scholarly journals Targeted Isolation of Xenicane Diterpenoids from Taiwanese Soft Coral Asterospicularia laurae

Marine Drugs ◽  
2021 ◽  
Vol 19 (3) ◽  
pp. 123
Author(s):  
Yu-Chi Lin ◽  
Yi-Jen Chen ◽  
Shu-Rong Chen ◽  
Wan-Ju Lien ◽  
Hsueh-Wei Chang ◽  
...  
Keyword(s):  
Cytotoxic Effect ◽  
Soft Coral ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Analyses ◽  
Potential Source ◽  
First Case ◽  
The Family ◽  
Mcf 7

Application of LC-MS/MS-based molecular networking indicated the ethanol extract of octocoral Asterospicularia laurae is a potential source for the discovery of new xenicane derivatives. A natural product investigation of this soft coral resulted in the isolation of four new xenicane diterpenoids, asterolaurins O‒R (1‒4), together with six known compounds, xeniolide-A (5), isoxeniolide-A (6), xeniolide-B (7), 7,8-epoxyxeniolide-B (8), 7,8-oxido-isoxeniolide-A (9), and 9-hydroxyxeniolide-F (10). The structures of isolated compounds were characterized by employing spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Asterolaurin O is the first case of brominated tricarbocyclic type floridicin in the family Xeniidae. Concerning bioactivity, the cytotoxic activity of those isolates was evaluated. As a result, compounds 1 and 2 demonstrated a selective cytotoxic effect against the MCF-7 cell line at IC50 of 14.7 and 25.1 μM, respectively.

scholarly journals New Biscembranoids Sardigitolides A–D and Known Cembranoid-Related Compounds from Sarcophyton digitatum: Isolation, Structure Elucidation, and Bioactivities

Marine Drugs ◽  
2020 ◽  
Vol 18 (9) ◽  
pp. 452 ◽  
Author(s):  
Tzu-Yin Huang ◽  
Chiung-Yao Huang ◽  
Chih-Hua Chao ◽  
Chi-Chien Lin ◽  
Chang-Feng Dai ◽  
...  
Keyword(s):  
Soft Coral ◽  
2D Nmr ◽  
Inflammatory Factor ◽  
Chemical Examination ◽  
Chemical Structures ◽  
Spectroscopic Analyses ◽  
Ic50 Values ◽  
Inhibitory Potential ◽  
Related Compounds ◽  
Mcf 7

Chemical examination from the cultured soft coral Sarcophyton digitatum resulted in the isolation and structural identification of four new biscembranoidal metabolites, sardigitolides A–D (1–4), along with three previously isolated biscembranoids, sarcophytolide L (5), glaucumolide A (6), glaucumolide B (7), and two known cembranoids (8 and 9). The chemical structures of all isolates were elucidated on the basis of 1D and 2D NMR spectroscopic analyses. Additionally, in order to discover bioactivity of marine natural products, 1–8 were examined in terms of their inhibitory potential against the upregulation of inflammatory factor production in lipopolysaccharide (LPS)-stimulated murine macrophage J774A.1 cells and their cytotoxicities against a limited panel of cancer cells. The anti-inflammatory results showed that at a concentration of 10 µg/mL, 6 and 8 inhibited the production of IL-1β to 68 ± 1 and 56 ± 1%, respectively, in LPS-stimulated murine macrophages J774A.1. Furthermore, sardigitolide B (2) displayed cytotoxicities toward MCF-7 and MDA-MB-231 cancer cell lines with the IC50 values of 9.6 ± 3.0 and 14.8 ± 4.0 µg/mL, respectively.

scholarly journals Additional New Tetracyclic Tetraterpenoid: Methyl Tortuoate D from Soft Coral Sarcophyton tortuosum

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Wen-Jian Lan ◽  
Shou-Liang Wang ◽  
Hou-Jin Li
Keyword(s):  
Mass Spectrometry ◽  
South China Sea ◽  
Electrospray Ionization ◽  
South China ◽  
Soft Coral ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Techniques ◽  
Direct Infusion ◽  
Relative Stereochemistry

