scholarly journals Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog

2014 ◽  
Vol 10 ◽  
pp. 316-322 ◽  
Author(s):  
Werner Telle ◽  
Gerhard Kelter ◽  
Heinz-Herbert Fiebig ◽  
Peter G Jones ◽  
Thomas Lindel
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Human Cancer ◽  
Phenyl Group ◽  
Marine Natural Product ◽  
Human Cancer Cell ◽  
Peptide Coupling ◽  
Human Cancer Cell Lines ◽  
First Time ◽  
Compare Analysis

The marine natural product malevamide D from the cyanobacterium Symploca hydnoides was synthesized for the first time. The final peptide coupling linked the dolaisoleuine and dolaproine subunits. The phenyl group of malevamide D was also functionalized with a photoreactive diazirine moiety, which was carried through seven reaction steps. Comprehensive assessment of the cytotoxicity in a panel of 42 human cancer cell lines revealed a geomean IC70 value of 1.5 nM (IC50 0.7 nM) for malevamide D, whereas the photoreactive derivative proved to be less active by a factor of at least 200. COMPARE analysis indicated tubulin interaction as likely mode of action of malevamide D.

scholarly journals Total synthesis of panicein A2

2015 ◽  
Vol 11 ◽  
pp. 1991-1996 ◽  
Author(s):  
Lili Yeung ◽  
Lisa I Pilkington ◽  
Melissa M Cadelis ◽  
Brent R Copp ◽  
David Barker
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Cell Lines ◽  
Tumour Cell ◽  
Human Cancer ◽  
In Vitro Cytotoxicity ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Tumour Cell Lines

The first total synthesis of the unusual aromatic sesquiterpene panicein A2 is reported and the structure of the natural product has been confirmed. When tested by the NCI against a range of human cancer cell lines, it was found that panicein A2 exhibits very little antiproliferative activity at 10 μM – an observation that is at odds with the earlier report that stated panicein A2 exhibits in vitro cytotoxicity against a number of tumour cell lines.

Cytotoxic constituents of Alocasia macrorrhiza

2017 ◽  
Vol 72 (1-2) ◽  
pp. 21-25 ◽  
Author(s):  
Marwa Elsbaey ◽  
Kadria F.M. Ahmed ◽  
Mahmoud F. Elsebai ◽  
Ahmed Zaghloul ◽  
Mohamed M.A. Amer ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Spectroscopic Data ◽  
Human Cancer ◽  
Indole Alkaloid ◽  
Acid Methyl Ester ◽  
2D Nmr ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Acid Methyl ◽  
First Time

AbstractAn indole alkaloid, 2-(5-hydroxy-1H-indol-3-yl)-2-oxo-acetic acid (1) isolated for the first time from nature, in addition to the nine known compounds 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (2), alocasin B (3), hyrtiosin B (4), α-monopalmitin (5), 1-O-β-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (6), 3-epi-betulinic acid (7), 3-epi-ursolic acid (8),β-sitosterol (9) andβ-sitosterol 3-O-β-D-glucoside (10) were isolated from the rhizomes ofAlocasia macrorrhiza(Araceae). Their structures were elucidated by 1D and 2D NMR spectroscopic data. Of these compounds,6exhibited the strongest cytotoxicity against the four tested human cancer cell lines (IC50of about 10 µM against Hep-2 larynx cancer cells).

scholarly journals Four New ent-Kaurane Diterpene Glycosides from Isodon henryi

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2736 ◽  
Author(s):  
Liu ◽  
Zhang ◽  
Wu ◽  
Chen ◽  
Li ◽  
...  
Keyword(s):  
Cell Lines ◽  
Human Cancer ◽  
Spectroscopic Methods ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Aerial Parts ◽  
Ic50 Values ◽  
Hct 116 ◽  
Relationship Of ◽  
First Time

