Nguyen Manh Cuong

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Department of Bioactive Products
Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology



Phytochemistry (isolation and structural elucidation of natural compounds), semisynthesis of natural compounds, pharmaceutical and medicinal chemistry


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Scopus Publications

  • Design, synthesis, structure, in vitro cytotoxic activity evaluation and docking studies on target enzyme GSK-3β of new indirubin-3ʹ-oxime derivatives
    Nguyen Trong Dan, Hoang Duc Quang, Vuong Van Truong, Do Huu Nghi, Nguyen Manh Cuong, To Dao Cuong, Tran Quoc Toan, Long Giang Bach, Nguyen Huu Thuan Anh, Nguyen Thi Mai, Ngo Thi Lan, Luu Van Chinh, and Pham Minh Quan

    Scientific Reports, eISSN: 20452322, Published: 1 December 2020 Springer Science and Business Media LLC
    The addition of chalcone and amine components into indirubin-3′-oxime resulted in 15 new derivatives with high yields. Structures of new derivatives were also elucidated through 1D, 2D-NMR and HR-MS(ESI) spectra and X-ray crystallography. All designed compounds were screened for cytotoxic activity against four human cancer cell lines (HepG2, LU-1, SW480 and HL-60) and one human normal kidney cell line (HEK-293). Compound 6f exhibited the most marked cytotoxicity meanwhile cytotoxicity of compounds 6e , 6h and 6l was more profound toward cancer cell lines than toward normal cell. These new derivatives were further analyzed via molecular docking studies on GSK-3β enzyme. Docking analysis shows that most of the derivatives exhibited potential inhibition activity against GSK-3β with characteristic interacting residues in the binding site. The fast pulling of ligand scheme was then employed to refine the binding affinity and mechanism between ligands and GSK-3β enzyme. The computational results are expected to contribute to predicting enzyme target of the trial inhibitors and their possible interaction, from which the design of new cytotoxic agents could be created in the future.

  • Vasorelaxing Activity of R -(-)-3′-Hydroxy-2,4,5-trimethoxydalbergiquinol from Dalbergia tonkinensis: Involvement of Smooth Muscle Ca <inf>V</inf> 12 Channels
    Nguyen Manh Cuong, Ninh The Son, Ngu Truong Nhan, Pham Ngoc Khanh, Tran Thu Huong, Nguyen Thi Thu Tram, Giampietro Sgaragli, Amer Ahmed, Alfonso Trezza, Ottavia Spiga, and Fabio Fusi

    Planta Medica, ISSN: 00320943, eISSN: 14390221, Pages: 284-293, Published: 1 March 2020 Georg Thieme Verlag KG
    Abstract Dalbergia species heartwood, widely used in traditional medicine to treat various cardiovascular diseases, might represent a rich source of vasoactive agents. In Vietnam, Dalbergia tonkinensis is an endemic tree. Therefore, the aim of the present work was to investigate the vascular activity of R-(−)-3′-hydroxy-2,4,5-trimethoxydalbergiquinol isolated from the heartwood of D. tonkinensis and to provide circular dichroism features of its R absolute configuration. The vascular effects of R-(−)-3′-hydroxy-2,4,5-trimethoxydalbergiquinol were assessed on the in vitro mechanical activity of rat aorta rings, under isometric conditions, and on whole-cell Ba2+ currents through CaV1.2 channels (IBa1.2) recorded in single, rat tail main artery myocytes by means of the patch-clamp technique. R-(−)-3′-Hydroxy-2,4,5-trimethoxydalbergiquinol showed concentration-dependent, vasorelaxant activity on both endothelium-deprived and endothelium intact rings precontracted with the α 1 receptor agonist phenylephrine. Neither the NO (nitric oxide) synthase inhibitor Nω-nitro-L-arginine methyl ester nor the cyclooxygenase inhibitor indomethacin affected its spasmolytic activity. R-(−)-3′-Hydroxy-2,4,5-trimethoxydalbergiquinol-induced vasorelaxation was antagonized by (S)-(−)-Bay K 8644 and unaffected by tetraethylammonium plus glibenclamide. In patch-clamp experiments, R-(−)-3′-hydroxy-2,4,5-trimethoxydalbergiquinol inhibited IBa1.2 in a concentration-dependent manner and significantly decreased the time constant of current inactivation. R-(−)-3′-Hydroxy-2,4,5-trimethoxydalbergiquinol likely stabilized the channel in its closed state, as suggested by molecular modelling and docking simulation to the CaV1.2 channel α 1c subunit. In conclusion, D. tonkinensis species may represent a source of agents potentially useful for the development of novel antihypertensive drugs.

  • Serine protease inhibitors and activators from Dalbergia tonkinensis species
    Ninh The Son, Midori Suenaga, Yoiichi Matsunaga, Luu Van Chinh, Miwa Kubo, Kenichi Harada, Nguyen Manh Cuong, and Yoshiyasu Fukuyama

    Journal of Natural Medicines, ISSN: 13403443, eISSN: 18610293, Pages: 257-263, Published: 1 January 2020 Springer Science and Business Media LLC
    The vulnerable plant Dalbergia tonkinensis Prain is a rare species in Vietnam. In the course of our studies on biologically active plants, we performed serine protease enzyme screenings. The results suggest that at concentrations of 25–250 ng/mL, methanol extracts of leaf and root, root ethanol extract and its dichloromethane fraction, and heartwood water decoction extract can serve as useful sources to stimulate trypsin enzyme activity. In addition, water decoction extracts of leaf and stem bark may explain unknown ethno-pharmacology due to the high inhibitory effects in enzyme assays using trypsin, chymotrypsin, and elastase. Among 23 isolated compounds and two semi-synthetic derivatives tested, quercetin (17) inhibits the activities of trypsin and chymotrypsin with IC50 9.7 µM. Flavonoids categorized as flavanone, isoflavanone, flavone, isoflavone, pretocarpan, aurone, and neoflavanone demonstrated variable activities. Several substitutions are closely correlated with protease actions, including hydroxylation at C-3 and C-3′ in flavone and C-5 and C-3′ in isoflavone, hydroxylation at C-3, C-5 and C-3′, carboxylation at C-6 and C-8, and 7-substitution in flavanone; 7-substitution and methoxylation at C-3′ in isoflavanone; and lactone ring opening in neoflavanone. In the assessment of casein cleavage, at a dose of 25 ng/mL, leaf water decoction extract demonstrates an inhibitory effect on casein cleavage by trypsin, whereas ethanol and methanol extracts of the root caused activation.

