Terpenoids from the octocorals Menella sp. (plexauridae) and Lobophytum crassum (alcyonacea)

Marine Drugs

Volumn 10, Issue 2, 2012, Pages 427-438

  Lee, Cheng Hung ^a,b,c   Kao, Chia Ying ^d,e   Kao, Shih Yao ^d,e   Chang, Chih Han ^a   Su, Jui Hsin ^d,e,f   Hwang, Tsong Long ^g   Kuo, Yueh Hsiung ^h   Wen, Zhi Hong ^f   Sung, Ping Jyun ^d,e,f  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^b HUNGKUANG UNIVERSITY   (Taiwan)

^c TAICHUNG VETERANS GENERAL HOSPITAL   (Taiwan)

^d NATIONAL DONG HWA UNIVERSITY   (Taiwan)

^e NATIONAL MUSEUM OF MARINE BIOLOGY AND AQUARIUM   (Taiwan)

^f NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^g CHANG GUNG UNIVERSITY   (Taiwan)

^h CHINA MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Cembrane; Elastase; Germacrane; Lobocrassin; Lobophytum; Menella; Menelloide

Indexed keywords

ELASTASE; LOBOCRASSIN F; MENELLOIDE E; O ACETYLLOBOCRASSIN F; SUPEROXIDE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CORAL; DRUG ACTIVITY; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME RELEASE; HUMAN; HUMAN CELL; IC 50; LOBOPHYTUM CRASSUM; MENELLA; NEUTROPHIL;

ALCYONACEA; LOBOPHYTUM; LOBOPHYTUM CRASSUM; MENELLA; PLEXAURIDAE;

EID: 84863234103     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md10020427     Document Type: Article

References (34)

