Chrysanolide A, an unprecedented sesquiterpenoid trimer from the flowers of Chrysanthemum indicum L

Gu, Qiong; Chen, Yaoyao; Cui, Hui; Huang, Dane; Zhou, Jingwei; Wu, Taizong; Shi, Lei; Xu, Jun

doi:10.1039/c3ra23172k

Cited by 27 publications

(34 citation statements)

References 19 publications

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“…Some known flavonoids (unpublished data) and new sesquiterpenoids were discovered. 17 Herein, a chemical modification method was performed in combination with bioactivity-guided isolation of a C. indicum extract to obtain four new 3,5-diarylpyrazole analogues (1−4) (Scheme 1). Furthermore, molecular docking was also used to study the binding modes of the active compounds 1−4 with Aβ 42 .…”

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confidence: 99%

3,5-Diarylpyrazole Derivatives Obtained by Ammonolysis of the Total Flavonoids from Chrysanthemum indicum Extract Show Potential for the Treatment of Alzheimer’s Disease

Jiang

Morris‐Natschke

et al. 2015

J. Nat. Prod.

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Four new 3,5-diarylpyrazole analogues (1-4) were isolated from an extract of the flowers of Chrysanthemun indicum using a combination of ammonolysis of the total flavonoid extract and an Aβ aggregation inhibitory activity guided purification procedure. All four compounds (1-4) showed moderate to potent activity against Aβ aggregation with EC50 values of 4.3, 15.8, 1.3, and 2.9 μM, respectively. Moreover, compound 3 showed low cytotoxicity and significant neuroprotective activity against Aβ-induced cytotoxicity in the SH-SY5Y cell line. This report is the first to show that 3,5-diarylpyrazole analogues can inhibit Aβ aggregation and exhibit neuroprotective activity with potential for the treatment of Alzheimer's disease. Taken together, the method presented here offers an alternative approach to yield bioactive compounds.

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confidence: 99%

3,5-Diarylpyrazole Derivatives Obtained by Ammonolysis of the Total Flavonoids from Chrysanthemum indicum Extract Show Potential for the Treatment of Alzheimer’s Disease

Jiang

Morris‐Natschke

et al. 2015

J. Nat. Prod.

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“…(+)-Rutamarin was used as control. 24 Among them,11 compounds (3,4,6,11,12,[15][16][17]20,22,and 24) exhibited more than 50% inhibition against EBV lytic replication. These 11 compounds were further analyzed to obtain their EC 50 , CC 50 , and SI values ( Table 4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The known compounds were identified as barbatellarine B (14), 19 scutebarbatine Y (15), 18 barbatin D (16), 20 scutebarbatine L (17), 21 6,7-di-O-acetoxbarbatin A (18), 22 scutebarbatine A (19), 11 scutebata J (20), 23 scutebarbatine K (21), 21 scutebata D (22), 8 scutebata F (23), 8 barbatine D (24), 11 barbatine A (25), 11 and barbatine B (26), 11 based on spectroscopic data analysis and comparison with literature values.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

neo-Clerodane Diterpenoids from Scutellaria barbata with Activity against Epstein–Barr Virus Lytic Replication

Wang

Jiang

et al. 2015

J. Nat. Prod.

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Bioassay-guided fractionation was conducted on an EtOAc-soluble extract of the whole plants of Scutellaria barbata, monitored by inhibition of Epstein-Barr virus (EBV) lytic replication. Twenty-six neo-clerodane diterpenoids were isolated, of which 13 are new (1-13, scutolides A-L) and 13 previously known (14-26). The structures of 1-13 were elucidated by analysis of their NMR and MS spectroscopic data. Furthermore, the configurations of the new compounds 1 and 11 were confirmed by single-crystal X-ray diffraction. All of the isolated compounds were evaluated for inhibitory effects against EBV lytic replication. Eleven compounds (3, 4, 6, 11, 12, 15, 16, 17, 20, 22, and 24) exhibited moderate to potent inhibition, with EC50 values from 3.2 to 23.6 μM and selective index (SI) values from 2.1 to 109.2. More specifically, the new compound 4 showed the most potent activity, with EC50 and SI values of 3.2 μM and 46.1, respectively, while compound 24 (EC50 = 16.4 μM) exhibited the highest SI of 109.2. This study is the first to report that neo-clerodane diterpenoids demonstrate significant inhibition against EBV lytic replication.

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“…More interestingly the anti-HBV activities increased with the increasing degree of aggregation. Compound 116 is a third guaianolide-type sesquiterpenoid trimer found in plant, its activity is better than that of the positive control drug, and its mechanism of anti-HBV is worthy of further exploration [43].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Chemistry and Pharmacological Activity of Sesquiterpenoids from the Chrysanthemum Genus

et al. 2021

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Plants from the Chrysanthemum genus are rich sources of chemical diversity and, in recent years, have been the focus of research on natural products chemistry. Sesquiterpenoids are one of the major classes of chemical constituents reported from this genus. To date, more than 135 sesquiterpenoids have been isolated and identified from the whole genus. These include 26 germacrane-type, 26 eudesmane-type, 64 guaianolide-type, 4 bisabolane-type, and 15 other-type sesquiterpenoids. Pharmacological studies have proven the biological potential of sesquiterpenoids isolated from Chrysanthemum species, reporting anti-inflammatory, antibacterial, antitumor, insecticidal, and antiviral activities for these interesting molecules. In this paper, we provide information on the chemistry and bioactivity of sesquiterpenoids obtained from the Chrysanthemum genus which could be used as the scientific basis for their future development and utilization.

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Chrysanolide A, an unprecedented sesquiterpenoid trimer from the flowers of Chrysanthemum indicum L

Cited by 27 publications

References 19 publications

3,5-Diarylpyrazole Derivatives Obtained by Ammonolysis of the Total Flavonoids from Chrysanthemum indicum Extract Show Potential for the Treatment of Alzheimer’s Disease

3,5-Diarylpyrazole Derivatives Obtained by Ammonolysis of the Total Flavonoids from Chrysanthemum indicum Extract Show Potential for the Treatment of Alzheimer’s Disease

neo-Clerodane Diterpenoids from Scutellaria barbata with Activity against Epstein–Barr Virus Lytic Replication

Chemistry and Pharmacological Activity of Sesquiterpenoids from the Chrysanthemum Genus

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