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Chung-yi Chen - One of the best experts on this subject based on the ideXlab platform.

  • Biofunctional Constituents from Michelia compressa var. lanyuensis with Anti-Melanogenic Properties.
    Molecules (Basel Switzerland), 2015
    Co-Authors: Chia-wei Chu, Chi-ming Liu, Mei-ing Chung, Chung-yi Chen
    Abstract:

    Seven compounds were extracted and purified from the roots of Michelia compressa var. lanyuensis. These compounds are Liriodenine, (−)-N-acetylanonaine, pressalanine A, p-dihydroxybenzaldehyde, 3,4-dihydroxybenzoic acid, (−)-bornesitol and β-sitostenone. These compounds were screened for anti-proliferation and anti-tyrosinase activities in B16F10 cells. Liriodenine, pressalanine A, (−)-bornesitol and β-sitostenone displayed cytotoxicity at high concentration (100 μM), but Liriodenine (5 μM), (−)-N-acetylanonaine (10 μM), and β-sitostenone (5 μM) inhibit tyrosinase activity and reduce the melanin content in B16F10 cells without cytotoxicity, suggesting that Liriodenine and β-sitostenone could be safe and potentially used in cosmetic skin whitening.

  • Review on pharmacological activities of Liriodenine
    African Journal of Pharmacy and Pharmacology, 2013
    Co-Authors: Chung-yi Chen, Wen-ying Chao, Chien-hsing Lee
    Abstract:

    This review describes the pharmacological properties of Liriodenine. This alkaloid has been isolated from plant species of many genera and exhibits a wide range of pharmacological activities that have been reported. This present paper enumerates an overview of pharmacological aspects that are useful to researchers for further exploration in order to develop the potential of this alkaloid.   Key words: Liriodenine, alkaloid, pharmacological activities, Liriodendron tulipifera L.

  • Liriodenine induces g1 s cell cycle arrest in human colon cancer cells via nitric oxide and p53 mediated pathway
    Process Biochemistry, 2012
    Co-Authors: Chung-yi Chen, Sing-ying Chen, Ching-hsein Chen
    Abstract:

    Abstract Liriodenine is an aporphine alkaloid compound extracted from the leaves of Michelia compressa var. lanyuensis . It had been reported to have an anti-colon cancer effect, but the mechanism remains unclear. In the present study, the antiproliferative mechanisms of Liriodenine were investigated in the human colon cancer SW480 cells. Flow cytometry analysis indicated that Liriodenine notably induced the G1/S phase arrest. The G1/S phase cycle-related proteins analysis illustrated that the expressions of cyclin-dependent kinase (CDK) 2, CDK4 and CDK6, and of cyclin D1 and A, as well as the phosphorylation of retinoblastoma tumor suppressor protein (ppRB) were found to be markedly reduced by Liriodenine, whereas the protein levels of the CDK inhibitors (CKIs), p21 and p27 were increased. Moreover, the intracellular nitric oxide (NO) production, protein levels of inducible NO synthase (iNOS) and, p53 were increased. The p53 overexpression was a downstream event of NO production in Liriodenine-induced G1/S-arrested SW480 cells, and the up-regulation of p21 and p27 was found to be mediated by a p53-dependent pathway. The inhibition of p53 by pifithrin-α (PFT-α), down-regulation of p21 and p27 by siRNA, or NO reduction by S-ethylisothiourea (ETU) entirely abolished the Liriodenine-induced G1/S phase arrest. We concluded that Liriodenine potently inhibited the cell cycle of SW480 cancer cells via NO- and p53-dependent G1/S phase arrest pathway. These results suggest that Liriodenine might be a powerful agent against colon cancer.

  • Bio-Functional Constituents from the Stems of Liriodendron tulipifera
    Molecules, 2012
    Co-Authors: Chien-chih Chiu, Han-lin Chou, Pei-fang Wu, Hui-min Wang, Hsin Liang Chen, Chung-yi Chen
    Abstract:

