全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...
Marine Drugs  2012 

Briarenolides F and G, New Briarane Diterpenoids from a Briareum sp. Octocoral

DOI: 10.3390/md10051156

Keywords: briarenolide, briarane, Briareum, superoxide anion

Full-Text   Cite this paper   Add to My Lib

Abstract:

Two new briarane diterpenoids, briarenolides, F ( 1) and G ( 2), were isolated from an octocoral identified as Briareum sp. The structures of briaranes 1 and 2 were established by spectroscopic methods and by comparison of the spectroscopic data with those of known briarane analogues. Briarenolide F was proven to be the first 6-hydroperoxybriarane derivative and this compound displayed a significant inhibitory effect on the generation of superoxide anion by human neutrophils.

References

[1]  Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.G.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2012, 29, 144–222, doi:10.1039/c2np00090c.
[2]  Berrue, F.; Kerr, R.G. Diterpenes from gorgonian corals. Nat. Prod. Rep. 2009, 26, 681–710, doi:10.1039/b821918b.
[3]  Hanson, J.R. Diterpenoids. Nat. Prod. Rep. 2009, 26, 1156–1171, doi:10.1039/b807311m.
[4]  Sung, P.-J.; Sheu, J.-H.; Xu, J.-P. Survey of briarane-type diterpenoids of marine origin. Heterocycles 2002, 57, 535–579, doi:10.3987/REV-01-546.
[5]  Sung, P.-J.; Chang, P.-C.; Fang, L.-S.; Sheu, J.-H.; Chen, W.-C.; Chen, Y.-P.; Lin, M.-R. Survey of briarane-related diterpenoids—Part II. Heterocycles 2005, 65, 195–204, doi:10.3987/REV-04-589.
[6]  Sung, P.-J.; Sheu, J.-H.; Wang, W.-H.; Fang, L.-S.; Chung, H.-M.; Pai, C.-H.; Su, Y.-D.; Tsai, W.-T.; Chen, B.-Y.; Lin, M.-R.; et al. Survey of briarane-type diterpenoids—Part III. Heterocycles 2008, 75, 2627–2648, doi:10.3987/REV-08-633.
[7]  Sung, P.-J.; Su, J.-H.; Wang, W.-H.; Sheu, J.-H.; Fang, L.-S.; Wu, Y.-C.; Chen, Y.-H.; Chung, H.-M.; Su, Y.-D.; Chang, Y.-C. Survey of briarane-type diterpenoids—Part IV. Heterocycles 2011, 83, 1241–1258.
[8]  Sheu, J.-H.; Sung, P.-J.; Huang, L.-H.; Lee, S.-F.; Wu, T.; Chang, B.-Y.; Duh, C.-Y.; Fang, L.-S.; Soong, K.; Lee, T.-J. New cytotoxic briaran diterpenes from the Formosan gorgonian Briareum sp. J. Nat. Prod. 1996, 59, 935–938.
[9]  Sheu, J.-H.; Sung, P.-J.; Cheng, M.-C.; Liu, H.-Y.; Fang, L.-S.; Duh, C.-Y.; Chiang, M.Y. Novel cytotoxic diterpenes, excavatolides A-E, isolated from the Formosan gorgonian Briareum excavatum. J. Nat. Prod. 1998, 61, 602–608, doi:10.1021/np970553w.
[10]  Sung, P.-J.; Su, J.-H.; Wang, G.-H.; Lin, S.-F.; Duh, C.-Y.; Sheu, J.-H. Excavatolides F-M, new briarane diterpenes from the gorgonian Briareum excavatum. J. Nat. Prod. 1999, 62, 457–463.
[11]  Sheu, J.-H.; Sung, P.-J.; Su, J.-H.; Wang, G.-H.; Duh, C.-Y.; Shen, Y.-C.; Chiang, M.Y.; Chen, I.-T. Excavatolides U-Z, new briarane diterpenes from the Gorgonian Briareum excavatum. J. Nat. Prod. 1999, 62, 1415–1420.
