Two New 11(15→1)Abeotaxanes with a 2,20-Epoxy Ring from the Needles of Taxus canadensis

Abstract Zanthoxylum nitidium (Roxb.) DC (Rutaceae) is well known for inhibiting the proliferation of human gastric, liver, kidney and lung cancer cells, though research on its potential use in treating leukaemia is relatively rare. Twenty-six compounds were isolated from the chloroform and petroleum ether extracts of the roots and leaves of Z. nitidium. They were (+)-9′-O-transferuloyl-5, 5′-dimethoxylaricriresinol (1), 8-(3′-oxobut-1′-en-1′-yl)-5, 7-dimethoxy-coumarin (2), 5, 7, 8-trimethoxy-coumarin (3), 5-(3′, 3′-dimethyl-2′-butenyloxy)-7, 8-dimethoxy-coumarin (4), 2-(5-methoxy-2-methyl-1H-indol-3-yl) methyl acetate (5), 2′-(5, 6-dihydrochleletrythrine-6-yl) ethyl acetate (6), 6-acetonyldi-hydrochelerythrine (7), 6β-hydroxymethyldihydronitidine (8), bocconoline (9), zanthoxyline (10), O-methylzanthoxyline (11), rhoifoline B (12), N-nornitidine (13), nitidine (14), chelerythrine (15), 4-hydroxyl-7,8-dimethoxy-furoquinoline (16), dictamnine (17), γ-fagarine (18), skimmianine (19), robustine (20), R-(+)-platydesmine (21), 4-methoxyl-1-methyl-2-quinoline (22), 4-methoxy-2-quinolone (23), liriodenine (24), aurantiamide acetate (25), 10-O-demethyl-12-O-methylarnottianamide (26). Four among them, compounds 4-6 and 16, were first confirmed in this study by UV, IR, 1D, 2D NMR and HR-ESI-MS spectra. Compounds 1-2 and 11 were isolated from Z. nitidium for the first time. Of the assayed compounds, 1, 2, 9, 10, 14, 15 and 24, exhibited good inhibitory activities in the leukaemia cell line HEL, whereas compound 14 (IC50: 3.59 µM) and compound 24 (IC50: 15.95 µM) exhibited potent inhibitory activities. So, to further investigate the possible mechanisms, cell cycle and apoptosis assays were performed, which indicated that compound 14 causes obvious S-phase arrest in HEL cells and induced apoptosis, whereas compound 24 only induced apoptosis. The present results suggested both compounds 14 and 24 are promising potential anti-leukaemia drug candidates.

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Active constituents of Zanthoxylum nitidium from Yunnan Province against leukaemia cells in vitro

BMC Chemistry ◽

10.1186/s13065-021-00771-0 ◽

2021 ◽

Vol 15 (1) ◽

Author(s):

Ying Deng ◽

Tongtong Ding ◽

Lulu Deng ◽

Xiaojiang Hao ◽

Shuzhen Mu

Keyword(s):

