Screening of several biological activities induced by different sesquiterpene lactones isolated from Centaurea behen L. and Rhaponticum repens (L.) Hidalgo

This study aims to evaluate the in vitro cytotoxic, in vitro and in ovo anti-angiogenic effects and antimicrobial activity of sesquiterpene lactones (SLs) from two plants Centaurea behen and Rhaponticum repens (L.). Five SLs, including cynaropicrin (1), 4β,15-dehydro-3-dehydrosolstitialin A (2), aguerin B (3), janerin (4), cebellin E (5), and a flavone hispidulin (6) were isolated from C. behen (compounds 1–3) and R. repens (compounds 4–6). Cynaropicrin (1) and aguerin B (3) were characterised by strong cytotoxic activities against A2780 cells with IC₅₀ values of 1.15 and 1.62 μg mL^?1, respectively, comparable to that of doxorubicin (IC₅₀ = 1.17 μg mL^?1). The anti-angiogenic study showed the remarkable inhibitory effect of cynaropicrin (1) and aguerin B (3) on the proliferation and migration of HUVECs. In addition, cynaropycrin and aguerin B exhibited significant angio-inhibitory effects in CAM assay. These findings may be useful for the development of novel chemotherapeutic agents for the treatment of cancer.     

A new compound with cytotoxic activities from the leaves of Panax ginseng C.A. Meyer

A new compound, 3,6,20（S）-trihydroxy- 12,23-epoxydammar-24-ene,6,20-di-O-β-D-glucopyranoside （1）, was isolated from the leaves of Panax ginseng C.A. Meyer, whose structural elucidation was carried out by means of spectral analysis （including IR, HR- FAB-MS and NMR）. This compound showed the moderate cytotoxic activities against U937 and HeLa cells by using the MTT method.     

New Sesquiterpene Lactones from Carpesium Lipskyi

ＮｏｐｒｅｖｉｏｕｓｗｏｒｋｏｎｔｈｅｃｈｅｍｉｃａｌｃｏｎｓｔｉｔｕｅｎｔｓｏｆＣａｒｐｅｓｉｕｍｌｉｐｓｋｙｉ（ｆａｍｉｌｙ：Ｃｏｍｐｏｓｉｔａｅ）,ｕｓｅｄａｓｆｏｌｋｍｅｄｉｃｉｎｅ,ｓｉｎｃｅａｎｃｉｅｎｔｔｉｍｅｓ,ｆｏｒｒｅｌｉｅｖｉｎ...     

Eupatozansins A – C,Sesquiterpene Lactones from Eupatorium chinense var. tozanense

Phytochemical investigation of Eupatorium chinense var. tozanense has resulted in the isolation of three new germacranolides, designated as eupatozansins A–C ( 1 – 3 ), along with five known compounds, (5S,6R,7R,8R)‐8‐angeloyloxy‐2‐oxoguaia‐1(10),3,11(13)‐trien‐12,6‐olide ( 4 ), costunolide ( 5 ), leptocarpin ( 6 ), 2α‐hydroxyeupatolide 8‐O‐angelate ( 7 ), and quercetin ( 8 ). The structures of the new compounds were identified by 1D and 2D NMR experiments, as well as high‐resolution mass spectrometry. The in vitro cytotoxic activities of compounds 1 – 8 were evaluated.     

Sesquiterpene Lactones from Anthemis melanolepis

From the aerial parts of A. melanolepis, two new sesquiterpene lactones, melanolepin B ( = 1α,4β,8α‐trihydroxyeudesm‐11(13)‐en‐12,6α‐olide; 1 ) and melanolepin C (= 1α,10β‐epoxy‐8β‐hydroxygermacra‐4(15),11(13)‐dien‐12,6α‐olide; 2 ), were isolated, together with four known compounds, desacetyllaurenobiolide, dentatin A, taraxasterol, and (3S,5R)‐loliolide. Compound 1 was found to have the rare cis‐fused eudesmane skeleton. The structures of the isolated compounds were established by means of NMR (¹H, ¹H‐COSY, ¹H,¹³C‐HSQC, HMBC, NOESY) and MS analyses.     

Sesquiterpene Lactones from Notoseris Porphyrolepis

Two new sesquiterpene lactones, notoserolides A and B, along with 12 known compounds were isolated from the aerial parts of Notoseris porphyrolepis.By means of spectral methods including MS, NMR (1H NMR, 13C NMR, DEPT, HMQC, HMBC) and X-ray diffraction, as well as chemical reactions, the structures of notoserolides A and B were established as austricin 8-O-β-D-glucopyranoside and 8-O-senecioylaustricin, respectively.     

