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Cytotoxic 5a,8a-epidioxy sterols from the marine sponge Monanchora sp.
문보라,Weihong Wang,김희영,한동엽,양인호,원동환,김은희,이지혜,한철경,김현지,Merrick Ekins,남상집,최혁재,강헌중 대한약학회 2015 Archives of Pharmacal Research Vol.38 No.1
Three new sterols, 5a,8a-epidioxy-24-norcholesta-6,9(11),22-trien-3b-ol (1), 5a,8a-epidioxy-cholesta-6,9(11),24-trien-3b-ol (2), and 5a,8a-epidioxy-cholesta-6,23-dien-3b,25-diol (3), with four known sterols (4–7)were isolated from a marine sponge Monanchora sp. Theirchemical structures were elucidated by extensive spectroscopicanalysis. Compounds 1 and 3–7 showed moderatecytotoxicity against several human carcinoma cell linesincluding renal (A-498), pancreatic (PANC-1 and MIAPaCa-2), and colorectal (HCT 116) cancer cell lines.
( Dongyup Hahn ),( Hiyoung Kim ),( Inho Yang ),( Jungwook Chin ),( Hoosang Hwang ),( Dong Hwan Won ),( Byoungchan Lee ),( Sang Jip Nam ),( Merrick Ekins ),( Hyukjae Choi ),( Heonjoong Kang ) 영남대학교 약품개발연구소 2016 영남대학교 약품개발연구소 연구업적집 Vol.26 No.-
Three new structurally related depsipeptides, halieylindramides F-H (1-3), and two known halieylindra-mides were isolated from a Petrosia sp. marine sponge collected off the shore of Youngdeok-Gun, East Sea, Republic of Korea. Their planar structures were elucidated by extensive spectroscopic data analyses including ID and 2D NMR data as well as MS data. The absolute configurations of halicylin-drarnides F-H (1-3) were determined by Marfey``s method in combination with Edman degradation. The absolute config-urations at C-4 of the dioxyindolyl alanine (Dioia) residues of halieylindramides G (2) and H (3) were determined as 4S and 4R, respectively, based on ECD spectroscopy. The C-2 configurations of Dioia in 2 and 3 were speculated to both be 2R based on the shared biogenesis of the halicylindramides. Halieylindrarnides F (1), A (4), and C (5) showed human farnesoid X receptor (hFXR) antagonistic activities, but did not bind directly to hFXR.
Bioactive Sesterterpenoids from a Korean Sponge <i>Monanchora</i> sp.
Wang, Weihong,Mun, Bora,Lee, Yehee,Venkat Reddy, Mallepally,Park, Youngmin,Lee, Jihye,Kim, Hiyoung,Hahn, Dongyup,Chin, Jungwook,Ekins, Merrick,Nam, Sang-Jip,Kang, Heonjoong American Chemical Society and American Society of 2013 Journal of natural products Vol.76 No.2
<P>Chemical investigation of a Korean marine sponge, <I>Monanchora</I> sp., yielded nine new sesterterpenoids (<B>1</B>–<B>9</B>) along with phorbaketals A–C (<B>10</B>–<B>12</B>). The planar structures were established on the basis of NMR and MS analysis, and the absolute configurations of <B>1</B>–<B>9</B> were defined using the modified Mosher’s method and CD spectroscopic data analysis. Compounds <B>1</B>–<B>8</B>, designated as phorbaketals D–K, possess a spiroketal-modified benzopyran moiety such as phorbaketal A, and their structural variations are due to oxidation and/or reduction of the tricyclic core or the side chain. Compound <B>9</B>, designated as phorbin A, has a monocyclic structure and is proposed to be a possible biogenetic precursor of the phorbaketals. Compounds <B>1</B>–<B>9</B> were evaluated for cytotoxicity against four human cancer cell lines (A498, ACHN, MIA-paca, and PANC-1), and a few of them were found to exhibit cytotoxic activity.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2013/jnprdf.2013.76.issue-2/np300573m/production/images/medium/np-2012-00573m_0006.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np300573m'>ACS Electronic Supporting Info</A></P>
Tepoerau Mai,Jordan Toullec,Simon Van Wynsberge,Marc Besson,Stephanie Soulet,Sylvain Petek,Emmanuelle Aliotti,Merrick Ekins,Kathryn Hall,Dirk Erpenbeck,David Lecchini,Mehdi A. Beniddir,Denis Saulnier 한국수산과학회 2019 Fisheries and Aquatic Sciences Vol.22 No.4