  • Soluble epoxide hydrolase inhibitors from Docynia indica (Wall.) Decne.
    Le Xuan Duy, Vinh Le Ba, Dan Gao, Vu Dinh Hoang, Tran Quoc Toan, Seo Young Yang, Dao Duy Quang, Young Ho Kim, and Nguyen Manh Cuong

    Natural Product Research, ISSN: 14786419, eISSN: 14786427, Published: 2020 Informa UK Limited
    Nine bioactive compounds, including one new dihydroisocoumarin glycoside, 3S-thunberginol C 6-O-β-D-glucopyranoside (1a/1b), were isolated by chromatographic separation from the fruits of the Vietnamese medicinal plant Docynia indica (Wall.) Decne. 3S-thunberginol C 6-O-β-D-glucopyranoside was determined as a mixture of boat-like conformers based on NMR evidence and density functional theory (DFT) calculations. The in vitro inhibition of soluble epoxide hydrolase (sEH) by the isolated compounds was comparable to that of AUDA (positive control), yielding IC50 values ranging from 10.0 ± 0.6 to 88.4 ± 0.2 µM. Among isolated compounds, 3-methoxy-4-hydroxy-benzoic acid (7) and 2',6'-dihydroxy 3',4'-dimethoxychalcone (9) were identified as a potent inhibitor of sEH, with IC50 values of 19.3 ± 2.2 and 10.0 ± 0.6 mM, respectively. These results suggest that the fruits of D. indica may be useful as daily supplements for the prevention of cardiovascular and other sEH-related diseases.[Formula: see text].

  • Chemical Constituents of the Heartwood of Dalbergia tonkinensis
    Ninh The Son, Yoshiyasu Fukuyama, and Nguyen Manh Cuong

    Chemistry of Natural Compounds, ISSN: 00093130, eISSN: 15738388, Pages: 854-856, Published: 1 September 2019 Springer Science and Business Media LLC
    A new sesquiterpene, rel-(3R,6S,7S)-6α-hydroxycyclonerolidol (1), along with three known compounds, including neroplomacrol (2), naringin (3), and p-formylphenol (4), was isolated from the heartwood of Dalbergia tonkinensis. Their chemical structures were elucidated based on spectroscopic analysis.

  • Chemical constituents of the Vietnamese plants Dalbergia tonkinensis Prain and Cratoxylum formosum (Jack) Dyer in Hook and their DPPH radical scavenging activities
    Ninh The Son, Mari Kamiji, Tran Thu Huong, Miwa Kubo, Nguyen Manh Cuong, and Yoshiyasu Fukuyama

    Medicinal Chemistry Research, ISSN: 10542523, eISSN: 15548120, Pages: 1441-1447, Published: 1 September 2019 Springer Science and Business Media LLC
    Phytochemical investigations of the leaves and roots of Dalbergia tonkinensis led to the isolation of a new isoflavone glycoside derivative, isocaviunin 7-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (1), and a new scalemic sesquiterpene lactone, 3,7-dimethyl-3-vinylhexahydro-6,7-bifuran-3(2H)-one (2), along with the previously known compounds 3-16, and nine other known compounds 17-25 were isolated from the leaves of Cratoxylum formosum. The chemical structures of the isolated compounds were elucidated by 1D- and 2D-NMR analyses as well as MS spectroscopic data. The results suggest that flavonoids are characteristic of both plants. In the DPPH radical scavenging assay, (3 R)-vestitol (5) and isoquercetin (24) possessed the strongest antioxidative IC50 values of 42.20 µg/mL and 45.63 µg/mL, respectively, and their values were comparable to that of the positive control catechin (IC50 42.98 µg/mL).

  • Identification of soluble epoxide hydrolase inhibitors from the seeds of passiflora edulis cultivated in Vietnam
    To Dao Cuong, Hoang Thi Ngoc Anh, Tran Thu Huong, Pham Ngoc Khanh, Vu Thi Ha, Tran Manh Hung, Young Ho Kim, and Nguyen Manh Cuong

    Natural Product Sciences, ISSN: 12263907, eISSN: 22889027, Pages: 348-353, Published: 2019 The Korean Society of Pharmacognosy (KAMJE)
    − Soluble epoxide hydrolases (sEH) are enzymes present in all living organisms, metabolize epoxy fatty acids to 1,2-diols. sEH in the metabolism of polyunsaturated fatty acids plays a key role in inflammation. In addition, the endogenous lipid mediators in cardiovascular disease are also broken down to diols by the action of sEH that enhanced cardiovascular protection. In this study, sEH inhibitory guided fractionation led to the isolation of five phenolic compounds trans-resveratrol (1), trans-piceatannol (2), sulfuretin (3), (+)-balanophonin (4), and cassigarol E (5) from the ethanol extract of the seeds of Passiflora edulis Sims cultivated in Vietnam. The chemical structures of isolated compounds were determined by the interpretation of NMR spectral data, mass spectra, and comparison with data from the literature. The soluble epoxide hydrolase (sEH) inhibitory activity of isolated compounds was evaluated. Among them, trans-piceatannol (2) showed the most potent inhibitory activity on sEH with an IC50 value of 3.4 μM. This study marks the first time that sulfuretin (3) was isolated from Passiflora edulis as well as (+)-balanophonin (4), and cassigarol E (5) were isolated from Passiflora genus.

  • New Constituents from the Roots and Stems of Paramignya trimera
    Tran Thu Huong, Vu Thi Ha, To Dao Cuong, Ninh The Son, Tran Quoc Toan, Hoang Thi Ngoc Anh, Nguyen Thi Thu Tram, Sun Hee Woo, Young Ho Kim, and Nguyen Manh Cuong

    Natural Product Communications, ISSN: 1934578X, eISSN: 15559475, Pages: 1-5, Published: 2019 SAGE Publications
    Paramignya trimera (Oliv.) Guill. (Rutaceae), mostly distributed in the southern regions of Vietnam, has been used as a medicinal plant for treatment of liver diseases and cancer. From the methanol extract of the roots and stems of P. trimera, 3 new compounds (1-3) were isolated, including ninhvanin B (1), paramitrimerol (2), and parabacunoic acid (3), and a known alkaloid, citrusinine-I (4). The structures of these compounds were elucidated by electrospray ionization mass spectrometry and nuclear magnetic resonance spectral analysis, as well as by comparison with literature data.

