Cholinesterase inhibitory alkaloids from the rhizomes of <i>Coptis chinensis</i>

Cao, Thao Quyen,Ngo, Quynh-Mai Thi,Seong, Su Hui,Youn, Ui Joung,Kim, Jeong Ah,Kim, Junheon,Kim, Jin-Cheol,Woo, Mi Hee,Choi, Jae Sue,Min, Byung Sun Elsevier 2018 Bioorganic chemistry Vol.77 No.-

<P><B>Abstract</B></P> <P> <I>Coptis chinensis</I> has been used as a medicinal herb in traditional oriental medicine. In this study, chemical investigation of a water extract of <I>C. chinensis</I> identified two new quaternary protoberberines (<B>1</B>, <B>2</B>), a new tricyclic amide (<B>3</B>), together with five known compounds. Their chemical structures were elucidated by analysis with 1D and 2D NMR and high-resolution mass spectroscopy, as well as by comparison with those reported in the literature. Compounds <B>4</B>, <B>5</B>, and <B>7</B> showed potent inhibition against acetylcholinesterase (AChE) with IC<SUB>50</SUB> values of 1.1, 5.6, and 12.9 μM, respectively. Compounds <B>2</B> and <B>4</B> showed inhibition of butyrylcholinesterase (BChE) with IC<SUB>50</SUB> values of 11.5 and 27.8 μM, respectively. The kinetic activities were investigated to find out the type of enzyme inhibition involved. The types of AChE inhibition shown by compounds <B>5</B> and <B>7</B> were noncompetitive; BChE inhibition by compound <B>2</B> was also noncompetitive.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Two new protoberberines and a new amide were isolated from <I>Coptis chinensis</I>. </LI> <LI> Isolated compounds (<B>1−8</B>) were screened for their <I>in vitro</I> ChEs inhibitory effects. </LI> <LI> Compound <B>4</B> showed the most activity on AChE with IC<SUB>50</SUB> values of 1.1 µM. </LI> <LI> Compounds <B>2</B> showed strong inhibition of BChE with IC<SUB>50</SUB> values of 11.5 µM. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Anti-inflammatory and Immunosuppressive Effects of Panax notoginseng

Thao Quyen Cao,한재혁,이현수,HAMANH TUAN,우미희,민병선 한국생약학회 2019 Natural Product Sciences Vol.25 No.4

Here, we designed to examine the anti-inflammatory effects on RAW264.7 cells and the immunosuppressive effects by evaluating interleukin-2 (IL-2) production in Jurkat T cells using a MeOH extract of Panax notoginseng roots. The results showed that the MeOH extract inhibited the synthesis of nitric oxide (NO) in a dose-dependent manner (IC50 value of 7.08 µg/mL) and displayed effects on T cell activation at a concentration of 400 µg/mL. In efforts to identify the potent compounds, bioactivity-guided fractionation of the MeOH extract and chemical investigation of its active CH2Cl2-, EtOAc-, and butanol- soluble fractions led to the successful isolation and identification of eleven compounds, including two polyacetylenes (1, 2), a steroid saponin (3), seven dammarane-type ginsenosides (4 – 10), and an oleanane-type ginsenoside (11). Among them, compound 11 was isolated from this plant for the first time. Compound 2 exhibited potent inhibitory effects on NO synthesis and an immunosuppressive effect with IC50 values of 2.28 and 65.57 µM, respectively.

Cytotoxic Activity of Compounds from Styrax obassia

Cao, Thao Quyen,Lee, Bo Mi,Jung, Yeon Woo,Nguyen, Van Thu,Kim, Jeong Ah,Min, Byung Sun NATURAL PRODUCT COMMUNICATIONS 2017 Natural product communications Vol.12 No.2

<P>Cancer is a major public health burden in both developed and developing countries. Plant-derived compounds have played an important role in the development of useful anti-cancer agents. The current study was designed to evaluate the cytotoxic activity of chemical compounds from the stem bark of Styrax obassia. Seven known compounds (1-7) were isolated and identified. Compound 2 exhibited cytotoxic activity against the breast cancer cell line MCF-7 with an IC50 of 27.9 mu M, followed by the human cervical cancer cell line Hela with an IC50 of 23.3 mu M, and the human promyelocytic leukemia cell line HL-60 with an IC50 of 47.8 mu M. Compound 7 exhibited cytotoxicity against Hela cells with an IC50 of 16.8 mu M, followed by MCF-7 cells with an IC50 of 53.5 mu M. This is the first study to investigate the significant anti-tumor properties of isolated compounds from the stem bark of S. obassia.</P>

Quantification of Allantoin in Yams (Dioscorea sp.) Using a ¹H NMR Spectroscopic Method

( Thao Quyen Cao ),( Dongyup Hahn ) 한국미생물생명공학회 2023 Journal of microbiology and biotechnology Vol.33 No.5

