Prostaglandin Derivatives: Nonaromatic Phosphodiesterase‑4 Inhibitors from the Soft Coral Sarcophyton ehrenbergi
Ten new prostaglandin derivatives (PGs), sarcoehrendins A–J (1–10), together with five known analogues (11–15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4–8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurati...
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| Published in | Journal of natural products (Washington, D.C.) Vol. 77; no. 8; pp. 1928 - 1936 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society and American Society of Pharmacognosy
22.08.2014
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0163-3864 1520-6025 1520-6025 |
| DOI | 10.1021/np500394d |
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| Abstract | Ten new prostaglandin derivatives (PGs), sarcoehrendins A–J (1–10), together with five known analogues (11–15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4–8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a–11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13–15 exhibited inhibition with IC50 values less than 10 μM, and compound 15 (IC50 = 1.4 μM) showed comparable activity to the positive control rolipram (IC50 = 0.60 μM). The active natural PGs (2, 10, and 13–15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure–activity relationship is also proposed. |
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| AbstractList | Ten new prostaglandin derivatives (PGs), sarcoehrendins A–J (1–10), together with five known analogues (11–15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4–8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a–11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13–15 exhibited inhibition with IC₅₀ values less than 10 μM, and compound 15 (IC₅₀ = 1.4 μM) showed comparable activity to the positive control rolipram (IC₅₀ = 0.60 μM). The active natural PGs (2, 10, and 13–15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure–activity relationship is also proposed. Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4-8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a-11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13-15 exhibited inhibition with IC50 values less than 10 μM, and compound 15 (IC50 = 1.4 μM) showed comparable activity to the positive control rolipram (IC50 = 0.60 μM). The active natural PGs (2, 10, and 13-15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure-activity relationship is also proposed.Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4-8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a-11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13-15 exhibited inhibition with IC50 values less than 10 μM, and compound 15 (IC50 = 1.4 μM) showed comparable activity to the positive control rolipram (IC50 = 0.60 μM). The active natural PGs (2, 10, and 13-15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure-activity relationship is also proposed. Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4-8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a-11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13-15 exhibited inhibition with IC50 values less than 10 μM, and compound 15 (IC50 = 1.4 μM) showed comparable activity to the positive control rolipram (IC50 = 0.60 μM). The active natural PGs (2, 10, and 13-15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure-activity relationship is also proposed. Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4-8 represented the first examples of PGs featuring an 18 ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a-11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13-15 exhibited inhibition with IC50 values less than 10 microM, and compound 15 (IC50, = 1.4 microM) showed comparable activity to the positive control rolipram (IC50 = 0.60 microM). The active natural PGs (2, 10, and 13-15) represent the first examples of PDE4 inhibitors without an aromatic moiety and a preliminary structure-activity relationship is also proposed. Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4-8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a-11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13-15 exhibited inhibition with IC50 values less than 10 mu M, and compound 15 (IC50 = 1.4 mu M) showed comparable activity to the positive control rolipram (IC50 = 0.60 mu M). The active natural PGs (2, 10, and 13-15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure-activity relationship is also proposed. |
| Author | Fan, Cheng-Qi Cheng, Zhong-Bin Deng, Ya-Lin Luo, Hai-Bin Lin, Shu-Ling Yin, Sheng Han, Qing-Hua Tang, Gui-Hua |
| AuthorAffiliation | Chinese Academy of Fishery Sciences Sun Yat-sen University School of Pharmaceutical Sciences East China Sea Fisheries Research Institute |
| AuthorAffiliation_xml | – name: School of Pharmaceutical Sciences – name: Chinese Academy of Fishery Sciences – name: Sun Yat-sen University – name: East China Sea Fisheries Research Institute |
| Author_xml | – sequence: 1 givenname: Zhong-Bin surname: Cheng fullname: Cheng, Zhong-Bin – sequence: 2 givenname: Ya-Lin surname: Deng fullname: Deng, Ya-Lin – sequence: 3 givenname: Cheng-Qi surname: Fan fullname: Fan, Cheng-Qi – sequence: 4 givenname: Qing-Hua surname: Han fullname: Han, Qing-Hua – sequence: 5 givenname: Shu-Ling surname: Lin fullname: Lin, Shu-Ling – sequence: 6 givenname: Gui-Hua surname: Tang fullname: Tang, Gui-Hua – sequence: 7 givenname: Hai-Bin surname: Luo fullname: Luo, Hai-Bin email: luohb77@mail.sysu.edu.cn – sequence: 8 givenname: Sheng surname: Yin fullname: Yin, Sheng email: yinsh2@mail.sysu.edu.cn |
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| Snippet | Ten new prostaglandin derivatives (PGs), sarcoehrendins A–J (1–10), together with five known analogues (11–15) were isolated from the soft coral Sarcophyton... Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton... |
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| SubjectTerms | Animals Anthozoa - chemistry asthma Chemistry, Medicinal China corals Cyclic Nucleotide Phosphodiesterases, Type 4 - drug effects drugs inhibitory concentration 50 Life Sciences & Biomedicine Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pharmacology & Pharmacy Phosphodiesterase 4 Inhibitors - chemistry Phosphodiesterase 4 Inhibitors - isolation & purification Phosphodiesterase 4 Inhibitors - pharmacology Plant Sciences prostaglandins Prostaglandins - chemistry Prostaglandins - isolation & purification Prostaglandins - pharmacology Rolipram - pharmacology Sarcophyton Science & Technology spectral analysis Structure-Activity Relationship structure-activity relationships |
| Title | Prostaglandin Derivatives: Nonaromatic Phosphodiesterase‑4 Inhibitors from the Soft Coral Sarcophyton ehrenbergi |
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