2D Nmr ◽

Leukaemia Cell Line ◽

Drug Candidates ◽

Hel Cells ◽

Inhibitory Activities ◽

Induced Apoptosis ◽

Aurantiamide Acetate ◽

First Time ◽

Potential Use

AbstractZanthoxylum nitidium (Roxb.) DC (Rutaceae) is well known for inhibiting the proliferation of human gastric, liver, kidney and lung cancer cells, though research on its potential use in treating leukaemia is relatively rare. Twenty-six compounds were isolated from the chloroform and petroleum ether extracts of the roots and leaves of Z. nitidium (Zanthoxylum nitidium). They were ( +)-9′-O-transferuloyl-5, 5′-dimethoxylaricriresinol (1), 8-(3′-oxobut-1′-en-1′-yl)-5, 7-dimethoxy-coumarin (2), 5, 7, 8-trimethoxy-coumarin (3), 5-(3′, 3′-dimethyl-2′-butenyloxy)-7, 8-dimethoxy-coumarin (4), 2-(5-methoxy-2-methyl-1H-indol-3-yl) methyl acetate (5), 2′-(5, 6-dihydrochleletrythrine-6-yl) ethyl acetate (6), 6-acetonyldi-hydrochelerythrine (7), 6β-hydroxymethyldihydronitidine (8), bocconoline (9), zanthoxyline (10), O-methylzanthoxyline (11), rhoifoline B (12), N-nornitidine (13), nitidine (14), chelerythrine (15), 4-hydroxyl-7,8-dimethoxy-furoquinoline (16), dictamnine (17), γ-fagarine (18), skimmianine (19), robustine (20), R-( +)-platydesmine (21), 4-methoxyl-1-methyl-2-quinoline (22), 4-methoxy-2-quinolone (23), liriodenine (24), aurantiamide acetate (25), 10-O-demethyl-12-O-methylarnottianamide (26). Four among them, compounds 4 – 6 and 16, were first confirmed in this study by UV, IR, 1D, 2D NMR and HR-ESI–MS spectra. Compounds 1 – 2 and 11 were isolated from Z. nitidium for the first time. Of the assayed compounds, 1, 2, 9, 10, 14, 15 and 24, exhibited good inhibitory activities in the leukaemia cell line HEL, whereas compound 14 (IC50: 3.59 µM) and compound 24 (IC50: 15.95 µM) exhibited potent inhibitory activities. So, to further investigate the possible mechanisms, cell cycle and apoptosis assays were performed, which indicated that compound 14 causes obvious S-phase arrest in HEL cells and induced apoptosis, whereas compound 24 only induced apoptosis. The present results suggested both compounds 14 and 24 are promising potential anti-leukaemia drug candidates.

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Two new taxane-glycosides from the needles of Taxus canadensis

Zeitschrift für Naturforschung B ◽

10.1515/znb-2015-0074 ◽

2015 ◽

Vol 70 (11) ◽

pp. 829-835 ◽

Cited By ~ 1

Author(s):

Nan Li ◽

Jin Wang ◽

Hui-Min Yan ◽

Man-li Zhang ◽

Qing-Wen Shi ◽

...

Keyword(s):

Mass Spectrometry ◽

Data Analysis ◽

High Resolution ◽

Fast Atom Bombardment ◽

2D Nmr ◽

Taxus Canadensis ◽

Nmr Data ◽

First Time

AbstractTwo minor taxane glycosides were isolated for the first time from the needles of Taxus canadensis. Their structures were characterized as 2α,5α-diacetoxy-10β-(6′-O-acetyl-β-d-glucopyranosyl)oxy-14β-[(2′R,3′S)-3′-hydroxy-2′-methylbutanoyl]oxytaxa-4(20),11-diene (1) and 2α,14β-diacetoxy-10β-(β-d-glucopyranosyl)oxytaxa-4(20),11-dien-5β-ol (2) on the basis of 1D and 2D NMR data analysis and confirmed by high-resolution fast atom bombardment mass spectrometry.

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A New pseudo-Alkaloid Taxane and a New Rearranged Taxane from the Needles of Taxus canadensis

Zeitschrift für Naturforschung B ◽

10.1515/znb-2008-0814 ◽

2008 ◽

Vol 63 (8) ◽

pp. 1005-1011 ◽

Cited By ~ 4

Author(s):

Manli Zhang ◽

Changhong Huo ◽

Mei Dong ◽

Ligeng Li ◽

Françoise Sauriol ◽

...

