Pei-cheng Zhang

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Organization: Institute of Materia Medica

Department: State Key Laboratory of Bioactive Substance and Function of Natural Medicines

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TOPICS

Polymer

Polyacetylene Polyacetylene

Chemicals
References

Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium

Co-reporter:Peng-Fei Yang, Zi-Ming Feng, Ya-Nan Yang, Jian-Shuang Jiang, and Pei-Cheng Zhang

Journal of Natural Products April 28, 2017 Volume 80(Issue 4) pp:1028-1028

Publication Date(Web):March 1, 2017

DOI:10.1021/acs.jnatprod.6b01026

Three new caffeoylquinic acid derivatives, chrysanthemorimic acids A–C (1–3), and 11 known compounds (4–14) were isolated and characterized from the flowers of Chrysanthemum morifolium. Their structures were confirmed by spectroscopic data as well as by comparison of the experimental and calculated electronic circular dichroism spectra. Chrysanthemorimic acids A–C possess a rare 8-oxa-bicyclo[3.2.1]oct-3-en-2-one ring that is formed through a [5+2] cycloaddition of caffeoylquinic acid with a d-glucose derivative. Compounds 1–3, 6–8, 12, and 13 displayed significant effects against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells at 10 μM.

Nine compounds from the Root Bark of Lycium chinense and their anti-inflammatory activities

Co-reporter:Yanan Yang, Yawen An, Wei Wang, Ning Du, Jinghua Zhang, Ziming Feng, Jianshuang Jiang, Peicheng Zhang

Acta Pharmaceutica Sinica B 2017 Volume 7, Issue 4(Issue 4) pp:

Publication Date(Web):1 July 2017

DOI:10.1016/j.apsb.2017.04.004

Two new compounds, named lyciumlignan D (1) and lyciumphenyl propanoid A (2), along with seven known compounds, were isolated from the root bark of Lycium chinense. Their structures were elucidated using spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR, CD), as well as by comparison with those of the literature. Compounds 39 were isolated from this genus for the first time. In the in vitro assay, compounds 3, 6, and 7 exhibited stronger anti-inflammatory effects than the positive control curcumin at a concentration of 10 μmol/L.Nine compounds were isolated from the root bark of Lycium chinense. Among them, compounds 1 and 2 were two new compounds, named lyciumlignan D (1) and lyciumphenylpropanoid A (2). Compounds 3, 6, and 7 exhibited anti-inflammatory activities on BV2 microglial cells at 10 and 1 μmol/L.Download high-res image (216KB)Download full-size image

Neuroprotective phenylethanoid glycosides with dioxane units from the fruits of Forsythia suspensa

Co-reporter:Si-Yuan Shao, Fan Zhang, Zi-Ming Feng, Ya-Nan Yang, Jian-Shuang Jiang, Pei-Cheng Zhang

Tetrahedron 2017 Volume 73, Issue 44(Issue 44) pp:

Publication Date(Web):2 November 2017

DOI:10.1016/j.tet.2017.09.008

Six new phenylethanoid glycosides possessing dioxane moieties, named forsyoxasides A−F (1–6), together with four known such compounds (7–10) were isolated from the fruits of Forsythia suspensa. These structures were illustrated by extensive NMR spectroscopic techniques and by comparing their NMR data with the related literatures. Notably, forsyoxaside A (1) is a novel dioxane phenylethanoid glycoside with an axial aromatic ring, which is rare in the natural sources. Compounds 1, 4, 7 and 8 showed remarkable bioactivities against rotenone induced PC12 cell damage. Furthermore, 1 and 7 displayed strong activities against serum deprivation induced damage on the same cells.Download high-res image (215KB)Download full-size image

New heterocyclic compounds from Ranunculus ternatus Thunb.

Co-reporter:Zi-ming Feng, Zhi-lai Zhan, Ya-nan Yang, Jian-shuang Jiang, Pei-cheng Zhang

Bioorganic Chemistry 2017 Volume 74(Volume 74) pp:

Publication Date(Web):1 October 2017

DOI:10.1016/j.bioorg.2017.07.004

•Five new heterocyclic compounds were obtained from Ranunculus ternatus.•Compounds 1–3 are rarely occurring furfural fructosides in natural sources.•The structures of these compounds are similar to some anti-tuberculosis drugs.Five new heterocyclic compounds, 5-α-d-fructofuranosylmethyl-furfural (1), 5-β-d-fructofuranosylmethyl-furfural (2), 5-β-d-fructopyranosylmethyl-furfural (3), 4-(2-((2S-2,3-dihydroxypropoxy)methyl)-5-formyl-1H-pyrrol-1-yl)butanoic acid (4), and 3S,4S-4,5,8-trihydroxy-3-(prop-1-en-2-yl)isochroman-1-one (5), were obtained from the root of Ranunculus ternatus Thunb., which is a traditional Chinese anti-tuberculosis medicine. Their structures were elucidated by UV, IR, HRESIMS, NMR data, and the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Notably, compounds 1–3 are rarely occurring furfural fructosides in natural sources. These heterocyclic compounds could be further studied for the synthetic chemists and pharmacologists due to the source and structural properties.Download high-res image (44KB)Download full-size image

Forsythenethosides A and B: two new phenylethanoid glycosides with a 15-membered ring from Forsythia suspensa

Co-reporter:Si-Yuan Shao;Zi-Ming Feng;Ya-Nan Yang;Jian-Shuang Jiang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 33) pp:7034-7039

Publication Date(Web):2017/08/23

DOI:10.1039/C7OB01811H

Forsythenethosides A (1) and B (2), two new phenylethanoid glycosides with an unprecedented 15-membered carbon scaffold ring, were isolated from the fruits of Forsythia suspensa. Their structures, including their geometric configurations, were determined via extensive NMR spectroscopy techniques, especially using 2D NMR data combined with systematic conformational analysis. Forsythenethosides A and B showed strong neuroprotective activities against serum-deprivation-induced PC12 cell damage. Furthermore, they were active on rotenone-induced PC12 cell damage.

Direct Assignment of the Threo and Erythro Configurations in Polyacetylene Glycosides by 1H NMR Spectroscopy

Co-reporter:Kuo Xu, Peng-Fei Yang, Ya-Nan YangZi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng Zhang

Organic Letters 2017 Volume 19(Issue 3) pp:

Publication Date(Web):January 19, 2017

DOI:10.1021/acs.orglett.6b03855

An approach for discriminating the threo and erythro configurations of polyacetylene glycosides by 1H NMR spectroscopy was developed. Using acetic acid-d4/D2O as the solvent, a relatively larger 3JHH value (7.0 Hz) for the acyclic vicinal diol group was unambiguously assigned to the threo configuration, whereas the smaller value (3.5 Hz) was assigned to the erythro configuration. This convenient method requires no hydrolysis or derivatization and is suitable for micromolar concentrations of polyacetylene glycosides. The underlying mechanism is discussed via visualized conformations.

