Bioactive natural products from Chinese marine flora and fauna

Acta Pharmacologica Sinica

Volumn 33, Issue 9, 2012, Pages 1159-1169

  Zhou, Zhen Fang ^a   Guo, Yue Wei ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

algae; biological activity; mangrove; marine natural products; mollusks; soft coral; sponges

Indexed keywords

15 DEHYDROXY INTEGRACIN B; 3BETA HYDROXYAPLYSIN; DISULFIDE; INTEGRACIN A; INTEGRACIN B; LAUROKAMURENE A; LAUROKAMURENE B; LINGSHUIOLIDE A; LINGSHUIOLIDE B; NATURAL PRODUCT; PARACASEOLIDE A; SEA WATER; SESQUITERPENOID; UNCLASSIFIED DRUG;

APLYSIA; APLYSIA DACTYLOMELA; AQUATIC FAUNA; AQUATIC FLORA; BRUGUIERA GYMNORRHIZA; CAULERPA; CAULERPA TAXIFOLIA; CHINESE MEDICINE; CIRCULAR DICHROISM; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; DINOFLAGELLATE; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; EUPHORBIACEAE; LAURENCIA; LAURENCIA OKAMURAI; MANGROVE; MELIACEAE; MICROALGA; NONHUMAN; RED ALGA; REVIEW; RHIZOPHORACEAE; SALINITY; SARCOPHYTON; SECURINEGA SUFFRUTICOSA; SPONGE (PORIFERA); STEREOCHEMISTRY; TRITONIOPSIS ELEGANS; X RAY DIFFRACTION;

ANIMALS; BIOLOGICAL PRODUCTS; CHINA; DRUG DESIGN; DRUG DISCOVERY; HUMANS; MARINE BIOLOGY; PHARMACEUTICAL PREPARATIONS;

EID: 84865957698     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1038/aps.2012.110     Document Type: Review

References (50)