[12]  Sheu, J.-H.; Sung, P.-J.; Su, J.-H.; Liu, H.-Y.; Duh, C.-Y.; Chiang, M.Y. Briaexcavatolides A-J, new diterpenes from the gorgonian Briareum excavatum. Tetrahedron 1999, 55, 14555–14564.
[13]  Sung, P.-J.; Su, J.-H.; Duh, C.-Y.; Chiang, M.Y.; Sheu, J.-H. Briaexcavatolides K-N, new briarane diterpenes from the gorgonian Briareum excavatum. J. Nat. Prod. 2001, 64, 318–323.
[14]  Wu, S.-L.; Sung, P.-J.; Chiang, M.Y.; Wu, J.-Y.; Sheu, J.-H. New polyoxygenated briarane diterpenoids, briaexcavatolides O-R, from the gorgonian Briareum excavatum. J. Nat. Prod. 2001, 64, 1415–1420, doi:10.1021/np010253l.
[15]  Wu, S.-L.; Sung, P.-J.; Su, J.-H.; Sheu, J.-H. Briaexcavatolides S-V, four new briaranes from a Formosan gorgonian Briareum excavatum. J. Nat. Prod. 2003, 66, 1252–1256, doi:10.1021/np030102d.
[16]  Wu, S.-L.; Sung, P.-J.; Su, J.-H.; Wang, G.-H.; Sheu, J.-H. Briaexcavatolide W, a new diterpenoid from Briareum excavatum. Heterocycles 2004, 63, 895–898, doi:10.3987/COM-04-10004.
[17]  Sung, P.-J.; Hu, W.-P.; Wu, S.-L.; Su, J.-H.; Fang, L.-S.; Wang, J.-J.; Sheu, J.-H. Briaexcavatolides X-Z, three new briarane-related derivatives from the gorgonian coral Briareum excavatum. Tetrahedron 2004, 60, 8975–8979.
[18]  Sung, P.-J.; Hu, W.-P.; Fang, L.-S.; Fan, T.-Y.; Wang, J.-J. Briarenol A, a new diterpenoid from a gorgonian Briareum sp. (Briareidae). Nat. Prod. Res. 2005, 19, 689–694, doi:10.1080/14786410512331330611.
[19]  Sung, P.-J.; Chao, C.-H.; Chen, Y.-P.; Su, J.-H.; Hu, W.-P.; Sheu, J.-H. Briaexcavatins A and B, novel briaranes from the octocoral Briareum excavatum. Tetrahedron Lett. 2006, 47, 167–170.
[20]  Sung, P.-J.; Chen, Y.-P.; Hwang, T.-L.; Hu, W.-P.; Fang, L.-S.; Wu, Y.-C.; Li, J.-J.; Sheu, J.-H. Briaexcavatins C-F, four new briarane-related diterpenoids from the Formosan octocoral Briareum excavatum (Briareidae). Tetrahedron 2006, 62, 5686–5691.
[21]  Chen, Y.-P.; Wu, S.-L.; Su, J.-H.; Lin, M.-R.; Hu, W.-P.; Hwang, T.-L.; Sheu, J.-H.; Fan, T.-Y.; Fang, L.-S.; Sung, P.-J. Briaexcavatins G and H, two new briaranes from the octocoral Briareum excavatum. Bull. Chem. Soc. Jpn. 2006, 79, 1900–1905, doi:10.1246/bcsj.79.1900.
[22]  Su, J.-H.; Sung, P.-J.; Kuo, Y.-H.; Hsu, C.-H.; Sheu, J.-H. Briarenolides A-C, briarane diterpenoids from the gorgonian coral Briareum sp. Tetrahedron 2007, 63, 8282–8285.
[23]  Sung, P.-J.; Lin, M.-R.; Su, Y.-D.; Chiang, M.Y.; Hu, W.-P.; Su, J.-H.; Cheng, M.-C.; Hwang, T.-L.; Sheu, J.-H. New briaranes from the octocorals Briareum excavatum (Briareidae) and Junceella fragilis (Ellisellidae). Tetrahedron 2008, 64, 2596–2604.
[24]  Sung, P.-J.; Lin, M.-R.; Hwang, T.-L.; Fan, T.-Y.; Su, W.-C.; Ho, C.-C.; Fang, L.-S.; Wang, W.-H. Briaexcavatins M-P, four new briarane-related diterpenoids from cultured octocoral Briareum excavatum (Briareidae). Chem. Pharm. Bull. 2008, 56, 930–935, doi:10.1248/cpb.56.930.