  • In silico screening of anthraquinones from Prismatomeris memecyloides as novel phosphodiesterase type-5 inhibitors (PDE-5Is)
    Pham Ngoc Khanh, Tran Thu Huong, Ottavia Spiga, Alfonso Trezza, Ninh The Son, To Dao Cuong, Vu Thi Ha, and Nguyen Manh Cuong

    Revista Internacional de Andrologia, ISSN: 1698031X, eISSN: 16980409, Pages: 147-158, Published: October - December 2018 Elsevier BV
    OBJECTIVE Prismatomeris memecyloides Craib (Rubiaceae) is a medicinal plant traditionally used by ethnic minorities in Vietnam for the treatment of erectile dysfunction (ED). The aim of this study was to investigate the chemical compositions and screen in silico its possible inhibitory effect against PDE-5 which reduced cyclic guanosine-3',5'-monophosphate (cGMP) levels and indirectly caused the male ED. METHODS Separation of natural compounds were carried out on chromatographic column with silica gel or reversed phase materials, eluting with different solvent gradients. The structures of all isolated compounds were elucidated on the basis of spectroscopic data (HR-MS, 1D/2D-NMR). Docking simulation study of compound (1-7) was performed by using flexible side chains protocol based on Iterated Local Search Global Optimizer Algorithm of AutoDock/Vina v.1.1.2. Pharmacokinetic parameters and toxicity prediction were also calculated by appropriate softwares. RESULTS From the methanol extract of roots of P. memecyloides collected in Vietnam, seven compounds including four anthraquinone/one anthraquinone glycoside namely damnacanthal (1), lucidin-ω-methyl ether (2), 3-methylalizarin (3), rubiadin-3-methyl ether (4), and 1-O-methylrubiadin 3-O-primeveroside (5) along with two iridoid glucosides, asperulosidic acid (6) and aitchisonide A (7) were isolated. The molecular modeling results showed that 5 anthraquinone compounds possess the lowest binding energies to PDE-5. The anthraquinone glucoside 1-O-methylrubiadin 3-O-primeveroside (5) potentially inhibited PDE-5 similarly to commercial PDE-5Is sildenafil (SLD) and tadalafil (TLD). Calculated pharmacokinetic results like pIC50,pred; miLogP, TPSA, enzyme inhibitory of anthraquinone glucoside (5) were similar and even higher to those of the commercial PDE-5 inhibitors. Especially the predictive toxicity of 1-O-methylrubiadin 3-O-primeveroside (5) was even lower than those of SLD and TLD. CONCLUSION This is the first study to find a scientific-based evidence for the ethnic use of P. memecyloides as medicinal plant for the treatment of ED. The result indicates that the anthraquinones (damnacanthal (1), lucidin-ω-methyl ether (2), 3-methylalizarin (3) and rubiadin-3-methyl ether (4)), especially anthraquinone glycoside (1-O-methylrubiadin 3-O-primeveroside (5)) are compounds of potential novel drug class for the ED treatment.

  • Antimicrobial activity of the constituents of dalbergia tonkinensis and structural-bioactive highlights
    Ninh The Son, Masataka Oda, Naoki Hayashi, Daiki Yamaguchi, Yu Kawagishi, Fumi Takahashi, Kenichi Harada, Nguyen Manh Cuong, and Yoshiyasu Fukuyama

    Natural Product Communications, ISSN: 1934578X, eISSN: 15559475, Pages: 157-161, Published: February 2018 SAGE Publications
    The vulnerable plant Dalbergia tonkinensis Prain, is a rare species, native to Vietnam. Phytochemical investigations and biological evaluations of this species are quite limited. Antimicrobial screening has suggested that, at the low dose of 1.0 mg/mL, the methanol extracts of the leaf, stem bark, and root, as well as chloroform fraction of heartwood can serve as useful sources against seven gram-positive skin microbacteria, Bacillus cereus (ATCC27522), Escherichia coli (JM109), Staphylococcus aureus (ATCC25923), Staphylococcus epidermidis (ATCC14990), Streptococcus pneumonia (ATCC49619), Streptococcus pyogenes (ATCC12344), and Vibrio parahaemolyticus (RIMD2210010), and four oral gram-positive microbacteria Streptococcus mutans (ATCC 25175), Streptococcus mitis (ATCC903), Streptococcus sobrinus (ATCC 33478), and Porphyromonas gingivalis (ATCC33277), with an inhibitory percentage of 60-80% growth for several strains Bacillus cereus, Escherichia coli, and Streptococcus pneumonia. We further assessed antimicrobial activities of the enriched diverse flavonoids from chloroform fraction of its heartwood. Extensive structural activity relationship studies showed structure function closely related to the antimicrobial activity, in which methoxylation at C-2’, and 4’ in isoflavanones, hydroxylation at C-3’ in flavones, substitution at C-5 in isoflavones, and lactone opened ring in neoflavonoids were found to increase the effective inhibitions. In the second antimicrobial assessment, the isolated flavonoid liquiritigenin showed the MIC values of 50, and 100 μg/mL against the microbacterial strains Staphylococcus aureus subsp. aureus (ATCC 11632), and Aspergillus niger (439), respectively, whereas the MIC value of 100 μg/mL was assignable to biochanin A against microbacterium Staphylococcus aureus subsp. aureus.

