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1.
Nat Prod Res ; 32(21): 2535-2541, 2018 Nov.
Article in English | MEDLINE | ID: mdl-29350054

ABSTRACT

A new chromanone derivative, namely caloinophyllin A (1), along with eight known compounds (2-9), nobiletin (2), pentamethylquercetin (3), 3,5,7,4'-tetramethoxyflavone (4), 5,7,4'-trimethoxyflavone (5), 1,5-dihydroxyxanthone (6), 1,8-dimethoxy-2-hydroxyxanthone (7), 1,6-dihydroxy-7-methoxyxanthone (8) and 4-methoxycaffeic acid (9) were isolated from the roots of Calophyllum inophyllum. The structures of all the isolated compounds (1-9) were fully characterised using spectroscopic data, as well as comparison with the previous literature data. In addition, the quantum chemical calculation has been used to confirm the conformation of 1. Moreover, all isolated compounds were assessed for their in vitro cytotoxicity against five human cancer cell lines.


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Calophyllum/chemistry , Chromans/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Chromans/pharmacology , Humans , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Roots/chemistry , Thailand , Xanthones/chemistry , Xanthones/isolation & purification
2.
Nat Prod Commun ; 11(6): 709-10, 2016 Jun.
Article in English | MEDLINE | ID: mdl-27534097

ABSTRACT

Strychnuxin (1), a new non-glucosidic iridoid, together with four known compounds, IX (2), loganetin (3), loganin (4) and sweroside (5), were isolated from the roots of Strychnos nux-blanda. The structures of all isolated compounds (1-5) were elucidated through their physical properties and by the use of spectroscopic methods, as well as comparisons with the previous literature. To the best of our knowledge, this is the first isolation of compounds 1-5 from this plant. All isolated compounds were evaluated for their in vitro cytotoxicity against five human cancer cell lines.


Subject(s)
Drugs, Chinese Herbal/chemistry , Iridoids/chemistry , Strychnos/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Humans , Iridoids/isolation & purification , Iridoids/pharmacology , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Roots/chemistry
3.
Fitoterapia ; 111: 73-7, 2016 Jun.
Article in English | MEDLINE | ID: mdl-27102610

ABSTRACT

Two new depsidones, schomburgdepsidones A and B (1 and 2), and one new xanthone, schomburgxanthone A (3), together with eight known compounds (4-11) were isolated from the roots of Garcinia schomburgkiana. Their chemical structures were established on the basis of spectroscopic analysis. The in vitro cytotoxicity of all 11 compounds was evaluated against the KB, HeLa S-3, HT-29, MCF-7 and Hep G2 human cancer cell lines. Compound 7 performed a good cytotoxicity against the KB, Hela S-3 and MCF-7 cell lines with IC50 values in the range of 3.17-6.07µM. Compound 3 exhibited a good cytotoxicity against the KB cell line only, with an IC50 value of 8.14µM.


Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Depsides/chemistry , Garcinia/chemistry , Lactones/chemistry , Xanthones/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Depsides/isolation & purification , Humans , Inhibitory Concentration 50 , Lactones/isolation & purification , Molecular Structure , Plant Extracts/chemistry , Plant Roots/chemistry , Xanthones/isolation & purification
4.
Nat Prod Commun ; 11(9): 1287-1288, 2016 Sep.
Article in English | MEDLINE | ID: mdl-30807024

ABSTRACT

The chemical investigation of the crude ethyl acetate extract from Pterocarpus indicus stems led to isolation of a new coumarin, indicusane (1), together with eleven known compounds (2-12). To the best of our knowledge, all isolated coumarins (1-12) are reported for the first time from this plant. Their structures were identified on the basic of spectroscopic data (NMR, MS and ECD) as well as a chemical reaction (Mosher's method). In addition, all isolates were also evaluated for their cholinesterase (ChEs) inhibitory activities, in which only compound 4 exhibited the moderate activity toward AChE and BChE.


Subject(s)
Coumarins/pharmacology , Plant Extracts/chemistry , Plant Stems/chemistry , Pterocarpus/chemistry , Cholinesterase Inhibitors/isolation & purification , Cholinesterase Inhibitors/pharmacology , Coumarins/isolation & purification , Molecular Structure , Thailand
5.
Nat Prod Commun ; 10(4): 633-6, 2015 Apr.
Article in English | MEDLINE | ID: mdl-25973496

ABSTRACT

Chemical investigation of the CH2Cl2 and MeOH crude extracts of the roots of Melodorum fruticosum Lour. led to the isolation of 15 known compounds, of which 5, 10, and 12-15 are reported for the first time from this plant. In addition, melodorinol (7) was derivatized to afford six new (7a-7d and 7f-7g) analogues and one known compound (7e). Their structures were identified on the basic of spectroscopic data Most of them were evaluated for their cytotoxicity against KB, HeLa, MCF-7 and HepG-2 cell lines. Compounds 4 and 7b were the most potent to all cell lines.