Keyword(s):

Double Bond ◽

Nmr Spectroscopy ◽

High Resolution ◽

2D Nmr ◽

Side Chain ◽

2D Nmr Spectroscopy ◽

Taxus Canadensis ◽

First Time

A new taxane with an amino side chain on C-5 and a new 11(15→1)abeotaxane having a tetrahydrofuran ring along carbon atoms C-2, C-3, C-4, C-20 identified for the first time from the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as 2α,7β ,9α,10β ,13-pentaacetoxy-11β -hydroxy-5α-(2´ -hydroxy,3'-N,N-dimethylamino-3´- phenyl)-propionyloxytaxa-4(20),12-diene (1) and 13α,20β -diacetoxy-5α,7β ,9α,10β -tetrahydroxy- 2α,20-epoxy-11(15→1)abeotaxa-11,15-diene (2) on the basis of 1D, 2D NMR spectroscopy and high-resolution FABMS analysis. Taxane 1 contains a rare C-12, C-13 double bond and a basic side chain, while taxane 2 bears a rare isopropenyl group at C-1.

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Two New Phytoecdysteroids from the Needles of Taxus canadensis

Zeitschrift für Naturforschung B ◽

10.1515/znb-2010-1118 ◽

2010 ◽

Vol 65 (11) ◽

pp. 1401-1405 ◽

Cited By ~ 2

Author(s):

Yu Fang ◽

Zhi-Yu Ni ◽

Teiko Yamada ◽

Yu-Fang Wang ◽

Man-Li Zhang ◽

...

Keyword(s):

High Resolution ◽

2D Nmr ◽

Taxus Canadensis ◽

First Time ◽

Acetal Group ◽

Ponasterone A

Two new phytoecdysteroids with a 20,22-acetal group were identified for the first time from the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as ponasterone A 20,22-p-hydroxybenzylidene acetal (1) and ponasterone A 20,22-acetonide (2) on the basis of 1D, 2D NMR evidence and high-resolution FABMS analysis

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Active constituents of Zanthoxylum nitidum from Yunnan Province against leukemia cells in vitro

10.21203/rs.2.22293/v6 ◽

2021 ◽

Author(s):

Ying Deng ◽

Tongtong Ding ◽

Lulu Deng ◽

Xiaojiang Hao ◽

Shu Zhen Mu

Keyword(s):

2D Nmr ◽

Leukaemia Cell Line ◽

Drug Candidates ◽

Hel Cells ◽

Inhibitory Activities ◽

Induced Apoptosis ◽

Aurantiamide Acetate ◽

First Time ◽

Potential Use

Abstract Zanthoxylum nitidium (Roxb.) DC (Rutaceae) is well known for inhibiting the proliferation of human gastric, liver, kidney and lung cancer cells, though research on its potential use in treating leukaemia is relatively rare. Twenty-six compounds were isolated from the chloroform and petroleum ether extracts of the roots and leaves of Z. nitidium (Zanthoxylum nitidium). They were (+)-9′-O-transferuloyl-5, 5′-dimethoxylaricriresinol (1), 8-(3′-oxobut-1′-en-1′-yl)-5, 7-dimethoxy-coumarin (2), 5, 7, 8-trimethoxy-coumarin (3), 5-(3′, 3′-dimethyl-2′-butenyloxy)-7, 8-dimethoxy-coumarin (4), 2-(5-methoxy-2-methyl-1H-indol-3-yl) methyl acetate (5), 2′-(5, 6-dihydrochleletrythrine-6-yl) ethyl acetate (6), 6-acetonyldi-hydrochelerythrine (7), 6β-hydroxymethyldihydronitidine (8), bocconoline (9), zanthoxyline (10), O-methylzanthoxyline (11), rhoifoline B (12), N-nornitidine (13), nitidine (14), chelerythrine (15), 4-hydroxyl-7,8-dimethoxy-furoquinoline (16), dictamnine (17), γ-fagarine (18), skimmianine (19), robustine (20), R-(+)-platydesmine (21), 4-methoxyl-1-methyl-2-quinoline (22), 4-methoxy-2-quinolone (23), liriodenine (24), aurantiamide acetate (25), 10-O-demethyl-12-O-methylarnottianamide (26). Four among them, compounds 4-6 and 16, were first confirmed in this study by UV, IR, 1D, 2D NMR and HR-ESI-MS spectra. Compounds 1-2 and 11 were isolated from Z. nitidium for the first time. Of the assayed compounds, 1, 2, 9, 10, 14, 15 and 24, exhibited good inhibitory activities in the leukaemia cell line HEL, whereas compound 14 (IC50: 3.59 µM) and compound 24 (IC50: 15.95 µM) exhibited potent inhibitory activities. So, to further investigate the possible mechanisms, cell cycle and apoptosis assays were performed, which indicated that compound 14 causes obvious S-phase arrest in HEL cells and induced apoptosis, whereas compound 24 only induced apoptosis. The present results suggested both compounds 14 and 24 are promising potential anti-leukaemia drug candidates.