  • New records of potent in-vitro antidiabetic properties of dalbergia tonkinensis heartwood and the bioactivity-guided isolation of active compounds
    Van Nguyen, San-Lang Wang, Ngu Nhan, Thi Nguyen, Nguyen Nguyen, Do Nghi, and Nguyen Cuong

    Molecules, eISSN: 14203049, Published: 2018 MDPI AG
    Alpha-glucosidase inhibitory activity has been commonly used for the evaluation of antidiabetic property in vitro. The aim of this study is to investigate and characterize Dalbergia tonkinensis as a potential source of antidiabetic compounds. The screening of the active parts used, such as trunk bark, heartwood, and the leaves of Dalbergia tonkinensis indicated that all these extracted parts used with methanol demonstrated potent α-glucosidase inhibitory activity. The in vitro antidiabetic property of Dalbergia tonkinensis was notably recorded for the first time and showed activity (EC50 = 0.17–0.78 mg/mL) comparable to those of reported potent herbal extracts (EC50 = 0.25–4.0 mg/mL) and higher activity than that of acarbose, a commercial antidiabetic drug (EC50 = 1.21 mg/mL). The stability tests revealed that the heartwood of Dalbergia tonkinensis extract (HDT) possesses high pH stability with relative activity in the range of 80–98%. Further bioassay-guided purification led to the isolation of 2 active compounds identified as sativanone and formononetin from the ethyl acetate fraction and water fraction of HDT, respectively. These α-glucosidase inhibitors (aGIs) show promising inhibition against various types of α-glucosidases. Remarkably, these inhibitors were determined as new mammalian aGIs, showing good effect on rat α-glucosidase. The results suggest that Dalbergia tonkinensis is a potent source of aGIs and suggest promise in being developed as functional food with antidiabetic efficacy. The results of this study also enrich our knowledge concerning current biological activity and constituents of Dalbergia tonkinensis species.

  • Daltonkins A and B, Two New Carboxyethylflavanones from the Heartwood of Dalbergia tonkinensis
    Nguyen Manh Cuong, Ngu Truong Nhan, Ninh The Son, Do Huu Nghi, and To Dao Cuong

    Bulletin of the Korean Chemical Society, ISSN: 02532964, eISSN: 12295949, Pages: 1511-1514, Published: December 2017 Wiley

  • Two new carboxyethylflavanones from the heartwood of Dalbergia tonkinensis and their antimicrobial activities
    Ninh The Son, Kenichi Harada, Nguyen Manh Cuong, and Yoshiyasu Fukuyama

    Natural Product Communications, ISSN: 1934578X, eISSN: 15559475, Pages: 1721-1723, Published: November 2017 SAGE Publications
    Two new carboxyethylflavanone derivatives, (2 S)-8-carboxyethylnarigenin (2) and (2 S)-6,8-dicarboxyethylpinocembrin (3) were isolated from the heartwood of Dalbergia tonkinensis Prain, along with four known compounds 1, and 4-6. The chemical structures of two new compounds 2 and 3 were elucidated based on analyses of the spectroscopic data, including 1D and 2D NMR, HR-ESI-MS, IR, UV, and CD spectroscopies. By carrying out antimicrobial assay, CH3OH and CHCl3 fractions exhibited weak MIC value at 200 μg/mL against filamentous fungus A. niger (439), whereas the known flavanone 1 and the new carboxyethylflavanone 2 had MIC at 100 μg/mL.

  • Synthesis and in vitro cytotoxic evaluation of novel murrayafoline a derived β-amino alcohols
    Luu Van Chinh, Le Duc Anh, Nguyen Thi Nga, Nguyen Thi Ha Ly, Vu Thi Ha, Tran Quoc Toan, Nguyen Manh Cuong, and Tran Khac Vu

    Letters in Organic Chemistry, ISSN: 15701786, Pages: 603-611, Published: 1 October 2017 Bentham Science Publishers Ltd.

  • The hepatoprotective activity of a new derivative kaempferol glycoside from the leaves of Vietnamese Phyllanthus acidus (L.) Skeels
    Nguyen Cong Thuy Tram, Ninh The Son, Nguyen Thi Nga, Vu Thi Thu Phuong, Nguyen Thi Cuc, Do Thi Phuong, Gilles Truan, Nguyen Manh Cuong, and Do Thi Thao

    Medicinal Chemistry Research, ISSN: 10542523, eISSN: 15548120, Pages: 2057-2064, Published: 1 September 2017 Springer Science and Business Media LLC
    A new derivative kaempferol glycoside, kaempferol-3-O-(2-α-l-rhamnopyranosyl)-β-d-glucuronopyranosyl methyl ester (3), together with six other known kaempferol glycosides, kaempferol-3-O-[α-l-rhamnopyranosyl (1→2)]-β-d-galactopyranoside (1), kaempferol-3-O-(2-α-l-rhamnopyranosyl)-β-d-glucuronopyranoside (2), rutin (4), isoquercitrin (5), quercitrin (6), and myricitrin (7) were isolated from the leaves of Phyllanthus acidus (L.) Skeels (Phyllanthaceae). Here, is the first report described the isolation of compound (1) and (2) from the genus Phyllanthus. Compound (1) presents antioxidant activity in 2,2-diphenyl-1-picryl-hydrazyl-hydrate assay. Compound (2) and (3) performed no antioxidant activity in 2,2-diphenyl-1-picryl-hydrazyl-hydrate and thiobarbituric acid reactive substances assays (IC50 > 100 µM). However, compound (2) showed anti-inflammation activity through inhibiting interleukin 6 and tumor necrosis factor alpha production (P < 0.05). Compound (3) also exhibited cytokine modulating activities such as inhibiting tumor necrosis factor alpha, activating interleukin 10 at concentration of 10 µM (P < 0.05). The interleukin 6 cytokine level was also up or down-regulated by compound (3) at two time points; 24 and 48 h. This activeness of compound (3) might induce hepatoprotection in the acute-phase response by activating the signal transducer and activator of transcription 3(STAT3) through cytokine modulation. Together with other kaempferol glycosides, this new derivative compound may mediate the liver-protective activity of the Vietnamese medicinal plant Phyllanthus acidus.

  • Potent Inhibitor of Drug-Resistant HIV-1 Strains Identified from the Medicinal Plant Justicia gendarussa
    Hong-Jie Zhang, Emily Rumschlag-Booms, Yi-Fu Guan, Dong-Ying Wang, Kang-Lun Liu, Wan-Fei Li, Van H. Nguyen, Nguyen M. Cuong, Djaja D. Soejarto, Harry H. S. Fong, and Lijun Rong

    Journal of Natural Products, ISSN: 01633864, eISSN: 15206025, Pages: 1798-1807, Published: 23 June 2017 American Chemical Society (ACS)
    Justicia gendarussa, a medicinal plant collected in Vietnam, was identified as a potent anti-HIV-1 active lead from the evaluation of over 4500 plant extracts. Bioassay-guided separation of the extracts of the stems and roots of this plant led to the isolation of an anti-HIV arylnaphthalene lignan (ANL) glycoside, patentiflorin A (1). Evaluation of the compound against both the M- and T-tropic HIV-1 isolates showed it to possess a significantly higher inhibition effect than the clinically used anti-HIV drug AZT. Patentiflorin A and two congeners were synthesized, de novo, as an efficient strategy for resupply as well as for further structural modification of the anti-HIV ANL glycosides in the search for drug leads. Subsequently, it was determined that the presence of a quinovopyranosyloxy group in the structure is likely essential to retain the high degree of anti-HIV activity of this type of compounds. Patentiflorin A was further investigated against the HIV-1 gene expression of the R/U5 and U5/gag transcripts, and the data showed that the compound acts as a potential inhibitor of HIV-1 reverse transcription. Importantly, the compound displayed potent inhibitory activity against drug-resistant HIV-1 isolates of both the nucleotide analogue (AZT) and non-nucleotide analogue (nevaripine). Thus, the ANL glycosides have the potential to be developed as novel anti-HIV drugs.

