A seco-laurane sesquiterpene and related laurane derivatives from the red alga Laurencia okamurai Yamada

Phytochemistry

Volumn 103, Issue , 2014, Pages 162-170

  Yu, Xiao Qing ^a   He, Wen Fei ^b   Liu, Ding Quan ^a   Feng, Mei Tang ^a   Fang, Yi ^a   Wang, Bin ^a   Feng, Li Hua ^a   Guo, Yue Wei ^b   Mao, Shui Chun ^a  

^a NANCHANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Antifungal activity; Bisabolane sesquiterpene; Cytotoxicity; Laurane sesquiterpene; Laurencia; Laurencia okamurai; Laurokamurane sesquiterpene; Rhodomelaceae; seco Laurokamurane sesquiterpene

Indexed keywords

ANTIFUNGAL AGENT; SESQUITERPENE;

ASPERGILLUS FUMIGATUS; CANDIDA GLABRATA; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CRYPTOCOCCUS NEOFORMANS; DRUG EFFECTS; HUMAN; LAURENCIA; TRICHOPHYTON; TUMOR CELL LINE;

ANTIFUNGAL AGENTS; ASPERGILLUS FUMIGATUS; CANDIDA GLABRATA; CELL LINE, TUMOR; CELL SURVIVAL; CRYPTOCOCCUS NEOFORMANS; HUMANS; LAURENCIA; MOLECULAR STRUCTURE; SESQUITERPENES; TRICHOPHYTON;

EID: 84901189256     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.03.021     Document Type: Article

References (40)

