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Manzamine Alkaloids from an <i>Acanthostrongylophora</i> sp. Sponge
Kim, Chang-Kwon,Riswanto, Riswanto,Won, Tae Hyung,Kim, Heegyu,Elya, Berna,Sim, Chung J.,Oh, Dong-Chan,Oh, Ki-Bong,Shin, Jongheon American Society of Pharmacognosy 2017 Journal of natural products Vol.80 No.5
<P>Five new manzamine alkaloids (1 S) and new salt forms of two known manzamines (6 and 7), along with sven known compounds (8-14) of the same structural class, were isolated from an Indonesian Acanthostrongylophora sp. sponge. On the basis of the results of combined spectroscopic analyses, the structure of kepulauamine A (1) was determined to possess an unprecedented pyrrolizine moiety, while others were functional group variants of known maillamines, These compounds exhibited weak cytotoxicity, moderate antibacterial activity, and mild inhibition against the enzyme isocitrate lyase.</P>
Terpenylated coumarins as SIRT1 activators isolated from Ailanthus altissima.
Dao, Trong-Tuan,Tran, Tien-Lam,Kim, Jayeon,Nguyen, Phi-Hung,Lee, Eun-Hee,Park, Junsoo,Jang, Ik-Soon,Oh, Won-Keun American Society of Pharmacognosy ; American Chemi 2012 Journal of natural products Vol.75 No.7
<P>Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2'R,3'R)-7-(2',3'-dihydroxy-3',7'-dimethylocta-6'-enyloxy)-6,8-dimethoxycoumarin (1), 6,8-dimethoxy-7-(3',7'-dimethylocta-2',6'-dienyloxy)coumarin (2), (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2'R,3'R,4'S,5'S)-6,8-dimethoxy-7-(3',7'-dimethyl-4',5'-epoxy-2'-hydroxyocta-6'-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1 activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may serve as lead molecules for the treatment of some age-related disorders.</P>
Choi, Seul-Ki,Mun, Gil-Im,Choi, Eun,Kim, Seo-Young,Kwon, Youngjoo,Na, Younghwa,Lee, Yun-Sil American Society of Pharmacognosy 2017 Journal of natural products Vol.80 No.8
<P>Coniferyl aldehyde (1) is previously reported as a potent inducer of heat shock factor 1 (HSF1). Here, we further examined the active pharmacophore of 1 for activation of HSF1 using the derivatives coniferyl alcohol (2), 4-hydroxy-3-methoxyphenylpropanal (3), and 4-hydroxy-3-methoxyphenylpropanol (4). Both 1 and 2 resulted in increased survival days after a lethal radiation (IR) dose. The decrease in bone marrow (BM) cellularity and Ki67-positive BM cells by IR was also significantly restored by 1 or 2 in mice. These results suggested that the vinyl moiety of 1 and 2 is necessary for inducing HSF1, which may be useful for developing small molecules for cytoprotection of normal cells against damage by cytotoxic drugs and radiation.</P>
Choi, Byeoung-Kyu,Phan, Thi Hoai Trinh,Hwang, Sunghoon,Oh, Dong-Chan,Kang, Jong Soon,Lee, Hwa-Sun,Ngo, Thi Duy Ngoc,Tran, Thi Thanh Van,Shin, Hee Jae American Society of Pharmacognosy 2019 Journal of natural products Vol.82 No.11
<P>Two new glycosylated alkylresorcinols, resorcinosides A (<B>1</B>) and B (<B>2</B>), were isolated from a strain of the fungus <I>Penicillium janthinellum</I> derived from a marine sediment sample collected from Cu Lao Cham Island, Vietnam. The structures of <B>1</B> and <B>2</B> were established by interpretation of 1D and 2D NMR and high-resolution ESIMS data, and their absolute configurations were confirmed by the coupling constant of the anomeric proton, acid hydrolysis, subsequent HPLC analysis, Mosher’s method, and quantum-mechanics-based computational analysis of NMR chemical shifts. The structure elucidation indicated that <B>1</B> and <B>2</B> are new alkylresorcinols with <SMALL>D</SMALL>-glucose, and <B>2</B> has an α-pyrone moiety attached to the aromatic ring. Compound <B>1</B> exhibited cytotoxic activity against the NUGC-3 cancer cell line with a GI<SUB>50</SUB> value of 9.3 μM.</P> [FIG OMISSION]</BR>
Salternamides A-D from a Halophilic Streptomyces sp. Actinobacterium.
