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Yue-wei Guo - One of the best experts on this subject based on the ideXlab platform.
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further brominated polyacetylenes with pancreatic lipase inhibitory activity from chinese marine sponge Xestospongia testudinaria
Journal of Asian Natural Products Research, 2017Co-Authors: Min Yang, Linfu Liang, Ting Wang, Heyao Wang, Haili Liu, Yue-wei GuoAbstract:AbstractA new brominated polyacetylene, xestonariene I (1), along with three known related analogues (2–4), was obtained from Chinese marine sponge Xestospongia testudinaria. Its structure was determined on the basis of detailed spectroscopic analysis and by comparison with literature data. Compound 4 exhibited significant inhibitory activity against pancreatic lipase, which plays a key role in preventing obesity, with an IC50 value of 0.61 μM, being comparable to that of the positive control orlistat (IC50 = 0.78 μM).
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bioactive isoquinolinequinone alkaloids from the south china sea nudibranch jorunna funebris and its sponge prey Xestospongia sp
Future Medicinal Chemistry, 2016Co-Authors: Renyong Huang, Wenting Chen, Tibor Kurtan, Attila Mandi, Jian Ding, Yue-wei GuoAbstract:Background: Nudibranchs are slug-like invertebrates, well known as rich sources of biologically active secondary metabolites with highly chemical diversity and complexity. The production of such interesting metabolites was possibly influenced by their diet relationship with sponges such as Xestospongia. Results: Our continuous investigation of South China Sea nudibranch Jorunna funebris and its sponge-prey Xestospongia sp. led to the isolation of two new and eight known metabolites (1–10). The absolute configurations were determined by time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) method and by the comparison of ECD spectra. In bioassays, 1–4 and 7 showed strong NF-κB inhibitory activity, 4–6 exhibited considerable cytotoxicity against A549 and HL-60 tumor cell lines. Conclusion: Five unusual isoquinolinequinones (3, 7–10) were discovered from both two animals, further confirmed their predator–prey relationship. Preliminary bioassay results and structure–activity rel...
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new isoquinolinequinone alkaloids from the south china sea nudibranch jorunna funebris and its possible sponge prey Xestospongia sp
Fitoterapia, 2014Co-Authors: Meitang Feng, Margherita Gavagnin, Ernesto Mollo, Shuichun Mao, Yue-wei GuoAbstract:Abstract Two new renieramycin-type bistetrahydroisoquinolinequinone alkaloids, fennebricins A (1) and B (5), and one new isoquinolinequinone alkaloid, N-formyl-1,2-dihydrorenierol (7), were isolated from the skin of the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp., together with eight known metabolites, including three bistetrahydroisoquinolinequinones (2–4) and five isoquinolinequinones (8–12). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) and by comparison with data for related known compounds. All the metabolites except for 7 occurred simultaneously in the two animals, supporting recent ecological studies that the nudibranch J. funebris preys on the sponge of the genus Xestospongia.
Meitang Feng - One of the best experts on this subject based on the ideXlab platform.
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new isoquinolinequinone alkaloids from the south china sea nudibranch jorunna funebris and its possible sponge prey Xestospongia sp
Fitoterapia, 2014Co-Authors: Meitang Feng, Margherita Gavagnin, Ernesto Mollo, Shuichun Mao, Yue-wei GuoAbstract:Abstract Two new renieramycin-type bistetrahydroisoquinolinequinone alkaloids, fennebricins A (1) and B (5), and one new isoquinolinequinone alkaloid, N-formyl-1,2-dihydrorenierol (7), were isolated from the skin of the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp., together with eight known metabolites, including three bistetrahydroisoquinolinequinones (2–4) and five isoquinolinequinones (8–12). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) and by comparison with data for related known compounds. All the metabolites except for 7 occurred simultaneously in the two animals, supporting recent ecological studies that the nudibranch J. funebris preys on the sponge of the genus Xestospongia.
Naoki Saito - One of the best experts on this subject based on the ideXlab platform.
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Chemistry of Renieramycins. 15. Synthesis of 22‑O‑Ester Derivatives of Jorunnamycin A and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cells
2016Co-Authors: Natchanun Sirimangkalakitti, Naoki Saito, Kornvika Charupant, Supakarn Chamni, Pithi Chanvorachote, Nanae Mori, Khanit SuwanboriruxAbstract:Eighteen 22-O-ester derivatives of jorunnamycin A (2) were prepared via 2, and their cytotoxicity against human non-small-cell lung cancer (NSCLC) cells was evaluated. Preliminary study of the structure–cytotoxicity relationship revealed that the ester part containing a nitrogen-heterocyclic ring elevated the cytotoxicity of the 22-O-ester derivatives. Among them, 22-O-(4-pyridinecarbonyl) ester 6a is the most potent compound (IC50 1.1 and 1.6 nM), exhibiting 21-fold and 5-fold increases in cytotoxicity against the H292 and H460 NSCLC cell lines, respectively, relative to renieramycin M (1), the major cytotoxic bistetrahydroisoquinolinequinone alkaloid of the Thai blue sponge Xestospongia sp
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chemistry of renieramycins part 7 renieramycins t and u novel renieramycin ecteinascidin hybrid marine natural products from thai sponge Xestospongia sp
Tetrahedron Letters, 2009Co-Authors: Naomi Daikuhara, Surattana Amnuoypol, Khanit Suwanborirux, Yumiko Tada, Sachiyo Yamaki, Kornvika Charupant, Naoki SaitoAbstract:Abstract Two new bistetrahydroisoquinoline marine natural products, renieramycins T ( 1 ) and U ( 2 ), were isolated from the Thai blue sponge Xestospongia sp. and their structures were elucidated by comparing spectral data with those of renieramycin M ( 3a ) and ecteinascidin 770 ( 4a ). These compounds are the first reported examples of novel ecteinascidin–renieramycin hybrid natural products. Renieramycin T ( 1 ) showed strong cytotoxicity to several human cancer cell lines, its IC 50 values ranging from 4.7 to 98 nM.