  • Inhibitory effects of novel diarylheptanoids and other constituents of the rhizomes of Curcuma singularis on the catalytic activity of soluble epoxide hydrolase
    Nguyen Manh Cuong, Doan Thi Van, Ninh The Son, To Dao Cuong, Pham Ngoc Khanh, Nguyen Quoc Binh, Tran Thi Viet Thanh, Ji Sun Lee, Ah Reum Jo, and Young Ho Kim

    Bulletin of the Korean Chemical Society, eISSN: 12295949, Pages: 112-115, Published: 1 January 2017 Wiley

  • Inhibitory components from Glycosmis stenocarpa on pepper mild mottle virus
    Jang Hoon Kim, Ju-Yeon Yoon, Sun Jung Kwon, In Sook Cho, Nguyen Manh Cuong, Seung-Kook Choi, Young Ho Kim, and Gug Seoun Choi

    Journal of Microbiology and Biotechnology, ISSN: 10177825, eISSN: 17388872, Pages: 2138-2140, Published: December 2016 Korean Society for Microbiology and Biotechnology
    The goal of this study was to identify a source of natural plant compounds with inhibitory activity against pepper mild mottle virus (PMMoV). We showed, using a half-leaf assay, that murrayafoline-A (1) and isomahanine (2) isolated from the aerial parts of Glycosmis stenocarpa have inhibitory activity against PMMoV through curative, inactivation, and protection effects. Using a leaf-disk assay, we confirmed that 2 inhibited virus replication in Nicotiana benthamiana. Using electron microscopy, we found that a mixture of the virus with 2 resulted in damage to the rod-shaped virus.

  • Enhancement of contraction and L-type Ca <sup>2+</sup> current by murrayafoline-A via protein kinase C in rat ventricular myocytes
    Bojjibabu Chidipi, Min-Jeong Son, Joon-Chul Kim, Jeong Hyun Lee, Tran Quoc Toan, Nguyen Manh Cuong, Byung Ho Lee, and Sun-Hee Woo

    European Journal of Pharmacology, ISSN: 00142999, eISSN: 18790712, Volume: 784, Pages: 33-41, Published: 5 August 2016 Elsevier BV
    We previously reported that murrayafoline-A (1-methoxy-3-methyl-9H-carbazole, Mu-A) increases the contractility of ventricular myocytes, in part, via enhancing Ca(2+) influx through L-type Ca(2+) channels, and that it increases the Ca(2+) transients by activation of protein kinase C (PKC). In the present study, we further examined the cellular mechanisms for the enhancement of contractility and L-type Ca(2+) current (ICa,L) by Mu-A. Cell shortening and ICa,L were measured in rat ventricular myocytes using a video edge detection method and perforated patch-clamp technique, respectively. We found that the positive inotropic effect of Mu-A was not affected by pre-exposure to the β-adrenoceptor antagonist propranolol, the protein kinase A (PKA) inhibitors KT5720 or H-89, or the phospholipase C inhibitor U73122. Interestingly, the Mu-A-mediated increases in cell shortening and in the rate of contraction were completely suppressed by pre-treatment with the PKC inhibitor GF109203X. The stimulatory effect of Mu-A on ICa,L was not altered by inhibition of PKA (KT5720), G-protein coupled receptors (suramin), or α1-adrenoceptor (prazosin). However, pre-exposure to the PKC inhibitor, GF109203X or chelerythrine, abolished the Mu-A-induced increase in ICa,L. Pre-exposure to the Ca(2+)-calmodulin-dependent protein kinase II (CaMKII) inhibitor KN93 slightly reduced the stimulatory effects on contraction and ICa,L by Mu-A. Phosphorylation of PKC was enhanced by Mu-A in ventricular myocytes. These data suggest that Mu-A increases contraction and ICa,L via PKC in rat ventricular myocytes, and that the PKC-mediated responses in the presence of Mu-A may be partly mediated by CaMKII.

  • Inhibition of soluble epoxide hydrolase activity by compounds isolated from the aerial parts of Glycosmis stenocarpa
    Jang Hoon Kim, Abubaker M. A. Morgan, Bui Huu Tai, Doan Thi Van, Nguyen Manh Cuong, and Young Ho Kim

    Journal of Enzyme Inhibition and Medicinal Chemistry, ISSN: 14756366, eISSN: 14756374, Pages: 640-644, Published: 3 July 2016 Informa UK Limited
    Abstract The aim of this study is to search for soluble epoxide hydrolase (sEH) inhibitors from natural plants, bioassay-guided fractionation of lipophilic n-hexane and chloroform layers of an extract of the aerial parts of Glycosmis stenocarpa led to the isolation of 12 compounds (1–12) including murrayafoline-A (1), isomahanine (2), bisisomahanine (3), saropeptate (4), (24 S)-ergost-4-en-3,6-dione (5), stigmasta-4-en-3,6-dion (6), stigmast-4-en-3-one (7), β-sitosterol (8), 24-methylpollinastanol (9), trans-phytol (10), neosarmentol III (11) and (+)-epiloliolide (12). Their structures were elucidated on the basis of spectroscopic data. Among them, neosarmentol III (11) was isolated from nature for the first time. All the isolated compounds were evaluated for their inhibitory activity against sEH. Among isolated carbazole-type compounds, isomahanine (2) and bisisomahanine (3) were identified as a potent inhibitor of sEH, with IC50 values of 22.5 ± 1.7 and 7.7 ± 1.2 µM, respectively. Moreover, the inhibitory action of 2 and 3 represented mixed-type enzyme inhibition.