Allantoin is an abundant component of yams and has been known as a skin protectant due to its pharmacological activities. In previous methods for allantoin determination using high-performance liquid chromatography (HPLC), the separation was unsatisfactory. We herein developed a 1H quantitative nuclear magnetic resonance (qNMR) method for quantification of allantoin in the flesh and peel of yams. The method was carried out based on the relative ratio of signals integration of allantoin to a certain amount of the internal standard dimethyl sulfone (DMSO₂) and validated in terms of specificity, linearity (range 62.5-2000 μg/ml), sensitivity (limit of detection (LOD) and quantification (LOQ) 4.63 and 14.03 μg/ml, respectively), precision (RSD% 0.02-0.26), and recovery (86.35-92.11%). The method was then applied for the evaluation of allantoin in flesh and peel extracts of four different yams cultivated in Korea.

Development and Validation of Quantitative Analysis Method for Phenanthrenes in Peels of the Dioscorea Genus

Kim, Hunseong,Cao, Thao Quyen,Yeo, Chae-eun,Shin, Seung Ho,Kim, Hiyoung,Hong, Dong-Hyuck,Hahn, Dongyup The Korean Society for Microbiology and Biotechnol 2022 Journal of microbiology and biotechnology Vol.32 No.8

Phenanthrenes are bioactive phenolic compounds found in genus Dioscorea, in which they are distributed more in peel than in flesh. Recent studies on phenanthrenes from Dioscorea sp. peels have revealed the potential for valuable biomaterials. Herein, an analytical method using high-performance liquid chromatography (HPLC) for quantitation of bioactive phenanthrenes was developed and validated. The calibration curves were obtained using the phenanthrenes (1-3) previously isolated from Dioscorea batatas concentrations in the range of 0.625-20.00 ㎍/ml with a satisfactory coefficient of determination (R²) of 0.999. The limit of detection (LOD) and the limit of quantification (LOQ) values of the isolated phenanthrenes ranged from 0.78-0.89 and 2.38-2.71 ㎍/ml, respectively. The intraday and interday precision ranged from 0.25-7.58%. The recoveries of the isolated phenanthrenes were from 95 to 100% at concentrations of 1.25, 2.5, and 5.0 ㎍/ml. Additionally, phenanthrenes (1-3) were found in all investigated peel extracts. Hence, the developed method was encouraging for the quantitative analysis of phenanthrenes in genus Dioscorea.

Cytotoxic Triterpenoids from the Fruits of Ligustrum japonicum

Quynh-Mai Thi Ngo,Thao Quyen Cao,우미희,민병선,원권연 한국생약학회 2018 Natural Product Sciences Vol.24 No.2

Medicinal plants are potential sources of anticancer agents screening. A large number of phytochemicals, including triterpenoids, have been reported to have significant cytotoxic effects on cancer cells. From the fruits of Ligustrum japonicum Thunb., thirteen triterpenoids (1 - 13) were isolated and evaluated for their cytotoxic activity against Hela and HL-60 cells. As results, 8 (oleanolic acid) showed significant effects on Hela with IC50 values of 5.5 ?M, and moderate effects on HL-60 cells with IC50 values of 55.9 ?M. Meanwhile, 10 (oleanderic acid) and 11 (3b-acetoxy-urs-12-en-28-oic acid) exhibited moderate inhibitory effects on Hela with IC50 value of 55.0 and 68.8 ?M, respectively. Moreover, 10 showed cytotoxic effect on HL-60 cell line with IC50 value of 63.9 ?M. To our knowledge, this is the first report that oleanderic acid was isolated from L. japonicum and investigated in cytotoxic effects on Hela and HL-60 cells.

Cytotoxic Lactones from the Pericarps of Litsea japonica

Quynh-Mai Thi Ngo,Thao Quyen Cao,우미희,민병선 한국생약학회 2019 Natural Product Sciences Vol.25 No.1

From the pericarps of Litsea japonica (Thunb.) Jussieu, eighteen butanolide derivatives (1 - 18) were evaluated for their cytotoxic activity against HeLa, HL-60, and MCF-7 cells. Compounds 1 - 9 with 2-alkylidene-3-hydroxy-4-methylbutanolides structure exhibited cytotoxic activities against cancer-cell lines. Among them, compound 8 (litsenolide D2) exhibited the most potent cytotoxicity against the tested cell lines, including HeLa, HL-60, and MCF-7, with IC50 values of 17.6 ? 1.3, 4.2 ? 0.2, and 12.8 ? 0.0 ?M, respectively. Compound 8 induced apoptosis in a dose-dependent manner. Annexin V/Propidium Iodide (PI) double staining confirmed that 8 effectively induced apoptosis in MCF-7 cells. To the best of our knowledge, we have reported cytotoxic activity of butanolides from L. japonica against these cancer-cell lines for the first time.