Marine natural products isolated from the sponge Fascaplysinopsis cf reticulata, in French Polynesia, were investigated as an alternative to antibiotics to control pathogens in aquaculture. The overuse of antibiotics in aquaculture is largely considered to be an environmental pollution, because it supports the transfer of antibiotic resistance genes within the aquatic environment. One environmentally friendly alternative to antibiotics is the use of quorum sensing inhibitors (QSIs). Quorum sensing (QS) is a regulatory mechanism in bacteria which control virulence factors through the secretion of autoinducers (AIs), such as acyl-homoserine lactone (AHL) in gramnegative bacteria. Vibrio harveyi QS is controlled through three parallel pathways: HAI-1, AI-2, and CAI-1. Bioassayguided purification of F. cf reticulata extract was conducted on two bacterial species, i.e., Tenacibaculum maritimum and V. harveyi for antibiotic and QS inhibition bioactivities. Toxicity bioassay of fractions was also evaluated on the freshwater fish Poecilia reticulata and the marine fish Acanthurus triostegus. Cyclohexanic and dichloromethane fractions of F. cf reticulata exhibited QS inhibition on V. harveyi and antibiotic bioactivities on V. harveyi and T. maritimum, respectively. Palauolide (1) and fascaplysin (2) were purified as major molecules from the cyclohexanic and dichloromethane fractions, respectively. Palauolide inhibited QS of V. harveyi through HAI-1 QS pathway at 50 μg ml–1 (26 μM), while fascaplysin affected the bacterial growth of V. harveyi (50 μg ml–1) and T. maritimum (0.25 μg). The toxicity of fascaplysin-enriched fraction (FEF) was evaluated and exhibited a toxic effect against fish at 50 μg ml–1. This study demonstrated for the first time the QSI potential of palauolide (1). Future research may assess the toxicity of both the cyclohexanic fraction of the sponge and palauolide (1) on fish, to confirm their potential as alternative to antibiotics in fish farming.
Mai, Tepoerau,Toullec, Jordan,Wynsberge, Simon Van,Besson, Marc,Soulet, Stephanie,Petek, Sylvain,Aliotti, Emmanuelle,Ekins, Merrick,Hall, Kathryn,Erpenbeck, Dirk,Lecchini, David,Beniddir, Mehdi A.,Sau The Korean Society of Fisheries and Aquatic Scienc 2019 Fisheries and Aquatic Sciences Vol.22 No.12
Marine natural products isolated from the sponge Fascaplysinopsis cf reticulata, in French Polynesia, were investigated as an alternative to antibiotics to control pathogens in aquaculture. The overuse of antibiotics in aquaculture is largely considered to be an environmental pollution, because it supports the transfer of antibiotic resistance genes within the aquatic environment. One environmentally friendly alternative to antibiotics is the use of quorum sensing inhibitors (QSIs). Quorum sensing (QS) is a regulatory mechanism in bacteria which control virulence factors through the secretion of autoinducers (AIs), such as acyl-homoserine lactone (AHL) in gram-negative bacteria. Vibrio harveyi QS is controlled through three parallel pathways: HAI-1, AI-2, and CAI-1. Bioassay-guided purification of F. cf reticulata extract was conducted on two bacterial species, i.e., Tenacibaculum maritimum and V. harveyi for antibiotic and QS inhibition bioactivities. Toxicity bioassay of fractions was also evaluated on the freshwater fish Poecilia reticulata and the marine fish Acanthurus triostegus. Cyclohexanic and dichloromethane fractions of F. cf reticulata exhibited QS inhibition on V. harveyi and antibiotic bioactivities on V. harveyi and T. maritimum, respectively. Palauolide (1) and fascaplysin (2) were purified as major molecules from the cyclohexanic and dichloromethane fractions, respectively. Palauolide inhibited QS of V. harveyi through HAI-1 QS pathway at 50 ㎍ ml<sup>-1</sup> (26 μM), while fascaplysin affected the bacterial growth of V. harveyi (50 ㎍ ml<sup>-1</sup>) and T. maritimum (0.25 ㎍). The toxicity of fascaplysin-enriched fraction (FEF) was evaluated and exhibited a toxic effect against fish at 50 ㎍ ml<sup>-1</sup>. This study demonstrated for the first time the QSI potential of palauolide (1). Future research may assess the toxicity of both the cyclohexanic fraction of the sponge and palauolide (1) on fish, to confirm their potential as alternative to antibiotics in fish farming.