  • Alkylphloroglucinol derivatives and triterpenoids with soluble epoxide hydrolase inhibitory activity from Callistemon citrinus
    Pham Ngoc Khanh, Ho Viet Duc, Tran Thu Huong, Ninh The Son, Vu Thi Ha, Doan Thi Van, Bui Huu Tai, Ji Eun Kim, Ah Reum Jo, Young Ho Kim, and Nguyen Manh Cuong

    Fitoterapia, ISSN: 0367326X, eISSN: 18736971, Volume: 109, Pages: 39-44, Published: 1 March 2016 Elsevier BV
    Phytochemical analysis of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of two new alkylphloroglucinols, gallomyrtucommulone E and F (1 and 2), along with four other known alkylphloroglucinol derivatives, gallomyrtucommulone A (3), endoperoxide G3 (4), myrtucommulone B (5), callistenone B (6) and five known triterpenoids, including betulinic acid (7), 3β-acetylmorolic acid (8), 3β-hydroxy-urs-11-en-13(28)-olide (9), diospyrolide (10) and ursolic acid (11). The structures of the natural compounds were determined from the spectroscopic evidences including 1D-/2D-NMR and HR-MS spectrometry. All the isolated compounds were assessed for the effects on the sEH inhibitory activity. The acylphloroglucinols myrtucommulone B (5)/callistenone B (6) (in mixture), and two triterpenoids, ursolic acid (11) and 3β-hydroxy-urs-11-en-13(28)-olide (9) displayed strong inhibition of sEH activity, with IC50 values of 0.7, 11.2 and 24.8 μM, respectively.

  • Morinlongosides A-C, two new naphthalene glycoside and a new iridoid glycoside from the roots of Morinda longissima
    Nguyen Manh Cuong, Tran Thu Huong, Ninh The Son, To Dao Cuong, Doan Thi Van, Pham Ngoc Khanh, Vu Thi Ha, Nguyen Cong Thuy Tram, Pham Quoc Long, and Young Ho Kim

    Chemical and Pharmaceutical Bulletin, ISSN: 00092363, eISSN: 13475223, Pages: 1230-1234, Published: 2016 Pharmaceutical Society of Japan
    Two new naphthalene glycosides, morinlongosides A and B (1, 2) and a new iridoid glycoside, morinlongoside C (3), together with four known ones, geniposidic acid (4), (3R)-3-O-[β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl]-l-octen-3-ol (5), lucidin-3-O-β-primeveroside (6), and morindone-6-O-β-gentiobioside (7), were isolated from the roots of Morinda longissima Y. Z. RUAN. The structures of all isolated compounds (1-7) were elucidated on the basis of spectroscopic data (high resolution (HR)-MS, one and two dimensional (1/2D)-NMR).

  • Functional, electrophysiological and molecular docking analysis of the modulation of Ca<inf>v</inf>1.2 channels in rat vascular myocytes by murrayafoline A
    S Saponara, M Durante, O Spiga, P Mugnai, G Sgaragli, TT Huong, PN Khanh, NT Son, NM Cuong, and F Fusi

    British Journal of Pharmacology, ISSN: 00071188, eISSN: 14765381, Volume: 173, Pages: 292-304, Published: 1 January 2016 Wiley
    The carbazole alkaloid murrayafoline A (MuA) enhances contractility and the Ca2+ currents carried by the Cav1.2 channels [ICa1.2] of rat cardiomyocytes. As only few drugs stimulate ICa1.2, this study was designed to analyse the effects of MuA on vascular Cav1.2 channels.

  • Paratrimerins A and B, two new dimeric monoterpene-linked coumarin glycosides from the roots and stems of paramignya trimera
    Nguyen Manh Cuong, Tran Thu Huong, Pham Ngoc Khanh, Nguyen Van Tai, Vu Thi Ha, Ninh The Son, Bui Huu Tai, and Young Ho Kim

    Chemical and Pharmaceutical Bulletin, ISSN: 00092363, eISSN: 13475223, Pages: 945-949, Published: 1 November 2015 Pharmaceutical Society of Japan
    Two new dimeric monoterpene-linked coumarin glucosides, paratrimerins A (1) and B (2), and three known coumarins, 6-(6-hydroxy-3,7-dimethylocta-2,7-dienyl)-7-hydroxycoumarin (3), ostruthin (4), and ninhvanin (5), were isolated from the roots and stems of Paramignya trimera (OLIV.) GUILL. collected in Khanh Hoa province, Vietnam. Compound 1 comprises two 7-O-β-D-glucopyranoside coumarins linked at positions 6,6' via a 1,3,4,4-tetrasubstituted cyclohexene containing a monoterpene bridge, whereas compound 2 is a β-D-apiofuranosyl(1→6)-β-D-glucopyranosyl derivative of 1. The chemical structures of these compounds were determined by one dimensional (1D) and 2D-NMR and high resolution-electrospray ionization (HR-ESI)-MS spectroscopy.

  • Murrayafoline a induces a G<inf>0</inf>/G<inf>1</inf>-phase arrest in platelet-derived growth factor-stimulated vascular smooth muscle cells
    Joo-Hui Han, Yohan Kim, Sang-Hyuk Jung, Jung-Jin Lee, Hyun-Soo Park, Gyu-Yong Song, Nguyen Manh Cuong, Young Ho Kim, and Chang-Seon Myung

    Korean Journal of Physiology and Pharmacology, ISSN: 12264512, eISSN: 20933827, Pages: 421-426, Published: 1 September 2015 The Korean Physiological Society and The Korean Society of Pharmacology (KAMJE)
    The increased potential for vascular smooth muscle cell (VSMC) growth is a key abnormality in the development of atherosclerosis and post-angioplasty restenosis. Abnormally high activity of platelet-derived growth factor (PDGF) is believed to play a central role in the etiology of these pathophysiological situations. Here, we investigated the anti-proliferative effects and possible mechanism(s) of murrayafoline A, a carbazole alkaloid isolated from Glycosmis stenocarpa Guillamin (Rutaceae), on PDGF-BB-stimulated VSMCs. Murrayafoline A inhibited the PDGF-BB-stimulated proliferation of VSMCs in a concentration-dependent manner, as measured using a non-radioactive colorimetric WST-1 assay and direct cell counting. Furthermore, murrayafoline A suppressed the PDGF-BB-stimulated progression through G0/G1 to S phase of the cell cycle, as measured by [3H]-thymidine incorporation assay and cell cycle progression analysis. This anti-proliferative action of murrayafoline A, arresting cell cycle progression at G0/G1 phase in PDGF-BB-stimulated VSMCs, was mediated via down-regulation of the expression of cyclin D1, cyclin E, cyclin-dependent kinase (CDK)2, CDK4, and proliferating cell nuclear antigen (PCNA), and the phosphorylation of retinoblastoma protein (pRb). These results indicate that murrayafoline A may be useful in preventing the progression of vascular complications such as restenosis after percutaneous transluminal coronary angioplasty and atherosclerosis.