Sesquiterpenoid and C14-polyacetylene glycosides from the rhizomes of Atractylodes lancea

Co-reporter:Kuo Xu, Zi-Ming Feng, Jian-Shuang Jiang, Ya-Nan Yang, Pei-Cheng Zhang

Chinese Chemical Letters 2017 Volume 28, Issue 3(Volume 28, Issue 3) pp:

Publication Date(Web):1 March 2017

DOI:10.1016/j.cclet.2016.10.036

Four new glycosides including a eudesmane-type sesquiterpenoid (1), a guaiane-type sesquiterpenoid (2), and two C14-polyacetylenes (3, 4) were isolated from the rhizomes of Atractylodes lancea. Their structures were elucidated by means of spectroscopic and spectrometric analyses (UV, IR, 1D and 2D NMR, and HR-ESIMS). The absolute configurations of their aglycones were established based on the experimental and calculated electronic circular dichroism (ECD), whereas those of monosaccharide moieties were determined by the GC method after chiral derivatization. Compound 4 showed weak anti-inflammatory effects on the LPS-induced NO production in microglia BV2 cells at a concentration of 10 μmol L−1.Download high-res image (132KB)Download full-size imageTwo new sesquiterpenoid glycosides with a eudesmane (1) and a guaiane carbon skeleton (2), respectively, and two new C14-polyacetylene glycosides (3, 4) were isolated from Atractylodes lancea. Their anti-inflammatory effects were evaluated by the LPS-induced NO production in microglia BV2 cells.

Sophopterocarpan A, a novel pterocarpine derivative with a benzotetrahydrofuran-fused bicyclo [3.3.1] nonane from Sophora flavescens

Co-reporter:Hui Zhu;Ya-Nan Yang;Kuo Xu;Jing Xie;Zi-Ming Feng;Jian-Shuang Jiang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 26) pp:5480-5483

Publication Date(Web):2017/07/05

DOI:10.1039/C7OB01261F

Sophopterocarpan A (1), with a novel benzotetrahydrofuran-fused bicyclo [3.3.1] nonane ring, was isolated from the roots of Sophora flavescens Ait. Its unusual structure, including its stereochemistry, was determined on the basis of a comprehensive spectroscopic data analysis. A plausible biogenetic pathway for 1 is presented. Sophopterocarpan A was identified as a potential autophagy activator. Additionally, it was found that 1 exhibited cytotoxic activity in MCF-7 cells with an IC50 of 29.36 μM.

Phthalide derivatives from Ligusticum chuanxiong

Co-reporter:Xu Zhang;Bing Han;Zi-Ming Feng;Ya-Nan Yang;Jian-Shuang Jiang

RSC Advances (2011-Present) 2017 vol. 7(Issue 59) pp:37478-37486

Publication Date(Web):2017/07/24

DOI:10.1039/C7RA06813A

Eleven new phthalide derivatives (1–11) have been isolated from the rhizome of Ligusticum chuanxiong. In particular, 1 and 2 contain a mercaptopropionic acid moiety in the phthalide derivatives. All the structures, including their absolute configurations, were determined by UV, IR, HRESIMS, 1D and 2D NMR spectroscopic measurements, and by a comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. Results of a bioassay showed that compound 4 has a moderate neuroprotective activity on human neuroblastoma SH-SY5Y cell injury induced by H2O2 and oxygen glucose deprivation (OGD).

Four new phenylethanoid and flavonoid glycoside dimers from the fruits of Forsythia suspensa and their neuroprotective activities

Co-reporter:Fan Zhang;Ya-Nan Yang;Zi-Ming Feng;Jian-Shuang Jiang

RSC Advances (2011-Present) 2017 vol. 7(Issue 40) pp:24963-24969

Publication Date(Web):2017/05/05

DOI:10.1039/C7RA04229A

During our continuing study on the fruits of Forsythia suspensa, one new heterodimer (forsythoneoside E) containing a flavonoid and a phenethanoid glycoside formed through a pyran ring, one new phenylethanoid glycoside dimer (forsythoneoside F) with a C–O bond, along with a pair of flavonoid glycoside dimers (forsythobiflavone A and B) possessing different axial chirality, were obtained. Their chemical structures, including absolute configurations, were established by NMR, HRESIMS, UV, IR, and ECD spectroscopic data and comparison of experimental and calculated electronic circular dichroism (ECD) spectra. All of the compounds were evaluated for their neuroprotective effects against rotenone-induced neurotoxicity in PC12 cells at 1 μM.

Nine new compounds from the root bark of Lycium chinense and their α-glucosidase inhibitory activity

Co-reporter:Ya-Nan Yang;Ya-Wen An;Zhi-Lai Zhan;Jing Xie;Jian-Shuang Jiang;Zi-Ming Feng;Fei Ye

RSC Advances (2011-Present) 2017 vol. 7(Issue 2) pp:805-812

Publication Date(Web):2017/01/03

DOI:10.1039/C6RA24751B

Lycium chinense Mill. is a deciduous shrub in the Solanaceae family that is known for its fruits (Lycii fructus) and root bark (Lycii cortex). In our ongoing search for α-glucosidase inhibitors from the root bark of L. chinense, lyciumflavane A, one new flavane with an unusual benzofuran unit, one new amide possessing a naphthalene skeleton, one new sesquiterpene, three new lignan glucosides, and three new phenolic glucosides were isolated along with eight known compounds. Their structures were elucidated using NMR, HRESIMS, UV, ECD, and IR spectroscopic data. Their α-glucosidase inhibitory activity was screened using acarbose as a positive control (IC50 = 385 μM). Compound 1 showed strong inhibitory activity against α-glucosidase (IC50 = 20.89 μM).