    Four known compounds have been isolated from the stems of Liriodendron tulipifera, and the structures of these pure constituents were determined using spectroscopic analysis. Isolated compounds were screened for free radical scavenging ability, metal chelating power assay and ferric reducing antioxidant power assay (FRAP). The anti-tyrosinase effects of L. tulipifera compounds were calculated the inhibition of hydroxylation of L-tyrosine to L-dopa according to an in vitro mushroom tyrosinase assay. The study also examined the bio-effects of the four compounds on the human melanoma A375.S2, and showed that Liriodenine (1) and (-)-norglaucine (4) significantly inhibited the proliferation of melanoma cells in the cell viability assay. Wound healing results indicated that Liriodenine (1), (-)-glaucine (3) and (-)-norglaucine (4) exerted anti-migration potential. Interestingly, (-)-glaucine (3), neither Liriodenine (1) nor (-)-norglaucine (4) showed promising anti-migration potential without inducing significant cytotoxicity. Furthermore, a dramatically increased level of intracellular reactive oxygen species (ROS) was detected from (-)-glaucine (3). The cell cycle assessment demonstrated a moderate G2/M accumulation by (-)-glaucine (3). The above results revealed the anti-cancer effects of L. tulipifera compounds, especially on the anti-migration ability indicating the promising chemopreventive agents to human skin melanoma cells.

  • Liriodenine induces G1/S cell cycle arrest in human colon cancer cells via nitric oxide- and p53-mediated pathway
    Process Biochemistry, 2012
    Co-Authors: Chung-yi Chen, Sing-ying Chen, Ching-hsein Chen
    Abstract:

    Abstract Liriodenine is an aporphine alkaloid compound extracted from the leaves of Michelia compressa var. lanyuensis . It had been reported to have an anti-colon cancer effect, but the mechanism remains unclear. In the present study, the antiproliferative mechanisms of Liriodenine were investigated in the human colon cancer SW480 cells. Flow cytometry analysis indicated that Liriodenine notably induced the G1/S phase arrest. The G1/S phase cycle-related proteins analysis illustrated that the expressions of cyclin-dependent kinase (CDK) 2, CDK4 and CDK6, and of cyclin D1 and A, as well as the phosphorylation of retinoblastoma tumor suppressor protein (ppRB) were found to be markedly reduced by Liriodenine, whereas the protein levels of the CDK inhibitors (CKIs), p21 and p27 were increased. Moreover, the intracellular nitric oxide (NO) production, protein levels of inducible NO synthase (iNOS) and, p53 were increased. The p53 overexpression was a downstream event of NO production in Liriodenine-induced G1/S-arrested SW480 cells, and the up-regulation of p21 and p27 was found to be mediated by a p53-dependent pathway. The inhibition of p53 by pifithrin-α (PFT-α), down-regulation of p21 and p27 by siRNA, or NO reduction by S-ethylisothiourea (ETU) entirely abolished the Liriodenine-induced G1/S phase arrest. We concluded that Liriodenine potently inhibited the cell cycle of SW480 cancer cells via NO- and p53-dependent G1/S phase arrest pathway. These results suggest that Liriodenine might be a powerful agent against colon cancer.

Cheming Teng - One of the best experts on this subject based on the ideXlab platform.

  • Antiplatelet and Vasorelaxing Actions of Some Aporphinoids
    Planta medica, 1996
    Co-Authors: Keh Shaw Chen, Cheming Teng
    Abstract:

    A series of aporphines and oxoaporphines was tested for antiplatelet and vasorelaxing actions. (+)-N-Methylactinodaphnine, (-)-norannuradhapurine x HBr, xylopine, actinodaphnine, and N-methylnandigerine showed strong inhibition of adenosine 5'-diphosphate (ADP)-induced platelet aggregation. Boldine, (+)-N-methylactinodaphnine, (-)-norannuradhapurine x HBr, xylopine, N-acetyllaurolitsine, N-methyllaurotetanine, actinodaphnine, N-methylnandigerine, O-methylbulbocapnine, and Liriodenine showed strong inhibition of arachidonic acid (AA)-induced platelet aggregation. (+)-N-Methylactinodaphnine, fissoldine x HCIO4, (-)-norannuradhapurine x HBr, xlylopine, N-methyllaurotetanine, actinodaphnine, N-methylnandigerine, O-methylbulbocapnine, and Liriodenine showed strong inhibiton of collagen-induced platelet aggregation. (-)-Norannuradhapurine x HBr, xylopine, N-methyllaurotetanine, and actinodaphnine showed strong inhibition of platelet-activating factor (PAF; 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine)-induced platelet aggregation. (+)-N-Methylactinodaphnine, laurotetanine, N-methylactinodaphnine N-oxide, oxoglaucine, boldine, and actinodaphnine showed vasorelaxing action in rat thoracic aorta. The results are discussed on the basis of structure-activity relationships.