Under the guidance of chemical prescreening by direct infusion electrospray ionization mass spectrometry (DI ESI-MS), a new tetracyclic tetraterpenoid, methyl tortuoate D (1) was isolated from the soft coral Sarcophyton tortuosum collected from the South China Sea. Its structure and relative stereochemistry were established by MS, and 1D- and 2D-NMR spectroscopic techniques.

scholarly journals High performance thin-layer chromatography and in vitro cytotoxic studies on ethanol extract of Matricaria chamomilla L (Asteraceae) flowers

2021 ◽  
Vol 18 (9) ◽  
pp. 1969-1976
Author(s):  
Mohammed Al Bratty ◽  
Lalitha K. Govindaram ◽  
Lalitha K. Govindaram ◽  
Neelaveni Thangavel ◽  
Hassan A. Alhazmi ◽  
...  
Keyword(s):  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Mtt Assay ◽  
High Performance ◽  
Cytotoxic Effect ◽  
Ethanol Extract ◽  
Matricaria Chamomilla ◽  
Layer Chromatography ◽  
Mcf 7

Purpose: To develop a high performance thin-layer chromatography (HPTLC procedure for quantitation of apigenin in ethanol extract of Matricaria chamomilla (Babunaj) flowers, and to evaluate the extract for in vitro cytotoxic effect on MCF-7 cell lines. Methods: Quantification of apigenin was carried out using a CAMAG TLC system. A combination of toluene, ethyl acetate and formic acid (4.5:3.5:0.2 v/v/v) was used as mobile phase, with densitometry detection at 336 nm. The HPTLC procedure was subjected to validation as per ICH guidelines. The cytotoxicity of the extract was assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Results: A sharp apigenin band at Rf of 0.51 was obtained, and the content of apigenin in the extract was 0.062 % w/w. The detection limit (LOD) and quantification limit (LOQ) were 0.19 and 0.57 ng/band, respectively. MTT assay results indicate that M. chamomilla was cytotoxic to Michigan Cancer Foundation-7 (MCF-7) cells, with half-maximal concentration (IC50) of 74 µg/mL. Conclusion: The developed HPTLC method is linear, precise, accurate and specific for the determination of apigenin. M. chamomilla exerts cytotoxic effect on MCF-7 cell line via induction of apoptosis.

scholarly journals Isolation of Lasiodiplodin and Evaluation of some Biological Activities of the Stem Barks of Phyllanthus Albizzioides (Kurz) Hook.f.

2019 ◽  
Vol 1 (4) ◽  
pp. 199-216 ◽  
Author(s):  
Khine Zar Wynn Lae ◽  
Su Swe Su ◽  
Nwet Nwet Win ◽  
Ni Ni Than ◽  
Hla Ngwe
Keyword(s):  
Biological Activities ◽  
Chemical Constituents ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Stem Bark ◽  
Chloroform Extract ◽  
Traditional System ◽  
Spectroscopic Analyses ◽  
Ethanol Extracts ◽  
Relative Structure

A large number of the plants are claimed to possess the antibiotic properties in the traditional system and are also used extensively by the tribal people throughout the world. It is now mostly thought that nature has given the cure of every disease in one form or another. Plants have been known to cure people from various diseases in Ayurveda. This research focused on the screening of phytochemicals and some biological activities of Phyllanthus albizzioides. The research showed that the ethanol extracts were found to be greater chemical constituents than watery extracts. Among the chemical constituents, steroid compounds were observed in highest amount in ethanol extract and the second highest in flavonoid compounds followed by tannin compounds and pheolic compounds. Furthermore, the ethanol extracts were more effective than the watery extracts in all tested biological activities such as antioxidant, anti-diabetic, cytotoxicity, antimicrobial, antitumor and NO inhibition activities. A cyclohexanone compound was isolated from the chloroform extract of the stem bark of P. albizzioides. The relative structure was determined to be 4,5-dihydroxy-3-methyl-cyclohex-2-enone on the basic of HRESIMS, 1H NMR and 13C NMR spectroscopic analyses, including 2D NMR experiments.