New iridoid glycosides from the fruits of Forsythia suspensa and their hepatoprotective activities

Co-reporter:Si-Yuan Shao, Ya-Nan Yang, Zi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng Zhang

Bioorganic Chemistry 2017 Volume 75(Volume 75) pp:

Publication Date(Web):1 December 2017

DOI:10.1016/j.bioorg.2017.10.006

•Six new iridoid glycosides were isolated from the fruits of Forsythia suspensa.•Compound 1 is a novel iridoid glycoside trimer existing in natural sources.•Compounds 5 and 6 have strong bioactivities against APAP-induced HepG2 cell damage.A novel iridoid glycoside trimer named forsydoitriside A (1) and five new iridoid glycosides (2–6) were isolated from the fruits of Forsythia suspensa together with two known compounds (7, 8). These new structures were elucidated by comprehensive spectroscopic data and the comparison of experimental and calculated electronic circular dichroism spectra. Compounds 1–8 were all assayed on acetaminophen-induced HepG2 cell damage. The results exhibited that compounds 2, 3, 5 and 6 possessed strong hepatoprotective activities against the damage in HepG2 cell.Download high-res image (75KB)Download full-size image

Eight new phenylethanoid glycoside derivatives possessing potential hepatoprotective activities from the fruits of Forsythia suspensa

Co-reporter:Si-Yuan Shao, Zi-Ming Feng, Ya-Nan Yang, Jian-Shuang Jiang, Pei-Cheng Zhang

Fitoterapia 2017 Volume 122(Volume 122) pp:

Publication Date(Web):1 October 2017

DOI:10.1016/j.fitote.2017.09.008

In our study to investigate components with hepatoprotective activities, eight new phenylethanoid glycoside derivatives (1–8) were isolated from the 75% EtOH–H2O extract of the fruits of Forsythia suspensa along with six known compounds (9–14). These new structures were elucidated through HRESIMS and extensive NMR spectroscopic techniques. The absolute configurations of their sugars were determined by GC analysis. The pharmacological assay showed that compounds 2, 3, and 9–11 displayed remarkable hepatoprotective activities against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage at the concentration of 10 μM (Bicyclol as positive contrast).Eight new phenylethanoid glycoside derivatives were isolated from the fruits of Forsythia suspensa. The bioactive assay suggested that some of them possessed potential hepatoprotective activities.Download high-res image (352KB)Download full-size image

An Approach for Determining the Absolute Configuration of C-2 in 2-Oxygenated Phenylethanoid Glycosides by 1H NMR Spectroscopy

Co-reporter:Si-Yuan Shao, Fan Zhang, Ya-Nan Yang, Zi-Ming Feng, Jian-Shuang Jiang, and Pei-Cheng Zhang

Organic Letters 2016 Volume 18(Issue 16) pp:4084-4087

Publication Date(Web):July 29, 2016

DOI:10.1021/acs.orglett.6b01978

The absolute configurations of 2-oxygenated phenylethanoid glycosides were conveniently determined by 1H NMR spectroscopy. A comparison of the chemical shift differences (Δδ) of the diastereotopic methylene protons (H-1) demonstrate that a large chemical shift difference corresponds to an R configuration and a small chemical shift difference indicates S for the 2-alkoxy form. However, the situation is contrary to that of the 2-hydroxy form. Furthermore, the mechanism underlying this result is discussed based on the visualized conformations of such compounds.

Bioactive Sesquiterpenoid and Polyacetylene Glycosides from Atractylodes lancea

Co-reporter:Kuo Xu; Jian-Shuang Jiang; Zi-Ming Feng; Ya-Nan Yang; Li Li; Cai-Xia Zang

Journal of Natural Products 2016 Volume 79(Issue 6) pp:1567-1575

Publication Date(Web):May 26, 2016

DOI:10.1021/acs.jnatprod.6b00066

Nine new sesquiterpenoids (1–9), five new polyacetylenes (10–14), and six known compounds were isolated from the rhizomes of Atractylodes lancea. These new chemical structures were established using NMR, MS, and ECD data. Notably, compounds 3–5, the aglycone of which possesses two stereogenic centers (C-5 and C-7), exhibited similar ECD spectra to compounds 1 and 2, the aglycone of which possesses one stereogenic center (C-7). Such a difference was supported by the experimental and calculated ECD data and single-crystallographic analyses of 3a. In addition, compound 3 inhibited lipopolysaccharide-induced NO production in BV2 cells with an IC50 value of 11.39 μM (positive control curcumin, IC50 = 4.77 μM); compound 4 showed better hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury than the positive drug (bicyclol) at a concentration of 10 μM (p < 0.001).

Bioactive Octahydroxylated C21 Steroids from the Root Bark of Lycium chinense

Co-reporter:Ya-Wen An; Zhi-Lai Zhan; Jing Xie; Ya-Nan Yang; Jian-Shuang Jiang; Zi-Ming Feng; Fei Ye

Journal of Natural Products 2016 Volume 79(Issue 4) pp:1024-1034

Publication Date(Web):March 16, 2016

DOI:10.1021/acs.jnatprod.5b01087

Lyciumsterols A–K (1–11), 11 new octahydroxylated C21 steroids, were isolated from the root bark of Lycium chinense, along with 15 known compounds. Characterization of these C21 steroids showed the presence of eight hydroxy groups on the C21 steroid skeleton with a (2E,4E)-5-phenyl-2,4-pentadienoate group at C-12 or C-20 and various 2,6-deoxy sugar residues at C-3. The structures of these compounds were elucidated using spectroscopic data interpretation. Compounds 2, 3, and 7 exhibited dose-dependent protective effects on pancreatic islet cells and may help to improve cell viability. In addition, it was found that compounds 7, 8, 9, and 11 exhibited autophagy activation.

A novel adduct of ECG fused to piceid and four new dimeric stilbene glycosides from Polygonum cuspidatum

Co-reporter:Ya-nan Yang, Fu-shuang Li, Fu Liu, Zi-ming Feng, Jian-shuang Jiang and Pei-cheng Zhang

RSC Advances 2016 vol. 6(Issue 65) pp:60741-60748

Publication Date(Web):17 Jun 2016

DOI:10.1039/C6RA11135A

Polyflavanostilbene B (1), an unusual adduct of epicatechin-3-O-gallate fused to piceid through a carbon–carbon bond, four new dimeric stilbene glycosides (2–5), three new stilbene glucosides (6–8), one new flavan glucoside (9), and six known compounds were isolated from the rhizome of Polygonum cuspidatum. The structures of these compounds were elucidated using spectroscopic data, including electronic circular dichroism (ECD) and Rh2(OCOCF3)4-induced CD spectra. All of the compounds were screened for their inhibitory activity against α-glucosidase using acarbose as a positive control (IC50 = 385 μM), and strong inhibitory activity against α-glucosidase was observed for compound 8 (IC50 = 3.04 μM).