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In Vitro Selective Growth-Inhibitory Activities of Phytochemicals, Synthetic Phytochemical Analogs, and Antibiotics against Diarrheagenic/Probiotic Bacteria and Cancer/Normal Intestinal Cells

Pharmaceuticals ◽

10.3390/ph13090233 ◽

2020 ◽

Vol 13 (9) ◽

pp. 233

Author(s):

Tomas Kudera ◽

Ivo Doskocil ◽

Hana Salmonova ◽

Miloslav Petrtyl ◽

Eva Skrivanova ◽

...

Keyword(s):

Cancer Cells ◽

Selective Growth ◽

Intestinal Cancer ◽

Zinc Pyrithione ◽

Chemical Structures ◽

Growth Inhibitory ◽

Increased Risk ◽

Broth Microdilution Method ◽

Inhibitory Activities

A desirable attribute of novel antimicrobial agents for bacterial diarrhea is decreased toxicity toward host intestinal microbiota. In addition, gut dysbiosis is associated with an increased risk of developing intestinal cancer. In this study, the selective growth-inhibitory activities of ten phytochemicals and their synthetic analogs (berberine, bismuth subsalicylate, ferron, 8-hydroxyquinoline, chloroxine, nitroxoline, salicylic acid, sanguinarine, tannic acid, and zinc pyrithione), as well as those of six commercial antibiotics (ceftriaxone, ciprofloxacin, chloramphenicol, metronidazole, tetracycline, and vancomycin) against 21 intestinal pathogenic/probiotic (e.g., Salmonella spp. and bifidobacteria) bacterial strains and three intestinal cancer/normal (Caco-2, HT29, and FHs 74 Int) cell lines were examined in vitro using the broth microdilution method and thiazolyl blue tetrazolium bromide assay. Chloroxine, ciprofloxacin, nitroxoline, tetracycline, and zinc pyrithione exhibited the most potent selective growth-inhibitory activity against pathogens, whereas 8-hydroxyquinoline, chloroxine, nitroxoline, sanguinarine, and zinc pyrithione exhibited the highest cytotoxic activity against cancer cells. None of the tested antibiotics were cytotoxic to normal cells, whereas 8-hydroxyquinoline and sanguinarine exhibited selective antiproliferative activity against cancer cells. These findings indicate that 8-hydroxyquinoline alkaloids and metal-pyridine derivative complexes are chemical structures derived from plants with potential bioactive properties in terms of selective antibacterial and anticancer activities against diarrheagenic bacteria and intestinal cancer cells.

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Active constituents of Zanthoxylum nitidum from Yunnan Province against leukemia

10.21203/rs.2.22293/v3 ◽

2020 ◽

Author(s):

Ying Deng ◽

Tongtong Ding ◽

Lulu Deng ◽

Xiaojiang Hao ◽

Shu Zhen Mu

Keyword(s):