scholarly journals Diterpenoid Alkaloids from Delphinium aemulans

2018 ◽  
Vol 13 (11) ◽  
pp. 1934578X1801301
Author(s):  
Nurfida Ablajan ◽  
Bo Zhao ◽  
Wenjuan Xue ◽  
Zukela Ruzi ◽  
Jiangyu Zhao ◽  
...  
Keyword(s):  
2D Nmr ◽  
Diterpenoid Alkaloids ◽  
Diterpenoid Alkaloid ◽  
Esi Ms ◽  
Mtt Method ◽  
Naturally Occurring ◽  
Spectroscopic Analyses ◽  
Type C ◽  
Mcf 7

A new naturally occurring lycoctonine-type C19-diterpenoid alkaloid aemulansine (1), together with ten known alkaloids (2–11), were isolated from the whole herb of Delphinium aemulans Navski. Their structures were elucidated by extensive spectroscopic analyses, including 1D, 2D NMR and HR-ESI-MS. Compounds 1–10 were also evaluated in vitro for cytotoxicity against A549, Hela and MCF-7 cells using the MTT method.

scholarly journals A New Xanthone from the Pericarp of Garcinia mangostana

2013 ◽  
Vol 8 (12) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Manqin Fu ◽  
Samuel X. Qiu ◽  
Yujuan Xu ◽  
Jijun Wu ◽  
Yulong Chen ◽  
...  
Keyword(s):  
Colorimetric Assay ◽  
Human Cancer ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Hep G2 ◽  
Garcinia Mangostana ◽  
Human Cancer Cell Lines ◽  
Mtt Colorimetric Assay ◽  
Mcf 7

A new prenylxanthone, garcimangostanol (1), was isolated from the EtOAc-soluble partition of the ethanol extract of the pericarp of Garcinia mangostana L., along with three known compounds, namely 8-deoxygartanin (2), 1-isomangostin (3), and garcinone C (4). The structure of compound 1 was elucidated on the basis of its 1D, 2D NMR and MS data. Compounds 1–4 exhibited either significant or moderate cytotoxicity against MCF-7, A549, Hep-G2 and CNE human cancer cell lines in vitro with IC50 values from 4.0 ± 0.3 to 23.6 ± 1.5 μM by MTT colorimetric assay.

scholarly journals Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4192
Author(s):  
Zhe Guo ◽  
Zhong-Mei Zou
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
Chemical Diversity ◽  
Ionization Mass ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Planar Structures ◽  
Ionization Mass Spectroscopy ◽  
Epigenetic Manipulation ◽  
New Compounds ◽  
Mcf 7

Overexpression of the histone acetyltransferase and the 1H NMR spectroscopic experiments of the endophytic fungus Monosporascus eutypoides resulted in the isolation of two new compounds, monosporasols A (1) and B (2), and two known compounds, pestaloficin C (3) and arthrinone (4). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds 1–2 were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.

Cytotoxic and Pro-apoptotic Activities of Diterpenoids from Zhumeria Majdae

2020 ◽  
Vol 17 ◽  
Author(s):  
Abolfazl Shakeri ◽  
Samira Navabi Nejad ◽  
Javad Asili ◽  
Milena Masullo ◽  
Mansoor Saeidi ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cytotoxic Effect ◽  
Therapeutic Agent ◽  
2D Nmr ◽  
Etoac Extract ◽  
Chemical Structures ◽  
Ic50 Value ◽  
Cytotoxic Compounds ◽  
First Time ◽  
Mcf 7

