scholarly journals New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 100
Author(s):  
Sherif Ebada ◽  
Werner Müller ◽  
Wenhan Lin ◽  
Peter Proksch
Keyword(s):  
Spectral Analysis ◽  
Marine Sponge ◽  
Parent Compound ◽  
2D Nmr ◽  
Chemical Structures ◽  
Nmr Data ◽  
Ic50 Values ◽  
Nanomolar Range ◽  
Mouse Lymphoma

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

scholarly journals Chemical Constituents from Scindapsus officinalis (Roxb.) Schott. and Their Anti–Inflammatory Activities

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2577 ◽  
Author(s):  
Hongjing Dong ◽  
Yanling Geng ◽  
Xueyong Wang ◽  
Xiangyun Song ◽  
Xiao Wang ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
No Production ◽  
Inhibitory Effects ◽  
Nmr Data ◽  
Extensive Analysis ◽  
Ic50 Values ◽  
Monoterpene Glycoside ◽  
Anti Inflammatory

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

scholarly journals Structure Revision and Protein Tyrosine Phosphatase Inhibitory Activity of Drazepinone

Marine Drugs ◽  
2021 ◽  
Vol 19 (12) ◽  
pp. 714
Author(s):  
Fei Cao ◽  
Li Pan ◽  
Wen-Bin Gao ◽  
Yun-Feng Liu ◽  
Cai-Juan Zheng ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Chemical Shifts ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Nmr Data ◽  
Structure Revision ◽  
Ic50 Values

From the marine-derived fungus Penicillium sumatrense (Trichocomaceae), a pair of enantiomers [(+)-1 and (−)-1] were isolated with identical 1D NMR data to drazepinone, which was originally reported to have a trisubstituted naphthofuroazepinone skeleton. In this study, we confirmed the structures of the two enantiomers as drazepinone and revised their structures by detailed analysis of extensive 2D NMR data and a comparison of the calculated 13C chemical shifts, ECD, VCD, and ORD spectra with those of the experiment ones. (+)-1 and (−)-1 were evaluated for their PTP inhibitory activity in vitro. (−)-1 showed selective PTP inhibitory activity against PTP1B and TCPTP with IC50 values of 1.56 and 12.5 μg/mL, respectively.

scholarly journals Ergosterol Peroxide and Stigmasterol from The Stembark of Aglaia simplicifolia (Meliaceae) and Their Cytotoxic against HeLa Cervical Cancer Cell Lines

2021 ◽  
Vol 1 (1) ◽  
pp. 46-51
Author(s):  
Nunung Kurniasih ◽  
Asep Supriadin ◽  
Desi Harneti ◽  
Rizky Abdulah ◽  
Mohamad Nurul Azmi bin Mohamad Taib ◽  
...  
Keyword(s):  
Cervical Cancer ◽  
2D Nmr ◽  
Cytotoxic Effects ◽  
Cytotoxicity Activity ◽  
Chemical Structures ◽  
Ergosterol Peroxide ◽  
Cervical Cancer Cells ◽  
Ic50 Values ◽  
Hela Cervical Cancer Cell

Two steroid compounds, ergosterol peroxide (1) and stigmasterol (2) have been isolated from the stembark of Aglaia simplicifolia belong to Meliaceae family. The chemical structures of 1 and 2 were identified based on spectroscopic evidence including UV, IR, 1D NMR, 2D NMR as well as mass spectra and by comparison with those previously reported spectra data. Both compounds were evaluated for their cytotoxic effects against cervical cancer HeLa cells in vitro. Compounds 1 and 2 showed cytotoxicity activity against HeLa cervical cancer cells with IC50 values of 0.80 and 26.42 µM, respectively.

scholarly journals Proposed Mechanism for the Antitrypanosomal Activity of Quercetin and Myricetin Isolated from Hypericum afrum Lam.: Phytochemistry, In Vitro Testing and Modeling Studies

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1009
Author(s):  
Farida Larit ◽  
Khaled M. Elokely ◽  
Manal A. Nael ◽  
Samira Benyahia ◽  
Francisco León ◽  
...  
Keyword(s):  
2D Nmr ◽  
Ionization Mass ◽  
Isolation And Identification ◽  
Chemical Structures ◽  
Modeling Studies ◽  
Antitrypanosomal Activity ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
Molecular Modeling Studies

