Skip to main content

Advertisement

Log in

On the biogenesis of marine isoprenoids

  • Published:
Phytochemistry Reviews Aims and scope Submit manuscript

Abstract

The isoprenoids comprise an important group among the marine natural products which are mainly obtained from soft corals, sponges and algae. The cembranes, xenia metabolites from soft corals and rearranged spongans from sponges are examples of marine diterpenoids obtained directly from GeGePP or after remarkable changes. Biogenesis, suggested biosynthesis, based on the structure and mainly known terrestrial biosynthesis, is proposed for diterpenoids and higher isoprenoids. Examples include the sipholanes, sodwanones and other triterpenoids as well as antheliolide and the T. toxius phenylhexaprenoide metabolites of mixed biogenetic origin.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • J Blunt (2002) “Marinlit” Database University of Canterbury Christchurch, New Zealand

    Google Scholar 

  • A Butler (1999) ArticleTitleMechanistic considerations of the vanadium haloperoxidases Coord. Chem. Rev. 187 17–35

    Google Scholar 

  • S Carmely Y Kashman (1983) ArticleTitleThe sipholanes: a novel group of triterpenes from the marine sponge Siphonochalina siphonella J. Org. Chem. 48 3517–3525

    Google Scholar 

  • S Carmely Y Loya Y Kashman (1983) ArticleTitleSiphonellinol a new triterpene from the marine sponge Siphonochalina siphonella Tetrahedron Lett 24 3673–3676

    Google Scholar 

  • S Carmely Y Kashman (1986a) ArticleTitleThe study of sipholanes by 2D NMR spectroscopy Magn. Reson. Chem. 24 332–336

    Google Scholar 

  • S Carmely Y Kashman (1986b) ArticleTitleNeviotine - A, a new triterpene from the Red Sea sponge Siphonochalina siphonella J Org. Chem. 51 784–788

    Google Scholar 

  • S Carmely M Cojocaru Y Loya Y Kashman (1988) ArticleTitleTen new rearranged spongian diterpenes from two Dysidae spp J. Org Chem. 53 4801–4807

    Google Scholar 

  • G Cimino A Crispino A Madaio E Trivellone (1993) ArticleTitleRaspacionin B, a further triterpenoid from the Mediterranean sponge Raspaciona aculeata J Nat. Prod. 56 534–538

    Google Scholar 

  • EJ Corey SPT Matsuda (1987) ArticleTitleGenerality of marine prostanoid biosynthesis by the 2-oxidopentadienyl cation pathway Tetrahedron Lett. 28 4247–4250

    Google Scholar 

  • PM Dewick (1999) ArticleTitleThe biosynthesis of C5–C25 terpenoid compounds Nat Prod. Rep. 16 97–130

    Google Scholar 

  • Faulkner, D.J. (2002) Marine natural products. Nat. Prod. Rep. 1–48 and previous reports in this series.

  • A Fontana G Villani G Cimino (2000) ArticleTitleTerpene biosynthesis in marine molluscs: incorporation of glucose in drimane esters of Dendrodoris nudibranches via classical mevalonat pathway Tetrahedron Lett. 41 2429–2433

    Google Scholar 

  • A Fontana MT Kelly J.D. Prasad R.J. Andersen (2001) ArticleTitleEvidence for the biosynthesis of squalene via the methylerythritol phosphate pathway in a Streptomyces sp. obtained from a marine sediment J. Org. Chem. 66 6202–6206

    Google Scholar 

  • E Fridkovsky A Rudi Y Benayahu Y Kashman (1996) ArticleTitleSarcoglane a new cytotoxic diterpene from Sarcophyton glaucum. Tetrahedron Lett. 37 6909–6910

    Google Scholar 

  • N Fusetani M Asano S Matsunaga K Hashimoto (1986) ArticleTitleBioactive marine metabolites. Isolation of aplysinopsin from the scleractinian coral Tubastrea aurea as as inhibitor of development of fertelized sea urchin eggs Comp. Biochem. Physiol. 85B IssueID4 845–846

    Google Scholar 

  • D Green S Carmeli Y Benayahu Y Kashman (1988) ArticleTitleAntheliolide A & B: two new C24 acetoacetylated diterpenoids of the soft coral Anthelia glauca Tetrahedron Lett 29 1605–1608

