Isolation, Structure Elucidation, and Synthesis of Eudistomides A and B, Lipopeptides from a Fijian Ascidian Eudistoma Sp

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2008 Dec 5

PMID 19053188

Citations 7

Authors

Emily L Whitson

Anokha S Ratnayake

Tim S Bugni

Mary Kay Harper

Chris M Ireland

Affiliations

Soon will be listed here.

Abstract

Eudistomides A (1) and B (2), two new cyclic peptides, were isolated from a Fijian ascidian Eudistoma sp. These five-residue cystine-linked cyclic peptides are flanked by a C-terminal methyl ester and a 12-oxo- or 12-hydroxy-tetradecanoyl moiety. The complete structures of the eudistomides were determined using a combination of spectroscopic and chemical methods. Chiral HPLC analysis revealed that all five amino acid residues in 1 and 2 had the L-configuration. Total synthesis of eudistomides A (1) and B (2) confirmed the proposed structures. Enantioselective lipase-catalyzed hydrolysis of a mixture of C-35 acetoxy epimers indicated a 35R absolute configuration for 2.

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References

Williams D, Moore R, Paul V . The structure of ulithiacyclamide B. Antitumor evaluation of cyclic peptides and macrolides from Lissoclinum patella. J Nat Prod. 1989; 52(4):732-9. DOI: 10.1021/np50064a011. View

Kalinovskaya N, Kuznetsova T, Ivanova E, Romanenko L, Voinov V, Huth F . Characterization of surfactin-like cyclic depsipeptides synthesized by Bacillus pumilus from ascidian Halocynthia aurantium. Mar Biotechnol (NY). 2004; 4(2):179-88. DOI: 10.1007/s10126-001-0084-4. View

Badre A, Boulanger A, Abou-Mansour E, Banaigs B, Combaut G, Francisco C . Eudistomin U and isoeudistomin U, new alkaloids from the Caribbean ascidian Lissoclinum fragile. J Nat Prod. 1994; 57(4):528-33. DOI: 10.1021/np50106a016. View

Smyrniotopoulos V, Abatis D, Tziveleka L, Tsitsimpikou C, Roussis V, Loukis A . Acetylene sesquiterpenoid esters from the green alga Caulerpa prolifera. J Nat Prod. 2003; 66(1):21-4. DOI: 10.1021/np0202529. View

Schupp P, Poehner T, Edrada R, Ebel R, Berg A, Wray V . Eudistomins W and X, two new beta-carbolines from the micronesian tunicate Eudistoma sp. J Nat Prod. 2003; 66(2):272-5. DOI: 10.1021/np020315n. View

Siemion I, Wieland T, Pook K . Influence of the distance of the proline carbonyl from the beta and gamma carbon on the 13C chemical shifts. Angew Chem Int Ed Engl. 1975; 14(10):702-3. DOI: 10.1002/anie.197507021. View

Hawkins C, Lavin M, Marshall K, Van Den Brenk A, Watters D . Structure-activity relationships of the lissoclinamides: cytotoxic cyclic peptides from the ascidian Lissoclinum patella. J Med Chem. 1990; 33(6):1634-8. DOI: 10.1021/jm00168a016. View

Schmitz F, Yasumoto T . The 1990 United States-Japan seminar on bioorganic marine chemistry, meeting report. J Nat Prod. 1991; 54(6):1469-90. DOI: 10.1021/np50078a001. View

Williams D, Austin P, Diaz-Marrero A, Van Soest R, Matainaho T, Roskelley C . Neopetrosiamides, peptides from the marine sponge Neopetrosia sp. that inhibit amoeboid invasion by human tumor cells. Org Lett. 2005; 7(19):4173-6. DOI: 10.1021/ol051524c. View

10.

Perez Baz J, Canedo L, Fernandez Puentes J, Silva Elipe M . Thiocoraline, a novel depsipeptide with antitumor activity produced by a marine Micromonospora. II. Physico-chemical properties and structure determination. J Antibiot (Tokyo). 1997; 50(9):738-41. DOI: 10.7164/antibiotics.50.738. View

11.

Orjala J, Nagle D, Gerwick W . Malyngamide H, an ichthyotoxic amide possessing a new carbon skeleton from the Caribbean cyanobacterium Lyngbya majuscula. J Nat Prod. 1995; 58(5):764-8. DOI: 10.1021/np50119a019. View

12.

Fu X, Do T, Schmitz F, Andrusevich V, Engel M . New cyclic peptides from the ascidian Lissoclinum patella. J Nat Prod. 1998; 61(12):1547-51. DOI: 10.1021/np9802872. View

13.

Degnan B, Hawkins C, Lavin M, McCaffrey E, Parry D, Van Den Brenk A . New cyclic peptides with cytotoxic activity from the ascidian Lissoclinum patella. J Med Chem. 1989; 32(6):1349-54. DOI: 10.1021/jm00126a034. View

14.

Nagle D, McClatchey W, Gerwick W . New glycosphingolipids from the marine sponge Halichondria panicea. J Nat Prod. 1992; 55(7):1013-7. DOI: 10.1021/np50085a032. View

15.

Rashid M, Gustafson K, Boyd M . New cytotoxic N-methylated beta-carboline alkaloids from the marine ascidian Eudistoma gilboverde. J Nat Prod. 2001; 64(11):1454-6. DOI: 10.1021/np010214+. View

16.

Neuhof T, Schmieder P, Preussel K, Dieckmann R, Pham H, Bartl F . Hassallidin A, a glycosylated lipopeptide with antifungal activity from the cyanobacterium Hassallia sp. J Nat Prod. 2005; 68(5):695-700. DOI: 10.1021/np049671r. View

17.

Rinehart K, Kishore V, Bible K, Sakai R, Sullins D, Li K . Didemnins and tunichlorin: novel natural products from the marine tunicate Trididemnum solidum. J Nat Prod. 1988; 51(1):1-21. DOI: 10.1021/np50055a001. View

18.

Van Wagoner R, Jompa J, Tahir A, Ireland C . Trypargine alkaloids from a previously undescribed Eudistoma sp. ascidian. J Nat Prod. 1999; 62(5):794-7. DOI: 10.1021/np9805589. View

19.

Rowley D, Kelly S, Kauffman C, Jensen P, Fenical W . Halovirs A-E, new antiviral agents from a marine-derived fungus of the genus Scytalidium. Bioorg Med Chem. 2003; 11(19):4263-74. DOI: 10.1016/s0968-0896(03)00395-x. View

20.

Makarieva T, Dmitrenok A, Dmitrenok P, Grebnev B, Stonik V . Pibocin B, the first N-O-methylindole marine alkaloid, a metabolite from the Far-Eastern ascidian Eudistoma species. J Nat Prod. 2002; 64(12):1559-61. DOI: 10.1021/np010161w. View