1. Fraga, B.M. Natural sesquiterpenoids. Nat. Prod. Rep. 2011, 28, 1580-1610.
2. Blunt, J.W.; Copp, B.R.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2011, 28, 196-268.
3. Harper, M.K.; Bugni, T.S.; Copp, B.R.; James, R.D.; Lindsay, B.S.; Richardson, A.D.; Schnabel, P.C.; Tasdemir, D.; VanWagoner, R.M.; Verbitski, S.M.; Ireland, C.M. Introduction to the Chemical Ecology of Marine Natural Products. In Marine Chemical Ecology; McClintock, J.B., Baker, B.J., Eds.; CRC Press: Washington, DC, USA, 2001; pp. 3-69.
4. Bayer, F.M. Key to the genera of Octocorallia exclusive of Pennatulacea (Coelenterata: Anthozoa), with diagnoses of new taxa. Proc. Biol. Soc. Wash. 1981, 94, 902-947.
5. Fabricius, K.; Alderslade, P. Soft Corals and Sea Fans - A Comprehensive Guide to the Tropical Shallow-Water Genera of the Central-West Pacific, the Indian Ocean and the Red Sea, 1st ed.; Australian Institute of Marine Science: Queensland, Australia, 2001; pp. 49-50, 59-60, 94-97, 206-207.
6. Deng, S.; Peng, S.; Li, F.; Tan, X.; Chen, J. A study on chemical constituents of South China Sea gorgonian Menella spinifera Kukenthal (I). Guangzhou Chem. 1993, 44-47.
7. Li, F.; Deng, S.; Rao, Z.; Wu, H.; Xu, J. Studies on chemical constituents of South China Sea gorgonian Menella spinifera Kukenthal (II). Guangzhou Chem. 1996, 49-51.
8. Deng, S.; Li, F.; Peng, S.; Rao, Z.; Wu, H.; Xu, J. Chemical constituents of the South China Sea gorgonian Menella spinifera Kukenthal. Chin. J. Appl. Chem. 1997, 14, 80-82.
9. Zhang, W.; Guo, Y.-W.; Mollo, E.; Cimino, G. Menverins A-D, new highly oxygenated guaiane lactones from Hainan gorgonian Menella verrucosa (Brundin). Helv. Chim. Acta 2004, 87, 2919-2925. (Pubitemid 40037242)
10. Zhang, W.; Huang, H.; Ding, Y.; Gavagnin, M.; Mollo, E.; Cimino, G.; Guo, Y.-W. Three new polyoxygenated steroids from two species of the South China Sea gorgonian Muricella flexuosa and Menella verrucosa Brundin. Helv. Chim. Acta 2006, 89, 813-820.
11. Li, L.; Wang, C.-Y.; Huang, H.; Mollo, E.; Cimino, G.; Guo, Y.-W. Further highly oxygenated guaiane lactones from the South China Sea gorgonian Menella sp. Helv. Chim. Acta 2008, 91, 111-117. (Pubitemid 351196087)
12. Chai, X.-Y.; Sun, J.-F.; Tang, L.-Y.; Yang, X.-W.; Li, Y.-Q.; Huang, H.; Zhou, X.-F.; Yang, B.; Liu, Y. A novel cyclopentene derivative and a polyhydroxylated steroid from a South China Sea gorgonian Menella sp. Chem. Pharm. Bull. 2010, 58, 1391-1394.
13. Kao, S.-Y.; Chang, Y.-C.; Su, J.-H.; Lu, M.-C.; Chen, Y.-H.; Sheu, J.-H.; Wen, Z.-H.; Wang, W.-H.; Kuo, Y.-H.; Hwang, T.-L.; Sung, P.-J. (-)-Hydroxylindestrenolide, a new sesquiterpenoid from a gorgonian coral Menella sp. (Plexauridae). Chem. Pharm. Bull. 2011, 59, 1048-1050.
14. Kao, S.-Y.; Su, J.-H.; Hwang, T.-L.; Sheu, J.-H.; Su, Y.-D.; Lin, C.-S.; Chang, Y.-C.; Wang, W.-H.; Fang, L.-S.; Sung, P.-J. Discovery of novel sesquiterpenoids from a gorgonian Menella sp. Tetrahedron 2011, 67, 7311-7315.
15. Kao, S.-Y.; Su, J.-H.; Hwang, T.-L.; Sheu, J.-H.; Wen, Z.-H.; Wu, Y.-C.; Sung, P.-J. Menelloides C and D, new sesquiterpenoids from the gorgonian coral Menella sp. Mar. Drugs 2011, 9, 1534-1542.
16. Sung, P.-J.; Kao, S.-Y.; Kao, C.-Y.; Chang, Y.-C.; Chen, Y.-H.; Su, Y.-D. Seco-germacrane anhydride: Occurrence of a sesquiterpene lactone in the gorgonian coral Menella sp. (Plexauridae). Biochem. Syst. Ecol. 2012, 40, 53-55.
17. Imbs, A.B.; Demidkova, D.A.; Dautova, T.N.; Latyshev, N.A. Fatty acid biomarkers of symbionts and unusual inhibition of tetracosapolyenoic acid biosynthesis in corals (octocorallia). Lipids 2009, 44, 325-335.
