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 Cytotoxic Furan- and Pyrrole-Containing Scalarane Sesterterpenoids Isolated from the Sponge Scalarispongia sp.

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 840 ◽  
Author(s):  
Yeon-Ju Lee ◽  
Su Kim ◽  
Hansol Choi ◽  
Hyi-Seung Lee ◽  
Jong Lee ◽  
...  
Keyword(s):  
Natural Products ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Silica Column ◽  
Synthetic Derivative ◽  
High Cytotoxicity ◽  
First Time

Three furan-containing scalarane sesterterpenoids (1–3) and a novel pyrrole-containing analog (4) were isolated from the sponge Scalarispongia species. Compound 3, reported in the literature as a synthetic derivative of furoscalarol 2, was for the first time isolated from a natural source. During the separation performed using a silica column in the presence of methanol, 16-methoxy derivatives (5, 6) were obtained from the unintended reaction of 2. The isolated natural products 3 and 4 and the artifact 5 showed moderate to high cytotoxicity against six human cancer cell lines, whereas compound 6, the C-16 epimer of 5, showed no cytotoxicity at a concentration of 60 μΜ.

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 Design and synthesis of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone conjugates: study on their apoptosis inducing ability and tubulin polymerization inhibition

2020 ◽  
Vol 11 (11) ◽  
pp. 1295-1302
Author(s):  
Kesari Lakshmi Manasa ◽  
Sowjanya Thatikonda ◽  
Dilep Kumar Sigalapalli ◽  
Sowmya Vuppaladadium ◽  
Ganthala Parimala Devi ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Lines ◽  
Proliferative Potential ◽  
Tubulin Polymerization ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Design And Synthesis ◽  
Substituted 1

Herein, we have designed and synthesized a library of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone derivatives (10aa–ef) and evaluated for their anti-proliferative potential against a panel of human cancer cell lines.

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.

Pyrazole–oxadiazole conjugates: synthesis, antiproliferative activity and inhibition of tubulin polymerization

2014 ◽  
Vol 12 (40) ◽  
pp. 7993-8007 ◽  
Author(s):  
Ahmed Kamal ◽  
Anver Basha Shaik ◽  
Sowjanya Polepalli ◽  
Vangala Santosh Reddy ◽  
G. Bharath Kumar ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Antiproliferative Activity ◽  
Human Cancer ◽  
Cancer Cell Lines ◽  
Tubulin Polymerization ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines

A library of pyrazole–oxadiazole conjugates were synthesized and investigated for their antiproliferative activity in human cancer cell lines.

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.

Evaluation of the Cytotoxic Potential of Natural Products Employing a Battery of Human Cancer Cell Lines

Planta Medica ◽  
1990 ◽  
Vol 56 (06) ◽  
pp. 673-673
Author(s):  
J. Pezzuto ◽  
C. Beattie ◽  
K Lowell ◽  
W. Mar ◽  
S. Swanson ◽  
...  
Keyword(s):  
Natural Products ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Lines ◽  
Human Cancer Cell ◽  
Cytotoxic Potential ◽  
Human Cancer Cell Lines

scholarly journals Synthesis of mycalazol and mycalazal analogs with potent antiproliferating activities

2011 ◽  
Vol 83 (3) ◽  
pp. 489-493 ◽  
Author(s):  
Yasser M. A. Mohamed ◽  
Trond Vidar Hansen
Keyword(s):  
Natural Products ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Coupling Reaction ◽  
Human Cancer Cell ◽  
Stille Coupling ◽  
Human Cancer Cell Lines ◽  
Stille Coupling Reaction ◽  
Nanomolar Range

Four 2,5-disubstituted pyrrole and two 2-disubstituted thiophene analogs of the natural products mycalazol 5 and mycalazal 2 have been prepared using the Stille coupling reaction. All four analogs displayed potent antiproliferating activity against several human cancer cell lines with IC50 values in the nanomolar range.

Sign in / Sign up

Export Citation Format

Share Document