Absolute Configuration of a New Phenethylcyclohexanetriol and a New Natural Bibenzyl From Amomum celsum

Methanol extracts of the rhizomes or fruit of Amomum celsum Lamxay & M.F. Newman (Zingiberaceae) yielded 5 compounds one of which, 1,3 S,5 S-trihydroxy-1-(4-hydroxyphenylethyl)cyclohexane (2), is new and one, 4-hydroxybibenzyl (1), is reported as a natural product for the first time. In addition, 3 known compounds, 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (3), 3,5-diacetoxy-1,7- bis(3,4-dihydroxyphenyl)heptane (4), and 1,4-hydroquinone (5), were also isolated. Their structures were determined by performing extensive analysis of high-resolution electrospray ionization-mass spectrometry and nuclear magnetic resonance spectroscopic data. The absolute configuration of 2 was unambiguously established by X-ray crystallography and Mosher’s method. Cytotoxicity of compounds 1 and 2 against MCF-7 and Hep-G2 human cancer cell lines were tested in the sulforhodamine B cytotoxic assay. A plausible biosynthesis of 1 and 2 in A. celsum was proposed.

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Synthesis of novel amide and Schiff’s base functionalized novel pyrido[1,2-a] pyrimidin-4-one derivatives and their anticancer activity studies.

Letters in Organic Chemistry ◽

10.2174/1570178618666210512021950 ◽

2021 ◽

Vol 18 ◽

Author(s):

Sailu Betala ◽

Chiranjeevi Abba ◽

Hanumandlu Racha

Keyword(s):

Anticancer Activity ◽

Hydrazine Hydrate ◽

Human Cancer ◽

Aromatic Aldehydes ◽

Human Cancer Cell ◽

Hep G2 ◽

Schiff’S Base ◽

Human Cancer Cell Lines ◽

Amide Derivatives ◽

Mcf 7

Abstract: A series of novel amide and Schiffs base functionalized novel pyrido[1,2-a]pyrimidin-4-one derivatives were prepared starting from 6-(thiophene-2-yl)/phenyl-4-(trifluoromethyl) pyridin-2-amine 1a and 1b. These compounds on reaction with EMME, to afford compounds 2a and 2b, followed by cyclization to afford compounds 3a and 3b. Treatment of compound 3a and 3b with hydrazine hydrate to get compounds 4a and 4b, compounds 4a and 4b on reaction with different substituted aromatic aldehydes to get Schiff’s base derivatives 5a-j, in another way compounds 3a, 3b on reaction with aliphatic amines to get amide derivatives 6a-f. All the compounds 5a-j and 6a-f were screened against four human cancer cell lines (HeLa, COLO205, Hep G2, and MCF 7), among all the derivatives, compounds 5c, 5e, 6a, and 6b showed promising anticancer activity.

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New 9α-Hydroxy-5α,6α-epoxysterols from the Vietnamese Marine Sponge Ircinia echinata

Marine Drugs ◽

10.3390/md16110424 ◽

2018 ◽

Vol 16 (11) ◽

pp. 424 ◽

Cited By ~ 1

Author(s):

Thi Trinh ◽

Bich Truong ◽

Arlette Longeon ◽

Thi Doan ◽

Alexandre Deville ◽

...

Keyword(s):