  • pharmacological characteristics of Liriodenine isolated from fissistigma glaucescens a novel muscarinic receptor antagonist in guinea pigs
    British Journal of Pharmacology, 1994
    Co-Authors: Chienhuang Lin, Gwojyh J Chang, Cheming Teng
    Abstract:

    1. The pharmacological activities of Liriodenine, isolated from Fissistigma glaucescens, were determined in isolated trachea, ileum and cardiac tissues of guinea-pigs. 2. Liriodenine was found to be a muscarinic receptor antagonist in guinea-pig trachea as revealed by its competitive antagonism of carbachol (pA2 = 6.22 +/- 0.08)-induced smooth muscle contraction. It was slightly more potent than methoctramine (pA2 = 5.92 +/- 0.05), but was less potent than atropine (pA2 = 8.93 +/- 0.07), pirenzepine (pA2 = 7.02 +/- 0.09) and 4-diphenylacetoxy-N-methylpiperidine (4-DAMP, pA2 = 8.72 +/- 0.07). 3. Liriodenine was also a muscarinic antagonist in guinea-pig ileum (pA2 = 6.36 +/- 0.10) with a pA2 value that closely resembled that obtained in the trachea. 4. Liriodenine was 10 fold less potent in atrial preparations (left atria, pA2 = 5.24 +/- 0.04; right atria, pA2 = 5.35 +/- 0.09 and 5.28 +/- 0.07 for inotropic and chronotropic effects, respectively) than in smooth muscle preparations. 5. High concentration of Liriodenine (300 microM) partially depressed the contractions induced by U-46619, histamine, prostaglandin F2 alpha, neurokinin A, leukotriene C4 and high K+ in the guinea-pig trachea. The inhibitions were characterized by a rightward shift in the concentration-response curves with suppression of their maximal contraction. 6. High concentration of Liriodenine (300 microM) did not affect U-46619- or neurokinin A-induced tracheal contraction in the presence of nifedipine (1 microM) or in Ca(2+)-free (containing 0.2 mM EGTA) medium. 7. Neither cyclic AMP nor cyclic GMP content of guinea-pig trachealis was changed by Liriodenine (30-300 microM). 8. It is concluded that Liriodenine is a selective muscarinic receptor antagonist in isolated trachea, ileum and cardiac tissues of guinea-pigs. It is more potent in smooth muscle than in cardiac preparations. It also acts as a blocker of voltage-dependent Ca2+ channels at a high concentration (300 microM).

  • Pharmacological characteristics of Liriodenine, isolated from Fissistigma glaucescens, a novel muscarinic receptor antagonist in guinea-pigs.
    British journal of pharmacology, 1994
    Co-Authors: Chienhuang Lin, Gwo‐jyh ‐j Chang, Cheming Teng
    Abstract:

    Abstract 1. The pharmacological activities of Liriodenine, isolated from Fissistigma glaucescens, were determined in isolated trachea, ileum and cardiac tissues of guinea-pigs. 2. Liriodenine was found to be a muscarinic receptor antagonist in guinea-pig trachea as revealed by its competitive antagonism of carbachol (pA2 = 6.22 +/- 0.08)-induced smooth muscle contraction. It was slightly more potent than methoctramine (pA2 = 5.92 +/- 0.05), but was less potent than atropine (pA2 = 8.93 +/- 0.07), pirenzepine (pA2 = 7.02 +/- 0.09) and 4-diphenylacetoxy-N-methylpiperidine (4-DAMP, pA2 = 8.72 +/- 0.07). 3. Liriodenine was also a muscarinic antagonist in guinea-pig ileum (pA2 = 6.36 +/- 0.10) with a pA2 value that closely resembled that obtained in the trachea. 4. Liriodenine was 10 fold less potent in atrial preparations (left atria, pA2 = 5.24 +/- 0.04; right atria, pA2 = 5.35 +/- 0.09 and 5.28 +/- 0.07 for inotropic and chronotropic effects, respectively) than in smooth muscle preparations. 5. High concentration of Liriodenine (300 microM) partially depressed the contractions induced by U-46619, histamine, prostaglandin F2 alpha, neurokinin A, leukotriene C4 and high K+ in the guinea-pig trachea. The inhibitions were characterized by a rightward shift in the concentration-response curves with suppression of their maximal contraction. 6. High concentration of Liriodenine (300 microM) did not affect U-46619- or neurokinin A-induced tracheal contraction in the presence of nifedipine (1 microM) or in Ca(2+)-free (containing 0.2 mM EGTA) medium. 7. Neither cyclic AMP nor cyclic GMP content of guinea-pig trachealis was changed by Liriodenine (30-300 microM).(ABSTRACT TRUNCATED AT 250 WORDS)