[25]  Hwang, T.-L.; Lin, M.-R.; Tsai, W.-T.; Yeh, H.-C.; Hu, W.-P.; Sheu, J.-H.; Sung, P.-J. New polyoxygenated briaranes from octocorals Briareum excavatum and Ellisella robusta. Bull. Chem. Soc. Jpn. 2008, 81, 1638–1646, doi:10.1246/bcsj.81.1638.
[26]  Sung, P.-J.; Lin, M.-R.; Chiang, M.Y. The structure and absolute stereochemistry of briaexcavatin U, a new chlorinated briarane from a cultured octocoral Briareum excavatum. Chem. Lett. 2009, 38, 154–155.
[27]  Sung, P.-J.; Lin, M.-R.; Chiang, M.Y.; Hwang, T.-L. Briaexcavatins V-Z, discovery of new briaranes from a cultured octocoral Briareum excavatum. Bull. Chem. Soc. Jpn. 2009, 82, 987–996, doi:10.1246/bcsj.82.987.
[28]  Sung, P.-J.; Su, Y.-D.; Li, G.-Y.; Chiang, M.Y.; Lin, M.-R. Excavatoids A-D, new polyoxygenated briaranes from the octocoral Briareum excavatum. Tetrahedron 2009, 65, 6918–6924.
[29]  Sung, P.-J.; Chen, B.-Y.; Lin, M.-R.; Hwang, T.-L.; Wang, W.-H.; Sheu, J.-H.; Wu, Y.-C. Excavatoids E and F: Discovery of two new briaranes from the cultured octocoral Briareum excavatum. Mar. Drugs 2009, 7, 472–482, doi:10.3390/md7030472.
[30]  Sung, P.-J.; Chen, B.-Y.; Chiang, M.Y.; Hou, C.-H.; Su, Y.-D.; Hwang, T.-L.; Chen, Y.-H.; Chen, J.-J. Excavatoids G-K, new 8,17-epoxybriaranes from the cultured octocoral Briareum excavatum (Briareidae). Bull. Chem. Soc. Jpn. 2010, 83, 539–545, doi:10.1246/bcsj.20090306.
[31]  Su, J.-H.; Chen, B.-Y.; Hwang, T.-L.; Chen, Y.-H.; Huang, I.-C.; Lin, M.-R.; Chen, J.-J.; Fang, L.-S.; Wang, W.-H.; Li, J.-J.; et al. Excavatoids L-N, new 12-hydroxybriaranes from the cultured octocoral Briareum excavatum (Briareidae). Chem. Pharm. Bull. 2010, 58, 662–665.
[32]  Sung, P.-J.; Lin, M.-R.; Chiang, M.Y.; Syu, S.-M.; Fang, L.-S.; Wang, W.-H.; Sheu, J.-H. Briarenolide D, a new hydroperoxybriarane diterpenoid from a cultured octocoral Briareum sp. Chem. Lett. 2010, 39, 1030–1032.
[33]  Sung, P.-J.; Li, G.-Y.; Su, Y.-D.; Lin, M.-R.; Chang, Y.-C.; Kung, T.-H.; Lin, C.-S.; Chen, Y.-H.; Su, J.-H.; Lu, M.-C.; et al. Excavatoids O and P, new 12-hydroxybriaranes from the octocoral Briareum excavatum. Mar. Drugs 2010, 8, 2639–2646, doi:10.3390/md8102639.
[34]  Hong, P.-H.; Su, Y.-D.; Lin, N.-C.; Chen, Y.-H.; Kuo, Y.-H.; Hwang, T.-L.; Wang, W.-H.; Chen, J.-J.; Sheu, J.-H.; Sung, P.-J. Briarenolide E: The first 2-ketobriarane diterpenoid from an octocoral Briareum sp. (Briareidae). Tetrahedron Lett. 2012, 53, 1710–1712.
[35]  Yeh, T.-T.; Wang, S.-K.; Dai, C.-F.; Duh, C.-Y. Briacavatolides A-C, new briaranes from the Taiwanese octocoral Briareum excavatum. Mar. Drugs 2012, 10, 1019–1026.
[36]  Chang, Y.-C.; Huang, I.-C.; Chiang, M.Y.; Hwang, T.-L.; Kung, T.-H.; Lin, C.-S.; Sheu, J.-H.; Sung, P.-J. Briaviodiol A, a new cembranoid from a soft coral Briareum violacea. Chem. Pharm. Bull. 2010, 58, 1666–1668.
[37]  Sung, P.-J.; Chen, B.-Y.; Chen, Y.-H.; Chiang, M.Y.; Lin, M.-R. Loliolide: Occurrence of a carotenoid metabolite in the octocoral Briareum excavatum (Briareidae). Biochem. Syst. Ecol. 2010, 38, 116–118, doi:10.1016/j.bse.2009.12.028.