1. Huang XC, Zhao D, Guo YW, Wu HM, Trivellone E, Cimino G. Lingshuiols A and B, two new polyhydroxy compounds from the Chinese marine dinoflagellate Amphidinium sp. Tetrahedron Lett 2004; 45: 5501-4. (Pubitemid 38781889)
2. Huang XC, Zhao D, Guo YW, Wu HM, Lin LP, Wang ZH, et al. Lingshuiol, a novel polyhydroxyl compound with strongly cytotoxic activity from the marine dinoflagellate Amphidinium sp. Bioorg Med Chem Lett 2004; 14: 3117-20. (Pubitemid 38624574)
3. Doi Y, Ishibashi M, Nakamichi H, Kosaka T, Ishikawa T, Kobayashi J. Luteophanol A, a new polyhydroxyl compound from symbiotic marine dinoflagellate Amphidinium sp. J Org Chem 1997; 62: 3820-3.
4. Paul GK, Matsumori N, Murata M, Tachibana K. Isolation and chemical structure of amphidinol 2, a potent hemolytic compound from marine dinoflagellate Amphidinium klebsii. Tetrahedron Lett 1995; 36: 6279-82.
5. Satake M, Murata M, Yasumoto T, Fujita T, Naoki H. Amphidinol, a polyhydroxy-polyene antifungal agent with an unprecedented structure, from a marine dinoflagellate, Amphidinium klebsii. J Am Chem Soc 1991; 113: 9859-61.
6. Irie T, Suzuki M, Masamune T. Laurencin, a constituent from laurencia species. Tetrahedron Lett 1965; 6: 1091-9.
7. Mao SC, Guo YW. A laurane sesquiterpene and rearranged derivatives from the Chinese red alga Laurencia okamurai Yamada. J Nat Prod 2006; 69: 1209-11.
8. Mao SC, Guo YW. Sesquiterpenes from algae of the Genus Larencia: chemistry and biological activities. Chin Tradit Herb Drugs 2004; 35: 8-18.
9. Mao SC, Guo YW, Shen X. Two novel aromatic valerenane-type sesquiterpenes from the Chinese green alga Caulerpa taxifolia. Bioorg Med Chem Lett 2006; 16: 2947-50.
10. Wang BS, Liang SC, Zhang WY, Zan QJ. Mangrove Flora of the world. Acta Bot Sin 2003; 45: 644-53.
11. Li MY, Xiao Q, Pan JY, Wu J. Natural products from semi-mangrove flora: source, chemistry and bioactivities. Nat Prod Rep 2009; 26: 281-98.
12. Sun YQ, Guo YW. Gymnorrhizol, an unusual macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza. Tetrahedron Lett 2004; 45: 5533-5.
13. Sun YQ, Guo YW. Crystal structure of 1,2,6,7,11,12-hexathia- cyclopentadecane-4,9,14-triol, C9H18O3S6. Z Kristallogr NCS 2004; 219: 121-3.
14. Gong JX, Shen X, Yao LG, Jiang H, Krohn K, Guo YW. Total synthesis of gymnorrhizol, an unprecedented 15-membered macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza. Org Lett 2007; 9: 1715-6.
15. Huang XY, Wang Q, Liu HL, Zhang Y, Xin GR, Shen X, et al. Diastereoisomeric macrocyclic polydisulfides from the mangrove Bruguiera gymnorrhiza. Phytochemistry 2009; 70: 2096-100.
16. Jiang CS, Muller WE, Schroder HC, Guo YW. Disulfide-and multisulfide-containing metabolites from marine organisms. Chem Rev 2012; 112: 2179-207.
17. Cai YS, Kurtan T, Miao ZH, Mandi A, Komaromi I, Liu HL, et al. Palmarumycins BG1-BG7 and preussomerin BG1: establishment of their absolute configurations using theoretical calculations of electronic circular dichroism spectra. J Org Chem 2011; 76: 1821-30.
18. Wang L, Zhang CF, Wang ZT, Zhang M, Xu LS. Five new compounds from Dendrobium crystallinum. J Asian Nat Prod Res 2009; 11: 903-11.
19. Prajoubklang A, Sirithunyalug B, Charoenchai P, Suvannakad R, Sriubolmas N, Piyamongkol S, et al. Bioactive deoxypreussomerins and dimeric naphthoquinones from Diospyros ehretioides fruits: deoxypreussomerins may not be plant metabolites but may be from fungal epiphytes or endophytes. Chem Biodivers 2005; 2: 1358-67. (Pubitemid 41645370)
20. Ravindranath N, Ravinder Reddy M, Mahender G, Ramu R, Ravi Kumar K, Das B. Deoxypreussomerins from Jatropha curcas: are they also plant metabolites? Phytochemistry 2004; 65: 2387-90. (Pubitemid 39237257)
21. Kouam TNM, Lavaud C, Massiot G, Nuzillard JM, Connolly JD, Ryeroft DS. Bipendensin, an unusual phenolic acetal from Afzelia bipendensis. Nat Prod Lett 1993; 3: 299-303. (Pubitemid 2035755)
22. Cai YS, Guo YW, Krohn K. Structure, bioactivities, biosynthetic relationships and chemical synthesis of the spirodioxynaphthalenes. Nat Prod Rep 2010; 27: 1840-70.
23. Chen XL, Liu HL, Li J, Xin GR, Guo YW. Paracaseolide A, first alphaalkylbutenolide dimer with an unusual tetraquinane oxa-cage bislactone skeleton from Chinese mangrove Sonneratia paracaseolaris. Org Lett 2011; 13: 5032-5.
24. Hill RA, Sutherland A. Hot off the press. Nat Prod Rep 2011; 28: 1879-82.
25. Liu HL, Huang XY, Li J, Xin GR, Guo YW. Absolute configurations of integracins A, B, and 15?-dehydroxy-integracin B. Chirality 2012; 24: 459-62.
26. Wang JD, Zhang W, Li ZY, Xiang WS, Guo YW, Krohn K. Elucidation of excogallochaols A-D, four unusual diterpenoids from the Chinese mangrove Excoecaria agallocha. Phytochemistry 2007; 68: 2426-31. (Pubitemid 47429715)