  • Antimuscarinic action of Liriodenine, isolated from Fissistigma glaucescens, in canine tracheal smooth muscle.
    British journal of pharmacology, 1994
    Co-Authors: Chienhuang Lin, Chuen‐mao ‐m Yang, Cheming Teng
    Abstract:

    1. The antimuscarinic properties of Liriodenine, isolated from Fissistigma glaucescens, were compared with methoctramine (cardioselective M2 antagonist) and 4-diphenylacetoxy-N-methylpiperidine (4-DAMP, smooth muscle selective M3 antagonist) by radioligand binding tests, functional tests and measurements of second messenger generation in canine cultured tracheal smooth muscle cells. 2. Liriodenine, pirenzepine, methoctramine and 4-DAMP displaced [3H]-N-methyl scopolamine ([3H]-NMS) binding in a concentration-dependent manner with Ki values of 2.2 +/- 0.4 x 10(-6), 3.3 +/- 0.7 x 10(-7), 8.9 +/- 2.3 x 10(-8) and 2.3 +/- 0.6 x 10(-9) M, respectively. The curves for competitive inhibition of [3H]-NMS with Liriodenine, methoctramine and 4-DAMP were best fitted according to a two site model of binding, but pirenzepine was best fitted according to a model with one site. 3. Liriodenine and 4-DAMP displayed a high affinity for blocking tracheal contraction (pKB = 5.9 and 9.1, respectively) and inositol phosphate formation (pKB = 6.0 and 8.9, respectively), but a low affinity for antagonism of cyclic AMP inhibition (pKB = 4.7 and 7.8, respectively). 4. Methoctramine blocked cyclic AMP inhibition with a high affinity (pKB = 7.4), but it antagonized tracheal contraction and inositol phosphate formation with a low affinity (pKB = 6.1 and 6.0, respectively). 5. In conclusion, both M2 and M3 muscarinic receptor subtypes coexist in canine tracheal smooth muscle and are coupled to the inhibition of cyclic AMP formation and phosphoinositide breakdown, respectively. The antimuscarinic characteristics of Liriodenine are similar to those of 4-DAMP. It may act as a selective M3 receptor antagonist in canine tracheal smooth muscle.

Hong Liang - One of the best experts on this subject based on the ideXlab platform.

  • synthesis characterization and in vitro antitumor properties of gold iii compounds with the traditional chinese medicine tcm active ingredient Liriodenine
    Journal of Biological Inorganic Chemistry, 2012
    Co-Authors: Zhenfeng Chen, Xue Hong, Honghong Wang, Minmin Zhang, Yan Peng, Hong Liang
    Abstract:

    Liriodenine, an oxoaporphine alkaloid with anticancer activity isolated from Zanthoxylum nitidum (rutaceous anticancer traditional Chinese medicine), was selected as a bioactive ligand to react with HAuCl4 and NaAuCl4 to afford [LH][AuCl4] (1) and [AuCl3L] (2), respectively (where L is Liriodenine). The structures of 1 and 2 were characterized by IR spectroscopy, electrospray ionization mass spectrometry, 1H-NMR spectroscopy, and elemental analysis. The single-crystal X-ray diffraction analysis of 1 revealed that it is an ionic compound consisting of protonated Liriodenine cation [LH]+ and [AuCl4]− anion. The spectroscopic analysis showed that 2 is a coordination compound, in which one Liriodenine coordinates to gold via its 7-N donor. In aqueous solution, 1 is relatively stable, but 2 undergoes rapid hydrolysis. The in vitro cytotoxicity towards five human tumor cell lines shows that 1 and 2 manifest roughly similar biological behavior and appreciable antiproliferative properties, with IC50 values falling in the 2–16 μM range. The flow-cytometric analysis of 1 and 2 suggests that both compounds induced an S-phase arrest. Compounds 1 and 2 significantly poison topoisomerase I in vitro at low concentration (25 μM or less). DNA binding studies indicate that both 1 and 2 interact with DNA mainly via intercalation between the neighboring base pairs of the DNA double helix. Electrostatic interactions of 1 and 2 with the polyanionic DNA phosphate backbone may reinforce the intercalation because both 1 and 2 are composed of planar cationic species. Two Liriodenine (L) gold(III) compounds [LH][AuCl4] (1) and [AuCl3L] (2) were synthesized. The in vitro cytotoxicity towards five human tumor cell lines was tested and shows that 1 and 2 manifest appreciable antiproliferative properties, with IC50 values falling in the 2–16 μM range. Both 1 and 2 interact with DNA mainly via an intercalation mode, but electrostatic binding may exist. They both inhibit topoisomerase I activity at low concentration (25 μM or less).

