Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.

Shahan Khokhar; Yunjiang Feng; Marc R. Campitelli; Merrick G. Ekins; John N. A. Hooper; Karren D. Beattie; Martin C. Sadowski; Colleen C. Nelson; Rohan A. Davis

doi:10.1016/j.bmcl.2014.05.104

Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.

Shahan Khokhar
, Yunjiang Feng
, Marc R. Campitelli
, Merrick G. Ekins
, John N. A. Hooper
, Karren D. Beattie
, Martin C. Sadowski
, Colleen C. Nelson
, Rohan A. Davis

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

30 Citations (Scopus)

Abstract

Mass-guided fractionation of the MeOH extract from a specimen of the Australian marine sponge Hyrtios sp. resulted in the isolation of two new tryptophan alkaloids, 6-oxofascaplysin (2), and secofascaplysic acid (3), in addition to the known metabolites fascaplysin (1) and reticulatate (4). The structures of all molecules were determined following NMR and MS data analysis. Structural ambiguities in 2 were addressed through comparison of experimental and DFT-generated theoretical NMR spectral values. Compounds 1-4 were evaluated for their cytotoxicity against a prostate cancer cell line (LNCaP) and were shown to display IC50 values ranging from 0.54 to 44.9 Î¼M.

Original language	English
Pages (from-to)	3329-3332
Number of pages	4
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	24
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2014.05.104
Publication status	Published - 2014

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Australia
alkaloids
antineoplastic agents
cytotoxicity
sponges
tryptophan

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10.1016/j.bmcl.2014.05.104

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Khokhar, S., Feng, Y., Campitelli, M. R., Ekins, M. G., Hooper, J. N. A., Beattie, K. D., Sadowski, M. C., Nelson, C. C., & Davis, R. A. (2014). Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp. Bioorganic & Medicinal Chemistry Letters, 24(15), 3329-3332. https://doi.org/10.1016/j.bmcl.2014.05.104

@article{03bdff1443f24f539a727a955222a77f,

title = "Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.",

abstract = "Mass-guided fractionation of the MeOH extract from a specimen of the Australian marine sponge Hyrtios sp. resulted in the isolation of two new tryptophan alkaloids, 6-oxofascaplysin (2), and secofascaplysic acid (3), in addition to the known metabolites fascaplysin (1) and reticulatate (4). The structures of all molecules were determined following NMR and MS data analysis. Structural ambiguities in 2 were addressed through comparison of experimental and DFT-generated theoretical NMR spectral values. Compounds 1-4 were evaluated for their cytotoxicity against a prostate cancer cell line (LNCaP) and were shown to display IC50 values ranging from 0.54 to 44.9 {\^I}¼M.",

keywords = "Australia, alkaloids, antineoplastic agents, cytotoxicity, sponges, tryptophan",

author = "Shahan Khokhar and Yunjiang Feng and Campitelli, \{Marc R.\} and Ekins, \{Merrick G.\} and Hooper, \{John N. A.\} and Beattie, \{Karren D.\} and Sadowski, \{Martin C.\} and Nelson, \{Colleen C.\} and Davis, \{Rohan A.\}",

year = "2014",

doi = "10.1016/j.bmcl.2014.05.104",

language = "English",

volume = "24",

pages = "3329--3332",

journal = "Bioorganic \& Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "15",

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TY - JOUR

T1 - Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.

AU - Khokhar, Shahan

AU - Feng, Yunjiang

AU - Campitelli, Marc R.

AU - Ekins, Merrick G.

AU - Hooper, John N. A.

AU - Beattie, Karren D.

AU - Sadowski, Martin C.

AU - Nelson, Colleen C.

AU - Davis, Rohan A.

PY - 2014

Y1 - 2014

N2 - Mass-guided fractionation of the MeOH extract from a specimen of the Australian marine sponge Hyrtios sp. resulted in the isolation of two new tryptophan alkaloids, 6-oxofascaplysin (2), and secofascaplysic acid (3), in addition to the known metabolites fascaplysin (1) and reticulatate (4). The structures of all molecules were determined following NMR and MS data analysis. Structural ambiguities in 2 were addressed through comparison of experimental and DFT-generated theoretical NMR spectral values. Compounds 1-4 were evaluated for their cytotoxicity against a prostate cancer cell line (LNCaP) and were shown to display IC50 values ranging from 0.54 to 44.9 Î¼M.

AB - Mass-guided fractionation of the MeOH extract from a specimen of the Australian marine sponge Hyrtios sp. resulted in the isolation of two new tryptophan alkaloids, 6-oxofascaplysin (2), and secofascaplysic acid (3), in addition to the known metabolites fascaplysin (1) and reticulatate (4). The structures of all molecules were determined following NMR and MS data analysis. Structural ambiguities in 2 were addressed through comparison of experimental and DFT-generated theoretical NMR spectral values. Compounds 1-4 were evaluated for their cytotoxicity against a prostate cancer cell line (LNCaP) and were shown to display IC50 values ranging from 0.54 to 44.9 Î¼M.

KW - Australia

KW - alkaloids

KW - antineoplastic agents

KW - cytotoxicity

KW - sponges

KW - tryptophan

UR - http://handle.uws.edu.au:8081/1959.7/uws:34157

U2 - 10.1016/j.bmcl.2014.05.104

DO - 10.1016/j.bmcl.2014.05.104

M3 - Article

SN - 0960-894X

VL - 24

SP - 3329

EP - 3332

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 15

ER -

Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.

Abstract

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Keywords

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