dihydro-5,6,7-trihydroxy-1-](/data/chemimg/1175500/28196-46-5.png)
![β-D-Glucopyranose, cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 4-[4-hydrogen (3-carboxy-3,4-dihydro-5,6,7-trihydroxy-1-](/data/chemimg/1175500/28196-46-5_b.png)
![Butanedioic acid,[(3S,4S)-3-carboxy-3,4-dihydro-5,6,7-trihydroxy-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-](http://img.cochemist.com/ccimg/23800/23725-05-5.png)
![Butanedioic acid,[(3S,4S)-3-carboxy-3,4-dihydro-5,6,7-trihydroxy-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-](http://img.cochemist.com/ccimg/23800/23725-05-5_b.png)
![b-D-Glucopyranose, cyclic3,6-[(1R)-4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate]1-(3,4,5-trihydroxybenzoate), cyclic 2?5:4?1-ester with(2S)-[(3S,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioicacid, stereoisomer](http://img.cochemist.com/ccimg/23100/23094-71-5.png)
![b-D-Glucopyranose, cyclic3,6-[(1R)-4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate]1-(3,4,5-trihydroxybenzoate), cyclic 2?5:4?1-ester with(2S)-[(3S,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioicacid, stereoisomer](http://img.cochemist.com/ccimg/23100/23094-71-5_b.png)
![[1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid](http://img.cochemist.com/ccimg/22300/22255-40-9.png)
![[1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid](http://img.cochemist.com/ccimg/22300/22255-40-9_b.png)
![(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]cyclohexanecarboxylic acid](http://img.cochemist.com/ccimg/17400/17365-11-6.png)
![(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]cyclohexanecarboxylic acid](http://img.cochemist.com/ccimg/17400/17365-11-6_b.png)
![[(2r,3r,4s,5r,6s)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate](http://img.cochemist.com/ccimg/15000/14937-32-7.png)
![[(2r,3r,4s,5r,6s)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate](http://img.cochemist.com/ccimg/15000/14937-32-7_b.png)
![Benzoic acid,3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-](http://img.cochemist.com/ccimg/600/536-08-3.png)
![Benzoic acid,3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-](http://img.cochemist.com/ccimg/600/536-08-3_b.png)
![Phenol,4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-](http://img.cochemist.com/ccimg/500/487-36-5.png)
![Phenol,4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-](http://img.cochemist.com/ccimg/500/487-36-5_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/482-39-3.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/482-39-3_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/480-10-4.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/480-10-4_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/17700/17650-84-9.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/17700/17650-84-9_b.png)
![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9.png)
![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9_b.png)
