Twelve new and 10 known protostane triterpenoids were isolated from the rhizome of Alisma orientale. Their structures were elucidated based on physical data analyses, including UV, HRESIMS, NMR experiments ((1)H, (13)C NMR, (1)H-(1)H COSY, HSQC, HMBC, and NOESY), and induced electronic circular dichroism. New compounds 1-12 were classified as protostanes (1-10), 29-norprotostane (11), and 24-norprotostane (12) by structure analyses. Furthermore, the inhibitory effects on human carboxylesterases (hCE-1, hCE-2) of compounds 1-22 were evaluated. Compounds 2, 6, 9, and 11 showed moderate inhibitory activities and were selective toward hCE-2 enzymes, with IC50 values of 8.68, 4.72, 4.58, and 2.02 μM, respectively. The inhibition kinetics of compound 11 toward hCE-2 were established, and the Ki value was determined as 1.76 μM using a mixed inhibition model. The interaction of bioactive compound 11 with hCE-2 was shown using molecular docking.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.jnatprod.5b00321 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Methyl jasmonate induces the regulation of protostane triterpene biosynthesis by microRNAs in Alisma orientale.
Protoplasma
January 2025
School of Pharmacy, Nanjing University of Chinese Medicine, 138 Xianlin Avenue, Nanjing, 210023, China.
Protostane triterpenes are medicinally important components found in members of the Alismataceae botanical family, notably Alisma orientale. Methyl jasmonate (MeJA) is known to regulate protostane triterpene biosynthesis in A. orientale, but the microRNA (miRNA) mechanism underlying MeJA response to promote triterpene biosynthesis remains unknown.
View Article and Find Full Text PDFTwo Undescribed Protostane Triterpenoids from the Rhizome of Alisma plantago-aquatica.
Chem Biodivers
March 2024
State Key Laboratory of Natural and Biomimetic Drugs and Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, 38 Xueyuan Road, Beijing, 100191, P. R. China.
Two undescribed protostane triterpenoids, 11-deoxy-13(17),15-dehydro-alisol B 23-acetate (2) and alisol S (3), together with 21 known ones (1, 4-23), were isolated from the dried rhizome of Alisma plantago-aquatica. Of these compounds, 13(17),15-Dehydro-alisol B 23-acetate (1) and 11-deoxy-13(17),15-dehydro-alisol B 23-acetate (2) are two protostane triterpenoids containing conjugated double bonds in the five-membered ring D that are rarely found from nature resource, while alisol S (3) is a protostane triterpenoid with undescribed tetrahydrofuran moiety linked via C -O-C at the side chain. Additionally, compound 18 is a new natural product, and cycloartenol triterpenoid 23 is a non protostane triterpenoid firstly isolated from genus Alisma.
View Article and Find Full Text PDFMechanism of triterpenoids from Alismatis Rhizoma against liver fibrosis based on an integrated approach using network pharmacology, molecular docking, and luciferase assay.
Nat Prod Res
November 2022
The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai, China.
Protostane-type triterpenoids are antifibrotic nature components with unique structures in Alismatis Rhizoma. However, the underlying mechanisms of them against liver fibrosis are not well illustrated. The present study aims to study the targets and mechanisms of Alismatis Rhizoma triterpenes responsible for their antifibrotic effects by network pharmacology, molecular docking, and luciferase assay.
View Article and Find Full Text PDFPharmacological Properties and Molecular Targets of Alisol Triterpenoids from Rhizoma.
Biomedicines
August 2022
OncoWitan, Scientific Consulting Office, 59290 Lille (Wasquehal), France.
More than 100 protostane triterpenoids have been isolated from the dried rhizomes of species, designated rhizoma (AR), commonly used in Asian traditional medicine to treat inflammatory and vascular diseases. The main products are the alisols, with the lead compounds alisol-A/-B and their acetate derivatives being the most abundant products in the plant and the best-known bioactive products. The pharmacological effects of Ali-A, Ali-A 24-acetate, Ali-B, Ali-B 23-acetate, and derivatives have been analyzed to provide an overview of the medicinal properties, signaling pathways, and molecular targets at the origin of those activities.
View Article and Find Full Text PDFNovel triterpenoids from Alisma plantago-aquatica with influence on LDL uptake in HepG2 cells by inhibiting PCSK9.
Phytomedicine
October 2022
National Engineering Research Center of TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Haike Road #501, Shanghai 201203, China. Electronic address:
Background: Proprotein convertase subtilisin/kexin type 9 (PCSK9) has been regarded as an effective and exciting target in the treatment of atherosclerotic cardiovascular disease since 2003. Only two monoclonal antibodies have been approved in the market which, however, were also criticized for their high cost to $9000 per dose and delivery route. Exploration of natural new effective and cheaper small molecule alternatives with effective PCSK9 inhibition is feasible and desired.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!