Marine Sponge ◽

Breast Cancer Cells ◽

Mass Spectra ◽

Human Cancer ◽

Selective Inhibition ◽

2D Nmr ◽

Human Breast ◽

Hep G2 ◽

Human Cancer Cell Lines ◽

Mcf 7

Chemical investigation of the methanol extract of the Vietnamese marine sponge Ircinia echinata led to the isolation of six new 9α-hydroxy-5α,6α-epoxysterols: 5α,6α-epoxycholesta-7,22(E)-dien-3β,9α-diol (1), 5α,6α-epoxycholesta-7,24(28)-dien-3β,9α-diol (2), (24R)-5α,6α-epoxy-24-ethyl-cholesta-7-en-3β,9α-diol (3), 5α,6α-epoxycholesta-7-en-3β,9α-diol (4), (24S)-5α,6α-epoxyergosta-7,22-dien-3β,9α-diol (5), and (24R)-5α,6α-epoxy-24-methyl-cholesta-7-en-3β,9α-diol (6) along with the known 5α-6α-epoxysterols: 5α,6α-epoxystigmasta-7-en-3β-ol (7), 5α,6α-epoxystigmasta-7,22-dien-3β-ol (8), and 5α,6α-epoxyergosta-7-en-3β-ol (9). Their structures and their configurations were established on the basis of high resolution mass spectra and extensive 1D and 2D NMR spectroscopic data and by comparison with the literature. Their cytotoxic activity, evaluated against three human cancer cell lines, MCF-7, Hep-G2 and LU-1, revealed that only compounds 3 and 4 exhibited significant antiproliferative activity and compound 3 showed a selective inhibition towards the MCF-7 human breast cancer cells.

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Conjugated Polyene Ketones From the Marine Sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and Their Cytotoxic Activity

Natural Product Communications ◽

10.1177/1934578x211043732 ◽

2021 ◽

Vol 16 (9) ◽

pp. 1934578X2110437

Author(s):

Bui H. Tai ◽

Dan T. Hang ◽

Do T. Trang ◽

Pham H. Yen ◽

Phan T. T. Huong ◽

...

Keyword(s):

Cytotoxic Activity ◽

Marine Sponge ◽

Human Cancer ◽

2D Nmr ◽

Ionization Mass ◽

Hep G2 ◽

Human Cancer Cells ◽

Resolution Electron ◽

New Compounds ◽

First Time

Five conjugated polyene ketones (1-5) were isolated from the methanol extract of the marine sponge Clathria ( Thalysias) reinwardti (Vosmaer, 1880) living in the coastal waters of Vietnam. Their structures were determined to be 8-(2′,3′,4′-trimethylphenyl)-6-methyl-oct-3( E),5( E),7( E)-trien-2-one (1), 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo- β-ionone (4), and 4-(2′,3′,4′-trimethylphenyl)-but-3( E)-en-2-one (5), by extensive analysis of high-resolution electron spray ionization mass spectrum (HR-ESI-MS), one-dimensional, and two-dimensional (2D) nuclear magnetic resonance (NMR) spectra, as well as by comparison of the spectral data with those reported in the literature. Compound 1 was new, compounds 2 to 4 were isolated from nature for the first time, and the chemical structure as well as the NMR assignments, of 5 were indicated by 2D NMR for the first time. Additionally, compound 5 exhibited cytotoxic activity against the human cancer cells SK-LU-1, SK-Mel-2, MCF-7, and Hep-G2 with half-minimal inhibitory concentration (IC50) values of 15.12 ± 3.43, 17.41 ± 2.83, 33.12 ± 3.39, and 34.38 ± 3.52 µM, respectively, but displayed only a weak cytotoxic effect on the normal HEK-239A cells (IC50 64.67 ± 3.67 µM). Compound 5 also significantly increased Caspase-3 activity in SK-LU-1 cells at concentrations of 10, 15, and 20 µM.

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STUDY ON CHEMICAL CONSTITUENTS AND CYTOTOXICITY OF ASPIDISTRA LETREAE

HUE UNIVERSITY JOURNAL OF SCIENCE NATURAL SCIENCE ◽

10.26459/hueuni-jns.v129i2a.5656 ◽

2020 ◽

Vol 129 (1B) ◽

Author(s):

Duc Viet Ho

Keyword(s):

Methanol Extract ◽

Human Cancer ◽

Chemical Constituents ◽

Hep G2 ◽

Pure Compound ◽

Human Cancer Cell Lines ◽

Phytochemical Investigation ◽

Reported Data ◽

First Time

A phytochemical investigation of whole Aspidistra letreae plants led to the isolation of 2H-chromen-2-one (1), α-tocopherol (2), (E)-phytol (3), asparenydiol (4) and (25S)-spirost-1β,3α,5β-triol (5). Their structures were determined on the basis of NMR spectral evidences and in comparison with the reported data. Of these, asparenydiol (4) was isolated from the genus Aspidistra for the first time. This is also the first report on the separation and structural determination of (25S)-spirost-1β,3α,5β-triol (5) as a pure compound. The methanol extract exhibited a moderate cytotoxicity against the LU-1, HeLa, MDA-MB-231, Hep-G2, and MKN-7 human cancer cell lines with IC50 values ranging from 52.58 ± 3.65 to 64.78 ± 4.89 μg/mL.