The in vitro activity of L. donovani (promastigotes, axenic amastigotes and intracellular amastigotes in THP1 cells) and T. brucei, from the fractions obtained from the hydroalcoholic extract of the aerial part of Hypericum afrum and the isolated compounds, has been evaluated. The chloroform, ethyl acetate and n-butanol extracts showed significant antitrypanosomal activity towards T. brucei, with IC50 values of 12.35, 13.53 and 12.93 µg/mL and with IC90 values of 14.94, 19.31 and 18.67 µg/mL, respectively. The phytochemical investigation of the fractions led to the isolation and identification of quercetin (1), myricitrin (2), biapigenin (3), myricetin (4), hyperoside (5), myricetin-3-O-β-d-galactopyranoside (6) and myricetin-3’-O-β-d-glucopyranoside (7). Myricetin-3’-O-β-d-glucopyranoside (7) has been isolated for the first time from this genus. The chemical structures were elucidated by using comprehensive one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) spectroscopic data, as well as high-resolution electrospray ionization mass spectrometry (HR-ESI–MS). These compounds have also been evaluated for their antiprotozoal activity. Quercetin (1) and myricetin (4) showed noteworthy activity against T. brucei, with IC50 and IC90 values of 7.52 and 5.71 µM, and 9.76 and 7.97 µM, respectively. The T. brucei hexokinase (TbHK1) enzyme was further explored as a potential target of quercetin and myricetin, using molecular modeling studies. This proposed mechanism assists in the exploration of new candidates for novel antitrypanosomal drugs.

scholarly journals Ergosterol Peroxide and Stigmasterol from The Stembark of Aglaia simplicifolia (Meliaceae) and Their Cytotoxic against HeLa Cervical Cancer Cell Lines

2021 ◽  
Vol 7 (1) ◽  
pp. 46-51
Author(s):  
Nunung Kurniasih ◽  
Asep Supriadin ◽  
Desi Harneti ◽  
Rizky Abdulah ◽  
Mohamad Nurul Azmi bin Mohamad Taib ◽  
...  
Keyword(s):  
Cervical Cancer ◽  
2D Nmr ◽  
Cytotoxic Effects ◽  
Cytotoxicity Activity ◽  
Chemical Structures ◽  
Ergosterol Peroxide ◽  
Cervical Cancer Cells ◽  
Ic50 Values ◽  
Hela Cervical Cancer Cell

Two steroid compounds, ergosterol peroxide (1) and stigmasterol (2) have been isolated from the stembark of Aglaia simplicifolia belong to Meliaceae family. The chemical structures of 1 and 2 were identified based on spectroscopic evidence including UV, IR, 1D NMR, 2D NMR as well as mass spectra and by comparison with those previously reported spectra data. Both compounds were evaluated for their cytotoxic effects against cervical cancer HeLa cells in vitro. Compounds 1 and 2 showed cytotoxicity activity against HeLa cervical cancer cells with IC50 values of 0.80 and 26.42 µM, respectively.

Antifungal and allelopathic activities of sesquiterpenes from Solidago canadensis

2021 ◽  
Vol 25 ◽  
Author(s):  
Na Liu ◽  
Meina Song ◽  
Yulin Sun ◽  
Fengying Yang ◽  
Haina Yu ◽  
...  
Keyword(s):  
Candida Albicans ◽  
Seed Germination ◽  
Invasive Plant ◽  
2D Nmr ◽  
Solidago Canadensis ◽  
Significant Activity ◽  
Inhibitory Effects ◽  
Ic50 Values ◽  
Allelopathic Effects

: One new eudesmane sesquiterpene (1) and one new chromolaevane sesquiterpene (2), along with 19 known compounds, have been isolated from the invasive plant Solidago canadensis. Their structures were established by spectroscopic means including 1D/2D-NMR and HR-ESIMS analyses. Compounds 10 and 12, in combination with fluconazole, showed significant activity in an in vitro synergistic antifungal assay against Candida albicans, with FIC values of <0.15625 and <0.28125, respectively. Meanwhile, the allelopathic effects of these sesquiterpenes on Arabidopsis seed germination were also tested. Compounds 5, 7, 17 and 18 retarded the seed germination of Arabidopsis with IC50 values ranging from 9.1 to 41 μg/mL, while other compounds showed no obvious inhibitory effects.

scholarly journals New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

Marine Drugs ◽  
2019 ◽  
Vol 17 (3) ◽  
pp. 167 ◽  
Author(s):  
Pierre-Eric Campos ◽  
Emmanuel Pichon ◽  
Céline Moriou ◽  
Patricia Clerc ◽  
Rozenn Trépos ◽  
...  
Keyword(s):  
Plasmodium Falciparum ◽  
Minimum Inhibitory Concentration ◽  
Marine Sponge ◽  
Nmr Spectra ◽  
Inhibitory Concentration ◽  
Chemical Study ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
2D Nmr Spectra ◽  
Ic50 Values

Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively.