Six new compounds from Atractylodes lancea and their hepatoprotective activities

Co-reporter:Kuo Xu, Ya-Nan Yang, Zi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng Zhang

Bioorganic & Medicinal Chemistry Letters 2016 Volume 26(Issue 21) pp:5187-5192

Publication Date(Web):1 November 2016

DOI:10.1016/j.bmcl.2016.09.069

Two new phenolic glycosides with a rare β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl moiety (1, 2), one new dihydrobenzofuran derivative (3), one new pyrazine derivative (4), two new furofuran lignan glycosides (5, 6), and six known compounds (7–12) were isolated from the rhizomes of Atractylodes lancea. The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh2(OCOCF3)4-induced circular dichroism for configurational assignments. Notably, compounds 1–3 showed significant hepatoprotective activities against N-acetyl-p-aminophenol-induced HepG2 cell injury. This study is also the first Letter on the isolation of furofuran lignans and pyrazine derivatives (4–7) from the genus Atractylodes.Download high-res image (131KB)Download full-size image

Seven New Acyl Glycosides from Erycibe obtusifolia

Co-reporter:Zi-Ming Feng;Zhao-Zhen Liu;Kuo Xu;Ya-Nan Yang;Jian-Shuang Jiang

Helvetica Chimica Acta 2016 Volume 99( Issue 3) pp:197-203

Publication Date(Web):

DOI:10.1002/hlca.201500143

Seven new acyl glycosides, benzyl 5-O-vanilloyl-β-d-apiofuranosyl-(16)-β-d-glucopyranoside (1), 4-hydroxy-3-methoxyphenyl 5-O-syringoyl-β-d-apiofuranosyl-(16)-β-d-glucopyranoside (2), isopentyl 5-O-syringoyl-β-d-apiofuranosyl-(16)-β-d-glucopyranoside (3), 3,4,5-trimethoxyphenyl 5-O-sinapoyl-β-d-apiofuranosyl-(16)-β-d-glucopyranoside (4), 6-methoxy-7-[(6-O-sinapoyl-β-d-glucopyranosyl)oxy]coumarin (5), 6-methoxy-7-[(2-O-sinapoyl-β-d-glucopyranosyl)oxy]coumarin (6), and isopentyl β-d-apiofuranosyl-(16)-[5-O-syringoyl-β-d-apiofuranosyl-(12)]-β-d-glucopyranoside (7), were isolated from Chinese folk herb Erycibe obtusifolia. Their structures were elucidated on the basis of extensive spectroscopic analysis, including UV, IR, MS, and 1D- and 2D-NMR techniques. Further, these compounds were evaluated against HCT-8 (human colon carcinoma), Bel-7402 (human liver carcinoma), BGC-823 (human stomach carcinoma), A549 (human lung carcinoma), and A2780 (human ovarian carcinoma) cell lines, however, none of them exhibited a significant bioactivity (IC₅₀ > 10 μm).

Two new quinic acid derivatives and one new lignan glycoside from Erycibe obtusifolia

Co-reporter:Zi-ming Feng, Zhao-zhen Liu, Peng-fei Yang, Ya-nan Yang, Jian-shuang Jiang, Pei-cheng Zhang

Phytochemistry Letters 2016 Volume 17() pp:45-49

Publication Date(Web):September 2016

DOI:10.1016/j.phytol.2016.06.010

⿢New quinic acid derivatives and lignan glycoside were isolated from Erycibe obtusifolia.⿢Their structures were elucidated on the basis of extensive spectroscopic analysis.⿢No cytotoxicities of them supported the literature⿿s report that it is safe through oral administration.Three new compounds, 4-{erythro-2-[3-(4-hydroxyl-3-methoxyphenyl)-3-O-β-d-glucopyranosyl-propan-1-ol]}-O-medioresinol (1), (7⿳E,9⿳E,1⿳R*,3⿳S*,5⿳R*,6⿳S*)-5-O-caffeoyl-3-O-dihydrophaseicoylquinic acid (2), and (7⿳E,9⿳E,1⿳R*,3⿳S*,5⿳R*,6⿳S*)-5-O-caffeoyl-4-O-dihydrophaseicoylquinic acid (3), were isolated from Chinese folk herb Erycibe obtusifolia together with six known compounds (4⿿9). Their structures were elucidated on the basis of comparisons of literatures and extensive spectroscopic analysis, including UV, IR, HRMS, and 1D and 2D NMR techniques. Further, the cytotoxicities of these compounds were evaluated against five cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780), but they were inactive against these tumor cell lines (IC50 > 10 μmol/L).

Forsythoneosides A–D, Neuroprotective Phenethanoid and Flavone Glycoside Heterodimers from the Fruits of Forsythia suspensa

Co-reporter:Fan Zhang; Ya-Nan Yang; Xiu-Yun Song; Si-Yuan Shao; Zi-Ming Feng; Jian-Shuang Jiang; Li Li; Nai-Hong Chen

Journal of Natural Products 2015 Volume 78(Issue 10) pp:2390-2397

Publication Date(Web):September 30, 2015

DOI:10.1021/acs.jnatprod.5b00372

Forsythoneosides A–D (1–4), four unusual adducts of a flavonoid unit fused to a phenylethanoid glycoside through a pyran ring or carbon–carbon bond, and four new phenylethanoid glycosides (5–8) were isolated from the fruits of Forsythia suspensa, together with nine known compounds. The structures of 1–8, including their absolute configurations, were elucidated by spectroscopic data as well as experimental and calculated electronic circular dichroism analysis. Compounds 2 and 4 inhibited PC12 cell damage induced by rotenone, and increased cell viability from 53.9 ± 7.1% to 70.1 ± 4.0% and 67.9 ± 5.2% at 0.1 μM, respectively.

New Butyrolactone Type Lignans from Arctii Fructus and Their Anti-inflammatory Activities

Co-reporter:Ya-Nan Yang, Xiao-Ying Huang, Zi-Ming Feng, Jian-Shuang Jiang, and Pei-Cheng Zhang

Journal of Agricultural and Food Chemistry 2015 Volume 63(Issue 36) pp:7958-7966

Publication Date(Web):August 27, 2015

DOI:10.1021/acs.jafc.5b02838

Arctiidilactone (1), a novel rare butyrolactone lignan with a 6-carboxyl-2-pyrone moiety, and 11 new butyrolactone lignans (2–12) were isolated from the fruits of Arctium lappa L., together with 5 known compounds (13–17). Their structures were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, UV, IR, ORD, and HRESIMS) and comparison to literature data. The absolute configurations of compounds 1–12 were determined by a combination of rotating-frame nuclear Overhauser effect spectroscopy (ROESY), circular dichroism (CD) spectroscopy, and Rh2(OCOCF3)4-induced CD spectroscopy. All of the compounds were tested for their anti-inflammatory properties in terms of suppressing the production of NO in lipopolysaccharide-induced BV2 cells. Compounds 1, 6, 8, and 10 exhibited stronger anti-inflammatory effects than the positive control curcumin, particularly 1, which exhibited 75.51, 70.72, and 61.17% inhibition at 10, 1, and 0.1 μM, respectively.