Chienhuang Lin - One of the best experts on this subject based on the ideXlab platform.

  • pharmacological characteristics of Liriodenine isolated from fissistigma glaucescens a novel muscarinic receptor antagonist in guinea pigs
    British Journal of Pharmacology, 1994
    Co-Authors: Chienhuang Lin, Gwojyh J Chang, Cheming Teng
    Abstract:

    1. The pharmacological activities of Liriodenine, isolated from Fissistigma glaucescens, were determined in isolated trachea, ileum and cardiac tissues of guinea-pigs. 2. Liriodenine was found to be a muscarinic receptor antagonist in guinea-pig trachea as revealed by its competitive antagonism of carbachol (pA2 = 6.22 +/- 0.08)-induced smooth muscle contraction. It was slightly more potent than methoctramine (pA2 = 5.92 +/- 0.05), but was less potent than atropine (pA2 = 8.93 +/- 0.07), pirenzepine (pA2 = 7.02 +/- 0.09) and 4-diphenylacetoxy-N-methylpiperidine (4-DAMP, pA2 = 8.72 +/- 0.07). 3. Liriodenine was also a muscarinic antagonist in guinea-pig ileum (pA2 = 6.36 +/- 0.10) with a pA2 value that closely resembled that obtained in the trachea. 4. Liriodenine was 10 fold less potent in atrial preparations (left atria, pA2 = 5.24 +/- 0.04; right atria, pA2 = 5.35 +/- 0.09 and 5.28 +/- 0.07 for inotropic and chronotropic effects, respectively) than in smooth muscle preparations. 5. High concentration of Liriodenine (300 microM) partially depressed the contractions induced by U-46619, histamine, prostaglandin F2 alpha, neurokinin A, leukotriene C4 and high K+ in the guinea-pig trachea. The inhibitions were characterized by a rightward shift in the concentration-response curves with suppression of their maximal contraction. 6. High concentration of Liriodenine (300 microM) did not affect U-46619- or neurokinin A-induced tracheal contraction in the presence of nifedipine (1 microM) or in Ca(2+)-free (containing 0.2 mM EGTA) medium. 7. Neither cyclic AMP nor cyclic GMP content of guinea-pig trachealis was changed by Liriodenine (30-300 microM). 8. It is concluded that Liriodenine is a selective muscarinic receptor antagonist in isolated trachea, ileum and cardiac tissues of guinea-pigs. It is more potent in smooth muscle than in cardiac preparations. It also acts as a blocker of voltage-dependent Ca2+ channels at a high concentration (300 microM).

  • Pharmacological characteristics of Liriodenine, isolated from Fissistigma glaucescens, a novel muscarinic receptor antagonist in guinea-pigs.
    British journal of pharmacology, 1994
    Co-Authors: Chienhuang Lin, Gwo‐jyh ‐j Chang, Cheming Teng
    Abstract:

