scholarly journals New Flavan and Alkyl α,β-Lactones from the Stem Bark of Horsfieldia Superba

2013 ◽  
Vol 8 (4) ◽  
pp. 1934578X1300800
Author(s):  
Nabil Ali Al-Mekhlafi ◽  
Khozirah Shaari ◽  
Faridah Abas ◽  
Ethyl Jeyaseela Jeyaraj ◽  
Johnson Stanslas ◽  
...  
Keyword(s):  
Optical Rotation ◽  
2D Nmr ◽  
Stem Bark ◽  
Cytotoxic Activities ◽  
Dihydroxybenzoic Acid ◽  
Vitro Assay ◽  
Phytochemical Investigation ◽  
Ache Inhibitory Activity ◽  
Hct 116

In the present study phytochemical investigation of the methanol extract of the stem bark of Horsfieldia superba led to the isolation of twenty compounds (1-20), of which three (1-3) were new. However, compounds 2 and 3 were previously reported as synthetic α, β-lactones. The compounds were characterized as (-)-3,4′,7-trihydroxy-3′-methoxyflavan (1), (-)-5,6-dihydro-6-undecyl-2 H-pyran-2-one (2), and (-)-5,6-dihydro-6-tridecyl-2 H-pyran-2-one (3). Seventeen other known compounds were also isolated and identified as (-)-viridiflorol (4), hexacosanoic acid (5), β-sitosterol (6), methyl 2,4-dihydroxy-6-methylbenzoate (methylorsellinate) (7), methyl 2,4-dihydroxy-3,6-dimethylbenzoate (8), (-)-4′-hydroxy-7-methoxyflavan (9), (-)-4′,7-dihydroxyflavan (10), (-)-4′,7-dihydroxy-3′-methoxyflavan (11), (+)-3,4′,7-trihydroxyflavan (12), (-)-catechin (13), (-)-epicatechin (14), (-)-7-hydroxy-3′,4′-methylenedioxyflavan (15), 2′,3,4-trihydroxy-4′-methoxydihydrochalcone (16), 3′,4′,7-trihydroxyflavone (17), (+)-4′-hydroxy-7-methoxyflavanone (18), hexadecanoic acid (palmitic acid) (19) and 3,4-dihydroxybenzoic acid (20). The structures of the compounds were fully characterized by various physical methods (melting point, optical rotation), spectral (UV, IR, ID and 2D NMR) and mass spectrometric techniques. In vitro assay of compounds 2 and 3 demonstrated moderate cytotoxic activities against human prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cells, while the chloroform and ethyl acetate fractions of H. superba were found to exhibit moderate AChE inhibitory activity (IC50 72 and 60 μg/mL).

scholarly journals Four New Pterosins from Pteris cretica and Their Cytotoxic Activities

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2767
Author(s):  
Jian Lu ◽  
Caiying Peng ◽  
Shuang Cheng ◽  
Jianqun Liu ◽  
Qinge Ma ◽  
...  
Keyword(s):  
Human Tumor ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Aerial Parts ◽  
Pteris Cretica ◽  
Phytochemical Investigation ◽  
Hct 116 ◽  
Hct 116 Cells ◽  
New Compounds

Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin 3-O-β-d-glucopyranoside (4), together with five known pterosins 5–9. Their structures were identified mainly on the basis of 1D and 2D NMR spectral data, ESI-MS and literature comparisons. Compounds 1 and 3 were new type of petrosins with a six membered ring between C-14 and C-15. The new compounds were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Results showed that compounds 1 and 2 exhibited cytotoxic activity against HCT-116 cells with IC50 value of 22.4 μM and 15.8 μM, respectively.

scholarly journals Triterpenoids from Vitellaria paradoxa Stem Barks Reduce Nitrite Levels in LPS-Stimulated Macrophages

Plants ◽  
2021 ◽  
Vol 10 (5) ◽  
pp. 1006
Author(s):  
Carmina Sirignano ◽  
Pascal Nadembega ◽  
Ferruccio Poli ◽  
Barbara Romano ◽  
Giuseppe Lucariello ◽  
...  
Keyword(s):  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Stem Bark ◽  
Inhibitory Effect ◽  
Vitellaria Paradoxa ◽  
Free Alcohol ◽  
Nmr Data ◽  
Phytochemical Investigation ◽  
New Compounds