Bioactive Alkaloids from the Tropical Marine Sponge Axinella carteri

1995 ◽  
Vol 50 (9-10) ◽  
pp. 669-674 ◽  
Author(s):  
A. Supriyono ◽  
B. Schwarz ◽  
V. Wray ◽  
L. Witte ◽  
W. E. G. Müller ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Insecticidal Activity ◽  
De Novo ◽  
The Philippines ◽  
De Novo Synthesis ◽  
Mouse Lymphoma Cells ◽  
Guanidine Alkaloids ◽  
Neonate Larvae ◽  
Mouse Lymphoma

Abstract Analysis of the tropical marine sponge Axinella carteri afforded six unusual alkaloids, including the new brominated guanidine derivative 3-bromo-hymenialdisine. The structure elucidation of the new alkaloid is described. The alkaloid patterns of sponges collected in Indonesia or in the Philippines were shown to be qualitatively identical suggesting de novo synthesis by the sponge or by endosymbiontic microorganisms rather than uptake by filterfeeding. All alkaloids were screened for insecticidal activity as well as for cytotoxicity. The guanidine alkaloids hymenialdisine and debromohymenialdisine exhibited insecticidal activity towards neonate larvae of the polyphagous pest insect Spodoptera littoralis (LD50s of 88 and 125 ppm, respectively), when incorporated into artificial diet and offered to the larvae in a chronic feeding bioassay. The remaining alkaloids, including the new compound, were inactive in this bioassay. Cytotoxicity was studied in vitro using L5178y mouse lymphoma cells. Debromohymenialdisine was again the most active compound (ED50 1.8 μg/ml) followed by hymenialdisine and 3-bromohymenialdisine, which were essentially equitoxic and exhibited ED50s of 3.9 μg/ml in both cases. The remaining alkaloids were inactive against this cell line

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 New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 439 ◽  
Author(s):  
Li ◽  
Peifer ◽  
Janussen ◽  
Tasdemir
Keyword(s):  
Anticancer Activity ◽  
Deep Sea ◽  
Topoisomerase I ◽  
Active Sites ◽  
Binding Potential ◽  
Chemical Structures ◽  
Ic50 Values ◽  
Ft Ir ◽  
The Antarctic

The sponge genus Latrunculia is a prolific source of discorhabdin type pyrroloiminoquinone alkaloids. In the continuation of our research interest into this genus, we studied the Antarctic deep-sea sponge Latrunculia biformis that showed potent in vitro anticancer activity. A targeted isolation process guided by bioactivity and molecular networking-based metabolomics yielded three known discorhabdins, (−)-discorhabdin L (1), (+)-discorhabdin A (2), (+)-discorhabdin Q (3), and three new discorhabdin analogs (−)-2-bromo-discorhabdin D (4), (−)-1-acetyl-discorhabdin L (5), and (+)-1-octacosatrienoyl-discorhabdin L (6) from the MeOH-soluble portion of the organic extract. The chemical structures of 1–6 were elucidated by extensive NMR, HR-ESIMS, FT-IR, [α]D, and ECD (Electronic Circular Dichroism) spectroscopy analyses. Compounds 1, 5, and 6 showed promising anticancer activity with IC50 values of 0.94, 2.71, and 34.0 µM, respectively. Compounds 1–6 and the enantiomer of 1 ((+)-discorhabdin L, 1e) were docked to the active sites of two anticancer targets, topoisomerase I-II and indoleamine 2,3-dioxygenase (IDO1), to reveal, for the first time, the binding potential of discorhabdins to these proteins. Compounds 5 and 6 are the first discorhabdin analogs with an ester function at C-1 and 6 is the first discorhabdin bearing a long-chain fatty acid at this position. This study confirms Latrunculia sponges to be excellent sources of chemically diverse discorhabdin alkaloids.

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