  • Optimization and purification of α-glucosidase inhibitor from Bacillus subtilis YT20
    TTD Tien Cuong Nguyen, Thanh Hoang Le, Van Hien Mai, Thi Yen Hoang, Thi ...
    Vietnam Journal of Science and Technology 59 (2), 179-188 2021

  • Optimization of Murrayafoline A ethanol extraction process from the roots of Glycosmis stenocarpa, and evaluation of its Tumorigenesis inhibition activity on Hep-G2 cells
    TNPDTNP Quoc Toan Tran, The Dan Pham, Thanh Duong Nguyen, Van Huyen Luu, Huu ...
    Open Chemistry 19 (1) 2021

  • Vasorelaxing Activity of R-(−)-3′-Hydroxy-2, 4, 5-trimethoxydalbergiquinol from Dalbergia tonkinensis: Involvement of Smooth Muscle CaV1. 2 Channels
    FF Nguyen Manh Cuong, Ninh The Son, Ngu Truong Nhan, Pham Ngoc Khanh, Tran ...
    Planta Medica 86 (04), 284-293 2020

  • Investigation of anti-Helicobacter pylori activity and chemical constituents of Ludwigia hyssopifolia aerial parts
    Nguyen Thi Thu Tram, Huynh Thi Thanh Thuy, Pham Thanh Trong, Phan Hoang Duy ...
    Vietnam Journal of Science and Technology 58 (6A), 35-40 2020

  • Antimicrobial, antioxidant and cytotoxic activity on human breast cancer cells of essential oil from Pinus sylvestris. var mongolica needle
    Javzmaa Namshir, Altantsetseg Shatar, Oyukhan Khandaa, Rentsenkhand ...
    Mong. J. Chem. 21 (47), 19-26 2020

  • Initial study on SARS-COV-2 main protease inhibition mechanism of some potential drugs using molecular docking simulation
    PQL Pham Minh Quan, Le Thi Thuy Huong, Tran Quoc Toan, Ngo Son Tung, Nguyen ...
    Vietnam Journal of Science and Technology 58 (6), 665-675 2020

  • Constituents of essential oils from the leaves and rhizomes of Ophiopogon fruticulosus Aver., N.Tanaka & K.S. Nguyen from Vietnam
    Pham Ngoc Khanh, Hoang Thi Ngoc Anh, Tran Thu Huong, Vu Thi Ha, DinhThi Thu ...
    American Journal of Essential Oils and Natural Products 8 (4), 19-23 2020

  • New method for preparing purity β-D-glucans (beta-Glucan) from baker’s yeast (Saccharomyces cerevisiae)
    Pham Ngoc Khanh, Nguyen Duy Nhut, Nguyen Manh Cuong
    Science & Technology Development Journal 23 (3), 673-678 2020

  • Ha thực vật v tc dụng dược l cc loi trong chi Trắc
    PTHT Ngũ Trường Nhn, Nguyễn Mạnh Cường, Đỗ Hữu Nghị, Nguyễn Thị Thảo ...
    Nh Xuất bản Đại học Sư phạm TP Hồ Ch Minh 2020

  • Design, synthesis, structure, in vitro cytotoxic activity evaluation and docking studies on target enzyme GSK‑3β of new indirubin‑3ʹ‑oxime derivatives
    NT Dan, HD Quang, VV Truong, DH Nghi, NM Cuong, TD Cuong, ...
    Scientific Reports 10 (11429) 2020

  • Soluble epoxide hydrolase inhibitors from Docynia indica (Wall.) Decne
    NMC Le Xuan Duy, Le Ba Vinh, Gao Dan, Vu Dinh Hoang, Tran Quoc Toan, Seo ...
    Natural Products Research 2020

  • Serine protease inhibitors and activators from Dalbergia tonkinensis species
    M Suenaga, Y Matsunaga, L Van Chinh, M Kubo, K Harada, NM Cuong, ...
    Journal of natural medicines 74 (1), 257-263 2020

    TD Cuong, DL Phuong, NVT Anh, PN Khanh, TT Huong, NM Cuong
    Vietnam Journal of Science and Technology 57 (5), 551-551 2019

  • Chemical Constituents of the Heartwood of Dalbergia tonkinensis
    Y Fukuyama, NM Cuong
    Chemistry of Natural Compounds 55 (5), 854-856 2019

  • Chemical constituents of the Vietnamese plants Dalbergia tonkinensis Prain and Cratoxylum formosum (Jack) Dyer in Hook and their DPPH radical scavenging activities
    M Kamiji, TT Huong, M Kubo, NM Cuong, Y Fukuyama
    Medicinal Chemistry Research 28 (9), 1441-1447 2019

  • Optimization of microwave-assisted extraction of total phenolic and total flavonoid contents from fruits of Docynia indica (Wall.) Decne. using response surface methodology
    XD Le, MC Nguyen, DH Vu, MQ Pham, QL Pham, QT Nguyen, TA Nguyen, ...
    Processes 7 (8), 485 2019

  • New Constituents From the Roots and Stems of Paramignya trimera
    TT Huong, VT Ha, TD Cuong, NT Son, TQ Toan, HTN Anh, NTT Tram, ...
    Natural Product Communications 14 (6), 1934578X19861015 2019

    PN Khanh, BH Tai, TT Huong, TD Cuong, YH Kim, NM Cuong
    Vietnam Journal of Science and Technology 57 (2), 139-139 2019