Vitellaria paradoxa C. F. Gaertn is widely used in African traditional medicine as an anti-inflammatory remedy to treat rheumatism, gastric problems, diarrhea, and dysentery. The phytochemical investigation of the ethyl acetate extract of V. paradoxa stem bark collected in Burkina Faso led to the isolation of eight known and two triterpenes undescribed to date (7 and 10), in the free alcohol form or as acetyl and cinnamyl ester derivatives. The stereostructures of the new compounds were elucidated using HR-ESIMS and 1D and 2D NMR data. The isolated compounds were evaluated in vitro for their inhibitory effect on nitrite levels on murine macrophages J774 stimulated with the lipopolysaccharide (LPS). Among all the compounds tested, lupeol cinnamate (3) and betulinic acid (5) showed a beneficial effect in reducing nitrite levels produced after LPS stimulation.

scholarly journals A New Terminal Cyano Group-containing Benzodiazepine Alkaloid from the Mangrove Endophytic Fungus Penicillium sp

2015 ◽  
Vol 10 (9) ◽  
pp. 1934578X1501000
Author(s):  
Jing Li ◽  
Yi-sheng Zhong ◽  
Jie Yuan ◽  
Xun Zhu ◽  
Yong-jun Lu ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Structure Elucidation ◽  
Human Cancer ◽  
Cyano Group ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Mangrove Endophytic Fungus ◽  
Hct 116

A new benzodiazepine alkaloid containing terminal cyano group has been isolated from a mangrove endophytic fungus, Penicillium 299#. Structure elucidation was determined by 1D and 2D NMR spectroscopy and the absolute configuration was determined by electronic circular dichroism (ECD). The new compound showed no cytotoxic activities in vitro against human cancer lines MDA-MB-435, HepG2, HCT-116, and Calu-3.

scholarly journals Semi-Synthesis of Harringtonolide Derivatives and Their Antiproliferative Activity

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1380
Author(s):  
Xiutao Wu ◽  
Lijie Gong ◽  
Chen Chen ◽  
Ye Tao ◽  
Wuxi Zhou ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Normal Cell ◽  
Selectivity Index ◽  
Cytotoxic Activities ◽  
Structure Activity ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Hct 116 ◽  
Systematic Structure

Harringtonolide (HO), a natural product isolated from Cephalotaxus harringtonia, exhibits potent antiproliferative activity. However, little information has been reported on the systematic structure−activity relationship (SAR) of HO derivatives. Modifications on tropone, lactone, and allyl positions of HO (1) were carried out to provide 17 derivatives (2–13, 11a–11f). The in vitro antiproliferative activity against four cancer cell lines (HCT-116, A375, A549, and Huh-7) and one normal cell line (L-02) was tested. Amongst these novel derivatives, compound 6 exhibited comparable cell growth inhibitory activity to HO and displayed better selectivity index (SI = 56.5) between Huh-7 and L-02 cells. The SAR results revealed that the tropone and lactone moieties are essential for the cytotoxic activities, which provided useful suggestions for further structural optimization of HO.

Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha

2021 ◽  
Vol 76 (5-6) ◽  
pp. 213-218
Author(s):  
Usama W. Hawas ◽  
Lamia T. Abou El-Kassem ◽  
Radwan Al-farawati ◽  
Fekri M. Shaher
Keyword(s):  
2D Nmr ◽  
Cytotoxic Activities ◽  
Dpph Radical ◽  
Srb Assay ◽  
Phenolic Metabolites ◽  
2D Nmr Spectra ◽  
New Compounds ◽  
Benzaldehyde Derivatives ◽  
Mcf 7

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.

Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

Planta Medica ◽  
2021 ◽  
Author(s):  
Julianna Max ◽  
Jörg Heilmann
Keyword(s):  
Petroleum Ether Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Ionization Mass ◽  
2D Nmr Spectroscopy ◽  
Vitro Assay ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Adamantane Skeleton

Abstract 1H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1–14), while 5 further compounds showed an adamantane skeleton (15–19). Except for hookerione C (15), all isolated metabolites are hitherto unknown. While structurally-related metabolites have been isolated from other Hypericum species, it is the first report of admantan and homoadamantan type acylphloroglucinols in section Taeniocarpium Jaub. & Spach (Hypericaceae). The isolated compounds have been tested in a crystal violet-based in vitro assay on their properties to reduce the proliferation of human microvascular endothelial cells compared to hyperforin as the positive control. They showed a moderate reduction of proliferation with IC50 values in the range ~ 3 – 22 µM, with the homoadamantane-based compounds 2 and 4 being the most active. In addition, inhibition of the TNF-α-induced ICAM-1 expression was determined for 1 – 5, 7, and 10 – 12. Substances 3 and 12 reduced the ICAM-1 expression significantly (to 46.7% of control for 3, 62.3% for 12, at 50 µM).