    Abstract 1. The pharmacological activities of Liriodenine, isolated from Fissistigma glaucescens, were determined in isolated trachea, ileum and cardiac tissues of guinea-pigs. 2. Liriodenine was found to be a muscarinic receptor antagonist in guinea-pig trachea as revealed by its competitive antagonism of carbachol (pA2 = 6.22 +/- 0.08)-induced smooth muscle contraction. It was slightly more potent than methoctramine (pA2 = 5.92 +/- 0.05), but was less potent than atropine (pA2 = 8.93 +/- 0.07), pirenzepine (pA2 = 7.02 +/- 0.09) and 4-diphenylacetoxy-N-methylpiperidine (4-DAMP, pA2 = 8.72 +/- 0.07). 3. Liriodenine was also a muscarinic antagonist in guinea-pig ileum (pA2 = 6.36 +/- 0.10) with a pA2 value that closely resembled that obtained in the trachea. 4. Liriodenine was 10 fold less potent in atrial preparations (left atria, pA2 = 5.24 +/- 0.04; right atria, pA2 = 5.35 +/- 0.09 and 5.28 +/- 0.07 for inotropic and chronotropic effects, respectively) than in smooth muscle preparations. 5. High concentration of Liriodenine (300 microM) partially depressed the contractions induced by U-46619, histamine, prostaglandin F2 alpha, neurokinin A, leukotriene C4 and high K+ in the guinea-pig trachea. The inhibitions were characterized by a rightward shift in the concentration-response curves with suppression of their maximal contraction. 6. High concentration of Liriodenine (300 microM) did not affect U-46619- or neurokinin A-induced tracheal contraction in the presence of nifedipine (1 microM) or in Ca(2+)-free (containing 0.2 mM EGTA) medium. 7. Neither cyclic AMP nor cyclic GMP content of guinea-pig trachealis was changed by Liriodenine (30-300 microM).(ABSTRACT TRUNCATED AT 250 WORDS)

  • Antimuscarinic action of Liriodenine, isolated from Fissistigma glaucescens, in canine tracheal smooth muscle.
    British journal of pharmacology, 1994
    Co-Authors: Chienhuang Lin, Chuen‐mao ‐m Yang, Cheming Teng
    Abstract:

    1. The antimuscarinic properties of Liriodenine, isolated from Fissistigma glaucescens, were compared with methoctramine (cardioselective M2 antagonist) and 4-diphenylacetoxy-N-methylpiperidine (4-DAMP, smooth muscle selective M3 antagonist) by radioligand binding tests, functional tests and measurements of second messenger generation in canine cultured tracheal smooth muscle cells. 2. Liriodenine, pirenzepine, methoctramine and 4-DAMP displaced [3H]-N-methyl scopolamine ([3H]-NMS) binding in a concentration-dependent manner with Ki values of 2.2 +/- 0.4 x 10(-6), 3.3 +/- 0.7 x 10(-7), 8.9 +/- 2.3 x 10(-8) and 2.3 +/- 0.6 x 10(-9) M, respectively. The curves for competitive inhibition of [3H]-NMS with Liriodenine, methoctramine and 4-DAMP were best fitted according to a two site model of binding, but pirenzepine was best fitted according to a model with one site. 3. Liriodenine and 4-DAMP displayed a high affinity for blocking tracheal contraction (pKB = 5.9 and 9.1, respectively) and inositol phosphate formation (pKB = 6.0 and 8.9, respectively), but a low affinity for antagonism of cyclic AMP inhibition (pKB = 4.7 and 7.8, respectively). 4. Methoctramine blocked cyclic AMP inhibition with a high affinity (pKB = 7.4), but it antagonized tracheal contraction and inositol phosphate formation with a low affinity (pKB = 6.1 and 6.0, respectively). 5. In conclusion, both M2 and M3 muscarinic receptor subtypes coexist in canine tracheal smooth muscle and are coupled to the inhibition of cyclic AMP formation and phosphoinositide breakdown, respectively. The antimuscarinic characteristics of Liriodenine are similar to those of 4-DAMP. It may act as a selective M3 receptor antagonist in canine tracheal smooth muscle.

Zhenfeng Chen - One of the best experts on this subject based on the ideXlab platform.

