Mangostanaxanthone VIII,a new xanthone from Garcinia mangostana and its cytotoxic activity

A new prenylated xanthone, mangostanaxanthone VIII (7) and six known metabolites: gartanin (1), 1,3,8-trihydroxy-2-(3-methyl-2-butenyl)-4-(3-hydroxy-3-methylbutanoyl)-xanthone (2), rubraxanthone (3), 1,3,6,7-tetrahydroxy-8-prenylxanthone (4), garcinone C (5), and xanthone I (9-hydroxycalabaxanthone) (6) were separated from the EtOAc-soluble fraction of the air-dried pericarps of Garcinia mangostana (Clusiaceae). Their structures have been verified on the basis of spectroscopic data analysis as well as comparison with the literature. The cytotoxic activity of 7 was assessed against MCF7, A549, and HCT116 cell lines using sulforhodamine B (SRB) assay. Compound 7 showed significant cytotoxic potential against MCF7 and A549 cell lines with IC₅₀s 3.01 and 1.96 μM, respectively compared to doxorubicin (0.06 and 0.44 μM, respectively). However, it exhibited moderate activity towards HCT116 cell line.     

A Novel Xanthone from Garcinia oligantha

One novel xanthone, oliganthone A ( 1 ), was isolated from the stems of the plant Garcinia oligantha. It features the O‐bearing C(3)‐atom and absence of C(4) compared with the structures of related known xanthones, which have never been reported before. The structure of this compound was elucidated by spectroscopic analysis. Compound 1 showed strong HeLa cell growth‐inhibiting effects with IC₅₀ values below 10 μM .     

Xanthones from the green branch of Garcinia dulcis

Two new prenylated xanthones, namely dulcisxanthone H and dulcisxanthone I along with garciniaxanthone C, were isolated from the dichloromethane extract of the green branch of Garcinia dulcis. Their structures were elucidated by the analysis of 1-D and 2-D NMR spectral data. Their antibacterial activities were also examined.     

Two new xanthones from the pericarp of Garcinia mangostana

Two new xanthones, designated garcimangosxanthone F (1) and garcimangosxanthone G (2), were isolated from the EtOAc-soluble fraction of ethanolic extract from the pericarp of Garcinia mangostana. Their structures were established as 1,6,7-trihydroxy-5-(3-methylbut-2-enyl)-8-(3-hydroxy-3-methylbutyl)-6′,6′-dimethylpyrano[2′,3′:3,2]xanthone and 1,6,7-trihydroxy-5-(3-methylbut-2-enyl)-8-(3-hydroxy-3-methylbutyl)-6′,6′-dimethyl-4′,5′-dihydropyrano[2′,3′:3,2]xanthone, respectively, on the basis of their 1D, 2D NMR and MS data interpretation.     

A new cytotoxic caged polyprenylated xanthone from the resin of Garcinia hanburyi

A new caged polyprenylated xanthone, gambogic aldehyde （1）, was isolated from the resin of Garcinia hanburyi. Its structure was elucidated on the basis of spectral data including 1D and 2D NMR data. In addition, the antiproliferative ability of compound 1 was determined in mouse leukemia P388 and P388/ADR cells.     

人面果树皮中口 山 酮 化合物及其DPPH自由基的清除活性

从人面果乙酸乙酯提取物中分离出5个新的口 山 酮 化合物garcinenone A (1), B (3), C (4), D (7) and E (8)和7个已知化合物,其结构经过波谱技术,特别是2D-NMR技术来鉴定。Jacareubin (2), 1,4,6-trihydroxy-5-methoxy-7-(3-methyl-2-buteny1)xanthone (6), subeliptenone B (11) 和symphoxanthone (12)为首次从该植物中分离出来。在DPPH自由基的清除活性实验中,所有的化合物都显示抗氧化活性,其IC50的值在 6.0-23.2 mM。结果表明人面果是潜在的有前景的天然抗氧化剂。     

Phenylpropanoid Derivatives from the Tuber of Asparagus cochinchinensis with Anti-Inflammatory Activities