scholarly journals In vivo Neurological, Analgesic and In vitro Antioxidant and Cytotoxic Activities of Ethanolic Extract of Leaf and Stem Bark of Wedelia chinensis

2019 ◽  
Vol 22 (1) ◽  
pp. 18-26
Author(s):  
Sayema Khanum ◽  
Md Shahid Sarwar ◽  
Mohammad Safiqul Islam
Keyword(s):  
Body Weight ◽  
Oral Administration ◽  
Radical Scavenging ◽  
Ethanolic Extract ◽  
Ethanol Extract ◽  
Pharmaceutical Journal ◽  
Stem Bark ◽  
Cytotoxic Activities

Wedelia chinensis is a widely used anti-inflammatory and hepatoprotective medicinal plant in Bangladesh. In this study, analgesic, neurological, antioxidant and cytotoxic activities of the ethanolic extract of leaf and stem bark of W. chinensis were investigated. Oral administration of the ethanolic extract of W. chinensis (200- and 300-mg/kg body weight) was investigated on animal model for neurological activity using open field test and hole cross test. Acetic acid induced writhing method was used to assess the analgesic activity. DPPH (1,1-diphenyl, 2-picryl hydrazyl) radical scavenging assay was used for determining the antioxidant activity, while brine shrimp lethality bioassay was used for investigating cytotoxicity. The ethanol extract of the plant produced significant reduction (P<0.05) of locomotion in both doses (200- and 300-mg/kg body weight) indicating pronounced neurological activity. Oral administration of alcoholic leaves and stem extracts significantly (p < 0.05) inhibited writhing response in mice. The percentage of scavenging of DPPH free radical was found to be concentration dependent with IC50 value of 44.10 ± 0.65 and 38.96 ± 0.50 μg/ml for leaves and stem extracts, respectively. Our findings indicate that W. chinensis may be a source of natural antioxidant with potent analgesic, neurological and cytotoxic activities. Bangladesh Pharmaceutical Journal 22(1): 18-26, 2019

scholarly journals Antiplasmodial and Cytotoxic Activities of Extracts of Selected Medicinal Plants Used to Treat Malaria in Embu County, Kenya

2020 ◽  
Vol 2020 ◽  
pp. 1-12
Author(s):  
Bibianne Waiganjo ◽  
Gervason Moriasi ◽  
Jared Onyancha ◽  
Nelson Elias ◽  
Francis Muregi
Keyword(s):  
Side Effects ◽  
Medicinal Plants ◽  
Stem Bark ◽  
Antiplasmodial Activity ◽  
Chloroquine Resistance ◽  
Cytotoxic Activities ◽  
Aqueous Extracts ◽  
Methanolic Extracts

Malaria is a deadly disease caused by a protozoan parasite whose mode of transmission is through a female Anopheles mosquito. It affects persons of all ages; however, pregnant mothers, young children, and the elderly suffer the most due to their dwindled immune state. The currently prescribed antimalarial drugs have been associated with adverse side effects ranging from intolerance to toxicity. Furthermore, the costs associated with conventional approach of managing malaria are arguably high especially for persons living in low-income countries, hence the need for alternative and complementary approaches. Medicinal plants offer a viable alternative because of their few associated side effects, are arguably cheaper, and are easily accessible. Based on the fact that studies involving antimalarial medicinal plants as potential sources of efficacious and cost-effective pharmacotherapies are far between, this research was designed to investigate antiplasmodial and cytotoxic activities of organic and aqueous extracts of selected plants used by Embu traditional medicine practitioners to treat malaria. The studied plants included Erythrina abyssinica (stem bark), Schkuhria pinnata (whole plant), Sterculia africana (stem bark), Terminalia brownii (leaves), Zanthoxylum chalybeum (leaves), Leonotis mollissima (leaves), Carissa edulis (leaves), Tithonia diversifolia (leaves and flowers), and Senna didymobotrya (leaves and pods). In vitro antiplasmodial activity studies of organic and water extracts were carried out against chloroquine-sensitive (D6) and chloroquine-resistance (W2) strains of Plasmodium falciparum. In vivo antiplasmodial studies were done by Peter’s four-day suppression test to test for their in vivo antimalarial activity against P. berghei. Finally, cytotoxic effects and safety of the studied plant extracts were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) rapid calorimetric assay technique. The water and methanolic extracts of T. brownii and S. africana and dichloromethane extracts of E. abyssinica, S. pinnata, and T. diversifolia leaves revealed high in vitro antiplasmodial activities (IC50≤10 μg/ml). Further, moderate in vivo antimalarial activities were observed for water and methanolic extracts of L. mollissima and S. africana and for dichloromethane extracts of E. abyssinica and T. diversifolia leaves. In this study, aqueous extracts of T. brownii and S. africana demonstrated high antiplasmodial activity and high selectivity indices values (SI≥10) and were found to be safe. It was concluded that T. brownii and S. africana aqueous extracts were potent antiplasmodial agents. Further focused studies geared towards isolation of active constituents and determination of in vivo toxicities to ascertain their safety are warranted.