Subject(s)
Alkenes/chemistry , Annonaceae/chemistry , Plant Roots/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Humans , Molecular Structure
6.
Nat Prod Commun ; 9(9): 1253-4, 2014 Sep.
Article in English | MEDLINE | ID: mdl-25918785

ABSTRACT

Trichostemonoate (1), a new tirucallane, together with four known compounds, 11α,20-dihydroxydammar-24-ene-3-one (2), sapelin E acetate (3), grandifolinolenenone (4) and α-mangostin (5), were isolated from the stem bark of Walsura trichostemon. The structural assignment of the new compound was based on spectroscopic methods. All isolated compounds were evaluated for their cytotoxicity against five cancer cell lines.


Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Meliaceae/chemistry , Plant Bark/chemistry , Plant Extracts/chemistry , Triterpenes/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Humans , Molecular Structure , Plant Extracts/pharmacology , Triterpenes/pharmacology
7.
Nat Prod Commun ; 9(9): 1323-6, 2014 Sep.
Article in English | MEDLINE | ID: mdl-25918803

ABSTRACT

From the chemical investigation of the methanolic extract of the roots of the Thai dipterocarp, Dipterocarpus tuberculatus, two new oligostilbene glycosides, dipterostilbenes A (1) and B (2), were isolated together with four known stilbenes. Their structures and relative configurations were determined on the basis of spectroscopic data. From an evaluation of cytotoxic activity against KB and HeLa cell lines, α-viniferin (5) and (-)-hopeaphenol (6) showed potent activity, but less than that of doxorubicin.


Subject(s)
Glycosides/chemistry , Magnoliopsida/chemistry , Plant Extracts/chemistry , Stilbenes/chemistry , Cell Line , Cell Proliferation/drug effects , Glycosides/pharmacology , Humans , Molecular Structure , Plant Extracts/pharmacology , Stilbenes/pharmacology
8.
J Nat Med ; 68(2): 436-41, 2014 Apr.
Article in English | MEDLINE | ID: mdl-24293387

ABSTRACT

Three new apotirucallanes (1-3) were isolated from the leaves of Walsura trichostemon. Their structures were identified by interpretation of their spectroscopic data as well as comparison with those reported in the literature. In addition, all isolated compounds were evaluated for their cytotoxicity against KB and HeLa cells.


Subject(s)
Antineoplastic Agents/chemistry , Meliaceae/chemistry , Triterpenes/chemistry , Antineoplastic Agents/toxicity , Cell Line, Tumor , HeLa Cells , Humans , Plant Leaves/chemistry , Triterpenes/toxicity
9.
Fitoterapia ; 92: 270-3, 2014 Jan.
Article in English | MEDLINE | ID: mdl-24333260

ABSTRACT

Three new furoquinoline alkaloids, leptanoines A-C (1-3) along with three known compounds (4-6) were isolated from the leaves of Evodia lepta. Their structures were identified by interpretation of their spectroscopic data as well as comparison with those reported in the literature. In addition, all isolated compounds were evaluated for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities. Compound 4 showed the highest inhibitory activity towards BChE with an IC50 value of 47.9 µM. On the other hand, Compound 5 showed the highest inhibitory activity towards AChE with an IC50 value of 69.1 µM.


Subject(s)
Cholinesterase Inhibitors/isolation & purification , Evodia/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Acetylcholinesterase/metabolism , Butyrylcholinesterase/metabolism , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Inhibitory Concentration 50 , Molecular Structure
10.
Nat Prod Commun ; 8(10): 1371-2, 2013 Oct.
Article in English | MEDLINE | ID: mdl-24354177

ABSTRACT

A new 3beta-O-vanilloyl-taraxerol, microcisin (1) and eight known compounds, 3beta-taraxerol acetate (2), 3beta-taraxerol (3), cholest-4-en-3-one (4), cholest-4-en-6beta-ol-3-one (5), beta-sitosterol (6), 7-hydroxycadalene (7), mellein (8) and vanillin (9), were isolated from the roots of Microcos tomentosa. The structures were determined by extensive analysis of their spectroscopic data. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cells.