In vitro antiplasmodial and cytotoxic activities of sesquiterpene lactones from Vernonia fimbrillifera Less. (Asteraceae)

Due to the in vitro antiplasmodial activity of leaf extracts from Vernonia fimbrillifera Less. (Asteraceae), a bioactivity-guided fractionation was carried out. Three sesquiterpene lactones were isolated, namely 8-(4’-hydroxymethacrylate)-dehydromelitensin (1), onopordopicrin (2) and 8α-[4’-hydroxymethacryloyloxy]-4-epi-sonchucarpolide (3). Their structures were elucidated by spectroscopic methods (1D and 2D NMR and MS analyses) and by comparison with published data. The isolated compounds exhibited antiplasmodial activity with IC₅₀ values ≤ 5 μg/mL. Cytotoxicity of the compounds against a human cancer cell line (HeLa) and a mouse lung epithelial cell line (MLE12) was assessed to determine selectivity. Compound 3 displayed promising selective antiplasmodial activity (SI > 10).     

Cytotoxic and chemotaxonomic study of isolated metabolites from Centaurea aegyptiaca

The aerial parts of Centaureaa egyptiaca afforded 10 secondary metabolites including four sesquiterpene lactones; chlorohyssopifolin A (centaurepensin) ( 1 ), rediolpidetriol ( 2 ), linichlorinA ( 3 ), and sinaicin ( 4 ), one monoterpene; loliolid ( 5 ), one phenolic: tyrosol ( 6 ), three lignans; arctigenin ( 7 ), matairesinol ( 8 ), and pinoresinol ( 9 ), and one steroid; ergosta‐5,22‐dien‐3‐ol ( 10 ). The cluster analysis of 32 Centaurea species revealed that C. aegyptiaca is closely related to C. repens and C. solstitialise. The isolated compounds ( 1 – 10 ) were screened against CCRF‐CEM‐leukemia, MDA‐MB‐231‐pcDNA3 breast cancer, and HCT116 (p53⁺/⁺) colon carcinoma cell lines. Compounds 1 and 2 were the most potent compounds against both leukemia and breast carcinoma cell lines.     

牛尾蒿中—新倍半萜结构的确定

牛尾蒿中—新倍半萜结构的确定李瑜，杨立，师彦平（兰州大学应用有机化学国家重点实验室，兰州，７３００００）关键词牛尾蒿，倍半萜，牛尾蒿酮牛尾蒿（ＡｒｔｅｍｉｓｉａＳｕｂｄｉｇｉｔａｔａ）是菊科蒿属的一种多年生草本植物，广布于华北、东北、西北和西南等地区...     

Phytoquinoids and Secoprezizaane‐Type Sesquiterpenes from Illicium arborescens

A phytochemical investigation of the MeOH extract of Illicium arborescens yielded the two new phytoquinoid epimers, 2,3‐didehydro‐5‐O‐methyl‐11‐epiillifunone E ( 1 ) and 2,3‐didehydro‐5‐O‐methylillifunone E ( 2 ), as well as five new sesquiterpene lactones (8,9‐secoprezizaane‐type sesquiterpenes). Two of them, i.e., 3 and 4 , were minwanensin‐type sesquiterpenes, the other two, i.e., 5 and 6 , had the anisatin‐type (or floridanolide type) skeleton, and the fifth, i.e., 7 , was a dunnianin‐type sesquiterpene. Their structures were established by analyses of 1D‐ and 2D‐NMR, HR‐MS, and chemical evidence. The in vitro cytotoxic activity of compounds 1 – 7 was tested against four human tumor cell lines, including HeLa (cervical epitheloid), WiDr (colon), Daoy (medulloblastoma), and Hep2 (liver carcinoma) human‐tumor cells.     

Cytotoxic germacrane-type sesquiterpene lactones from the whole plant of Inula cappa

Phytochemical investigation on the whole plant of Inula cappa led to the isolation of two new germacrane-type sesquiterpene lactones,ineupatolides D and E(1 and 2),together with three known analogs.The structures of the new compounds were established by extensive analysis of 1Dand 2DNMR spectra,as well as MS data.Their absolute configurations were determined by CD spectra.All compounds showed moderate inhibitory effects on A431,A549,BGC-823,HL-60,HT-29,and MCF-7 cancer cell lines with IC_(50) values ranging from 2.1 to 36.3 μM.     

A New Bisabolane Sesquiterpene from Cremanthodium Discoideum

ThegenusCremanthodium(ComPositae)isaTibetan-traditionalmedicineusedforanti-inflanunation,painreliefandcuringaPoplexy'.Incontinuationofourstudies0nCremanthodiumplantS',wenowreport0ntheisolahonandstrUctUreelucidationofanewbisabolanesesquiterpenefromCremanth0diumdiscotheum.ComPound1,gum,[a]io53.3(cl.0,CHCl3),TheFABmassspectrUmsh0wedaquasim0lecularionpeak559[M H] anditSisotopicpeakofll3intensityatInlz56l,whichsuggestedthemolecularformulatobeC28ffi3O9Clinagreementwiththe13CNMRandDEPTsp…     

Sesquiterpene lactones from Artemisia austroyunnanensis suppresses ROS production and reduces cytokines,iNOS and COX-2 levels via NF-KB pathway in vitro

Abstract

The inhibitory effects of six sesquiterpene lactones (1–6) isolated from Artemisia austroyunnanensis Ling & Y. R. Ling were studied on the LPS-induced inflammatory mediator production in RAW264.7 cells. The results showed they can decrease the level of ROS in a concentration-dependent response. The compounds down-regulate the expression of iNOS and COX-2 and a series of classical inflammatory factors, including TNF-α, IL-1β, IL-6 and IL-10. These effects can be partially explained by the supression of the phosphorylation of NF-κB. Additionally, the relationship between their structures and inflammatory factors was analyzed and discussed.     

Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically

Ten new derivatives of isophorone were obtained through a five-step synthesis. Among the products were several unsaturated, bicyclic lactones with three or four methyl groups. These lactones were used as the substrates for biotransformation mediated by selected fungal strains (Fusarium species, Syncephalastrum racemosum, Cunninghamella japonica, Penicillium species, Absidia species, and Pleurotus ostreatus). Four new hydroxylactones were obtained as a result of biotransformation. Because the unsaturated lactone with four methyl groups was a diastereoisomeric mixture, a structural analysis was conducted. The hydroxylactones were also included in this analysis. Both the unsaturated lactones and hydroxylactones were examined for their antimicrobial activity. It was found that some of these compounds exhibited growth inhibition against pathogenic strains of bacteria (Staphylococcus aureus, Pseudomonas fluorescens), yeasts (Candida albicans) and filamentous fungi (Alternaria sp., Penicillium sp.). All obtained compounds were also subjected to scent analysis.     

Comparative analysis of sesquiterpene lactones from <Emphasis Type="Italic">Mikania cordifolia</Emphasis> collected from three different locations

The sesquiterpene lactone composition of extracts of Mikania cordifolia collected from Ribeirao Preto-SP (Brazil), Sao Carlos-SP (Brazil), and Campos de Jordao-SP (Brazil) were comparatively analyzed by HPLC. The results indicate that all specimens have the melampolide type sesquiterpene lactones analyzed and this kind of structure can be used as taxonomic marker for M. cordifolia. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 117–118, March–April, 2007.     

Two new sesquiterpene lactones from the fruits of Illicium jiadifengpi

Two new seco-prezizaane-type sesquiterpenes, 3,4-dehydroneomajucin (1) and 1,2,3,4-tetradehydroneomajucin (2), were isolated from the fruits of Illicium jiadifengpi. The structure of these compounds was determined using 1D and 2D NMR and ESI-MS. The isolates were evaluated for their anti-hepatitis B virus activities on the Hep G2.2.15 cell line. The inhibitory rates of compounds 1 and 2 on the HBeAg and HBsAg expression were 30.08 ± 3.09% and 11.43 ± 1.92% at a concentrations of 68.00 μM and 7.88 ± 1.21% and 16.96 ± 4.24% at a concentration of 68.50 μM, respectively.     

New Sesquiterpene Formamides from the Marine Sponge Axinyssa sp.

Chemical investigation of an extract of the marine sponge Axinyssa sp., collected from the South China Sea, led to the isolation and identification of two new sesquiterpene formamides, (4R*,5R*,10R*)‐4‐formamidoeudesm‐7‐ene ( 1 ) and (4R*,5R*,7S*,10R*)‐4‐formamidoeudesman‐11‐ol ( 2 ), together with the known 4α‐formamidogorgon‐11‐ene ( 3 ). Their structures were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR spectroscopy, high‐resolution ESI‐TOF mass spectrometry, as well as X‐ray single‐crystal diffraction experiments. Possible biosynthetic pathways for 1 – 3 were also proposed. The human nasopharyngeal cancer cell line CNE‐2, human cervical cancer cell line HeLa, and human normal liver cell line L02 were used to examine the cytotoxic activities of 1 – 3 in vitro. As the results, 1 showed significant cytotoxic activity against CNE‐2, HeLa, and L02 cell lines with the IC₅₀ values of 13.8, 7.5, and 38.0 μg/ml, resp.     

Phytochemical Analysis and Anti-Cancer Properties of Extracts of Centaurea castriferrei Borbás & Waisb Genus of Centaurea L

The Centaurea L. (Asteraceae) genus includes many plant species with therapeutic properties. Centaurea castriferrei Borbás & Waisb is one of the least known and least described plants of this genus. The aim of the study was the phytochemical analysis of water and methanol–water extracts (7:3 v/v) obtained from the aerial parts of the plant as well as evaluation of their anticancer activity. Quantitative determinations of phenolic compounds and flavonoids were performed, and the antioxidant potential was measured using the CUPRAC method. The RP-HPLC/DAD analysis and HPLC-ESI-QTOF-MS mass spectroscopy were performed, to determine the extracts’ composition. The antiproliferative activity of the obtained extracts was tested in thirteen cancer cell lines and normal skin fibroblasts using MTT test. Regardless of the extraction method and the extractant used, similar cytotoxicity of the extracts on most cancer cell lines was observed. However, the methanol–water extracts (7:3 v/v) contained significantly more phenolic compounds and flavonoids as well as showing stronger antioxidant properties in comparison to water extracts. Centaurea castriferrei Borbás & Waisb is a rich source of apigenin and its derivatives. In all tested extracts, chlorogenic acid and centaurein were also identified. In vitro research revealed that this plant may be a potential source of compounds with anticancer activity.