  • Tổng hợp v đnh gi hoạt tnh chống ung thư in vitro cc dẫn xuất mới indirubin
    Nguyễn Trọng Dn, Nguyễn Mạnh Cường, Lưu Văn Chnh
    Vietnam Journal of Chemistry 54 (4E3), 50-54 2019

  • Tổng hợp dẫn xuất mới indirubin với cc chalcone
    Nguyễn Trọng Dn, Nguyễn Mạnh Cường, Lưu Văn Chnh
    Tạp ch Ha học 57 (4E3), 55-60 2019


  • Antioxidative and anti-inflammatory effect of quercetin and its glycosides isolated from mampat (Cratoxylum formosum)
    SJ Choi, BH Tai, NM Cuong, YH Kim, HD Jang
    Food Science and biotechnology 21 (2), 587-595 2012
    Citations: 61

  • Oleanane-type triterpenoids from Panax stipuleanatus and their anticancer activities
    C Liang, Y Ding, NH Tung, JA Kim, HJ Boo, HK Kang, NM Cuong, YH Kim
    Bioorganic & Medicinal Chemistry Letters 20 (23), 7110-7115 2010
    Citations: 61

  • A new dimeric carbazole alkaloid from Glycosmis stenocarpa roots
    NM Cuong, TQ Hung, T Van Sung, WC Taylor
    Chemical and pharmaceutical bulletin 52 (10), 1175-1178 2004
    Citations: 51

  • Murrayafoline A attenuates the Wnt/β-catenin pathway by promoting the degradation of intracellular β-catenin proteins
    H Choi, J Gwak, M Cho, MJ Ryu, JH Lee, SK Kim, YH Kim, GW Lee, ...
    Biochemical and biophysical research communications 391 (1), 915-920 2010
    Citations: 40

  • Mechanism of osthole inhibition of vascular Cav1. 2 current
    F Fusi, G Sgaragli, LM Ha, NM Cuong, S Saponara
    European journal of pharmacology 680 (1-3), 22-27 2012
    Citations: 39

  • Total peroxynitrite scavenging capacity of phenylethanoid and flavonoid glycosides from the flowers of Buddleja officinalis
    BH Tai, BY Jung, NM Cuong, PT Linh, NH Tung, NX Nhiem, TT Huong, ...
    Biological and Pharmaceutical Bulletin 32 (12), 1952-1956 2009
    Citations: 39

  • A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity
    BTT Luyen, BH Tai, NP Thao, SY Yang, NM Cuong, YI Kwon, HD Jang, ...
    Bioorganic & medicinal chemistry letters 24 (17), 4120-4124 2014
    Citations: 29

  • New pyrano-pyrone from Goniothalamus tamirensis enhances the proliferation and differentiation of osteoblastic MC3T3-E1 cells
    BH Tai, VT Huyen, TT Huong, NX Nhiem, EM Choi, JA Kim, PQ Long, ...
    Chemical and Pharmaceutical Bulletin 58 (4), 521-525 2010
    Citations: 28

  • 1-O-Substituted derivatives of murrayafoline A and their antifungal properties
    NM Cuong, H Wilhelm, A Porzel, N Arnold, L Wessjohann
    Natural product research 22 (16), 1428-1432 2008
    Citations: 28

  • Antimicrobial Activity of the Constituents of Dalbergia tonkinensis and Structural-Bioactive Highlights
    YF Ninh The Son, Masataka Oda, Naoki Hayashi, Daiki Yamaguchi, Yu Kawagishi ...
    Natural Product Communications 13 (2), 157-161 2018
    Citations: 24

  • Paratrimerins A and B, two new dimeric monoterpene-linked coumarin glycosides from the roots and stems of Paramignya trimera
    NM Cuong, TT Huong, PN Khanh, N Van Tai, VT Ha, BH Tai, YH Kim
    Chemical and Pharmaceutical Bulletin 63 (11), 945-949 2015
    Citations: 24

  • Oleanane-triterpenoids from Panax stipuleanatus inhibit NF-κB
    C Liang, Y Ding, SB Song, JA Kim, NM Cuong, JY Ma, YH Kim
    Journal of ginseng research 37 (1), 74 2013
    Citations: 22

  • A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis
    BH Tai, NX Nhiem, TH Quang, NTT Ngan, NH Tung, Y Kim, JJ Lee, ...
    Bioorganic & medicinal chemistry letters 21 (11), 3462-3466 2011
    Citations: 22

  • Glypetelotine, a sulphur-containing indole alkaloid from Glycosmis petelotii
    NM Cuong, WC Taylor, T Van Sung
    Phytochemistry 52 (8), 1711-1714 1999
    Citations: 22

  • New Records of Potent In-Vitro Antidiabetic Properties of Dalbergia tonkinensis Heartwood and the Bioactivity-Guided Isolation of Active Compounds
    NMC Van Bon Nguyen, San-Lang Wang, Ngu Truong Nhan, Thi Hanh Nguyen, Nguyen ...
    Molecules 23, 1589 2018
    Citations: 21

  • Inhibition of soluble epoxide hydrolase activity by compounds isolated from the aerial parts of Glycosmis stenocarpa
    JH Kim, AMA Morgan, BH Tai, DT Van, NM Cuong, YH Kim
    Journal of enzyme inhibition and medicinal chemistry 31 (4), 640-644 2016
    Citations: 21

  • Oleanolic triterpene saponins from the roots of Panax bipinnatifidus
    NH Tung, TH Quang, NTT Ngan, C Van Minh, BK Anh, PQ Long, ...
    Chemical and Pharmaceutical Bulletin 59 (11), 1417-1420 2011
    Citations: 21

  • Chrysoeriol isolated from the leaves of Eurya ciliata stimulates proliferation and differentiation of osteoblastic MC3T3-E1 cells
    BH Tai, NM Cuong, TT Huong, EM Choi, JA Kim, YH Kim
    Journal of Asian natural products research 11 (9), 817-823 2009
    Citations: 21

  • Alkylphloroglucinol derivatives and triterpenoids with soluble epoxide hydrolase inhibitory activity from Callistemon citrinus
    PN Khanh, HV Duc, TT Huong, NT Son, VT Ha, DT Van, BH Tai, JE Kim, ...
    Fitoterapia 109, 39-44 2015
    Citations: 20

  • Flavanoids from Carya tonkinensis
    NM Cuong, TV Sung, C Kamperdick, G Adam
    Pharmazie 51 (2), 127-128 1996
    Citations: 20