Neuroprotective naphthalene and flavan derivatives from Polygonum cuspidatum

Co-reporter:Fu Liu, Fu-shuang Li, Zi-ming Feng, Ya-nan Yang, Jian-shuang Jiang, Li Li, Pei-cheng Zhang

Phytochemistry 2015 110() pp: 150-159

Publication Date(Web):

DOI:10.1016/j.phytochem.2014.12.007

Saffloflavonesides A and B, Two Rearranged Derivatives of Flavonoid C-glycosides with a Furan–Tetrahydrofuran Ring from Carthamus tinctorius

Co-reporter:Jun He, Ya-Nan Yang, Jian-shuang Jiang, Zi-Ming Feng, and Pei-Cheng Zhang

Organic Letters 2014 Volume 16(Issue 21) pp:5714-5717

Publication Date(Web):October 21, 2014

DOI:10.1021/ol502789x

Two new rearranged derivatives of flavonoid C-glycosides, saffloflavonesides A (1) and B (2), were isolated from the florets of Carthamus tinctorius. Their structures were determined using UV, IR, HRESIMS, and 1D and 2D NMR data and by comparing experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 1 and 2 were unprecedented chalcone and flavanone derivatives possessing a furan conjoining tetrahydrofuran ring. A potential biosynthetic pathway was proposed. At 10 μM, 1 and 2 both showed strong inhibitory activity against PC12 cell damage induced by rotenone.

Hepatoprotective Activity of Twelve Novel 7′-Hydroxy Lignan Glucosides from Arctii Fructus

Co-reporter:Ya-Nan Yang, Xiao-Ying Huang, Zi-Ming Feng, Jian-Shuang Jiang, and Pei-Cheng Zhang

Journal of Agricultural and Food Chemistry 2014 Volume 62(Issue 37) pp:9095-9102

Publication Date(Web):September 2, 2014

DOI:10.1021/jf501859x

Twelve novel 7′-hydroxy lignan glucosides (1–12), including two benzofuran-type neolignans, two 8-O-4′ neolignans, two dibenzylbutyrolactone lignans, and six tetrahydrofuranoid lignans, together with six known lignan glucosides (13–18), were isolated from the fruit of Arctium lappa L. (Asteraceae), commonly known as Arctii Fructus. Their structures were elucidated using spectroscopy (1D and 2D NMR, MS, IR, ORD, and UV) and on the basis of chemical evidence. The absolute configurations of compounds 1–12 were confirmed using rotating frame nuclear overhauser effect spectroscopy (ROESY), the circular dichroic (CD) exciton chirality method, and Rh2(OCOCF3)4-induced CD spectrum analysis. All of the isolated compounds were tested for hepatoprotective effects against d-galactosamine-induced cytotoxicity in HL-7702 hepatic cells. Compounds 1, 2, 7–12, and 17 showed significantly stronger hepatoprotective activity than the positive control bicyclol at a concentration of 1 × 10–5 M.

Hepatoprotective acyl glycosides obtained from Erycibe hainanesis

Co-reporter:Ziming Feng, Shuang Song, Yawen An, Yanan Yang, Jianshuang Jiang, Peicheng Zhang

Phytochemistry Letters 2014 Volume 9() pp:163-167

Publication Date(Web):September 2014

DOI:10.1016/j.phytol.2014.06.006

•We focused on acyl glycosides from Erycibe hainanesis.•Three new acyl glycosides along with a new lignan glycoside were obtained.•The new compounds showed moderate hepatoprotective activities.An ongoing search for naturally occurring hepatoprotective constituents has identified three new acyl glycosides (1–3) and a new lignan glycoside (4) in the roots and stems of Erycibe hainanesis using various column chromatography methods. The structures of these compounds have been determined based on chemical and spectroscopic evidence, and the following bioassay indicates that all four glycosides have moderate hepatoprotective activities against d-galactosamine induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

Polyflavanostilbene A, a New Flavanol-Fused Stilbene Glycoside from Polygonum cuspidatum

Co-reporter:Fushuang Li, Zhilai Zhan, Fu Liu, Yanan Yang, Li Li, Ziming Feng, Jianshuang Jiang, and Peicheng Zhang

Organic Letters 2013 Volume 15(Issue 3) pp:674-677

Publication Date(Web):January 15, 2013

DOI:10.1021/ol3035033

Polyflavanostilbene A, a new flavanol-fused stilbene glycoside, was isolated from the rhizome of Polygonum cuspidatum. Its unusual structure, including its absolute stereochemistry, was determined by UV, IR, HRESIMS, and 1D and 2D NMR data and by the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Polyflavanostilbene A has an unprecedented rearranged flavanol skeleton fused to stilbene via a hexahydrocyclopenta[c]furan moiety. Polyflavanostilbene A showed strong inhibitory activity against α-glucosidase with an IC50 value of 17.7 μM.

Ternatusine A, a New Pyrrole Derivative with an Epoxyoxepino Ring from Ranunculus ternatus

Co-reporter:Zhilai Zhan, Ziming Feng, Yanan Yang, Li Li, Jianshuang Jiang, and Peicheng Zhang

Organic Letters 2013 Volume 15(Issue 8) pp:1970-1973

Publication Date(Web):April 4, 2013

DOI:10.1021/ol400643q

Ternatusine A (1), a novel alkaloid with an unprecedented epoxyoxepino[4,5-c] pyrrole ring, was isolated from the roots of Ranunculus ternatus Thunb. Its unusual structure, including its absolute stereochemistry, was determined using UV, IR, HRESIMS, and 1D and 2D NMR data and through comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. A possible biosynthetic pathway for ternatusine A was postulated.

