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Melanogenesis inhibitory pregnane glycosides from <i>Cynanchum atratum</i>
Jin, Qinghao,Han, Xiang Hua,Yun, Cheong-Yong,Lee, Chul,Lee, Jin Woo,Lee, Dongho,Lee, Mi Kyeong,Jung, Sang-Hun,Hong, Jin Tae,Kim, Youngsoo,Hwang, Bang Yeon Elsevier 2018 Bioorganic & medicinal chemistry letters Vol.28 No.7
<P><B>Abstract</B></P> <P>Bioassay-guided fractionation of the methanolic extract from the roots of <I>Cynanchum atratum</I> has resulted in the isolation of three new pregnane glycosides (<B>1</B>–<B>3</B>) along with four known compounds (<B>4</B>–<B>7</B>). Their structures were identified by analysis of the spectroscopic data including extensive 2D NMR. All of the isolates were evaluated for their potential to inhibit the melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Of these, compounds <B>4</B>–<B>7</B> dose-dependently inhibited the melanin production with the IC<SUB>50</SUB> values ranging from 4 μM to 33 μM.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Jin, Qinghao,Lee, Chul,Lee, Jin Woo,Yeon, Eung Tae,Lee, Dongho,Han, Sang Bae,Hong, Jin Tae,Kim, Youngsoo,Lee, Mi Kyeong,Hwang, Bang Yeon American Chemical Society and American Society of 2014 Journal of natural products Vol.77 No.7
<P>Two new 2-phenoxychromones <B>1</B> and <B>2</B> and two prenylflavonoids <B>3</B> and <B>4</B> along with 12 known compounds (<B>5–16</B>) were isolated from the CH<SUB>2</SUB>Cl<SUB>2</SUB>-soluble fraction of a methanol extract of <I>Epimedium koreanum</I>. Compounds <B>1</B>, <B>4</B>, <B>6</B>, <B>7</B>, <B>9</B>, <B>10</B>, <B>12</B>, and <B>15</B> exhibit inhibitory effects on nitric oxide production with IC<SUB>50</SUB> values ranging from 16.8 to 49.3 μM. Compounds <B>1</B>, <B>4</B>, <B>7</B>, and <B>12</B> also showed inhibitory effects on interleukin-1β production with IC<SUB>50</SUB> values ranging from 8.6 to 38.9 μM in RAW 264.7 macrophages.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2014/jnprdf.2014.77.issue-7/np400831p/production/images/medium/np-2013-00831p_0004.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np400831p'>ACS Electronic Supporting Info</A></P>
Dimeric- and trimeric sesquiterpenes from the flower of <i>Inula japonica</i>
Jin, Qinghao,Lee, Jin Woo,Jang, Hari,Lee, Hye Lim,Kim, Jun Gu,Wu, Wanying,Lee, Dongho,Kim, Eun-Hee,Kim, Youngsoo,Hong, Jin Tae,Lee, Mi Kyeong,Hwang, Bang Yeon Elsevier 2018 Phytochemistry Vol.155 No.-
<P><B>Abstract</B></P> <P>An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of <I>Inula japonica</I>. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data as well as HRESIMS data. Inulajaponicolide A has an undescribed carbon skeleton comprising of one xanthanolide and two guaianolide units with the linkage mode of C-11/C-3ʹ and C-11ʹ/C-1ʹʹ via a Diels-Alder cycloaddition reaction. Inulajaponicolides C and D exhibited moderate cytotoxic activity against A 549 and NCI-H460 human cancer cell lines with IC<SUB>50</SUB> values ranging from 8.5 to 17.8 μM. Inulajaponicolides A-D and lineariifolianoid A possessed significant inhibitory potency against nitric oxide production in LPS-induced RAW264.7 cells with IC<SUB>50</SUB> values ranging from 1.0 to 4.1 μM.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Four sesquiterpenes were isolated from <I>Inula japonica.</I> </LI> <LI> Inulajaponicolide A is an unprecedented sesquiterpene trimer formed by both endo- and exo-type 1,3-linked Diels-Alder cycloaddition. </LI> <LI> Inulajaponicolides B-D are biogenetically related sesquiterpene dimers. </LI> <LI> Some of the isolates were showed cytotoxic and NO inhibitory activities. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of <I>Inula japonica</I>. Some of the isolates were showed cytotoxic and NO inhibitory activities.</P> <P>[DISPLAY OMISSION]</P>
Jin, Qinghao,Lee, Jin Woo,Jang, Hari,Choi, Ji Eun,Lee, Dongho,Hong, Jin Tae,Kim, Youngsoo,Lee, Mi Kyeong,Hwang, Bang Yeon American Chemical Society and American Society of 2016 Journal of natural products Vol.79 No.6
<P>Eight new sesquiterpenes (1-8), along with seven known sesquiterpenes (9-15), were isolated from a methanol extract of the flowers of Inula japonica. Their structures were elucidated by a combination of 1D and 2D NMR spectroscopic and HRESIMS data. All of isolates were evaluated for their inhibitory effects on nitric oxide production in LPS-induced RAW 264.7 cells, with their IC50 values ranging from 1.9 to 15.4 mu M.</P>
Two New <i>C</i>‐<i>seco</i> Limonoids from the Fruit of <i>Melia azedarach</i>
Jin, Qinghao,Lee, Chul,Woo ,Lee, Jin,Yeon ,Choi, Jeong,Tae ,Hong, Jin,Kim, Youngsoo,Kyeong ,Lee, Mi,Yeon ,Hwang, Bang WILEY‐VCH Verlag 2014 Helvetica chimica acta Vol.97 No.8
<P><B>Abstract</B></P><P>A phytochemical investigation of the fruits of <I>Melia azedarach</I> led to the isolation of two new C‐<I>seco</I>‐nimbolinin‐type limonoids, 3<I>α</I>‐acetoxy‐1<I>α</I>,7<I>α</I>‐dihydroxy‐12<I>α</I>‐methoxynimbolinin (<B>1</B>) and 3<I>α</I>‐acetoxy‐1<I>α</I>,12<I>α</I>‐dihydroxy‐7<I>α</I>‐(2‐methylprop‐2‐enoyl)nimbolinin (<B>2</B>), together with eleven known compounds, <B>3</B>–<B>13</B>. Their structures were elucidated on the basis of extensive spectroscopic analysis, including <SUP>1</SUP>H‐ and <SUP>13</SUP>C‐NMR, HMQC, HMBC, NOESY, and HR‐FAB‐MS.</P>
A New Apotirucallane-type Triterpenoid from the Fruit of Melia azedarach
Qinghao Jin,황방연,Chul Lee,이진우,이미경,이문순 한국생약학회 2013 Natural Product Sciences Vol.19 No.4
A new apotirucallane-type triterpenoid, 3a-tigloylsapelin D (1) together with five known triterpenoids such as meliasenin B (2), sendanolactone (3), (-)-12b-hydroxykulactone (4), cinamodiol (5), and 3a-hydroxytirucalla-7,24(25)-dien-6-oxo-21,16-olide (6) were isolated from the fruits of Melia azedarach. Their structures were established on the basis of various NMR spectroscopic analyses including 2D-NMR techniques (HSQC, HMBC, and NOESY) and HR-FAB-MS data.