Subject(s)
Oleanolic Acid/analogs & derivatives , Tiliaceae/chemistry , Drug Screening Assays, Antitumor , HeLa Cells , Humans , KB Cells , Oleanolic Acid/chemistry , Oleanolic Acid/isolation & purification , Plant Roots/chemistry , Plants, Medicinal/chemistry
11.
Fitoterapia ; 82(3): 489-92, 2011 Apr.
Article in English | MEDLINE | ID: mdl-21238549

ABSTRACT

A new resveratrol dimer, roxburghiol A (1) together with eleven known compounds were isolated from the roots of Shorea roxburghii. Their structures were identified on the basis of spectroscopic evidence and physicochemical properties. All isolated compounds were evaluated for their cytotoxicity (KB and HeLa cells). Compounds 8 and 9 showed potent cytotoxicity against both KB and HeLa cell lines with IC(50) values of 6.5, 8.5 and 8.7, 10.1 µg/mL, respectively.


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Dipterocarpaceae/chemistry , Neoplasms/drug therapy , Phytotherapy , Plant Extracts/chemistry , Stilbenes/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/therapeutic use , HeLa Cells , Humans , Inhibitory Concentration 50 , KB Cells , Molecular Structure , Plant Extracts/pharmacology , Plant Extracts/therapeutic use , Plant Roots , Stilbenes/chemistry , Stilbenes/pharmacology , Stilbenes/therapeutic use
12.
Fitoterapia ; 82(3): 422-5, 2011 Apr.
Article in English | MEDLINE | ID: mdl-21130146

ABSTRACT

A new dimeric aporphine, artabotrysine along with five known compounds was isolated from the roots of Artabotrys spinosus. Their structures were fully established on the basis of spectral evidence. All isolated compounds were evaluated for their cytotoxicity on HeLa and KB cells.


Subject(s)
Annonaceae/chemistry , Aporphines/isolation & purification , Plant Extracts/chemistry , Aporphines/chemistry , Aporphines/pharmacology , HeLa Cells , Humans , KB Cells , Molecular Structure , Plant Extracts/pharmacology , Plant Roots
13.
Fitoterapia ; 81(7): 894-6, 2010 Oct.
Article in English | MEDLINE | ID: mdl-20554005

ABSTRACT

A new 1-azaanthraquinone, named laoticuzanone A (1), and a synthetically known 3-methyl-1H-1-azaanthracene-2,9,10-trione (2), together with four known compounds, Griffithazanone A (3), methyl sinapate (4), methyl p-coumarate (5), and p-hydroxyphenylethyl p-coumarate (6) were isolated from the stems of Goniothalamus laoticus. Their structures were established on the basis of spectroscopic data as well as comparisons with the previous literature data. Compound 1 showed the highest cytotoxicity against KB and HeLa cells with IC(50) values of 0.68 and 0.50 µg/ml, respectively.


Subject(s)
Anthraquinones/therapeutic use , Antineoplastic Agents, Phytogenic/therapeutic use , Carcinoma, Squamous Cell/drug therapy , Goniothalamus/chemistry , Mouth Neoplasms/drug therapy , Plant Extracts/therapeutic use , Uterine Cervical Neoplasms/drug therapy , Anthraquinones/chemistry , Anthraquinones/isolation & purification , Anthraquinones/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Female , HeLa Cells , Humans , Inhibitory Concentration 50 , KB Cells , Molecular Structure , Phytotherapy , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Stems
14.
Fitoterapia ; 81(7): 830-3, 2010 Oct.
Article in English | MEDLINE | ID: mdl-20472039

ABSTRACT

A pair of new isomeric indole alkaloids, naucleaorals A (1) and B (2) were isolated from the roots of Nauclea orientalis. The structures of compounds 1 and 2 were fully characterized using spectroscopic data, and were tested for their cytotoxicity (HeLa and KB cells) and antimalarial activity. Compound 1 showed significant cytotoxicity to HeLa cells with an IC(50) value of 4.0 µg/mL, while compound 2 exhibited very modest cytotoxicity to both cell lines with IC(50) values of 7.8 and 9.5 µg/mL, respectively. Both compounds proved to be inactive in antimalarial assays (IC(50)>10.00 µg/mL).


Subject(s)
Antineoplastic Agents, Phytogenic/therapeutic use , Carcinoma, Squamous Cell/drug therapy , Indole Alkaloids/therapeutic use , Phytotherapy , Plant Extracts/therapeutic use , Rubiaceae/chemistry , Uterine Cervical Neoplasms/drug therapy , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Female , HeLa Cells , Humans , Indole Alkaloids/chemistry , Indole Alkaloids/isolation & purification , Indole Alkaloids/pharmacology , KB Cells , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Roots
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