NMR Solution Structure Study of the Representative Component Hydroxysafflor Yellow A and Other Quinochalcone C-Glycosides from Carthamus tinctorius

Co-reporter:Zi-Ming Feng ; Jun He ; Jian-Shuang Jiang ; Zhong Chen ; Ya-Nan Yang

Journal of Natural Products 2013 Volume 76(Issue 2) pp:270-274

Publication Date(Web):February 6, 2013

DOI:10.1021/np300814k

Hydroxysafflor yellow A (HSYA), a representative component of Carthamus tinctorius, has attracted much attention because of its remarkable cardiovascular activities. Its structure was originally reported in 1993 and has been widely cited to date. In our experiments, its solution structure was studied using NMR techniques in different solvents, including DMSO-d6, pyridine-d5, and CD3OH. The results indicate that the structure of HSYA is different than the previously described 1b, with 3-enol-1,7-diketo form. The structure has two keto–enol tautomers (2a and 2b), and 2a, with the 1-enol-3,7-diketo form, is the preferred tautomer. On the basis of this finding, other published quinochalcone C-glycoside structures were revised. Furthermore, a trend in the 13C NMR data of the (E)-olefinic carbons of quinochalcone C-glycosides is summarized, and a hypothesis is proposed for the relationship between the features of the molecular structure and the preferred keto–enol tautomer.

Dibenzoyl and Isoflavonoid Glycosides from Sophora flavescens: Inhibition of the Cytotoxic Effect of d-Galactosamine on Human Hepatocyte HL-7702

Co-reporter:Yi Shen, Zi-Ming Feng, Jian-Shuang Jiang, Ya-Nan Yang, and Pei-Cheng Zhang

Journal of Natural Products 2013 Volume 76(Issue 12) pp:2337-2345

Publication Date(Web):December 2, 2013

DOI:10.1021/np400784v

Twelve new dibenzoyl derivatives sophodibenzoside A–L (1–12) and five new isoflavone glycosides (13–17) have been isolated from the roots of Sophora flavescens together with eight known compounds (18–25). Notably, the use of acetic acid-d4 was required to enable identification of the dibenzoyl glycoside structures. Compounds 1, 2, 13, 14, and 19 exhibited weak inhibition of the cytotoxic effect of d-galactosamine on the human hepatic cell line HL-7702.

Rapid Identification of Unstable Acyl Glucoside Flavonoids of Oxytropis racemosa Turcz by High-performance Liquid ChromatographyDiode Array DetectionElectrospray Ionisation/Multi-stage Mass Spectrometry

Co-reporter:Shuang Song;Xiu-Ping Zheng;Wei-Dong Liu;Rui-Fang Du;Zi-Ming Feng;Li-Fu Bi

Phytochemical Analysis 2013 Volume 24( Issue 2) pp:155-161

Publication Date(Web):

DOI:10.1002/pca.2395

Abstract

Introduction

Oxytropis racemosa Turcz is an important minority medicine that is used mainly to improve children's indigestion, especially in inner Mongolia and Tibet. Previous studies indicated that the characteristic constituents of this plant are acylated flavonoids.

Objective

Rapidly identify the characteristic chemical constituents of O. racemosa by high-performance liquid chromatography–diode array detection–electrospray ionisation/multi-stage mass spectrometry (HPLC–DAD–ESI/MSⁿ) and suggest a useful method to control the quality of this medicinal plant.

Methods

In the HPLC fingerprint, 32 flavonoids were tentatively identified by a detailed analysis of their mass spectra, UV spectra and retention times. Furthermore, 13 flavonoids were confirmed by comparison with previously isolated compounds obtained from O. racemosa.

Results

In total, 32 flavonoids, including 13 flavonoids with 3-hydroxy-3-methylglutaric acid (HMG) moieties and four flavonoids with 3-malonyl moieties, were identified in the extract of O. racemosa. Among the compounds identified, 10 were characterised as new compounds for their particular acylated sugar moieties.

Conclusions

The method described is effective for obtaining a comprehensive phytochemical profile of plants containing unstable acylated flavonoids. The method is also useful for constructing the chromatographic fingerprint of the minority medicine –O. racemosa Turcz for quality control. Copyright © 2012 John Wiley & Sons, Ltd.

Acyl glycosides lignans, coumarins, and terpenes from the stems of Erycibe obtusifolia

Co-reporter:Zhao-zhen Liu, Zhi-lai Zhan, Fu Liu, Ya-nan Yang, Zi-ming Feng, Jian-shuang Jiang, Pei-cheng Zhang

Carbohydrate Research 2013 Volume 372() pp:47-54

Publication Date(Web):3 May 2013

DOI:10.1016/j.carres.2013.02.006

Nine new acyl glycosides, obtusifosides A–I (1–9), and eight known compounds have been isolated from an EtOH extract of the stems of Erycibe obtusifolia. Their structures were elucidated on the basis of a spectroscopic data analysis (NMR, HRESIMS, and CD) and chemical evidence. The hepatoprotective effects of some of the compounds from d-galactosamine-induced cytotoxicity in HL-7702 hepatic cells were evaluated. Compounds 1, 10, 11, 13, 16, and 17 showed significant hepatoprotective activities compared with the positive control bicyclol at concentrations of 1 × 10−5 M.Graphical abstractHighlights► Nine new acyl glycosides, obtusifosides A–I (1–9) from Erycibe obtusifolia were elucidated. ► Subsequently, their hepatoprotective effects were evaluated and some of them showed significant hepatoprotective activities.

Acyl glycosides with rare β-d-apiofuranosyl-β-d-glucopyranosyl-β-d-apiofuranosyl from Erycibe hainanesis

Co-reporter:Zi-ming Feng, Shuang Song, Jun He, Ya-nan Yang, Jian-shuang Jiang, Pei-cheng Zhang

Carbohydrate Research 2013 380() pp: 59-63

Publication Date(Web):

DOI:10.1016/j.carres.2013.07.011

Lignans from the Root of Rhodiola crenulata

Co-reporter:Ya-nan Yang, Zhao-zhen Liu, Zi-ming Feng, Jian-shuang Jiang, and Pei-cheng Zhang

Journal of Agricultural and Food Chemistry 2012 Volume 60(Issue 4) pp:964-972

Publication Date(Web):January 6, 2012

DOI:10.1021/jf204660c

Rhodiola crenulata L. is an important species in genus Rhodiola widely used as a health food to reinforce immunity, improve memory and learning, scavenge active-oxygen species, and relieve altitude sickness. Eleven new lignans and a new benzonitrile compound, crenulatanoside A, were isolated from the roots of R. crenulata L. along with 25 known compounds, including 12 lignans. The structures of these compounds were elucidated by spectroscopic data and chemical evidence. Among them, compounds 1–4 and 5–7 were determined to be optical isomers of two 8-O-4′ neolignan glycosides. Compounds 8–11 were aryl tetralin type lignans, and compounds 12 and 13 were dihydrobenzofuran neolignans. All of the isolated compounds were evaluated for their inhibitory activity against α-glucosidase. From the data obtained, compound 37 showed strong inhibitory activity against α-glucosidase with an IC50 value of 96.8 μM.