    Google Scholar 

  • D Green Y Benayahu Y Kashman (1992a) ArticleTitleSecondary metabolites of the yellow and gray morphs of the soft coral P. fulvum fulvum comparitive aspects J. Nat. Prod. 55 1186–1196

    Google Scholar 

  • D Green I Goldberg Z Stein M Ilan Y Kashman (1992b) ArticleTitleCyanthiwigin A–D, novel cytotoxic diterpenes from the sponge Epipolasis reiswigi Nat. Prod. Lett. 1 193–199

    Google Scholar 

  • A Groweiss Y Kashman (1978) ArticleTitleXeniculin, xeniaphyllenol and xeniaphyllenol oxide new diterpenoids from the soft coral Xenia macrospiculata Tetrahedron Lett. 1978 2205–2208

    Google Scholar 

  • A Groweiss Y Kashman (1983) ArticleTitleEight new xenia diterpenoids from three soft corals of the Red Sea Tetrahedron 39 3385–3396

    Google Scholar 

  • S Isaacs Y Kasbman (1992) ArticleTitleShaagrockol B and C; two hexaprenylhydroquinone disulfates from the Red Sea sponge Toxiclona toxius Tetrahedron Lett. 33 2227–2230

    Google Scholar 

  • S Isaacs A Hizi Y Kashman (1993) ArticleTitleToxicols A–C and toxiusol–new bioactive hexaprenoid hydroquinones from Toxiclona toxius Tetrahedron Lett 49 4275–4282

    Google Scholar 

  • RR Izac W Fenical B Tagle J Clardy (1981) ArticleTitleNeolemnane and eremophilane sesquiterpenoids from the pacific soft coral Lemnalia africana Tetrahedron 37 2569–2573

    Google Scholar 

  • Y Kashman A Groweiss (1978) ArticleTitleXeniolide A and Xeniolide B, two new diterpenoids from the soft coral Xenia macrospiculata Tetrahedron Lett. 1978 4833–4836

    Google Scholar 

  • Y Kashman A Groweiss (1980) ArticleTitleNew diterpenoids from the soft corals Xenia macrospiculata and Xenia obscuronata J. Org Chem. 45 3814–3824

    Google Scholar 

  • Y Kashman M Saltoun A Rudi Y Benayahu (1994) ArticleTitleXeniafaraunol A and B and Faraunatin; three new cytotoxic diterpenes from the soft coral Xenia faraunensis Tetrahedron Lett 35 8855–8858

    Google Scholar 

  • Y Kashman T Yosief S Carmeli (2001) ArticleTitleNew triterpenoids from the Red Sea sponge Siphonochalina siphonella J. Nat. Prod. 64 175–180

    Google Scholar 

  • D Kelman Y Benayahu Y Kashman (2000) ArticleTitleVariation in secondary metabolite concentrations in yellow and grey morphs of the Red Sea soft coral Parerythropodium fulvum fulvum J. Chem. Ecol. 26 1123–1133

    Google Scholar 

  • S Ketzinel A Rudi M Schleyer Y Benayahu Y Kashman (1996) ArticleTitleSarcodictyin A and two novel diterpenoid glycosides, eleuthosides A and B, from the soft coral Eleuthrobia aurea J. Nat. Prod. 59 873–875

    Google Scholar 

  • E Kho DK Imagawa M Rohmer Y Kashman C Djerassi (1981) ArticleTitleSterols in marine invertebrates 22 J. Org Chem. 46 1836–1839

    Google Scholar 

  • G Koren-Goldshlager P Klein A Rudi Y Benayahu M Schleyer Y Kashman (1996) ArticleTitleSindurol and nephthoside: new tetraprenyltoluquinols from the soft corals Sinularia dura and Nephthea sp J. Nat. Prod. 59 262–266

    Google Scholar 

  • Kuniyoshi S, Marma MS, Higa T, Berndinelli G & Jefford C (2000) Bromobarekoxide, an unusual diterpene from Laurencia luzonesis. Chem. Commun.2000: 1155–1156.