  • synthesis characterization and in vitro antitumor properties of gold iii compounds with the traditional chinese medicine tcm active ingredient Liriodenine
    Journal of Biological Inorganic Chemistry, 2012
    Co-Authors: Zhenfeng Chen, Xue Hong, Honghong Wang, Minmin Zhang, Yan Peng, Hong Liang
    Abstract:

    Liriodenine, an oxoaporphine alkaloid with anticancer activity isolated from Zanthoxylum nitidum (rutaceous anticancer traditional Chinese medicine), was selected as a bioactive ligand to react with HAuCl4 and NaAuCl4 to afford [LH][AuCl4] (1) and [AuCl3L] (2), respectively (where L is Liriodenine). The structures of 1 and 2 were characterized by IR spectroscopy, electrospray ionization mass spectrometry, 1H-NMR spectroscopy, and elemental analysis. The single-crystal X-ray diffraction analysis of 1 revealed that it is an ionic compound consisting of protonated Liriodenine cation [LH]+ and [AuCl4]− anion. The spectroscopic analysis showed that 2 is a coordination compound, in which one Liriodenine coordinates to gold via its 7-N donor. In aqueous solution, 1 is relatively stable, but 2 undergoes rapid hydrolysis. The in vitro cytotoxicity towards five human tumor cell lines shows that 1 and 2 manifest roughly similar biological behavior and appreciable antiproliferative properties, with IC50 values falling in the 2–16 μM range. The flow-cytometric analysis of 1 and 2 suggests that both compounds induced an S-phase arrest. Compounds 1 and 2 significantly poison topoisomerase I in vitro at low concentration (25 μM or less). DNA binding studies indicate that both 1 and 2 interact with DNA mainly via intercalation between the neighboring base pairs of the DNA double helix. Electrostatic interactions of 1 and 2 with the polyanionic DNA phosphate backbone may reinforce the intercalation because both 1 and 2 are composed of planar cationic species. Two Liriodenine (L) gold(III) compounds [LH][AuCl4] (1) and [AuCl3L] (2) were synthesized. The in vitro cytotoxicity towards five human tumor cell lines was tested and shows that 1 and 2 manifest appreciable antiproliferative properties, with IC50 values falling in the 2–16 μM range. Both 1 and 2 interact with DNA mainly via an intercalation mode, but electrostatic binding may exist. They both inhibit topoisomerase I activity at low concentration (25 μM or less).

  • catena-Poly[[(Liriodenine-κ2N,O)lead(II)]-di-μ-chlorido]
    Acta Crystallographica Section E Structure Reports Online, 2009
    Co-Authors: Yan-tao Qin, Lu Tao, Yan-cheng Liu, Zhenfeng Chen
    Abstract:

    The title compound, [PbCl2(C17H9NO3)]n, was synthesized by the hydro­thermal reaction of PbCl2 and Liriodenine. The lead(II) atom has a distorted octa­hedral environment made up of the O and N atoms of the Liriodenine ligand [Pb—O 2.666 (4) A, Pb—N 2.587 (5) A, O—Pb—N 61.78 (14)°] and four bridging chloro ligands, which link the complex mol­ecules into infinite chains along the a axis. Both crystallographically independent chloro-bridges are asymmetric, so that the Pb atom participates in two short [2.6872 (18) and 2.7952 (18) A] and two noticeably longer Pb—Cl bonds [2.9626 (18) and 3.031 (2) A].

  • Potential new inorganic antitumour agents from combining the anticancer traditional Chinese medicine (TCM) Liriodenine with metal ions, and DNA binding studies.
    Dalton transactions (Cambridge England : 2003), 2008
    Co-Authors: Zhenfeng Chen, Yan-cheng Liu, Li-min Liu, Heng-shan Wang, San-hai Qin, Bo-long Wang, He-dong Bian, Bin Yang, Hoong-kun Fun, Hua-gang Liu
    Abstract:

    Liriodenine (L), an active component of the anticancer traditional Chinese medicine (TCM), was isolated from Zanthoxylum nitidum. Its reactions with Pt(II) and Ru(II) afforded three metal complexes: cis-[PtCl2(L)] (1), cis-[PtCl2(L)(DMSO)] (2), and cis-[RuCl2(L)(DMSO)2]·1.5H2O (3), the crystal structures of L, 2 and 3 were determined by single-crystal X-ray diffraction methods. These complexes were fully characterized by elemental analysis, IR spectrophotometry, 1H and 13C NMR spectroscopies, and ES mass spectrometry. The in vitro cytotoxicity of L and complexes 1–3 against 11 human tumour cell lines was assayed. The metal-based compounds exhibit enhanced cytotoxicity vs. free L, suggesting that these compounds display synergy in the combination of metal ions and Liriodenine. The binding properties of L and its complexes 1–3 to ct-DNA were investigated through UV-vis, fluorescence, CD spectra, viscosity and agarose gels electrophoretic measurements.