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Chemical constituents and cytotoxicity of Aspidistra letreae

HUE UNIVERSITY JOURNAL OF SCIENCE NATURAL SCIENCE ◽

10.26459/hueuni-jns.v129i1b.5656 ◽

2020 ◽

Vol 129 (1B) ◽

pp. 31-39

Author(s):

Duc Viet Ho ◽

Hanh Nhu Thi Hoang ◽

Khue Minh Vo ◽

Anh Tuan Le ◽

Hoai Thi Nguyen

Keyword(s):

Human Cancer ◽

Chemical Constituents ◽

Hep G2 ◽

Human Cancer Cell Lines ◽

Phytochemical Investigation ◽

Ic50 Values ◽

Reported Data ◽

Whole Plants ◽

First Time

A phytochemical investigation of whole Aspidistra letreae plants led to the isolation of 2H-chromen-2-one (1), α-tocopherol (2), (E)-phytol (3), asparenydiol (4) and (25S)-spirost-1β,3α,5β-triol (5). Their structures were determined on the basis of NMR spectral evidences and in comparison with the reported data. Of these, asparenydiol (4) was isolated from the genus Aspidistra for the first time. This is also the first report on the separation and structural determination of (25S)-spirost-1β,3α,5β-triol (5) as a pure compound. The methanol extract from the whole plants of Aspidistra letreae exhibits moderate cytotoxicity against the LU-1, HeLa, MDA-MB-231, Hep-G2, and MKN-7 human cancer cell lines with IC50 values ranging from 52.58 ± 3.65 to 64.78 ± 4.89 μg/mL.

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Two New Cytotoxic Steroidal Alkaloids from Sarcococca Hookeriana

Molecules ◽

10.3390/molecules24010011 ◽

2018 ◽

Vol 24 (1) ◽

pp. 11 ◽

Cited By ~ 1

Author(s):

Shaojie Huo ◽

Jichun Wu ◽

Xicheng He ◽

Lutai Pan ◽

Jiang Du

Keyword(s):

Cell Lines ◽

Human Cancer ◽

Cytotoxic Activities ◽

Steroidal Alkaloids ◽

X Ray ◽

Human Cancer Cell Lines ◽

X Ray Crystallography ◽

Ic50 Values ◽

Mcf 7

Two new steroidal alkaloids, named hookerianine A (1) and hookerianine B (2) were isolated from the stems and roots of Sarcococca hookeriana Baill., along with two known compounds, sarcorucinine G (3) and epipachysamine D (4). On the basis of spectroscopic methods and by comparison with literature data, their structures were determined. As well as X-ray crystallography was performed to confirm compound 4. To identify novel antitumor inhibitors, all compounds were performed a CCK-8 assay against five human cancer cell lines SW480, SMMC-7721, PC3, MCF-7 and K562 in vitro. Compound 2 exhibited moderate cytotoxic activities to all cell lines with IC50 values in the range of 5.97–19.44 μM. Compound 3 was the most effective one against SW480 and K562 cell lines with IC50 values of 5.77 and 6.29 μM, respectively.

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A New Xanthone from the Pericarp of Garcinia mangostana

Natural Product Communications ◽

10.1177/1934578x1300801219 ◽

2013 ◽

Vol 8 (12) ◽

pp. 1934578X1300801 ◽

Cited By ~ 2

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.