Hepatoprotective glycosides from Leonurus japonicus Houtt.

Co-reporter:Yixiu Li, Zhong Chen, Ziming Feng, Yanan Yang, Jianshuang Jiang, Peicheng Zhang

Carbohydrate Research 2012 Volume 348() pp:42-46

Publication Date(Web):1 February 2012

DOI:10.1016/j.carres.2011.10.034

Two new phenylethanoid glycosides 1 and 2 named leonoside E and leonoside F, and one new sesquiterpene glycoside (3) identified as 7α (H)-eudesmane-4,11 (12)-diene-3-one-2β-hydroxy-13-β-d-glucopyranoside, together with seven known glycosides (4–10), were isolated from the aerial part of Leonurus japonicus Houtt. Their structures were elucidated on the basis of spectroscopic data and chemical evidence. When tested in in vitro assays, compounds 1, 2, 4, and 6 exhibited potent hepatoprotective activity against d-galactosamine-induced toxicity in HL-7702 cells at concentration of 1 × 10−5 M.Graphical abstractTwo new phenylethanoid glycosides 1 and 2 named leonoside E and leonoside F, and one new sesquiterpene glycoside 3 identified as 7α (H)-eudesmane-4,11 (12)-diene-3-one-2β-hydroxy-13-β-d-glucopyranoside, together with seven known glycosides (4–10), were isolated from the aerial part of Leonurus japonicus Houtt.Highlights► Three new compounds were isolated from Leonurus japonicus Houtt. ► Their structures were identified by spectroscopic data and chemical evidence. ► Compounds 1, 2, 4, and 6 exhibited potent hepatoprotective activity.

New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities

Co-reporter:Jun He, Yi Shen, Jian-Shuang Jiang, Ya-Nan Yang, Zi-Ming Feng, Pei-Cheng Zhang, Shao-Peng Yuan, Qi Hou

Carbohydrate Research 2011 Volume 346(Issue 13) pp:1903-1908

Publication Date(Web):27 September 2011

DOI:10.1016/j.carres.2011.06.015

Eight new linear polyacetylene glucosides (1–8), containing two C10-, one C13- and five C14-acetylenes, together with three known polyacetylenes (9–11) were isolated from the florets of Carthamus tinctorius L. Their structures were elucidated by means of spectroscopic methods and chemical evidence. The absolute configurations of compounds 3–9 were confirmed by Snatzke and Gerards’s method, observing the induced circular dichroism after addition of dirhodium tetrakis (trifluoroacetate) [Rh2(OCOCF3)4] in CHCl3. All the isolated compounds (1–11) were also tested for inhibitory activities against LPS-induced NO production in murine macrophages and just showed weak activities at concentrations of 1 × 10−5 M.

Two New Quinochalcones from the Florets of Carthamus tinctorius

Co-reporter:Jian-Shuang Jiang, Jun He, Zi-Ming Feng and Pei-Cheng Zhang

Organic Letters 2010 Volume 12(Issue 6) pp:1196-1199

Publication Date(Web):February 19, 2010

DOI:10.1021/ol902971w

Two new quinochalcone compounds, named saffloquinoside A (1) and saffloquinoside B (2), were isolated from the florets of Carthamus tinctorius. Their unusual structures including their absolute stereochemistry were elucidated based on UV, IR, HRESIMS, 1D and 2D NMR data, and CD spectrum. Saffloquinoside A has an uncommon six−five member dioxaspirocycle and saffloquinoside B has a cyclohexatrione skeleton with a benzyl group and two C-glycosyl units. Saffloquinoside A exhibited middling anti-inflammatory activity.

Hepatoprotective Constituents from the Roots and Stems of Erycibe hainanesis

Co-reporter:Shuang Song, Yixiu Li, Ziming Feng, Jianshuang Jiang and Peicheng Zhang

Journal of Natural Products 2010 Volume 73(Issue 2) pp:177-184

Publication Date(Web):January 21, 2010

DOI:10.1021/np900593q

Eleven new diglycosides, erycibosides A−K (1−11), four new chlorogenic acid derivatives (14−17), and a new bis-coumarin (18), together with 21 known compounds, have been isolated from an EtOH extract of the roots and stems of Erycibe hainanesis. Their structures were elucidated by means of spectroscopic methods and chemical evidence. Inhibitory activities of some of the compounds on d-galactosamine-induced cytotoxicity in WB-F344 rat hepatic epithelial stem-like cells were screened, and compounds 2, 6, 10, 18, and 32 showed potent hepatoprotective activities at concentrations of 1 × 10−5 to 1 × 10−4 M.

Synthesis and cytotoxic activity of heterocycle-substituted phthalimide derivatives

Co-reporter:Ya Jun Yang, Ya Nan Yang, Jian Shuang Jiang, Zi Ming Feng, Hong Yan Liu, Xian Dao Pan, Pei Cheng Zhang

Chinese Chemical Letters 2010 Volume 21(Issue 8) pp:902-904

Publication Date(Web):August 2010

DOI:10.1016/j.cclet.2010.03.039

A series of heterocycle-substituted phthalimide derivatives were synthesized. Structurally diverse derivatives with heterocyclic rings, including furan, imidazo[1,2-a]pyridine, 1,3,4-thiadiazine, imidazo[2,1-b][1,3,4]thiadiazine, pyrazole, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine, thiazole and thiazoline, were obtained by the reactions of α-bromoketone intermediate with various nucleophiles containing oxygen, nitrogen and sulfur atom. Their cytotoxic activity was also evaluated against five human cancer cell lines in vitro.

Three New Sesquiterpenoids from Chrysanthemum indicum L.

Co-reporter:Zi-Ming Feng;Shuang Song;Peng-Fei Xia;Jian-Shuang Jiang

Helvetica Chimica Acta 2009 Volume 92( Issue 9) pp:1823-1828

Publication Date(Web):

DOI:10.1002/hlca.200900017

Abstract

Phytochemical investigation of the flowers of Chrysanthemum indicum L. led to the isolation of three new sesquiterpenoids, indicumolide A (1), indicumolide B (2), and indicumolide C (3). Their structures were elucidated by various spectroscopic methods.