scholarly journals Two New p-Terphenyl Derivatives from the Marine Fungal Strain Aspergillus sp. AF119

2012 ◽  
Vol 7 (8) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Shao-Song Liu ◽  
Bao-Bing Zhao ◽  
Chun-Hua Lu ◽  
Jing-Jing Huang ◽  
Yue-Mao Shen
Keyword(s):  
Cell Lines ◽  
Human Tumor ◽  
2D Nmr ◽  
Strand Break ◽  
Fungal Strain ◽  
Cytotoxic Activities ◽  
Cycle Arrest ◽  
Dna Double Strand Break ◽  
Aspergillus Sp

Two new p-terphenyl derivatives (1, 2), together with six known ones (3 - 8), have been isolated from the marine fungal strain Aspergillus sp. AF119. The structures for terphyl acid (1) and terphyl diacid (2) were determined on the basis of HR Q-TOF-MS, and 1D- and 2D-NMR spectroscopic data. The in vitro cytotoxic activities of compounds 1 – 8 were tested against human tumor cell lines HeLa, HepG-2 and MDA-MB-435; only compounds 5 – 8 exhibited inhibitory activity against the tested cell lines with IC50 values < 20 μM. Moreover, compound 5 showed a mechanism of inducing cell cycle arrest and apoptosis mediated by the generation of ROS and subsequent DNA double-strand break.

scholarly journals In VitroandIn VivoAntimalarial Evaluations of Myrtle Extract, a Plant Traditionally Used for Treatment of Parasitic Disorders

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Farzaneh Naghibi ◽  
Somayeh Esmaeili ◽  
Noor Rain Abdullah ◽  
Mehdi Nateghpour ◽  
Mahdieh Taghvai ◽  
...  
Keyword(s):  
Cell Lines ◽  
Mammalian Cell ◽  
Methanolic Extract ◽  
Cytotoxic Activities ◽  
Traditional Use ◽  
Aerial Parts ◽  
Mammalian Cell Lines ◽  
Phytochemical Investigation

Based on the collected ethnobotanical data from the Traditional Medicine and Materia Medica Research Center (TMRC), Iran,Myrtus communisL. (myrtle) was selected for the assessment ofin vitroandin vivoantimalarial and cytotoxic activities. Methanolic extract of myrtle was prepared from the aerial parts and assessed for antiplasmodial activity, using the parasite lactate dehydrogenase (pLDH) assay against chloroquine-resistant (K1) and chloroquine-sensitive (3D7) strains ofPlasmodium falciparum. The 4-day suppressive test was employed to determine the parasitemia suppression of the myrtle extract againstP. berghei  in vivo. The IC50values of myrtle extract were 35.44 µg/ml against K1 and 0.87 µg/ml against 3D7. Myrtle extract showed a significant suppression of parasitaemia (84.8 ± 1.1% at 10 mg/kg/day) in mice infected withP. bergheiafter 4 days of treatment. Cytotoxic activity was carried out against mammalian cell lines using methyl thiazol tetrazolium (MTT) assay. No cytotoxic effect on mammalian cell lines up to 100 µg/mL was shown. The results support the traditional use of myrtle in malaria. Phytochemical investigation and understanding the mechanism of action would be in our upcoming project.

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