Three undescribed phenylpropanoid derivatives, including two new bibenzyl constituents (1–2), one new stilbene constituent (3), together with five known compounds stilbostemin F (4), dihydropinosylvin (5), 2-(4-hydroxyphenyl)ethyl benzoate (6), 1-(4-hydroxybenzoyl)ethanone (7), and 4-hydroxy-3-prenylbenzoic acid (8), were isolated from the tuber of Asparagus cochinchinensis. The structures of 1–8 were elucidated according to UV, IR, HRMS, 1D and 2D-NMR methods together with the published literature. All of the isolated compounds were assessed for anti-inflammatory activity by acting on lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells in vitro. The results showed that compounds 2 and 5 were found to inhibit the production of nitric oxide (NO) with the IC₅₀ value of 21.7 and 35.8 µM, respectively. In addition, further studies found that compound 2 demonstrated concentration-dependent suppression of the protein expression of iNOS and exerted anti-inflammatory activity via the NF-κB signalling pathway. The present data suggest that phenylpropanoid derivatives from the tuber of A. cochinchinensis might be used as a potential source of natural anti-inflammatory agents.     

A novel xanthone dimer derivative with antibacterial activity isolated from the bark of Garcinia mangostana

A novel xanthone dimer derivative, garmoxanthone (1), together with 10 known compounds (2–11), were isolated from bark of Garcinia mangostana. Their structures were established through spectroscopic methods. Garmoxanthone exhibited strong inhibitory activities against MRSA ATCC 43300 and MRSA CGMCC 1.12409 (with MIC values of both 3.9 μg/mL) and moderate activities against tested strains of Vibrio (with MIC values ranging from 15.6 to 31.2 μg/mL). Garmoxanthone is a unique xanthone dimer with linkage of a fused 5/6 ring system and its absolute configuration was elucidated on the basis of experimental and calculated electronic circular dichroism. Garmoxanthone exhibited strong antibacterial activity which partially validated the ethnobotanical use of G. mangostana in the treatment of infections.     

Four New Gallate Derivatives from Wine-Processed Corni Fructus and Their Anti-Inflammatory Activities

Four new gallate derivatives—ornusgallate A, ent-cornusgallate A, cornusgallate B and C (1a, 1b, 2, 3)—were isolated from the wine-processed fruit of Cornus officinalis. Among them, 1a and 1b are new natural compounds with novel skeletons. Their chemical structures were elucidated by comprehensive spectroscopy methods including NMR, IR, HRESIMS, UV, ECD spectra and single-crystal X-ray diffraction analysis. The in vitro anti-inflammatory activities of all compounds were assayed in RAW 264.7 cells by assessing LPS-induced NO production. As the result, all compounds exhibited anti-inflammatory activities at attested concentrations. Among the tested compounds, compound 2 exhibited the strongest anti- inflammatory activity.     

藤黄化学成分的研究

传统中药藤黄通过各种色谱方法分离纯化, 得到15个化合物, 根据其理化性质和光谱方法鉴定其结构分别为: 2α-羟基-3β-乙酰氧基白桦酯酸(1), 10α-羟基表藤黄酸(2), 藤黄酸(3), 异藤黄酸(4), gambogin (5), gambogoic acid B (6), desoxymorellin (7), isomorellin (8), gambogenic acid (9), isogambogenin (10), gambogellic acid (11), desoxygambogenin (12), morellic acid (13), isomorellic acid (14), 30-hydroxygambogic acid (15). 其中化合物1和2为新化合物.     

异维A酸二茂铁基衍生物的合成及其细胞毒活性的研究

为降低异维A酸的毒副作用并提高其癌细胞毒活性以及增加其在生物体内的吸收, 通过Mitsunobu反应, 以高于80%的收率合成了8种新异维A酸二茂铁基衍生物, 并进行了结构表征与确认. 采用3-(4,5-二甲基噻唑-2)-2,5-二苯基四唑溴盐(MTT)法测试了它们对肺癌细胞(A549)等的癌细胞毒活性. 结果显示, 引入二茂铁基团后的异维A酸二茂铁基衍生物具有很好的癌细胞毒活性.     

二芳醚基哌嗪类衍生物的合成及细胞毒活性研究

根据拼合原理, 设计并合成了21个未见报道的新的二芳醚基哌嗪类衍生物, 其结构用1H NMR, ESI-MS, HRMS进行了确证, 初步生物活性测定实验证明部分目标化合物具有良好的细胞毒活性. 化合物4i分别对人食管癌(Eca109)细胞株和人鼻咽癌(CNE)细胞株的IC50为7.13和4.54 μmol•L－1, 与对照品顺铂(DDP)相近. 化合物5d对人鼻咽癌细胞株也表现较好的活性, 其IC50为8.49 μmol•L－1.     