  • S Loya R Tal A Hizi S Isaacs Y Kashman Y Loya (1993) ArticleTitleHexaprenoid hydroquinones, novel inhibitors of the reverse transcriptase of human immunodeficiency virus type 1 J. Nat. Prod. 56 2120–2125

    Google Scholar 

  • S Loya M Bakhanashvili Y Kashman A Hizi (1995) ArticleTitlePeyssonols A and B, two novel inhibitors of the reverse transcritptases of human immunodeficiency virus types 1 and 2 Arch. Biochem. Biophys. 316 789–796

    Google Scholar 

  • I Ohtani T Kusumi Y Kashman H Kakisawa (1991) ArticleTitleHigh-field FT NMR application of Mosher’s method. The absolute configuration of marine terpenoids J. Am. Chem. Soc. 113 4092–4096

    Google Scholar 

  • A Rudi Y Kashman (1990) ArticleTitleThree new norrisolide related rearranged spongians Tetrahedron Lett. 46 4019–4022

    Google Scholar 

  • A Rudi Y Kashman (1992) ArticleTitleChelodane, barekoxide and zaatirin–three new diterpenoids from the marine sponge Chelonaplysilla erecta J. Nat. Prod. 55 1408–1414

    Google Scholar 

  • A Rudi Y Kashman Y Benayahu M Schleyer (1994) ArticleTitleSodwanones A–F, new triterpenes from the marine sponge Axinella weltneri J. Nat. Prod. 57 1416–1423

    Google Scholar 

  • A Rudi S Ketzinel I Goldberg Z Stein Y Kashman Y benayahu M Schleyer (1995a) ArticleTitleAntheliatin and zahavins A & B, three new cytotoxic xenicane diterpenes from two soft corals J. Nat. Prod. 58 1581–1586

    Google Scholar 

  • A Rudi I Goldberg Z Stein Y Kasbman Y Benayahu M Schleyer M Garcia Gravalos (1995b) ArticleTitleSodwanones G, H and I, new cytotoxic triterpenes from a marine sponge J. Nat. Prod. 58 1702–1712

    Google Scholar 

  • A Rudi M Aknin EM Gaydou Y Kasbman (1997) ArticleTitleSodwanones K, L and M, new triterpenes from the marine sponge Axinella weltneri J. Nat. Prod. 60 700–703

    Google Scholar 

  • A Rudi T Lev-Ari Dayan M Aknin E.M. Gaydou Y Kashman (1998a) ArticleTitleSeveral new isoprenoids from the soft coral Sinularia erecta J. Nat. Prod. 61 872–875

    Google Scholar 

  • A Rudi Z Stein I Goldberg T Yosief Y Kasbman (1998b) ArticleTitleYardenone and Abudinol two new triterpenes from the marine sponge Ptilocaulis spiculifer Tetrahedron Lett. 39 1445–1448

    Google Scholar 

  • A Rudi T Yosief M Schleyer Y Kasbman (1999a) ArticleTitleBilosespenes A and B: two novel cytotoxic sesterpenes from the marine sponge Dysidea cinerea Organic Lett 1 471–472

    Google Scholar 

  • A Rudi T Yosief M Schleyer Y Kasbman (1999b) ArticleTitleSeveral new isoprenoids from two marine sponges of the family Axinellidae Tetrahedron 55 5555–5566

    Google Scholar 

  • A Rudi T Yosief S Loya A Hizi M Schleyer Y Kashman (2001) ArticleTitleClathsterol, a novel anti-HIV RT sulfated sterol from the sponge Clathria sp J. Nat. Prod. 64 1451–1453

    Google Scholar 

  • M Shatz T Yosief Y Kashman (2000) ArticleTitleBacteriohopanehexol, a new triterpene from the marine sponge Petrosia sp J. Nat. Prod. 63 1554–1556

    Google Scholar 

  • U Shmueli S Carmeli A Groweiss Y Kashman (1981) ArticleTitleSipholenol and sipholenone, two new triterpenes from the marine sponge Siphonochalina siphonella (Levi) Tetrahedron Lett. 22 709–712

    Google Scholar 

  • AB Smith PJ Carroll Y Kashman D Green (1989) ArticleTitleRevised structures of antheliolides A and B Tetrahedron Lett. 30 3363–3364

    Google Scholar 

  • B Sullivan JD Faulkner (1984) ArticleTitleMetabolites of the marine sponge Dendrill sp J. Org. Chem. 49 3204–3206

    Google Scholar 

  • R Talpir A Rudi Y Kashman (1994) ArticleTitleThree new sesquiterpene hydroquinones from marine origin Tetrahedron 50 4179–4184

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yoel Kashman.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kashman, Y., Rudi, A. On the biogenesis of marine isoprenoids. Phytochem Rev 3, 309–323 (2004). https://doi.org/10.1007/s11101-004-8062-x

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11101-004-8062-x

Keywords

Navigation