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A New Optical Biflavonoid, (2″R)-2″,3″-Dihydrorobustaflavone 7,4′-Dimethyl Ether, and Other Constituents from Selaginella trichoclada Alsto

Natural Product Communications ◽

10.1177/1934578x19887885 ◽

2019 ◽

Vol 14 (12) ◽

pp. 1934578X1988788

Author(s):

Peng Yang ◽

Mei-Long Lu ◽

Ke Li ◽

Qun Zhou

Keyword(s):

Dimethyl Ether ◽

Spectroscopic Data ◽

High Performance ◽

Human Cancer ◽

Ethanol Extract ◽

Racemic Compound ◽

Chiral Phase ◽

Human Cancer Cell Lines ◽

First Time ◽

Mcf 7

A new optical biflavonoid, (2” R)-2″,3″-dihydrorobustaflavone 7,4′-dimethyl ether (1), and 6 known compounds (2-7) were isolated for the first time from the 70% ethanol extract of Selaginella trichoclada Alsto. The structures of the compounds were confirmed by extensive spectroscopic data analyses. Racemic compound 1 was separated by chiral-phase high-performance liquid chromatography, and the absolute configurations of (±)-1 were defined by circular dichroism spectroscopic data. Compound 1 exhibited moderate cytotoxicity against MCF-7, A549, and HepG2 human cancer cell lines.

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Ochroborbone, A New Cytotoxic Indole Alkaloid from Ochrosia borbonica

Natural Product Communications ◽

10.1177/1934578x1701200407 ◽

2017 ◽

Vol 12 (4) ◽

pp. 1934578X1701200

Author(s):

Yan-Ping Liu ◽

A-Hong Chen ◽

Ruo-Heng Li ◽

Hui-Wen Yang ◽

Hai-Nan Bao ◽

...

Keyword(s):

Human Cancer ◽

Indole Alkaloid ◽

Spectroscopic Methods ◽

Inhibitory Effects ◽

Human Cancer Cell Lines ◽

Stems And Leaves ◽

Monoterpenoid Indole Alkaloid ◽

First Time ◽

Mcf 7

A new monoterpenoid indole alkaloid, ochroborbone (1), along with five known alkaloids (2–6), were isolated from the stems and leaves of Ochrosia borbonica. Among them, ochroborbone (1) is a rare C17-nor monoterpenoid indole alkaloid, and the known compounds (2-6) were isolated from Ochrosia for the first time. These structures were established on the basis of extensive spectroscopic methods. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1 and 2 exhibited inhibitory effects with IC50 values comparable with those of cisplatin.

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Two New Taxane Diterpenoids From Taxus baccata

Natural Product Communications ◽

10.1177/1934578x20953280 ◽

2020 ◽

Vol 15 (9) ◽

pp. 1934578X2095328

Author(s):

Qi Ding ◽

Dong-Mei Fang ◽

Xiao-Huan Li ◽

Feng Gao

Keyword(s):

Mass Spectrometry ◽

Human Cancer ◽

Ionization Mass ◽

Taxus Baccata ◽

Human Cancer Cell ◽

Human Cancer Cell Lines ◽

Nuclear Magnetic Resonance Spectra ◽

Taxane Diterpenoids ◽

Taxane Diterpenoid ◽

Mcf 7

Two new diterpenoids named 13-oxo-wollifoliane-10,15-olide (1) and 19-acetoxy-7,9,10-deacetyl-baccatin VI (2), along with 14 known taxanes (3-16), were isolated from Taxus baccata. The structures of these compounds were elucidated by 1-dimensional and 2-dimensional nuclear magnetic resonance spectra, high-resolution electrospray ionization-mass spectrometry, and infrared spectroscopy. Structurally, 13-oxo-wollifoliane-10,15-olide (1) is the first taxane diterpenoid possessing an unusual carbonyl group at the C-13 position of the 11(15→1),11(10→9)bis- abeo-taxane structure (5/6/6/6/4 skeleton), and 19-acetoxy-7,9,10-deacetyl-baccatin VI (2) is a new compound containing an acetoxy group at the C-19 position of 6/8/6/4-taxane. Among the 14 known taxane compounds 3-16, compounds 7 and 9 were first isolated and reported from T. baccata. Several compounds (3-16) were evaluated for cytotoxicity against MCF-7 and HCT116 human cancer cell lines, but none of them showed considerable cytotoxic activity.

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