Xanthones from the bark of Garcinia Xanthochymus

Two novel xanthones, 1,6-dihydroxy-4,5-dimethoxyxanthone (1) and 1,5,6-trihydroxy-7,8-di(3-methyl-2-butenyl)-60,60- dimethylpyrano(20,30:3,4)xanthone (2) were isolated from the bark of Garcinia xanthochymus by normal phase and reverse phase silica gel column chromatography. Their structures were elucidated by spectroscopic methods, especially 2D-NMR techniques.     

Structure elucidation and NMR spectral assignment of five new xanthones from the bark of Garcinia xanthochymus

Five new xanthones, namely Garcinexanthones A-E (1-5), were isolated from the barks of Garcinia xanthochymus. Their structures were elucidated by spectral analysis, primarily NMR, MS, and UV. The complete assignments of the (1)H NMR and (13)C NMR chemical shifts for the compounds were achieved by using 1D and 2D NMR techniques, including DEPT, HSQC, and HMBC NMR experiments.     

Chemical Constituents from the Bark of Garcinia xanthochymus and Their 1,1‐Diphenyl‐2‐picrylhydrazyl (DPPH) Radical‐Scavenging Activities

A new bis‐xanthone (xanthone=9H‐xanthen‐9‐one), named bigarcinenone A ( 1 ) which is the first example of a bis‐xanthone with the xanthone–xanthone linkage between an aromatic C‐atom and a C₅ side chain from a guttiferae plant, a new phloroglucinol (=benzene‐1,3,5‐triol) derivative, named garcinenone F ( 2 ), together with seven known xanthones were isolated from the bark of Garcinia xanthochymus. Their structures were elucidated by spectroscopic methods, especially 2D‐NMR techniques. Bigarcinenone A ( 1 ) exhibited potent antioxidant activity in the 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical‐scavenging test with a IC₅₀ value of 9.2 μM , compared to the positive control, the well‐known antioxidant butylated hydroxytoluene (BHT) with a IC₅₀ of 20 μM (Table 3).     

A new cytotoxic polycyclic polyprenylated acylphloroglucinol from Garcinia nujiangensis screened by the LC-PDA and LC-MS

Abstract

A new polycyclic polyprenylated acylphloroglucinol (1), nujiangefolin D, together with five known analogues (2–6), were isolated from the fruits of Garcinia nujiangensis. Compound 1 was screened by the LC-MS and LC-PDA. The structure of 1 was elucidated on the basis of extensive spectroscopic techniques including 1?D and 2?D NMR and MS analyses. The compounds isolated were evaluated for their cytotoxic activities against three cancer cell lines, 1 showed moderate cytotoxic activity against Hela, PANC-1, and MDA-MB-231 cell lines with IC₅₀ values of 5.6?±?0.1, 9.1?±?0.2, and 8.3?±?0.2?μM, respectively. The antitumor mechanism was explained via virtual docking of 1 to the main sites in the human serine/threonine-protein kinase mTOR (mTOR) crystal structure (PDB code: 4DRI). Furthermore, 1 may inhibit Hela cell proliferation through mTOR by the western blotting analysis. Taken together, 1 may be a potential mTOR inhibitor used for the treatment of cervical cancer.     

2,5-二酮哌嗪衍生物的一锅法合成及其细胞毒活性

以DMF为溶剂,Cs₂CO₃为碱, N,N-二乙酰基-2,5-二酮哌嗪,芳醛和卤代烷经一锅法合成了１10个2,5-二酮哌嗪类衍生物（4a~4j,其中4c, 4f和4i为新化合物）,收率54.2％～75.7％,其结构经¹H NMR, ¹³C NMR和ESI-MS确证。生物活性研究结果表明：（Z）-1-乙酰基-3-（1-亚甲基萘）-4-烯丙基-2,5-二酮哌嗪（4c）对U937, Hela和Du145等细胞具有一定的细胞毒活性。     

Phytochemical Profiles,Antioxidant, Cytotoxic,and Anti-Inflammatory Activities of Traditional Medicinal Plants: Centaurea pichleri subsp. pichleri,Conyza canadensis,and Jasminum fruticans