Chemical Constituents from the Fruits of Prunus mume
Qinghao Jin,Chul Lee,이진우,이인선,이미경,전원경,황방연,정일민 한국생약학회 2012 Natural Product Sciences Vol.18 No.3
The chromatographic separation of a methanol extract of Prunus mume (Rosaceae) led to the isolation of 5-hydroxymethyl-2-furaldehyde (1), 4-O-caffeoylquinic acid methyl ester (2), prunasin (3), 5-O-caffeoylquinic acid methyl ester (4), benzyl-O-b-D-glucopyranoside (5), and liquiritigenin-7-O-b-D-glucopyranoside (6). Their structures were determined by 1D, 2D-NMR and MS data analysis as well as by comparison of their data with the published values.
Lee, Jin Woo,Jin, Qinghao,Jang, Hari,Lee, Dongho,Han, Sang Bae,Kim, Youngsoo,Hong, Jin Tae,Lee, Mi Kyeong,Hwang, Bang Yeon Elsevier 2016 Bioorganic & medicinal chemistry letters Vol.26 No.14
<P><B>Abstract</B></P> <P>Bioactivity-guided fractionation of the MeOH extract from the roots of <I>Euphorbia kansui</I> resulted in the isolation of two new jatrophane-type diterpenoids, kanesulones A (<B>1</B>) and B (<B>2</B>), together with six known jatrophane-type diterpenoids (<B>3</B>–<B>8</B>) and ten known ingenane-type diterpenoids (<B>9</B>–<B>18</B>). Their chemical structures were elucidated on the basis of spectroscopic data interpretation, especially 1D and 2D NMR such as HMQC, HMBC, COSY and NOESY, and HRESIMS data as well as CD analysis. Compounds <B>1</B>–<B>8</B> and <B>11</B>–<B>18</B> exhibited the inhibitory effects on LPS-induced nitric oxide production with IC<SUB>50</SUB> values ranging from 0.7 to 46.5μM in RAW 264.7 macrophages.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Lee, Jin Woo,Mo, Eun Jin,Choi, Ji Eun,Jo, Yang Hee,Jang, Hari,Jeong, Ji Yeon,Jin, Qinghao,Chung, Hee Nam,Hwang, Bang Yeon,Lee, Mi Kyeong The Korean Society of Ginseng 2016 Journal of Ginseng Research Vol.40 No.3
Background: Extraction conditions greatly affect composition, as well as biological activity. Therefore, optimization is essential for maximum efficacy. Methods: Korean Red Ginseng (KRG) was extracted under different conditions and antioxidant activity, extraction yield, and ginsenoside Rg1 and phenolic content evaluated. Optimized extraction conditions were suggested using response surface methodology for maximum antioxidant activity and extraction yield. Results: Analysis of KRG extraction conditions using response surface methodology showed a good fit of experimental data as demonstrated by regression analysis. Among extraction factors, such as extraction solvent and extraction time and temperature, ethanol concentration greatly affected antioxidant activity, extraction yield, and ginsenoside Rg1 and phenolic content. The optimal conditions for maximum antioxidant activity and extraction yield were an ethanol concentration of 48.8%, an extraction time 73.3 min, and an extraction temperature of $90^{\circ}C$. The antioxidant activity and extraction yield under optimal conditions were 43.7% and 23.2% of dried KRG, respectively. Conclusion: Ethanol concentration is an important extraction factor for KRG antioxidant activity and extraction yield. Optimized extraction conditions provide useful economic advantages in KRG development for functional products.
장하리,Jin Woo Lee,Chul Lee,Qinghao Jin,Jeong Yeon Choi,이동호,한상배,김영수,Jin Tae HONG,Mi Kyeong Lee,황방연 대한약학회 2016 Archives of Pharmacal Research Vol.39 No.1
A new oplopane-type sesquiterpenoid tussilagofarin (1) and a new chromone tussilagofarol (2), along with 18 known compounds 3–20, were isolated from the flower buds of Tussilago farfara. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and HRESIMS data. Of the isolated compounds, oplopane- and bisabolane-type sesquterpenoids 1, 8–12, 15, and 16 were found to inhibit nitric oxide production in LPS-induced RAW 264.7 cells with IC50 values of 3.5–28.5 lM.