Antioxidant and cytotoxic lignans from the roots of Bupleurum chinense

In the search for biologically active compounds from the roots of Bupleurum chinense D C., phytochemical investigation of its ethanol extract led to the isolation and identification of a new 8-O-4′ neolignan glucoside, saikolignanoside A (1), along with eight known lignans (2–9). Their structures were determined on the basis of IR, UV, HRESIMS, and NMR spectroscopic analyses. The antioxidant and cytotoxic effects of isolated compounds were evaluated in vitro. The isolated compounds (IC₅₀ > 200 μM) did not display 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity. Whereas compounds 1–2, 5, 7, and 9 exhibited potent 2, 2′-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging properties with IC₅₀ values ranging from 8.34 to 15.24 μM, while compounds 3–4, 6, 8 showed moderate properties. In addition, all compounds were evaluated for cytotoxicities against A549, HepG2, U251, Bcap-37, and MCF-7 cell lines. Compounds 5 and 9 (IC_50?相似文献   

Chemical constituents from the roots of Tripterygium wilfordii and their cytotoxic activity

In our ongoing search for bioactive constituents, a new sesquiterpene polyol ester, named triptersinine U (1), together with five known triterpenes (2–6) and seven sesquiterpene pyridine alkaloids (7–13), were isolated from the roots of Tripterygium wilfordii Hook. f. Their chemical structures were elucidated using extensive spectroscopic analyses, including 1D and 2D NMR, and HRESIMS, as well as comparison with previously reported data. Cytotoxic activities of all compounds 1–13 were evaluated against six human tumor cell lines (HepG2, Hep3B, Bcap37, U251, MCF-7 and A549) using the MTT in vitro assay. The results showed that triterpenes exhibited moderate cytotoxic activities toward the tested cell lines.     

Leucanone A and naamine J,glycerol ether lipid and imidazole alkaloid from the marine sponge Leucandra sp.

Chemical investigation on CH₂Cl₂ extract of the marine sponge Leucandra sp. afforded two new compounds named leucanone A (1) and naamine J (2), together with eight known compounds (3–10). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of the compounds were evaluated against four cancer cell lines, and compound 2 showed mild cytotoxic activities against MCF-7, A549, HeLa, and PC9 cancer cell lines with IC₅₀ values in the range of 20.1–45.3 μM.     

Cytotoxic constituents of the leaves of Ixeris sonchifolia

The ethyl acetate extract of the leaves of Ixeris sonchifolia afforded two new and two known sesquiterpene lactone glucosides of the guaiane-type, together with a known alkenol glucoside. The known compounds were identified as ixerin Z (1), ixerin Z-6'-p-hydroxyphenylacetate (2), and (Z)-3-hexen-1-ol-beta-D-glucopyranoside (3), respectively. The structures of the new compounds were elucidated as 11,13a-dihydroixerin Z [4, 3-hydroxy-2-oxo-guaia-1(10), 3-dien-5alpha,6beta,7alpha, 11betaH-12,6-olide-3-O-beta-D-glucopyranoside], and 3,10beta-dihydroxy-2-oxo-guaia-3,11(13)-dien-1alpha,5alpha,6alpha,7aH-12,6-olide-10-O-beta-D-glucopyranoside (5), respectively. The cytotoxicity of these compounds against human hepatocellular carcinoma cell (HepG2) and human melanoma cell (SK-MEL-2) was evaluated.     

A new sesquiterpene lactone glucoside with inhibitory effect on K562 cells from Ixeris sonchifolia (Bge) Hance

A new minor sesquiterpene lactone glucoside, ixerin Z_A (1), together with 16 known compounds, were isolated from the whole plants of Ixeris sonchifolia (Bge) Hance. The structure of 1 was elucidated as 1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3-O-[6′-(p-metheoxyphenylacetyl)]-β-glucopyranoside on the basis of spectroscopic and chemical evidence. Compound 1 exhibited an inhibitory effect on K₅₆₂ cells.     

Three minor valepotriate isomers from Valeriana jatamansi and their cytotoxicity

Three new minor valepotriate isomers, jatamanvaltrates Z1 (1), Z2 (2), and Z3 (3), have been isolated from the whole plants of Valeriana jatamansi (syn. Valeriana wallichii.). Their structures were elucidated by extensive spectroscopic analysis, especially 2D NMR and ESI-MS/MSⁿ. All isolated compounds displayed moderate cytotoxicity against the lung adenocarcinoma (A549), metastatic prostate cancer (PC-3 M), colon cancer (HCT-8), and hepatoma (Bel7402) cell lines with IC₅₀ values of 2.8–8.3 μM.     