27. Qin S, Liang JY, Gu YC, Guo YW. Suffruticosine, a novel octacyclic alkaloid with an unprecedented skeleton from Securinega suffruticosa (Pall) Rehd. Tetrahedron Lett 2008; 49: 7066-9.
28. Wang JR, Liu HL, Kurtan T, Mandi A, Antus S, Li J, et al. Protolimonoids and norlimonoids from the stem bark of Toona ciliata var pubescens. Org Biomol Chem 2011; 9: 7685-96.
29. Jiang CS, Zhou R, Gong JX, Chen LL, Kur tan T, Shen X, et al. Synthesis, modification, and evaluation of (R)-de-O-methyllasiodiplodin and analogs as nonsteroidal antagonists of mineralocorticoid receptor. Bioorg Med Chem Lett 2011; 21: 1171-5.
30. Huang XC, Li J, Li ZY, Shi L, Guo YW. Sesquiterpenes from the Hainan Sponge Dysidea septosa. J Nat Prod 2008; 71: 1399-403.
31. Li Y, Zhang Y, Shen X, Guo YW. A novel sesquiterpene quinone from Hainan sponge Dysidea villosa. Bioorg Med Chem Lett 2009; 19: 390-2.
32. Zhang Y, Li Y, Guo YW, Jiang HL, Shen X. A sesquiterpene quinone, dysidine, from the sponge Dysidea villosa, activates the insulin pathway through inhibition of PTPases. Acta Pharmacol Sin 2009; 30: 333-45.
33. Mao SC, Manzo E, Guo YW, Gavagnin M, Mollo E, Ciavatta ML, et al. New diastereomeric bis-sesquiterpenes from Hainan marine sponges Axinyssa variabilis and Lipastrotethya ana. Tetrahedron 2007; 63: 11108-13. (Pubitemid 47464406)
34. Li L, Sheng L, Wang CY, Zhou YB, Huang H, Li XB, et al. Diterpenes from the Hainan soft coral Lobophytum cristatum Tixier-Durivault. J Nat Prod 2011; 74: 2089-94.
35. Zhang CX, Yan SJ, Zhang GW, Lu WG, Su JY, Zeng LM, et al. Cytotoxic diterpenoids from the soft coral Sinularia microclavata. J Nat Prod 2005; 68: 1087-9.
36. Li Y, Carbone M, Vitale RM, Amodeo P, Castelluccio F, Sicilia G, et al. Rare casbane diterpenoids from the Hainan soft coral Sinularia depressa. J Nat Prod 2010; 73: 133-8.
37. Jia R, Guo YW, Chen P, Yang YM, Mollo E, Gavagnin M, et al. Biscembranoids and their probable biogenetic precursor from the Hainan soft coral Sarcophyton tortuosum. J Nat Prod 2007; 70: 1158-66. (Pubitemid 47279909)
38. Yan XH, Gavagnin M, Cimino G, Guo YW. Two new biscembranes with unprecedented carbon skeleton and their probable biogenetic precursor from the Hainan soft coral Sarcophyton latum. Tetrahedron Lett 2007; 48: 5313-6. (Pubitemid 46992681)
39. Yan XH, Lin LP, Ding J, Guo YW. Methyl spongoate, a cytotoxic steroid from the Sanya soft coral Spongodes sp. Bioorg Med Chem Lett 2007; 17: 2661-3. (Pubitemid 46522522)
40. Gong JX, Miao ZH, Yao LG, Ding J, Kurtan T, Guo YW. Stereoselective synthesis of methyl spongoate, a new steroid with potent antitumor activities. Synlett 2010; 2010: 480-2.
41. Jiang CS, Huang CG, Feng B, Li J, Gong JX, Kurtan T, et al. Synthesis and antitumor evaluation of methyl spongoate analogs. Steroids 2010; 75: 1153-63.
42. Ciavatta ML, Manzo E, Mollo E, Mattia CA, Tedesco C, Irace C, et al. Tritoniopsins A-D, cladiellane-based diterpenes from the South China Sea nudibranch Tritoniopsis elegans and its prey Cladiella krempfi. J Nat Prod 2011; 74: 1902-7.
43. Gavagnin M, Mollo E, Docimo T, Guo YW, Cimino G. Scalarane metabolites of the nudibranch Glossodoris rufomarginata and its dietary sponge from the South China Sea. J Nat Prod 2004; 67: 2104-7. (Pubitemid 40092567)
44. Fontana A, Cavaliere P, Ungur N, D'Souza L, Parameswaram PS, Cimino G. New scalaranes from the nudibranch Glossodoris atromarginata and its sponge prey. J Nat Prod 1999; 62: 1367-70. (Pubitemid 29504096)
45. Terem B, Scheuer PJ. Scalaradial derivatives from the nudibranch chromodoris youngbleuthi and the sponge spongia oceania. Tetrahedron 1986; 42: 4409-12.
46. Manzo E, Gavagnin M, Bifulco G, Cimino P, Di MS, Ciavatta ML, et al. Aplysiols A and B, squalene-derived polyethers from the mantle of the sea hare Aplysia dactylomela. Tetrahedron 2007; 63: 9970-8. (Pubitemid 47268034)
47. Carbone M, Gavagnin M, Mattia CA, Lotti C, Castelluccio F, Pagano B, et al. Structure of onchidione, a bis-?-pyrone polypropionate from a marine pulmonate mollusk. Tetrahedron 2009; 65: 4404-9.
48. Wang JR, Carbone M, Gavagnin M, Mandi A, Antus S, Yao LG, et al. Assignment of absolute configuration of bis-?-pyrone polypropionates from marine pulmonate molluscs. Eur J Org Chem 2012; 2012: 1107-11.
49. Carbone M, Li Y, Irace C, Mollo E, Castelluccio F, Di Pascale A, et al. Structure and cytotoxicity of phidianidines A and B: first finding of 1,2,4-oxadiazole system in a marine natural product. Org Lett 2011; 13: 2516-9.
50. Manzo E, Carbone M, Mollo E, Irace C, Di Pascale A, Li Y, et al. Structure and synthesis of a unique isonitrile lipid isolated from the marine mollusk Actinocyclus papillatus. Org Lett 2011; 13: 1897-9.