Lactones from the pericarps of <i>Litsea japonica</i> and their anti-inflammatory activities

Ngo, Quynh-Mai Thi,Cao, Thao Quyen,Tran, Phi-Long,Kim, Jeong Ah,Seo, Sang-Tae,Kim, Jin-Cheol,Woo, Mi Hee,Lee, Jeong Hyung,Min, Byung Sun Elsevier 2018 Bioorganic & medicinal chemistry letters Vol.28 No.11

<P><B>Abstract</B></P> <P>Five new lactones, litsenolide F<SUB>1</SUB> (<B>1</B>), lisealactone H<SUB>1</SUB> (<B>10</B>), lisealactone H<SUB>2</SUB> (<B>11</B>), akolactone D (<B>13</B>), and akolactone E (<B>14</B>), along with thirteen known compounds were isolated from the pericarps of <I>Litsea japonica</I> (Thunb.) Jussieu. Their chemical structures were elucidated by extensive spectroscopic analyses, including 1D and 2D NMR, HRMS, and chemical methods. The isolated compounds were evaluated for their inhibitory effects on NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Among them, 2-alkylidene-3-hydroxy-4-methylbutanolide derivatives (compounds <B>1</B>–<B>9</B>) exhibited the most potent activity, with IC<SUB>50</SUB> values in the range of 2.9–12.8 μM. In additon, compounds <B>1</B>, <B>3</B>, <B>4</B>, and <B>6</B> showed inhibition of iNOS and COX-2 expression in concentration-dependent manner. Compound <B>3</B> suppresses mRNA expression of iNOS, COX-2, IL-6, and TNF-α in LPS-stimulated RAW264.7 cells. Based on these evidence, the isolated lactones from <I>L. japonica</I> could be promissing candidates for the development of new anti-inflammatory agents.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Five new lactones and thirteen known compounds were isolated from <I>Litsea japonica</I>. </LI> <LI> Compounds <B>1</B>–<B>9</B> exhibited potent inhibitory effects on NO production. </LI> <LI> Compounds <B>1</B>, <B>3</B>, <B>4</B> and <B>6</B> showed inhibition of iNOS and COX-2 expression. </LI> <LI> Compound <B>3</B> suppresses the expression of mRNA iNOS, COX-2, IL-6, and TNF-α. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Anti-inflammatory activity of compounds from the rhizome of Cnidium officinale

Huynh Nguyen Khanh Tran,Thao Quyen Cao,김정아,윤의중,김상희,우미희,민병선 대한약학회 2018 Archives of Pharmacal Research Vol.41 No.10

Five new compounds, 9,30-dimethoxyhierochin A (1), 6-oxo-trans-neocnidilide (2), (±)-(3E)-trans-6-hydroxy- 7-methoxydihydroligustilide (3), (±)-cnidiumin (4), and 6-(1-oxopentyl)-salicylic acid methyl ester (5), together with twenty known compounds (6–25), were isolated from the rhizome of Cnidium officinale. The chemical structures of new compounds were established by NMR spectroscopic techniques, mass spectrometry, Mosher’s method, and CD spectrum. Their anti-inflammatory activities were evaluated against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in macrophage RAW 264.7 cells. Compounds 7, 13, and 14 showed inhibitory effects with IC50 values of 5.1, 24.5, and 27.8 lM, respectively. In addition, compounds 7, 13, and 14 reduced LPS-induced inducible nitric oxide synthase (iNOS) expression and cyclooxygenase-2 (COX-2) protein in a concentration-dependent manner.

Biological Activity of Chemical Constituents Isolated from Strain Chlamydomonas sp. KSF108 (Chlamydomonadaceae)

Huynh Nguyen Khanh Tran,윤의중,김민지,Thao Quyen Cao,김정아,우미희,김상희,민병선 한국생약학회 2020 Natural Product Sciences Vol.26 No.1

This study focused on investigation of the immunosuppressive inhibitory effect through determination of IL-2 production of nine compounds (1 - 9) isolated from Chlamydomonas sp. KSF108. Among them, compounds 1, 5, and 6 displayed moderately inhibitory effects on IL-2 production at a concentration of 100 µM. In addition, the related ones including cytotoxic, anti-inflammatory, and anti-oxidant activities were also elucidated. 6 further displayed cytotoxic activity against the MCF-7 cell line, with an IC50 value of 17.2 µM and 4, 6 − 7, and 9 possessed significant DPPH radical scavenging activity, with IC50 values ranging from 3.1 to 4.4 µM. To the best of our knowledge, this is the first report on the bioactivity of isolated chemical constituents from the genus Chlamydomonas. Compounds 1 and 5 investigated for the first time in the activity of immunosuppressivity and 6 may come to serve as the most important marker in broad-spectrum activities of the secondary metabolites identified from C. sp. KSF108.