Abstract:: Since the ethylacetate (EtOAc) extract of the roots of Zhumeria majdae had the potent cytotoxic effect (IC50 < 50 μg/ml) on three cancer cell lines; MCF-7, PC3 and MDA-MB-231, therefore the purpous of this study is to isolation of the responcible cytotoxic compounds from the plant. Isolation of the extract led to the identification of four diterpenoids named as lanugon Q (1), 12,16-dideoxy aegyptinone B (2), 12-deoxy-salvipisone (3) and manool (4). The chemical structures have been determined on the basis of 1D and 2D NMR experiments. Compound 1 is reported for the first time in the plants of Zhumeria genus. The results of cytotoxic and apoptotic evaluation revealed that compound 2 had the strong cytotoxic effect with the IC50 value of 15.90 μg/ml against MCF-7 cell lines. Sub-G1 peak in flow cytometry histogram of cells treated with EtOAc axtract and compound 2 showed the induction of apoptosis. Changes in the Bax/Bcl-2 ratio and cleavage of PARP were observed. It is to be noted that owing to strong cytotoxic effect, Z. majdae extract could be represented as therapeutic agent against cancer.

scholarly journals Discovery of a Novel Diterpene in Brown Propolis from the State of Parana, Brazil

2016 ◽  
Vol 11 (2) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Shigemi Tazawa ◽  
Yasuko Arai ◽  
Sho Hotta ◽  
Taichi Mitsui ◽  
Hiroshi Nozaki ◽  
...  
Keyword(s):  
Human Cancer ◽  
2D Nmr ◽  
The State ◽  
The Novel ◽  
Human Cancer Cell Lines ◽  
Spectroscopic Analyses ◽  
Potent Inhibition ◽  
Plant Sources ◽  
Mcf 7

Propolis is a resinous substance collected by honeybees from certain plant sources. The components of propolis depend on the vegetation of the area in which apiculture is practiced. In Brazil, there are several types of propolis including ‘green,’ ‘red’ and ‘brown'. Brazilian brown propolis from the state of Parana characteristically includes diterpenes, and we discovered a novel clerodane diterpene, rel-(5 S,6 S,8 R,9 R,10 S,18 R,19 S)-18,19-epoxy-2-oxocleroda-3,12( E),14-triene-6,18,19-triol 18,19-diacetate 6-benzoate (3) and five known diterpenes (1, 2, 4, 5 and 6). The chemical structure of the novel diterpene 3 was determined using 1D- and 2D-NMR spectroscopic analyses. Furthermore, the activities of the isolated diterpenes on growth inhibition of several human cancer cell lines (LNCaP, MCF-7, DLD-1 and A549) were evaluated in vitro; diterpene 3 exhibited a potent inhibition of cell growth, and its activity was approximately 15 times higher than that of the other diterpenes.

scholarly journals Chemical constituents of ethanol extract of leaves and molluscicidal activity of crude extracts from vitex trifolia linn.

2013 ◽  
Vol 59 (4) ◽  
pp. 19-32 ◽  
Author(s):  
Jeet S. Jangwan ◽  
Rita P. Aquino ◽  
Teresa Mencherini ◽  
Patrizia Picerno ◽  
Raghubir Singh
Keyword(s):  
Ursolic Acid ◽  
Chemical Constituents ◽  
Ethanolic Extract ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Chloroform Extract ◽  
Biomphalaria Alexandrina ◽  
The Family ◽  
Hexane Extracts ◽  
First Time

Abstract β-sitosterol and two triterpenoids: ursolic acid acetate and platanic acid have been isolated from ethanolic extract of Vitex trifola leaves. β-sitosterol was previously isolated from the leaves, stem and seeds of Vitex trifolia. Ursolic acid acetate has been isolated for the first time in this plant species. Platanic acid has been reported for the first time in Vitex trifolia and even in the family of this plant: Verbenaceae. These compounds were characterized using spectroscopic methods including 1D-1HNMR, 13CNMR, ESIMS and 2D-NMR (HSQC, HMBC, COSY) experiments and confirmed by comparison of their NMR data with those from the literature. A preliminary molluscicidal test for ethanol, chloroform and n-hexane extracts of leaves of Vitex trifolia against Biomphalaria alexandrina adult snails showed that ethanol extract of leaves with LC50 value 26.42 mg/l (27.92 mg/l - 24.99 mg/l) was more effective than n-hexane extract with LC50 value 35.48 mg/l (43.81 mg/l - 28.72mg/l) and chloroform extract with LC50 value 46.77 mg/l (53.59 mg/l - 43.81 mg/l) after 24 h exposure.

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