Kim, Seong-Hwan,Shin, Yoonho,Lee, So-Hyoung,Oh, Ki-Bong,Lee, Sang Kook,Shin, Jongheon,Oh, Dong-Chan American Society of Pharmacognosy ; American Chemi 2015 Journal of natural products Vol.78 No.4
<P>Salternamides A-D (1-4), the first secondary metabolites discovered from saltern-derived actinomycetes, were isolated from a halophilic Streptomyces strain isolated from a saltern on Shinui Island in the Republic of Korea. The planar structures of the salternamides, which are new members of the manumycin family, were elucidated by a combination of spectroscopic analyses. The absolute configurations of the salternamides were determined by chemical and spectroscopic methods, including the modified Mosher's method, J-based configuration analysis, and circular dichroism spectroscopy. Salternamide A (1), which is the first chlorinated compound in the manumycin family, exhibited potent cytotoxicity against a human colon cancer cell line (HCT116) and a gastric cancer cell line (SNU638) with submicromolar IC50 values. Salternamides A and D were also determined to be weak Na(+)/K(+) ATPase inhibitors.</P>
Lee, IkSoo,Kim, Junghyun,Kim, Young Sook,Yoo, Nam Hee,Kim, Chan-Sik,Jo, Kyuhyung,Kim, Joo-Hwan,Bach, Tran The,Kim, Jin Sook American Society of Pharmacognosy ; American Chemi 2012 Journal of natural products Vol.75 No.7
<P>Six new cycloartane-type triterpenes (1-6), 24-methylenecycloartane-3관,6관,7관-triol (1), 24-methylenecycloartane-3관,6관,7관,16관-tetraol (2), 24-methylenecycloartane-3관,6관,16관-triol (3), 24-methylenecycloartane-3관,7관,16관-triol 3-O-관-d-xylopyranoside (4), 24-methylenecycloartane-3관,6관,16관-triol 3-O-관-d-xylopyranoside (5), and 24-methylenecycloartane-3관,6관,7관-triol 3-O-관-d-xylopyranoside (6), were isolated from the leaves of Homonoia riparia, together with one known compound, 24-methylenecycloartane-3관,6관,7관,16관-tetraol 3-O-관-d-xylopyranoside (7). The structures of the new triterpenes were established by spectroscopic studies and from chemical evidence, and the inhibitory effects of compounds 1 and 3-7 on VEGF-induced vascular permeability were examined in vivo in rats using the Miles assay. In addition, the inhibitory effect of 7 on VEGF-induced tube formation by HUVECs in vitro was investigated.</P>
Kim, Yu Jin,Kim, Hyun-Ju,Kim, Geon-Woo,Cho, Kyungyun,Takahashi, Shunya,Koshino, Hiroyuki,Kim, Won-Gon American Society of Pharmacognosy 2016 Journal of natural products Vol.79 No.9
<P>Two new potent anti-Gram negative compounds, coralmycins A (1) and B (2), were isolated from cultures of the myxobacteria Corallococcus coralloides M23, together with another derivative (3) that was identified as the very recently reported cystobactamid 919-2. Their structures including the relative stereochemistry were elucidated by interpretation of spectroscopic, optical rotation, and CD data. The relative stereochemistry of 3 was revised to 'S*R*' NMR analysis. The antibacterial activity of 1 was most potent against Gram-negative pathogens, including Escherichia coli, Pseudomonas aeruginosa, Acinetobacter baumanii, and Klebsiella pneumoniae. with MICs of 0.1-4 mu g/mL; these MICs were 4-10 and 40-100 times stronger than the antibacterial activities of 3 and 2, respectively. Thus, these data indicated that the beta-methoxyasparagine unit and the hydroxy group of the benzoic acid unit were critical for antibacterial activity.</P>
Nortriterpene glycosides of the sarasinoside class from the sponge Lipastrotethya sp.
Lee, Jung-Ho,Jeon, Ju-eun,Lee, Yeon-Ju,Lee, Hyi-Seung,Sim, Chung J,Oh, Ki-Bong,Shin, Jongheon American Society of Pharmacognosy ; American Chemi 2012 Journal of natural products Vol.75 No.7
<P>Five new nortriterpene glycosides, along with eight known compounds of the sarasinoside class, were isolated from the tropical sponge Lipastrotethya sp. collected from Chuuk, Micronesia. The structures of these new compounds, designated as sarasinosides N-R (9-13), were determined by combined spectroscopic and chemical methods. The aglycone portions of 10-13 were found to be unprecedented among nortriterpeneoids on the basis of extensive NMR analyses. Several of these compounds exhibited cytotoxicity against A549 and K562 cell lines as well as weak inhibitory activity against Na(+)/K(+)-ATPase.</P>
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>
Antiproliferative Pterocarpans and Coumestans from <i>Lespedeza bicolor</i>
Thuy, Nguyen Thi Thanh,Lee, Joo-Eun,Yoo, Hee Min,Cho, Namki American Society of Pharmacognosy 2019 Journal of natural products Vol.82 No.11
<P>Chromatographic purification of a methanol extract of the roots of <I>Lespedeza bicolor</I> led to the isolation of four new pterocarpans (<B>1</B>-<B>4</B>), two new coumestans (<B>6</B> and <B>7</B>), two new arylbenzofurans (<B>8</B> and <B>9</B>), and the known pterocarpan 1-methoxyerythrabyssin II (<B>5</B>). Their structures were identified using NMR spectroscopy, UV spectroscopy, and mass spectrometry. Cytotoxicity assays showed that compounds <B>1</B>-<B>9</B> exerted antiproliferative effects on blood cancer cells. Of these compounds, <B>1</B> and <B>6</B> induced mitochondrial depolarization and induced apoptosis in Jurkat cells. These compounds promoted cell death by inducing cell-cycle arrest at the G1 stage, reducing levels of BCL2, and increasing cleavage of PARP-1. These findings indicate that <B>1</B> and <B>6</B> are possible lead compounds for the treatment of human leukemia cells via intracellular signaling.</P> [FIG OMISSION]</BR>