[38]  Aoki, S.; Okano, M.; Matsui, K.; Itoh, T.; Satari, R.; Akiyama, S.-I.; Kobayashi, M. Brianthein A, a novel briarane-type diterpene reversing multidrug resistance in human carcinoma cell line, from the gorgonian Briareum excavatum. Tetrahedron 2001, 57, 8951–8957.
[39]  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, doi:10.1021/ja00467a001.
[40]  Guerriero, A.; D’Ambrosio, M.; Pietra, F. Slowly interconverting conformers of the briarane diterpenoids verecynarmin B, C, and D, isolated from the nudibranch mollusc Armina maculata and the Pennatulacean octocoral Veretillum cynomorium of East Pyrenean waters. Helv. Chim. Acta 1988, 71, 472–485, doi:10.1002/hlca.19880710221.
[41]  Anjaneyulu, A.S.R.; Rao, N.S.K. Juncins G and H: New briarane diterpenoids of the Indian Ocean gorgonian Junceella juncea Pallas. J. Chem. Soc. Perkin Trans. 1 1997, 959–962, doi:10.1039/a604271f.
[42]  Sung, P.-J.; Lin, M.-R.; Chen, W.-C.; Fang, L.-S.; Lu, C.-K.; Sheu, J.-H. Fragilide A, a novel diterpenoid from Junceella fragilis. Bull. Chem. Soc. Jpn. 2004, 77, 1229–1230, doi:10.1246/bcsj.77.1229.
[43]  Ospina, C.A.; Rodríguez, A.D. Bioactive compounds from the gorgonian Briareum polyanthes. Correction of the structures of four asbestinane-type diterpenes. J. Nat. Prod. 2006, 69, 1721–1727, doi:10.1021/np060317y.
[44]  Bayer, F.M. Key to the genera of octocorallia exclusive of Pennatulacea (Coelenterata: Anthozoa), with diagnoses of new taxa. Proc. Biol. Wash. Soc. 1981, 94, 902–947.
[45]  Benayahu, Y. Soft corals (Octocorallia: Alcyonacea) of the southern Ryukyu Archipelago: The families Tubiporidae, Clavulariidae, Alcyoniidae and Briareidae. Galaxea 2002, 4, 11–32, doi:10.3755/jcrs.2002.11.
[46]  Benayahu, Y.; Jeng, M.-S.; Perkol-Finkel, S.; Dai, C.-F. Soft corals (Octocorallia: Alcyonacea) from Southern Taiwan. II. Species diversity and distributional patterns. Zool. Stud. 2004, 43, 548–560.
[47]  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. 154–157.
[48]  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, doi:10.1016/j.freeradbiomed.2011.03.026.
[49]  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.
[50]  Dookran, R.; Maharaj, D.; Mootoo, B.S.; Ramsewak, R.; McLean, S.; Reynolds, W.F.; Tinto, W.F. Briarane and asbestinane diterpenes from Briareum asbestinum. Tetrahedron 1994, 50, 1983–1992.
[51]  Guerriero, A.; D’Ambrosio, M.; Pietra, F. Bis-allylic reactivity of the funicolides, 5,8(17)-diunsaturated briarane diterpenes of the sea pen Funiculina quadrangularis from the Tuscan Archipelago, leading to 16-nortaxane derivatives. Helv. Chim. Acta 1995, 78, 1465–1478, doi:10.1002/hlca.19950780606.
[52]  Xu, L.; Patrick, B.O.; Roberge, M.; Allen, T.; van Ofwegen, L.; Andersen, R.J. New diterpenoids from the octocoral Pachyclavularia violacea collected in Papua New Guinea. Tetrahedron 2000, 56, 9031–9037.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133