1. W.M. Abdel-Mageed, R. Ebel, F.A. Valeriote, and M. Jaspars Laurefurenynes A-F, new cyclic ether acetogenins from a marine red alga, Laurencia sp Tetrahedron 66 2010 2855 2862
2. W.M. Alarif, S.S. Al-Lihaibi, S.-E.N. Ayyad, M.H. Abdel-Rhman, and F.A. Badria Laurene-type sesquiterpenes from the Red Sea red alga Laurencia obtusa as potential antitumor-antimicrobial agents Eur. J. Med. Chem. 55 2012 462 466
3. M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, and M.R. Boyd Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay Cancer Res. 48 1988 589 601 (Pubitemid 18056527)
4. F. Cen-Pacheco, J.A. Villa-Pulgarin, F. Mollinedo, M. Norte, A.H. Daranas, and J.J. Fernandez Cytotoxic oxasqualenoids from the red alga Laurencia viridis Eur. J. Med. Chem. 46 2011 3302 3308
5. L.R. de Carvalho, M.T. Fujii, N.F. Roque, and J.H.G. Lago Aldingenin derivatives from the red alga Laurencia aldingensis Phytochemistry 67 2006 1331 1335 (Pubitemid 44080264)
6. C. Enzell, and H. Erdtman The chemistry of the natural order cupressales - XXI: cuparene and cuparenic acid, two sesquiterpenic compounds with a new carbon skeleton Tetrahedron 4 1958 361 368
7. C.J. Fletcher, D.J. Blair, K.M.P. Wheelhouse, and V.K. Aggarwal The total synthesis of (-)-aplysin via a lithiation-borylation-propenylation sequence Tetrahedron 68 2012 7598 7604
8. B.M. Howard, A.M. Nonomura, and W. Fenical Chemotaxonomy in marine algae: secondary metabolite synthesis by Laurencia in unialgal culture Biochem. Syst. Ecol. 8 1980 329 336
9. 15 Acetogenins from the red alga Laurencia obtusa Phytochemistry 59 2002 111 116 (Pubitemid 34073349)
10. T. Irie, and M. Suzuki Laurencin, a constituent from Laurencia species Tetrahedron Lett. 6 1965 1091 1099
11. M. Kladi, C. Vagias, P. Papazafiri, G. Furnari, D. Serio, and V. Roussis New sesquiterpenes from the red alga Laurencia microcladia Tetrahedron 63 2007 7606 7611 (Pubitemid 46970778)
12. G.M. Konig, and A.D. Wright Sesquiterpene contents of the antibacterial dichloromethane extract of the marine red alga Laurencia obtusa Planta Med. 63 1997 186 187 (Pubitemid 27196094)
13. C. Lhullier, M. Falkenberg, E. Ioannou, A. Quesada, P. Papazafiri, P.A. Horta, E.P. Schenkel, C. Vagias, and V. Roussis Cytotoxic halogenated metabolites from the Brazilian red alga Laurencia catarinensis J. Nat. Prod. 73 2010 27 32
14. X.-D. Li, F.-P. Miao, K. Li, and N.-Y. Ji Sesquiterpenes and acetogenins from the marine red alga Laurencia okamurai Fitoterapia 83 2012 518 522
15. X.-D. Li, F.-P. Miao, X.-L. Yin, J.-L. Liu, and N.-Y. Ji Sesquiterpenes from the marine red alga Laurencia composita Fitoterapia 83 2012 1191 1195
16. S.-C. Mao, and Y.-W. Guo Curparene-derived sesquiterpenes from the Chinese red alga Laurencia okamurai Yamada Helv. Chim. Acta 88 2005 1034 1039 (Pubitemid 40791161)
17. S.-C. Mao, and Y.-W. Guo A laurane sesquiterpene and rearranged derivatives from the Chinese red alga Laurencia okamurai Yamada J. Nat. Prod. 69 2006 1209 1211 (Pubitemid 44409797)
18. S.-C. Mao, and Y.-W. Guo Sesquiterpenes from Chinese red alga Laurencia okamurai Zhongguo Tianran Yaowu 8 2010 321 325
19. M. Masuda, T. Abe, S. Sato, T. Suzuki, and M. Suzuki Diversity of halogenated secondary metabolites in the red alga Laurencia nipponica (Rhodomelaceae, Ceramiales) J. Phycol. 33 1997 196 208 (Pubitemid 27253381)
20. M. Masuda, T. Abe, T. Suzuki, and M. Suzuki Morphological and chemotaxonomic studies on Laurencia composita and L. okamurae (Ceramiales, Rhodophyta) Phycologia 35 1996 550 562 (Pubitemid 126589265)
21. H. Nemoto, M. Nagamochi, H. Ishibashi, and K. Fukumoto A remarkable substituent effect on the enantioselectivity of tandem asymmetric epoxidation and enantiospecific ring expansion of cyclopropylidene alcohols: a new enantiocontrolled synthesis of (-)-debromoaplysin and (-)-aplysin J. Org. Chem. 59 1994 74 79 (Pubitemid 24095534)
22. G. Ohloff, W. Ciersch, R. Naf, and F. Delay The absolute configuration of β-bisabolol Helv. Chim. Acta 69 1986 698 703
23. A. Roy, and R.V. Venkateswaran Diverse reactivities of Corey-Chaykovsky ylides: synthesis of 10-hydroxyaplysin Synth. Commun. 42 2012 621 626
24. S. Sakemi, T. Higa, C.W. Jefford, and G. Bernardinelli Venustatriol. A new, anti-viral, triterpene tetracyclic ether from Laurencia venusta Tetrahedron Lett. 27 1986 4287 4290 (Pubitemid 16043572)
25. P.A. Skehan, R. Storeng, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl Cancer Inst. 82 1990 1107 1112 (Pubitemid 20213250)
26. A. Srikrishna, B. Beeraiah, and R.R. Babu Enantioselective total synthesis and assignment of the absolute configuration of (+)-laurokamurene B Tetrahedron Asymmetry 19 2008 624 627
27. A. Srikrishna, I.A. Khan, R.R. Babu, and A. Sajjanshetty The first total synthesis of (±)-laurokamurene B Tetrahedron 63 2007 12616 12620
28. J. Sun, L.-J. Han, D.-Y. Shi, X. Fan, S.-J. Wang, S. Li, Y.-C. Yang, and J.-G. Shi Sesquiterpene components of Laurencia tristicha Zhongcaoyao 37 2006 329 332 (Pubitemid 43670584)
29. J. Sun, D.-Y. Shi, S. Li, S.-J. Wang, L.-J. Han, X. Fan, Y.-C. Yang, and J.-G. Shi Chemical constituents of the red alga Laurencia tristicha J. Asian Nat. Prod. Res. 2007 9 2007 725 734 (Pubitemid 350130071)
30. M. Suzuki, M. Daitoh, C.S. Vairappan, T. Abe, and M. Masuda Novel halogenated metabolites from the Malaysian Laurencia pannosa J. Nat. Prod. 64 2001 597 602 (Pubitemid 32488675)
31. M. Suzuki, and E. Kurosawa New aromatic sesquiterpenoids from the red alga Laurencia okamurai Yamada Tetrahedron Lett. 19 1978 2503 2506
32. M. Suzuki, S. Nakano, Y. Takahashi, T. Abe, M. Masuda, H. Takahashi, and K. Kobayashi Brominated labdane-type diterpenoids from an Okinawan Laurencia sp J. Nat. Prod. 65 2002 801 804 (Pubitemid 34733980)
33. Y. Takahashi, M. Daitoh, M. Suzuki, T. Abe, and M. Masuda Halogenated metabolites from the New Okinawan red alga Laurencia yonaguniensis J. Nat. Prod. 65 2002 395 398 (Pubitemid 34260818)
34. S. Takano, M. Moriya, and K. Ogasawara Enantiocontrolled syntheses of the cuparene sesquiterpenes, (-)herbertene, (+)-β-cuparenone, (-)-debromoaplysin, and (-)-aplysin Tetrahedron Lett. 33 1992 329 332
35. J. Tallineau, G. Bashiardes, J.-M. Coustard, and F. Lecornue A one-pot preparation of aryl- and heteroarylcycloalkenes: application to the total synthesis of (±)-laurokamurene B Synlett 17 2009 2761 2764
36. J.-M. Tian, Y.-H. Shen, X.-W. Yang, S. Liang, L. Shan, H.-L. Li, R.-H. Liu, and W.-D. Zhang Antifungal cyclic peptides from Psammosilene tunicoides J. Nat. Prod. 73 2010 1987 1992
37. G. Topcu, Z. Aydogmus, S. Imre, A.C. Goeren, J.M. Pezzuto, J.A. Clement, and D.G.I. Kingston Brominated sesquiterpenes from the red alga Laurencia obtusa J. Nat. Prod. 66 2003 1505 1508 (Pubitemid 37490405)
38. C.S. Vairappan, M. Suzuki, T. Ishii, T. Okino, T. Abe, and M. Masuda Antibacterial activity of halogenated sesquiterpenes from Malaysian Laurencia spp Phytochemistry 69 2008 2490 2494
39. S. Yamamura, and Y. Hirata Structures of aplysin and aplysinol, naturally occurring bromo-compounds Tetrahedron 19 1963 1485 1496
40. F. Yang, M.T. Hamann, Y. Zou, M.-Y. Zhang, X.-B. Gong, J.-R. Xiao, W.-S. Chen, and H.-W. Lin Antimicrobial metabolites from the Paracel Islands sponge Agelas mauritiana J. Nat. Prod. 75 2012 774 778