Chemical constituents of the red alga Laurencia tristicha

Six new sesquiterpenes, 10-hydroxy-epiaplysin (1), 10-hydroxy-aplysin (2), 10-hydroxy-debromoepiaplysin (3), aplysin-9-ene (4), epiaplysinol (5) and debromoepiaplysinol (6), together with 13 known compounds (7–19), have been isolated from the red alga Laurencia tristicha. The structures of 1–6 were determined by spectroscopic methods including IR, EI-MS, HREI-MS, and 1D and 2D NMR techniques. All compounds were obtained from this species for the first time and were tested for cytotoxic activities against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), hepatoma (Bel 7402), colon cancer (HCT-8) and HeLa cell lines. Compound 6 showed selective cytotoxicity against HeLa cell line with IC₅₀ 15.5 μM, cholest-5-en-3β,7α-diol (14) was toxic to all tested cell lines with IC₅₀ values of 16.8, 5.1, 0.5, 0.5, and 0.3 μM, respectively, and other compounds were inactive (IC₅₀>10 μg/ml).     

A new bis-γ-pyrone polypropionate from a marine pulmonate mollusc Onchidium struma

A new bis-γ-pyrone polypropionate compound onchidione II (1), together with three known compounds, was isolated from a marine pulmonate mollusc Onchidium struma, collected at Hainan Island of China. The structure of new compound was determined by extensive spectroscopic analyses including IR, 1D and 2D NMR techniques, and chemical methods. Compounds 1–4 were evaluated for their cytotoxicity against human tumor cell lines HepG-2, A549, and MCF-2. The results showed that compounds 1 and 2 were moderate cytotoxic against HepG-2, A549, and MCF-2 cell lines, with IC₅₀ values from 13.2 to 22.4 μM.     

Ingenine E,a new cytotoxic β-carboline alkaloid from the Indonesian sponge Acanthostrongylophora ingens

A new β-carboline alkaloid ingenine E (4), along with three known metabolites annomontine (1), acanthomine A (2), and 1,2,3,4-tetrahydronorharman-1-one (3) were isolated from the Indonesian marine sponge Acanthostrongylophora ingens. Their structure characterization was unequivocally carried out using one- and two-dimensional NMR spectroscopy, as well as high-resolution mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated toward MCF7, A549, HCT116, PC12, and Hela cancer cell lines. Ingenine E (4) exhibited cytotoxic activity against MCF7, HCT116, and A549 cell lines with IC₅₀ values of 3.5, 0.67, and 2.15 μg/ml.     

Garcixanthone A,a new cytotoxic xanthone from the pericarps of Garcinia mangostana

A new prenylated xanthone, garcixanthone A (5), together with eight known compounds, mangostanaxanthones I (1) and II (2), garcinone E (3), β-mangostin (4), 8-hydroxycudraxanthone G (6), garcinone C (7), cudraxanthone G (8), and (-)-epicatechin (9) were isolated from the EtOAc-soluble fraction of the air-dried pericarps of Garcinia mangostana (family Clusiaceae). Their structures were verified on the basis of spectroscopic data interpretation as well as comparison with the literature. The cytotoxic and antimicrobial activities of the new compound were assessed using sulforhodamine B (SRB) and agar disk diffusion assays, respectively. Compound 5 showed significant cytotoxic potential against epithelial lung carcinoma (A549) and breast carcinoma (MCF7) cell lines with IC₅₀s 3.0 and 4.2 μM, respectively, compared to doxorubicin (0.74 and 0.41 μM, respectively).     

Phorbol ester-type diterpenoids from the twigs and leaves of Croton tiglium

Phytochemical investigation of the ethanol extract from the twigs and leaves of Croton tiglium led to the isolation of two new phorbol esters (1–2) and seven known ones (3–9). Their structures were elucidated by the analyses of extensive spectroscopic data (IR, MS, and 1D and 2D NMR) and comparing with related compounds. Meanwhile, compounds 1–9 were determined for their cytotoxic activities on human lung cancer cell line A549. Among them, 1–2 were inactive against the cell line A549 (IC₅₀ > 100 μM), but compounds 3 and 7 showed weak activities.     

A new elemanolide sesquiterpene lactone from Elephantopus scaber

A new elemanolide sesquiterpene lactone, named elescaberin (1), together with two known compounds, namely, isodeoxyelephantopin (2) and deoxyelephantopin (3), was isolated from the whole plant of Elephantopus scaber. The structure of 1 was elucidated on the basis of spectroscopic analysis. All three compounds exhibited significant inhibitory activities against human SMMC-7721 liver cancer cells in vitro (IC₅₀ 8.18–14.08 μmol/l).     

Two new sesquiterpenoid glycosides from the leaves of Lycium barbarum

Two new sesquiterpenoid glycosides, lyciumionosides A–B (1–2), together with four known compounds (3–6), were isolated from the leaves of Lycium barbarum. Their structures were mainly established on the basis of MS, 1D and 2D NMR spectroscopic techniques. The antiproliferative activities of compounds 1–5 were evaluated. Compound 1 showed highest inhibitory activity against A549 cells with IC₅₀ value of 32.6 ± 2.6 μM, compound 3 showed highest inhibitory activity against PC-3 cells with IC₅₀ value of 36.0 ± 2.9 μM, and compound 5 exhibited highest inhibitory activity against HeLa cells with IC₅₀ value of 32.3 ± 4.2 μM.     