Centaurea pichleri subsp. pichleri, Conyza canadensis, and Jasminum fruticans are traditionally used plants grown in Turkey. Methanol extracts were obtained from these plants and pharmacological activity studies and phytochemical analyses were carried out. To evaluate the phytochemical composition, spectrophotometric and chromatographic techniques were used. The extracts were evaluated for antioxidant activity by DPPH^●, ABTS^●+ radical scavenging, and FRAP assays. The cytotoxic effects of the extracts were investigated on DU145 prostate cancer and A549 lung cancer cell lines. The anti-inflammatory effects of extracts were investigated on the NO amount, TNF-α, IFN-γ, and PGE 2 levels in lipopolysaccharide-stimulated Raw 264.7 cells. The richest extract in terms of phenolic compounds (98.19 ± 1.64 mg_GAE/g_extract) and total flavonoids (21.85 ± 0.64 mg_CA/g_extract) was identified as C. pichleri subsp. pichleri methanol extract. According to antioxidant activity determinations, the C. pichleri subsp. pichleri extract was found to be the most active extract. Finally, the C. pichleri subsp. pichleri methanol extract was revealed to be the most effective inhibitor of viability in the cytotoxic activity investigation, and the extract with the best anti-inflammatory action. The findings point to C. pichleri subsp. pichleri as a promising source of bioactive compounds in the transition from natural sources to industrial uses, such as new medications, cosmeceuticals, and nutraceuticals.     

Secondary Metabolites from Hericium erinaceus and Their Anti-Inflammatory Activities

Hericium erinaceus, a culinary and medicinal mushroom, is widely consumed in Asian countries. Chemical investigation on the fruiting bodies of Hericium erinaceus led to the isolation of one new ergostane-type sterol fatty acid ester, erinarol K (1); and eleven known compounds: 5α,8α -epidioxyergosta-6,22-dien-3β-yl linoleate (2); ethyl linoleate (3); linoleic acid (4); hericene A (5); hericene D (6); hericene E (7); ergosta-4,6,8(14),22-tetraen-3-one (8); hericenone F (9); ergosterol (10); ergosterol peroxide (11); 3β,5α,6α,22E-ergosta-7,22-diene-3,5,6-triol 6-oleate (12). The chemical structures of the compounds were determined by 1D and 2D NMR (nuclear magnetic resonance) spectroscopy, mass spectra, etc. Anti-inflammatory effects of the isolated aromatic compounds (5–7, 9) were evaluated in terms of inhibition of pro-inflammatory mediator (TNF-α, IL-6 and NO) production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophage cells. The results showed that compounds 5 and 9 exhibited moderate activity against TNF-α (IC₅₀: 78.50 μM and 62.46 μM), IL-6 (IC₅₀: 56.33 μM and 48.50 μM) and NO (IC₅₀: 87.31 μM and 76.16 μM) secretion. These results supply new information about the secondary metabolites of Hericium erinaceus and their anti-inflammatory effects.     

Antioxidant and Anti-Inflammatory Activities of Six Flavonoids from Smilax glabra Roxb

This study aimed to isolate, prepare and identify the main flavonoids from a standardized Smilax glabra flavonoids extract (SGF) using preparative HPLC, MS, ¹H NMR and ¹³C NMR, determine the contents of these flavonoids using UPLC, then compare their pharmacological activities in vitro. We obtained six flavonoids from SGF: astilbin (18.10%), neoastilbin (11.04%), isoastilbin (5.03%), neoisoastilbin (4.09%), engeletin (2.58%) and (−)-epicatechin (1.77%). The antioxidant activity of six flavonoids were evaluated by determining the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2′-Azinobis (3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS⁺) radical scavenging activity and ferric reducing antioxidant power (FRAP). In addition, the anti-inflammatory activity of six flavonoids were evaluated by determining the production of cytokines (IL-1β, IL-6), nitric oxide (NO) using enzyme linked immunosorbent assay and the NF-κB p65 expression using Western blotting in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. The results showed that (−)-epicatechin, astilbin, neoastilbin, isoastilbin and neoisoastilbin had strong antioxidant activities, not only in DPPH and ABTS⁺ radicals scavenging capacities, but in FRAP system. Furthermore, all the six flavonoids could significantly inhibit the secretion of IL-1β, IL-6, NO (p < 0.01) and the protein expression of NF-κB p-p65 (p < 0.01) in LPS-stimulated RAW264.7 cells. This study preliminarily verified the antioxidant and anti-inflammatory activities of six flavonoids in S. glabra.