Kim, Hiyoung,Chin, Jungwook,Choi, Hyukjae,Baek, Kyungryul,Lee, Tae-Gu,Park, Seong Eon,Wang, Weihong,Hahn, Dongyup,Yang, Inho,Lee, Jihye,Mun, Bora,Ekins, Merrick,Nam, Sang-Jip,Kang, Heonjoong American Chemical Society 2013 Organic letters Vol.15 No.1
<P>Two unprecedented phosphorus-containing iodinated polyacetylenes, phosphoiodyns A and B (<B>1</B>–<B>2</B>), were isolated from a Korean marine sponge <I>Placospongia</I> sp. Their structures were elucidated by spectroscopic data analysis. Phosphoiodyn A exhibited potent agonistic activity on human peroxisome proliferator-activated receptor delta (hPPARδ) with an EC<SUB>50</SUB> of 23.7 nM.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2013/orlef7.2013.15.issue-1/ol3031318/production/images/medium/ol-2012-031318_0005.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol3031318'>ACS Electronic Supporting Info</A></P>
Cytotoxic scalarane sesterterpenes from a Korean marine sponge Psammocinia sp.
( Dongyup Hahn ),( Dong Hwan ),( Bora Mun ),( Hiyoung Kim ),( Chulkyeong Han ),( Weihong Wang ),( Taeho Chun ),( Sunhee Park ),( Dajeong Yoon ),( Hyukjae Choi ),( Sang Jip Nam ),( Merrick Ekins ),( Ju 영남대학교 약품개발연구소 2013 영남대학교 약품개발연구소 연구업적집 Vol.23 No.0
Three novel scalarane sesterterpenes were isolated from a Korean marine sponge, Psammocinia sp., along with four known derivatives. Their structures were elucidated on the basis of NMR, MS and IR spectroscopic data. The three new compounds are 12-deacetoxy-23-hydroxyscalaradial (1), 12-dehydroxy-23-hydroxyhyrtiolide (2) and 12-O-acetyl-16-deacetoxy-23-acetoxyscalarafuran (3), respectively, and the four known compounds are 12-deacetoxy-23-hydroxyheteronemin (4), 12-deacetoxy-23-acetoxy-19-O-acetylscalarin (5), 12-deacetoxy-23-O-acetoxyheteronemin (6) and 12-deacetoxyscalaradial (7). They exhibited cytotoxicity against intractable human cancer cell lines A498, ACHN, MIA-paca and PANC-1, with an IC50 range of 0.4-48 μM. ⓒ2013 Elsevier Ltd. All rights reserves.
( Hiyoung Kim ),( Jungwook Chin ),( Hyukjae Choi ),( Kyungryul Baek ),( Tae Gu Lee ),( Seong Eon Park ),( Weihong Wang ),( Dongyup Hahn ),( Inho Yang ),( Jihye Lee ),( Bora Mun ),( Merrick Ekins ),( S 영남대학교 약품개발연구소 2013 영남대학교 약품개발연구소 연구업적집 Vol.23 No.0
Two unprecedented phosphorus-containing iodinated polyacetylenes, phosphoiodyns A and B (1-2), were isolated from a Korean marine sponge Placospongia sp. Their structures were elucidated by spectroscopic data analysis. Phosphoiodyn A exhibited potent agonistic activity on human peroxisome proliferator-activated receptor delta (hPPARδ) with an EC(50) of 23.7 nM.
( Bora Mun ),( Wei Hong Wang ),( Hi Young Kim ),( Dong Yup Hahn ),( In Ho Yang ),( Dong Hwan Won ),( Eun Hee Kim ),( Ji Hye Lee ),( Chul Kyeong Han ),( Hyun Ji Kim ),( Merrick Ekins ),( Sang Jip Nam ) 영남대학교 약품개발연구소 2015 영남대학교 약품개발연구소 연구업적집 Vol.25 No.-
Three new sterols, 5α, 8α-epidioxy-24-norcho-lesta-6.9(11), 22-trien-3β-ol (1), 5α, 8α-epidioxy-cholesta-6.9(11), 24-trien-3β, 25-diol (3), with four known sterols (4-7) were isolated from a marine sponge Monanchora sp, Their chemical structures were elucidated by extensive spectro-scopic analysis. Compounds 1 and 3-7 showed moderate cytotoxicity against several human carcinoma cell lines including renal (A-498), pancreatic (PANC-1 and MLA paCa-2), and colorectal (HCT 116) cancer cell lines.