To obtain diterpene glycosides from an aqueous extract of the aerial parts of Isodon henryi and further investigate their cytotoxicities, in this study, a total of seven compounds were isolated, including six ent-kaurane diterpene glycosides (1–6) and one diterpene aglycon (7). Among the seven ent-kaurane diterpenes obtained, four were novel compounds, including ent-7,20-epoxy- kaur-16-en-1α,6β,7β,15β-tetrahydroxyl-11-O-β-d-glucopyranoside (1), ent-7,20-epoxy-kaur-16-en- 6β,7β,14β,15β-tetrahydroxyl-1-O-β-d-glucopyranoside (2), ent-7,20-epoxy-kaur-16-en-6β,7β,15β- trihydroxyl-1-O-β-d-glucopyranoside (3), and ent-7,20-epoxy-kaur-16-en-7β,11β,14α,15β-tetrahydr- oxyl-6-O-β-d-glucopyranoside (4), and three were isolated from this plant for the first time (5–7). Their structures were elucidated by utilizing spectroscopic methods and electronic circular dichroism analyses. Furthermore, the cytotoxicities of all seven compounds were investigated in four human cancer cell lines, including A2780, BGC-823, HCT-116, and HepG2. The IC50 values of these diterpenes ranged from 0.18 to 2.44 mM in the tested cell lines. In addition, the structure–cytotoxicity relationship of diterpene glycosides was also evaluated to study the effect of glycosylation on the cytotoxicity of diterpene compounds.

scholarly journals Bioactive Components of Fissistigma cupreonitens

2018 ◽  
Vol 13 (6) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
I-Hsiao Chen ◽  
Ming-Yi Yang ◽  
Shin-Hun Juang ◽  
Chia-Lin Lee ◽  
Tran-Dinh Thang ◽  
...  
Keyword(s):  
Cell Line ◽  
Human Cancer ◽  
Spectroscopic Methods ◽  
Human Cancer Cell ◽  
Bioactive Components ◽  
Standard Drug ◽  
Human Cancer Cell Lines ◽  
Chemical Structures ◽  
Phytochemical Investigation ◽  
First Time

Phytochemical investigation of Fissistigma cupreonitens (Annonaceae) led to the isolation of 34 compounds. The chemical structures of all compounds were determined by spectroscopic methods. Among the isolates, compounds 20–27 and 31–34 were reported from this genus for the first time. From the results of the cytotoxicity assay against three human cancer cell lines (NCI-H226, NPC-TW01, and Jurkat E6–1), oxoaporphine compounds oxoxylopine (1), oxocrebanine (3), kuafumine (4) and lysicamine (5), and the flavonoid adunctin E (26) displayed significant cytotoxicity against NCI-H226 cell line, with IC50 values of 8.45, 8.10, 8.54, 12.83 and 12.00 μM, respectively, in comparison with the standard drug, cisplatin with IC50 of 13.37 μM.

scholarly journals Chemical characterization and bioactive properties of Geranium molle L.: from the plant to the most active extract and its phytochemicals

2016 ◽  
Vol 7 (5) ◽  
pp. 2204-2212 ◽  
Author(s):  
V. C. Graça ◽  
Lillian Barros ◽  
Ricardo C. Calhelha ◽  
Maria Inês Dias ◽  
Ana Maria Carvalho ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Cell Lines ◽  
Human Cancer ◽  
Chemical Characterization ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Bioactive Properties ◽  
First Time ◽  
Geranium Molle

The phytochemical characterization, antioxidant activity and in vitro cytotoxicity against human cancer cell lines of Geranium molle L. extracts are reported for the first time.

Diterpenoid Hydroperoxides from the Far-Eastern Brown Alga Dictyota dichotoma

2009 ◽  
Vol 62 (9) ◽  
pp. 1185 ◽  
Author(s):  
Sophia A. Kolesnikova ◽  
Ekaterina G. Lyakhova ◽  
Anatoly I. Kalinovsky ◽  
Pavel S. Dmitrenok ◽  
Sergei A. Dyshlovoy ◽  
...  
Keyword(s):  
Cell Lines ◽  
Brown Alga ◽  
Human Cancer ◽  
Algal Species ◽  
Human Cancer Cell ◽  
Dictyota Dichotoma ◽  
Human Cancer Cell Lines ◽  
New Compounds ◽  
Far Eastern ◽  
First Time

Two new compounds, dictyohydroperoxide 1 and hydroperoxyacetoxycrenulide 2, (Scheme 1) containing hydroperoxyl groups rarely found in algal terpenoids were isolated from the Russian population of brown alga Dictyota dichotoma. The known compounds acetoxycrenulide 4 and squalene were also found in this algal species for the first time. Some of the isolated compounds showed moderate cytoxicity against human cancer cell lines.

