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Kang, Kyo Bin,Park, Eun Jin,Kim, Jinwoong,Sung, Sang Hyun American Society of Pharmacognosy 2017 Journal of natural products Vol.80 No.10
<P>Three compounds in a new class of 2-acetoxy-w-phenylpentaene fatty acid triglycosides, berchemiosides A-C (1-3), and a biosynthetically related phenolic glycoside (4) were isolated from the unripe fruits of Berchemia berchemiifolia, along with three flavonoid S-O-diglycosides (5-7) and three known flavonoids (8-10). Their chemical structures including absolute configurations were determined by spectroscopic analysis in combination with chemical derivatization. The pentaene group of 1 was found to have (6E,8E,10Z,12Z,14E)-geometry, whereas those of 2 and 3 exhibited all-E geometries. The isolated compounds were examined for their cytotoxicity and xanthine oxidase (XO) inhibitory activity; only compound 7 showed weak XO inhibitory activity.</P>
Comprehensive Profiling of Plant Specialized Metabolites with Computational Mass Spectrometry
Kyo Bin Kang 한국원예학회 2021 한국원예학회 학술발표요지 Vol.2021 No.10
Plants produce a myriad of specialized metabolites, also known as natural products, to overcome their sessile habit and combat biotic as well as abiotic stresses. Natural products have been a valuable source of drug discovery, due to their chemical diversity which has been shaped through the history of evolution. However, the chemical diversity of plant specialized metabolites has made itself to be difficult to investigate. Recent advances of analytical platforms, especially mass spectrometry, have revolutionized the comprehensive analysis of the chemical diversity of plant specialized metabolites. As the amount of data acquired from the untargeted metabolomics on the plant specialized metabolites is becoming massive, the importance of computational data analysis workflows is increasing. MS/MS molecular networking is a computational method calculating spectral similarities between tandem MS spectra for extrapolating them to structural similarities; which was introduced in 2012, and has become one of the most popular data analysis workflows for the untargeted metabolomics projects. In this talk, I will introduce some recent studies applying MS/MS molecular networking and related methodologies for metabolome mining of massive plant specialized metabolite datasets.
Cytotoxic Ceanothane- and Lupane-Type Triterpenoids from the Roots of <i>Ziziphus jujuba</i>
Kang, Kyo Bin,Kim, Jung Wha,Oh, Won Keun,Kim, Jinwoong,Sung, Sang Hyun American Chemical Society and American Society of 2016 Journal of natural products Vol.79 No.9
<P>Ziziphus jujuba, a plant in the family Rhamnaceae, is used in several Asian countries as a food and traditional medicine. Fifteen new ceanothane-type (1-15) and three new lupane-type triterpenoids (16-18) were isolated from the roots of Z. jujuba, as well, as 12 previously known triterpenoids (19-30). Their structures were elucidated by 1D and 2D NMR spectroscopic and HR mass spectrometric data analysis. Compounds 12 and 13 were found to possess a rare E-ring gamma-lactone structure, and 14 was assigned as the first 2,28-dinorlupane derivative isolated as a natural product. Twenty-five of the isolates were examined for cytotoxicity against human hepatocellular carcinoma HepG2 cells, and compounds 6-8, 14, 17, 23, 25, 29, and 30 showed cytotoxicity with IC50 values ranging from 1.9 to 5.9 mu M.</P>
Chemical and genomic diversity of six <i>Lonicera</i> species occurring in Korea
Kang, Kyo Bin,Kang, Shin-Jae,Kim, Mi Song,Lee, Dong Young,Han, Sang Il,Kim, Tae Bum,Park, Jee Young,Kim, Jinwoong,Yang, Tae-Jin,Sung, Sang Hyun Elsevier 2018 Phytochemistry Vol.155 No.-
<P><B>Abstract</B></P> <P> <I>Lonicera</I> spp. (Caprifoliaceae) are important not only as a common medicinal herb in East Asia but also as one of the most problematic invasive species in North America. In the present study, we performed a systemic analysis of genomic and chemical diversity among six <I>Lonicera</I> species occurring in Korea, <I>L. japonica</I>, <I>L. maackii</I>, <I>L. insularis</I>, <I>L. sachalinensis</I>, <I>L. praeflorens</I>, and <I>L. vesicaria</I>, using chloroplast DNA whole genome shotgun (WGS) sequencing and LC–MS analyses. The phylogenetic and phylochemical relationships did not coincide with each other, but partial consistency could be found among them. InDel-based cDNA marker for authentication was developed based on the genome sequences. Flavonoids, iridoids, and organic acids were identified in the LC–MS analyses, and their inter-species distribution and localization were also revealed.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Phylogeny between six <I>Lonicera</I> species was supposed based on chloroplast genome sequences. </LI> <LI> Specialized metabolites were profiled and compared by LC–MS. </LI> <LI> Partial consistency was found between genomic and chemical phylogeny. </LI> <LI> An Indel-based DNA barcode was developed for authentication of plants. </LI> <LI> Difference in chemotypes was suggested to be caused by ecological roles of iridoids. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
UHPLC-ESI-qTOF-MS Analysis of Cyclopeptide Alkaloids in the Seeds of Ziziphus jujuba var. spinos
( Kyo Bin Kang ),( Dae Sik Jang ),( Jinwoong Kim ),( Sang Hyun Sung ) 한국질량분석학회 2016 Mass spectrometry letters Vol.7 No.2
An UHPLC-ESI-qTOF-MS analytical method was developed for cyclopeptide alkaloids in the seeds of Ziziphus jujuba var. spinosa (Semen Ziziphi Spinosae), which is a commonly used herb in Chinese and Korean traditional medicines. Considering the basicity of cyclopeptide alkaloids, a specific separation method was developed for an UHPLC system. The compounds were detected by DAD and ESI-qTOF-MS, and their fragmentation patterns were also acquired by MS^{E} technologies. Peak-picking of major compounds was performed with nine previously isolated compounds and two reference standard compounds. Tandem MS fragmentation behaviors of type-Ia and -Ib cyclopeptide alkaloids were investigated with the acquired data to develop a strategy for dereplication of other cyclopeptide alkaloid compounds in Z. jujuba var. spinosa. Two more cyclopeptide alkaloids were tentatively identified with UHPLC-ESI-qTOF-MS using this method.