Yunnan Province ◽

2D Nmr ◽

Leukaemia Cell Line ◽

Drug Candidates ◽

Hel Cells ◽

Zanthoxylum Nitidum ◽

Inhibitory Activities ◽

Induced Apoptosis ◽

First Time ◽

Potential Use

Abstract Zanthoxylum nitidium (Roxb.) DC (Rutaceae) is well known for inhibiting the proliferation of human gastric, liver, kidney and lung cancer cells, though research on its potential use in treating leukaemia is relatively rare. Twenty-six compounds were isolated from the chloroform and petroleum ether extracts of the roots and leaves of Z. nitidium . Four among them, compounds 4-6 and 16 , were first confirmed in this study by UV, IR, 1D, 2D NMR and HR-ESI-MS spectra. Compounds 1-2 and 11 were isolated from Z. nitidium for the first time. Of the assayed compounds, 1 , 2 , 9 , 10 , 14 , 15 and 24, exhibited good inhibitory activities in the leukaemia cell line HEL, whereas compound 14 (IC 50 : 3.59 µM) and compound 24 (IC 50 : 15.95 µM) exhibited potent inhibitory activities. So, to further investigate the possible mechanisms, cell cycle and apoptosis assays were performed, which indicated that compound 14 causes obvious S-phase arrest in HEL cells and induced apoptosis, whereas compound 24 only induced apoptosis. The present results suggested both compounds 14 and 24 are promising potential anti-leukaemia drug candidates.

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Identification of a Proanthocyanidin from Litchi Chinensis Sonn. Root with Anti-Tyrosinase and Antioxidant Activity

Biomolecules ◽

10.3390/biom10091347 ◽

2020 ◽

Vol 10 (9) ◽

pp. 1347

Author(s):

Matthew Saive ◽

Manon Genva ◽

Thibaut Istasse ◽

Michel Frederich ◽

Chloé Maes ◽

...

Keyword(s):

Antioxidant Activities ◽

Biological Activities ◽

Chemical Characterization ◽

2D Nmr ◽

Ethnobotanical Study ◽

Traditional Use ◽

Litchi Chinensis ◽

Isolated Compound ◽

First Time

This work follows an ethnobotanical study that took place in the island of Mayotte (France), which pointed out the potential properties of Litchi chinensis Sonn. roots when used to enhance skin health and appearance. Through in vitro testing of a crude methanolic extract, high anti-tyrosinase (skin whitening effect) and antioxidant activities (skin soothing effect) could be measured. HPLC successive bio-guided fractionation steps allowed the purification of one of the compounds responsible for the biological activities. The isolated compound was characterized by UV, IR, MS and 2D-NMR, revealing, for the first time in Litchi chinensis Sonn. roots, an A-type proanthocyanidin and thus revealing a consensus among the traditional use shown by the ethnobotanical study, in vitro biological activities and chemical characterization.

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Cytotoxic Activity of Lomatiol and 7-(3′-Hydroxymethyl-3′-methylallyloxy)coumarin

Natural Product Communications ◽

10.1177/1934578x1601100322 ◽

2016 ◽

Vol 11 (3) ◽

pp. 1934578X1601100

Author(s):

Serena Fiorito ◽

Salvatore Genovese ◽

Francesco Epifano ◽

Veronique Mathieu ◽

Robert Kiss ◽

...

Keyword(s):

Structural Feature ◽

Colorimetric Assay ◽

Parent Compound ◽

Side Chain ◽

In Vitro Growth ◽

Mtt Colorimetric Assay ◽

Growth Inhibitory ◽

Inhibitory Activities ◽

Comparison Data

7-(3′-Hydroxymethyl-3′-methylallyloxy)coumarin, bearing a 3′-hydroxy-3′-methylallyl group as the O-side chain, and lomatiol, a lapachol derivative sharing the same structural feature, were tested for their in vitro growth inhibitory activities on six cancer cell lines using the MTT colorimetric assay, along with the respective 3′,3′-dimethylallyl derivatives and unprenylated products used for comparison. Data revealed that lomatiol displayed the strongest growth inhibitory activities in vitro although not as efficient as the parent compound lapachol. The oxidized O-prenylcoumarin recorded better growth inhibitory capacities than the prenylated and unprenylated parent products.

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