New Hepatoprotective Coumarinolignoids from Mallotus apelta

Co-reporter:Jian-Fu Xu;Zi-Ming Feng;Jian Liu

Chemistry & Biodiversity 2008 Volume 5( Issue 4) pp:591-597

Publication Date(Web):

DOI:10.1002/cbdv.200890055

Abstract

Three new coumarinolignoids, malloapelins A–C (1–3, resp.), together with three known coumarinolignoids, cleomiscosin A (4), cleomiscosin B (5), and 5′-demethylaquillochin (6), were isolated from the roots of Mallotus apeltaMuell.-Arg. Compounds 1–6 are three pairs of regioisomeric coumarinolignoids. Their structures were elucidated on the basis of spectral evidence. Compounds 3 showed promising hepatoprotective activity against D-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

Rare biscoumarins and a chlorogenic acid derivative from Erycibe obtusifolia

Co-reporter:Jian Liu, Ziming Feng, Jianfu Xu, Yinghong Wang, Peicheng Zhang

Phytochemistry 2007 Volume 68(Issue 13) pp:1775-1780

Publication Date(Web):July 2007

DOI:10.1016/j.phytochem.2007.05.001

Three coumarins, 7,7′-dihydroxy-6,6′-dimethoxy-3,3′-biscoumarin (1), 7,7′-dihydroxy-6,6′-dimethoxy-8,8′-biscoumarin (2) and 7-O-[4′-O-(3″,4″-dihydroxycinnamyl)-β-d-glucopyranosyl]-6-methoxycoumarin (3), and a chlorogenic acid derivative, methyl-3-O-(4″-hydroxy-3″,5″-dimethoxybenzoyl)-chlorogenate (4) were isolated from the roots of Erycibe obtusifolia along with four known coumarins, scopoletin (5), scopolin (6), cleomiscosin A (7) and cleomiscosin B (8). Their structures were elucidated by spectroscopic methods. Among them, compounds (1) and (2) are rare carbon–carbon linked symmetrical biscoumarins.Four compounds including two symmetrical biscoumarins were isolated from the roots of Erycibe obtusifolia. Their structures were elucidated by spectroscopic methods.

Flavonoid ketohexosefuranosides from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br.

Co-reporter:Pei-Cheng Zhang, Sui-Xu Xu

Phytochemistry 2001 Volume 57(Issue 8) pp:1249-1253

Publication Date(Web):August 2001

DOI:10.1016/S0031-9422(01)00170-4

Four flavonoid ketohexosefuranosides, pinnatifinoside A, pinnatifinoside B, pinnatifinoside C, and pinnatifinoside D were isolated from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br. Their structures were elucidated by spectroscopic analysis (UV, IR, MS and 1D, 2D NMR) and chemical evidence.Four flavonoid ketohexosefuranosides were isolated from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br. Their structures were elucidated by spectroscopic analysis and chemical evidence.

Protective effects of Forsythia suspense extract with antioxidant and anti-inflammatory properties in a model of rotenone induced neurotoxicity

Co-reporter:Shuai Zhang, Si-Yuan Shao, Xiu-Yun Song, Cong-Yuan Xia, Ya-Nan Yang, Pei-Cheng Zhang, Nai-Hong Chen

NeuroToxicology (January 2016) Volume 52() pp:72-83

Publication Date(Web):1 January 2016

DOI:10.1016/j.neuro.2015.09.009

•FS8, one of Forsythia suspense extracts, markedly protected PC12 cells against rotenone toxicity.•Four chemical compounds were identified in FS18.•FS8 protected dopamine neurons against rotenone toxicity via antioxidant and anti-inflammatory effects in rats.The present study investigated the neuroprotective effects of Forsythia suspense extract in a rotenone-induced neurotoxic model. FS8, one of the herbal extracts, markedly protected PC12 cells against rotenone toxicity and was selected for the in vivo study. Gavage administration of FS8 (50 and 200 mg/kg, but not 10 mg/kg) for 25 days significantly improved the behavior function, decreased the loss of dopaminergic neurons in substantia nigra (SN), and maintained the level of dopamine in striatum after unilateral infusion of rotenone in SN. Wherein, the protective effects of FS8 at the dose of 200 mg/kg were better than selegiline. Further study indicated the excellent antioxidant activity of FS8 on the 5th and 21st days after intranigral injection of rotenone. Moreover, FS8 could inhibit microglia activity and accumulation in SN, and obviously decreased the expression of pro-inflammatory molecules (IL-6, TNF-α, iNOS and COX-2), which indicated the anti-inflammatory effects of FS8. In the PI3K/Akt/NF-κB and MAPK pathways, FS8 significantly down-regulated the protein expression of p-PI3K, p-Akt, p-IκB, p-P65, cleaved Caspase 8, p-p38 and p-JNK but not p-mTOR, cleaved Caspase 3 and p-ERK. Therefore, FS8 protected dopamine neurons against rotenone toxicity via antioxidant and anti-inflammatory effects, which suggested the promising application of FS8 in the prevention and treatment of Parkinson disease.

NMR Spectroscopic Method for the Assignment of 3,5-Dioxygenated Aromatic Rings in Natural Products

Co-reporter:Ya-Nan Yang; Hui Zhu; Zhong Chen; Fu Liu; Ya-Wen An; Zi-Ming Feng; Jian-Shuang Jiang

Journal of Natural Products () pp:

Publication Date(Web):March 31, 2015

DOI:10.1021/np5008679

In recent years, certain “new” naturally occurring compounds (1–28) with 3,5-dioxygenated aromatic rings have been reported. A comparison of the NMR data of these compounds with the data of four model compounds (A–D) indicated that the structures of these “new” compounds were erroneous. The reason for the incorrect elucidation of the structures of 1–28 was attributed to “deceptively simple” 1H NMR spectra, which displayed two broad singlets with integrations of 1:2 for H-2 and H-5, H-6, respectively. To expose the misleading results from the spectra, serial 1H NMR experiments on compounds A–D were performed using various deuterated solvents and temperatures. The results revealed separated proton signals for the ABX system in certain deuterated solvents. Additionally, the characteristic differences between 3,4- and 3,5-dioxygenated aromatic rings in their 13C NMR spectra are summarized based on our experiment and data reported. This approach is useful for analyzing the patterns of dioxygenated aromatic rings in natural products, especially when “deceptively simple” 1H NMR spectra are displayed.

Sophopterocarpan A, a novel pterocarpine derivative with a benzotetrahydrofuran-fused bicyclo [3.3.1] nonane from Sophora flavescens

Co-reporter:Hui Zhu, Ya-Nan Yang, Kuo Xu, Jing Xie, Zi-Ming Feng, Jian-Shuang Jiang and Pei-Cheng Zhang

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 26) pp:NaN5483-5483

Publication Date(Web):2017/06/23

DOI:10.1039/C7OB01261F