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chemistry of renieramycins part 5 1 structure elucidation of renieramycin type derivatives o q r and s from thai marine sponge Xestospongia species pretreated with potassium cyanide
Journal of Natural Products, 2004Co-Authors: Surattana Amnuoypol, Khanit Suwanborirux, Sunibhond Pummangura, Akinori Kubo, Chieko Tanaka, Naoki SaitoAbstract:Four minor renieramycin-type derivatives, including renieramycins O (1o) and Q−S (1q−s), were isolated from the sponge Xestospongia sp. pretreated with potassium cyanide. Their structures were elucidated by comparison of spectral data with those of recently reported renieramycins M (1m) and N (1n). The results of transformation and cytotoxicity measurements are also described.
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chemistry of renieramycins part 3 1 isolation and structure of stabilized renieramycin type derivatives possessing antitumor activity from thai sponge Xestospongia species pretreated with potassium cyanide
Journal of Natural Products, 2003Co-Authors: Khanit Suwanborirux, Surattana Amnuoypol, Sunibhond Pummangura, Akinori Kubo, Chieko Tanaka, Anuchit Plubrukarn, Naoki SaitoAbstract:Renieramycins M (1m) and N (1n) were isolated from the Thai sponge Xestospongia sp., pretreated with potassium cyanide in methanolic buffer solution, and their structures and relative stereochemistries were elucidated on the basis of spectroscopic data. This strategy is the first example of the gram-scale preparation of this series of compounds and presents a potential solution for increasing the gram-scale supply of novel natural products from marine sources.
Renyong Huang - One of the best experts on this subject based on the ideXlab platform.
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bioactive isoquinolinequinone alkaloids from the south china sea nudibranch jorunna funebris and its sponge prey Xestospongia sp
Future Medicinal Chemistry, 2016Co-Authors: Renyong Huang, Wenting Chen, Tibor Kurtan, Attila Mandi, Jian Ding, Yue-wei GuoAbstract:Background: Nudibranchs are slug-like invertebrates, well known as rich sources of biologically active secondary metabolites with highly chemical diversity and complexity. The production of such interesting metabolites was possibly influenced by their diet relationship with sponges such as Xestospongia. Results: Our continuous investigation of South China Sea nudibranch Jorunna funebris and its sponge-prey Xestospongia sp. led to the isolation of two new and eight known metabolites (1–10). The absolute configurations were determined by time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) method and by the comparison of ECD spectra. In bioassays, 1–4 and 7 showed strong NF-κB inhibitory activity, 4–6 exhibited considerable cytotoxicity against A549 and HL-60 tumor cell lines. Conclusion: Five unusual isoquinolinequinones (3, 7–10) were discovered from both two animals, further confirmed their predator–prey relationship. Preliminary bioassay results and structure–activity rel...
M. Tailler - One of the best experts on this subject based on the ideXlab platform.
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The inositol 1,4,5-trisphosphate receptor regulates autophagy through its interaction with Beclin 1.
Cell Death and Differentiation, 2009Co-Authors: J. M. Vicencio, C. Ortiz, Alfredo Criollo, A. W. E. Jones, Olivier Kepp, L. Galluzzi, N. Joza, I. Vitale, E. Morselli, M. TaillerAbstract:The inositol 1,4,5-trisphosphate receptor (IP(3)R) is a major regulator of apoptotic signaling. Through interactions with members of the Bcl-2 family of proteins, it drives calcium (Ca(2+)) transients from the endoplasmic reticulum (ER) to mitochondria, thereby establishing a functional and physical link between these organelles. Importantly, the IP(3)R also regulates autophagy, and in particular, its inhibition/depletion strongly induces macroautophagy. Here, we show that the IP(3)R antagonist xestospongin B induces autophagy by disrupting a molecular complex formed by the IP(3)R and Beclin 1, an interaction that is increased or inhibited by overexpression or knockdown of Bcl-2, respectively. An effect of Beclin 1 on Ca(2+) homeostasis was discarded as siRNA-mediated knockdown of Beclin 1 did not affect cytosolic or luminal ER Ca(2+) levels. Xestospongin B- or starvation-induced autophagy was inhibited by overexpression of the IP(3)R ligand-binding domain, which coimmunoprecipitated with Beclin 1. These results identify IP(3)R as a new regulator of the Beclin 1 complex that may bridge signals converging on the ER and initial phagophore formation.