Three new sesquiterpenes from the stems of Nicotiana tabacum and their bioactivities

Three new sesquiterpenes, methyl 4-isopropyl-7-methoxy-6-methylnaphthalene-1-carboxylate (1), methyl 2-hydroxy-4-isopropyl-7-methoxy-6-methylnaphthalene-1-carboxylate (2), and methyl 2-hydroxy-6-(hydroxymethyl)-4-isopropyl-7-methoxynaphthalene-1-carboxylate (3), together with three known sesquiterpenes (4–6), were isolated from the stems of Nicotiana tabacum. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. The results showed that compounds 2, 3, and 5 exhibited high anti-TMV activity with inhibition rates of 33.6, 35.8, and 36.7%. Compounds 1–6 showed weak inhibitory activities against some tested human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7) with IC₅₀ values in the range of 6.7–9.6 μM.     

甘草次酸C3、C30衍生物的合成及其体外抗肿瘤活性研究

目的设计并合成甘草次酸C3、C30衍生物,并对其体外抗肿瘤活性进行研究。方法以甘草次酸为先导化合物,对其C3位羟基、C30位羧基进行结构修饰,并采用SRB法对目标化合物进行体外抗肿瘤活性研究。结果设计合成了12个新型甘草次酸衍生物,并利用MS、1H-NMR及元素分析确证了结构;体外实验中,目标化合物对MCF-7和A549肿瘤细胞的抑制活性均明显强于甘草次酸,其中化合物GA-I1、GA-I2和GA-II1对MCF-7和A549两种细胞表现出很好的抑制活性,明显高于对照药吉非替尼。结论甘草次酸衍生物具有良好的抗肿瘤活性,值得进一步研究。     

Cytotoxic monoterpenoid-type alkaloids from the aerial parts of Melodinus morsei

Three new monoterpenoid alkaloids, melomorines A–C (1–3), along with melohemsine B (4), were isolated from the 70% ethanol extract of the aerial parts of Melodinus morsei. Structural elucidation of all the compounds was performed on the basis of spectral data. All the compounds were tested in vitro for cytotoxic activities. As a result, alkaloids 1, 2, and 4 exhibited cytotoxicities against all the five tested tumor cell lines with IC₅₀ value of less than 20 μM.     

A new compound,brefeldin A formylate,from Penicillium sp. strain HLKG-44

A novel compound named as brefeldin A formylate (1), together with two known compounds, brefeldin A (2) and ergosterol (3), was isolated from the Penicillium sp. strain HLKG-44, which was isolated from polluted environment in Fujian Province. Their structures were identified based on the spectral and X-ray crystallographic analyses. The compound 1, brefeldin A formylate, exhibited moderate cytotoxic activity against the human lung cancer cell line A549 with IC₅₀ value of 18.9 μg/ml by the MTT assay protocol.     

Four new diterpenoids isolated from the Euphorbia rapulum

Four new diterpenoids named 1-epi-9-hydroxydepressin (1), 1-epi-8-hydroxydepressin (2), 2,13,9-trihydroxy-labda-8(17),12(E),14-triene (3) and tagalsin I (4) were isolated from Euphorbia rapulum. The structures of these compounds were elucidated by means of various spectroscopic methods. All the isolated compounds were evaluated for cytotoxic activities against HepG2, MCF-7, and C6 cell lines, and compound 4 showed moderate selective activity against MCF-7 cell line with an IC₅₀ value of 31.8 μM.     

A novel degraded sesquiterpene from the fresh stem of Aquilaria sinensis

A novel degraded sesquiterpene, named aquilarin B (1), together with two known compounds (2 and 3), was isolated from the EtOH extract of the fresh stem of Aquilaria sinensis (Lour.) Gilg. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR (HMQC, ¹H–¹H COSY, HMBC, and ROESY). The cytotoxic activities of the three compounds against three human tumor cell lines K562, SMMC-7721, and SGC-7901 were evaluated, and compound 3 exhibited obvious cytotoxic activity.     

Three new aaptamine derivatives from the South China Sea sponge Aaptos aaptos

Abstract

Three new aaptamine derivatives (1–3), together with six known related compounds (4–9), have been isolated from the South China Sea sponge Aaptos aaptos. The structures of all compounds were unambiguously elucidated on the basis of spectroscopic analyses. Compounds 1, 4, 5, 7, and 9 showed cytotoxic activities against HeLa, K562, MCF-7, and U937 cell lines with IC₅₀ values in the range of 0.90–12.32 μM.