Catechin-Bound Ceanothane-Type Triterpenoid Derivatives from the Roots of <i>Zizyphus jujuba</i>
Kang, Kyo Bin,Kim, Hyun Woo,Kim, Jung Wha,Oh, Won Keun,Kim, Jinwoong,Sung, Sang Hyun American Society of Pharmacognosy 2017 Journal of natural products Vol.80 No.4
<P>Three unprecedented ceanothane-type triterpenoids, ent-epicatechinoceanothic acid A (1), ent-epicatechinoceanothic acid B (2), and epicatechino-3-deoxyceanothetric acid A (3), containing C-C bond linkages with catechin moieties, were isolated from the roots of Zizyphus jujuba. Their chemical structures, including absolute configurations, were established by spectroscopic analysis and calculation of their ECD spectra. A possible biogenetic pathway for C-C bond formation between the catechin and the triterpenoid moieties is presented. Compound 1 was evaluated for its antiproliferalive activity on HSC-T6 hepatic stellate cells.</P>
UHPLC-ESI-qTOF-MS Analysis of Cyclopeptide Alkaloids in the Seeds of Ziziphus jujuba var. spinosa
Kang, Kyo Bin,Jang, Dae Sik,Kim, Jinwoong,Sung, Sang Hyun Korean Society for Mass Spectrometry 2016 Mass spectrometry letters Vol.7 No.2
An UHPLC-ESI-qTOF-MS analytical method was developed for cyclopeptide alkaloids in the seeds of Ziziphus jujuba var. spinosa (Semen Ziziphi Spinosae), which is a commonly used herb in Chinese and Korean traditional medicines. Considering the basicity of cyclopeptide alkaloids, a specific separation method was developed for an UHPLC system. The compounds were detected by DAD and ESI-qTOF-MS, and their fragmentation patterns were also acquired by MS<sup>E</sup> technologies. Peak-picking of major compounds was performed with nine previously isolated compounds and two reference standard compounds. Tandem MS fragmentation behaviors of type-Ia and -Ib cyclopeptide alkaloids were investigated with the acquired data to develop a strategy for dereplication of other cyclopeptide alkaloid compounds in Z. jujuba var. spinosa. Two more cyclopeptide alkaloids were tentatively identified with UHPLC-ESI-qTOF-MS using this method.
Kyo Bin Kang,이동영,성상현 한국생약학회 2021 Natural Product Sciences Vol.27 No.4
Aster species (Asteraceae) are widely distributed edible and medicinal plants, known to contain various specialized metabolites including polyphenols and saponins. However, systemic analysis on the chemical profiles of these plants have rarely been made. Here we analyzed the phytochemical constituents in leaves of 6 Aster species occurring in Korea, A. ageratoides, A. altaicus var. uchiyamae, A. glehnii, A. hispidus, A. incisus, and A. yomena, by applying a LC–MS/MS-based untargeted metabolomics approach. The analysis revealed that A. ageratoides, A. hispidus, and A. yomena are relatively rich in saponins most of which are expected to be previously unknown.
Tyrosinase Inhibitory Constituents of Morus bombycis Cortex
Kyo Bin Kang,Sang Du Kim,김태범,Eun Ju Jeong,Young Choong Kim,Jong Hyuk Sung,성상현 한국생약학회 2011 Natural Product Sciences Vol.17 No.3
Tyrosinase is one of the important enzymes in the mammalian melanin synthesis. In the process of melanin synthesis, tyrosine is oxidized to DOPA (3,4-dihydroxyphenylalanine), and DOPA is further oxidized to dopaquinone. Tyrosinase is an enzyme catalyzing this oxidation of tyrosine, so chemicals that inhibit the activity of tyrosinase can be used as skin whitening agents. In this study, we isolated five constituents from the 80% MeOH extract of Morus bombycis cortex by bioactivity-guided fractionation. We performed mushroom tyrosinase inhibition assay. As a result, 7,2',4'-trihydroxyflavanone (1), 2',4',2,4,-tetrahydroxychalcone (2), and oxyresveratrol (3) showed the more potent inhibitory effect compared to kojic acid, a well-known skin whitening agent with anti-tyrosinase effect. Moracinoside M (4) and moracin M-3'-O-b-D-glucopyranoside (5) also showed the moderate tyrosinase inhibitory activities.