18. Allinger, N.L. Conformational analysis. 130. MM2. A hydrocarbon force field utilizing V1 and V2 torsional terms. J. Am. Chem. Soc. 1977, 99, 8127-8134.
19. Duh, C.-Y.; Wang, S.-K.; Huang, B.-T.; Dai, C.-F. Cytotoxic cembrenolide diterpenes from the Formosan soft coral Lobophytum crassum. J. Nat. Prod. 2000, 63, 884-885. (Pubitemid 30452201)
20. Chao, C.-H.; Wen, Z.-H.; Wu, Y.-C.; Yeh, H.-C.; Sheu, J.-H. Cytotoxic and anti-inflammatory cembranoids from the soft coral Lobophytum crassum. J. Nat. Prod. 2008, 71, 1819-1824.
21. Lin, S.-T.; Wang, S.-K.; Cheng, S.-Y.; Duh, C.-Y. Lobocrasol, a new diterpenoid from the soft coral Lobophytum crassum. Org. Lett. 2009, 11, 3012-3014.
22. Liao, Z.-J.; Su, H.-J.; Shyue, Y.-C.; Wen, Z.-H.; Sheu, J.-H.; Su, J.-H. Two new cembranoids from the soft coral Lobophytum crassum. Bull. Chem. Soc. Jpn. 2011, 84, 653-655.
23. Tseng, Y.-J.; Wen, Z.-H.; Hsu, C.-H.; Dai, C.-F.; Sheu, J.-H. Bioactive cembranoids from the Dongsha atoll soft coral Lobophytum crassum. Bull. Chem. Soc. Jpn. 2011, 84, 1102-1106.
24. Kao, C.-Y.; Su, J.-H.; Lu, M.-C.; Hwang, T.-L.; Wang, W.-H.; Chen, J.-J.; Sheu, J.-H.; Kuo, Y.-H.; Weng, C.-F.; Fang, L.-S.; Wen, Z.-H.; Sung, P.-J. Lobocrassins A-E: New cembrane-type diterpenoids from the soft coral Lobophytum crassum. Mar. Drugs 2011, 9, 1319-1331.
25. Lee, N.-L.; Su, J.-H. Tetrahydrofuran cembranoids from the cultured soft coral Lobophytum crassum. Mar. Drugs 2011, 9, 2526-2536.
26. Lin, S.-T.; Wang, S.-K.; Duh, C.-Y. Cembranoids from the Dongsha atoll soft coral Lobophytum crassum. Mar. Drugs 2011, 9, 2705-2716.
27. Chao, C.-H.; Huang, H.-C.; Wu, Y.-C.; Lu, C.-K.; Dai, C.-F.; Sheu, J.-H. Glycolipids from the Formosan soft coral Lobophytum crassum. Chem. Pharm. Bull. 2007, 55, 1720-1723. (Pubitemid 350232544)
28. Cheng, S.-Y.; Lin, S.-T.; Wang, S.-K.; Duh, C.-Y. α-Tocopherols from the Formosan soft coral Lobophytum crassum. Bull. Chem. Soc. Jpn. 2011, 84, 783-787.
29. Lu, Y.; Huang, C.-Y.; Lin, Y.-F.; Wen, Z.-H.; Su, J.-H.; Kuo, Y.-H.; Chiang, M.Y.; Sheu, J.-H. Anti-inflammatory cembranoids from the soft coral Sinularia querciformis and Sinularia granosa. J. Nat. Prod. 2008, 71, 1754-1759.
30. Marrero, J.; Benítez, J.; Rodríguez, A.D.; Zhao, H.; Raptis, R.G. Bipinnatins K-Q, minor cembrane-type diterpenes from the West Indian gorgonian Pseudopterogorgia kallos: Isolation, structure assignment, and evaluation of biological activities. J. Nat. Prod. 2008, 71, 381-389. (Pubitemid 351549360)
31. Chen, S.-Y.; Wen, Z.-H.; Wang, S.-K.; Chiou, S.-F.; Hsu, C.-H.; Dai, C.-F.; Chiang, M.Y.; Duh, C.-Y. Unprecedented hemiketal cembranolides with anti-inflammatory activity from the soft coral Lobophytum durum. J. Nat. Prod. 2009, 72, 152-155.
32. Chao, C.-H.; Chou, K.-J.; Huang, C.-Y.; Wen, Z.-H.; Hsu, C.-H.; Wu, Y.-C.; Dai, C.-F.; Sheu, J.-H. Bioactive cembranoids from the soft coral Sinularia crassa. Mar. Drugs 2011, 9, 1955-1968.
33. Yu, H.-P.; Hsieh, P.-W.; Chang, Y.-J.; Chung, P.-J.; Kuo, L.-M.; Hwang, T.-L. 2-(2-Fluorobenzamido)benzoate ethyl ester (EFB-1) inhibits superoxide production by human neutrophils and attenuates hemorrhagic shock-induced organ dysfunction in rats. Free Radic. Biol. Med. 2011, 50, 1737-1748.
34. Hwang, T.-L.; Wang, C.-C.; Kuo, Y.-H.; Huang, H.-C.; Wu, Y.-C.; Kuo, L.-M.; Wu, Y.-H. The hederagenin saponin SMG-1 is a natural FMLP receptor inhibitor that suppresses human neutrophil activation. Biochem. Pharmacol. 2010, 80, 1190-1200.