Cytotoxic Thiophenes from the Root of Echinops grijisii Hance

2009 ◽  
Vol 64 (3-4) ◽  
pp. 193-196 ◽  
Author(s):  
Peng Zhang ◽  
Dong Liang ◽  
Wenrong Jin ◽  
Haibin Qu ◽  
Yiyu Cheng ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Spectroscopic Data ◽  
Human Cancer ◽  
Ethanol Extract ◽  
Cancer Cell Lines ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
First Time

A new thiophene, echinothiophenegenol (1), together with seven known thiophenes was isolated from the crude ethanol extract of roots of Echinops grijisii Hance. The structure of 1 was elucidated on the basis of spectroscopic data. Compounds 2 and 5, isolated from the plant for the first time, and compounds 1 - 7 were tested for their cytotoxicity against two human cancer cell lines, HL60 and K562. The thiophenes showed better activity than the bithiophenes

Synthesis and biological evaluation of sapinofuranones A,B and 1,2,3-triazole-sapinofuranone hybrids as cytotoxic agents

RSC Advances ◽  
2016 ◽  
Vol 6 (103) ◽  
pp. 101501-101512 ◽  
Author(s):  
K. Siva Nagi Reddy ◽  
Gowravaram Sabitha ◽  
Y. Poornachandra ◽  
C. Ganesh Kumar
Keyword(s):  
Total Synthesis ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Lines ◽  
Biological Evaluation ◽  
Cytotoxic Agents ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Synthesis And Biological Evaluation

The total synthesis of sapinofuranones A,B and ent-sapinofuranones A,B and L-factor and a series of novel 1,2,3-triazole-sapinofuranone hybrids is described and their cytotoxicity against four human cancer cell lines (A549, MDA-MB-231, DU145 and HepG2) was evaluated.

Canadensenes: Natural and semi-synthetic analogues

2003 ◽  
Vol 81 (5) ◽  
pp. 406-411 ◽  
Author(s):  
Qing-Wen Shi ◽  
Anastasia Nikolakakis ◽  
Françoise Sauriol ◽  
Orval Mamer ◽  
Lolita O Zamir
Keyword(s):  
Natural Products ◽  
Human Cancer ◽  
Side Chain ◽  
Taxus Chinensis ◽  
Tubulin Polymerization ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Taxus Canadensis ◽  
Taxus Mairei ◽  
First Time

The first bicyclic taxanes isolated in the needles of the Canadian yew were named canadensene 1 and 5-epi-canadensene 2. Four additional analogues (3–6), isolated previously in Taxus chinensis and Taxus mairei, and a new natural 5-epi-canadensene analog 7 with a C-20-cinnamoyl group, were characterized for the first time in the needles of Taxus canadensis. A bicyclic derivative 8 with a docetaxel side chain on C-20 was synthesized using 5-epi-canadensene 2 as starting material. The lack of bioactivities of these bicyclic analogues (tubulin polymerization and cytotoxicities against human cancer cell lines) is discussed.Key words: Taxus canadensis, Taxaceae, taxanes, natural products, semi-synthesis.

scholarly journals Chemical Constituents from the Fruit Body of Chlorophyllum Molybdites

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800
Author(s):  
Zushang Su ◽  
Ping Wang ◽  
Wei Yuan ◽  
Shiyou Li
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Chemical Constituents ◽  
Fruit Body ◽  
Cancer Cell Lines ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
First Time

A new glycoxyuracil and 15 known compounds were isolated from the fruit body of Chlorophyllum molybdites. The structures were determined from their NMR and MS data and by comparison with literature data. Compounds 2–5, 10–11, 13, and 15–16 were isolated from the genus Chlorophyllum for the first time. Compounds (1–9) did not show cytotoxicity against two human cancer cell lines, A549 and Panc-28 (GI50 > 50 μM).

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