Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring

Michael J. Somerville; Peter L. Katavic; Lynette K. Lambert; Gregory K. Pierens; Joanne T. Blanchfield; Guido Cimino; Ernesto Mollo; Margherita Gavagnin; Martin G. Banwell; Mary J. Garson

doi:10.1021/np300442s

Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring

Michael J. Somerville, Peter L. Katavic, Lynette K. Lambert, Gregory K. Pierens, Joanne T. Blanchfield, Guido Cimino, Ernesto Mollo, Margherita Gavagnin^*, Martin G. Banwell, Mary J. Garson

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO₃-impregnated silica gel. Thuridillins D-F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ^10,11- and Δ^11,12- isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and ¹H-¹H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).

Original language	English
Pages (from-to)	1618-1624
Number of pages	7
Journal	Journal of Natural Products
Volume	75
Issue number	9
DOIs	https://doi.org/10.1021/np300442s
Publication status	Published - 28 Sept 2012

Access to Document

10.1021/np300442s

Cite this

Somerville, M. J., Katavic, P. L., Lambert, L. K., Pierens, G. K., Blanchfield, J. T., Cimino, G., Mollo, E., Gavagnin, M., Banwell, M. G., & Garson, M. J. (2012). Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring. Journal of Natural Products, 75(9), 1618-1624. https://doi.org/10.1021/np300442s

@article{fc57c1d9e3c349f3a10bd7c41793045a,

title = "Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring",

abstract = "This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D-F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12- isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H-1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).",

author = "Somerville, {Michael J.} and Katavic, {Peter L.} and Lambert, {Lynette K.} and Pierens, {Gregory K.} and Blanchfield, {Joanne T.} and Guido Cimino and Ernesto Mollo and Margherita Gavagnin and Banwell, {Martin G.} and Garson, {Mary J.}",

year = "2012",

month = sep,

day = "28",

doi = "10.1021/np300442s",

language = "English",

volume = "75",

pages = "1618--1624",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "9",

}

Somerville, MJ, Katavic, PL, Lambert, LK, Pierens, GK, Blanchfield, JT, Cimino, G, Mollo, E, Gavagnin, M, Banwell, MG & Garson, MJ 2012, 'Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring', Journal of Natural Products, vol. 75, no. 9, pp. 1618-1624. https://doi.org/10.1021/np300442s

Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring. / Somerville, Michael J.; Katavic, Peter L.; Lambert, Lynette K. et al.
In: Journal of Natural Products, Vol. 75, No. 9, 28.09.2012, p. 1618-1624.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring

AU - Somerville, Michael J.

AU - Katavic, Peter L.

AU - Lambert, Lynette K.

AU - Pierens, Gregory K.

AU - Blanchfield, Joanne T.

AU - Cimino, Guido

AU - Mollo, Ernesto

AU - Gavagnin, Margherita

AU - Banwell, Martin G.

AU - Garson, Mary J.

PY - 2012/9/28

Y1 - 2012/9/28

N2 - This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D-F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12- isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H-1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).

AB - This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D-F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12- isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H-1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).

UR - http://www.scopus.com/inward/record.url?scp=84867015703&partnerID=8YFLogxK

U2 - 10.1021/np300442s

DO - 10.1021/np300442s

M3 - Article

SN - 0163-3864

VL - 75

SP - 1618

EP - 1624

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 9

ER -

Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; Relative configuration of the epoxylactone ring

Abstract

Access to Document

Other files and links

Fingerprint

Cite this