Purpurone, an inhibitor of ATP-citrate lyase: a novel alkaloid from the marine sponge Iotrochota sp

Chan, George; Francis, Terry; Thureen, Dean R.; Offen, Priscilla; Pierce, Nigel J.; Westley, John; Johnson, Randall K.; Faulkner, D. John

doi:10.1021/jo00061a031

Cited by 60 publications

(57 citation statements)

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“…Lamellarins can be biosynthesized from three molecules of tyrosine or DOPA [4,11], similarly to several related marine alkaloid families such as lukianols [12], ningalins [13], polycitones [14] and purpurone [15] ( Figure 1). Several reviews on lamellarins have recently been published [16].…”

Section: Fig (1) Structures Of Lamellarins O-r Lukianol a Ningalimentioning

confidence: 99%

Recent Advances in Lamellarin Alkaloids: Isolation, Synthesis and Activity

Plá¹,

Alberício²,

Álvarez

2008

ACAMC

105

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Lamellarins are a large family of marine alkaloids with potential anticancer activity that have been isolated from diverse marine organisms, mainly ascidians and sponges. All lamellarins feature a 3,4-diarylpyrrole system. Pentacyclic lamellarins, whose polyheterocyclic system has a pyrrole core, are the most active compounds. Some of these alkaloids are potently cytotoxic to various tumor cell lines. To date, Lam-D and Lam-H have been identified as lead compounds for the inhibition of topoisomerase I and HIV-1 integrase, respectively-nuclear enzymes which are over-expressed in deregulation disorders. Moreover, these compounds have been reported for their efficacy in treatment of multi-drug resistant (MDR) tumors cells without mediated drug efflux, as well as their immunomodulatory activity and selectivity towards melanoma cell lines. This article is an overview of recent literature on lamellarins, encompassing their isolation, recent synthetic strategies for their total synthesis, the preparation of their analogs, studies on their mechanisms of action, and their structure-activity relationships (SAR).

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Section: Fig (1) Structures Of Lamellarins O-r Lukianol a Ningalimentioning

confidence: 99%

Recent Advances in Lamellarin Alkaloids: Isolation, Synthesis and Activity

Plá¹,

Alberício²,

Álvarez

2008

ACAMC

105

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“…3 Lamellarins are featured with a benzopyrano-pyrrolo-isoquinolinone nucleus; 2,5-15 lukianols mainly consist of a naturally rare N-alkylpyrrolecarboxylic acid; 16 polyxitones and polycitons are a small group with an unprecedented molecular skeleton 6,17 assumed to be biogenetically derived from lamellarins; storniamides are of peptide origin, 16 while ningalins, among them purpurone (1, see Fig. 1) 18,19 and ningalin A (17), 18 are derived from the condensation of two, three, four, or five DOPA precursor units. The DOPA-derived alkaloids exhibit a wide array of significant biological activities, including cytotoxicity, HIV-1 integrase inhibition, 20 multidrug resistance reversal activity 21 and immunomodulatory activity.…”

Section: Introductionmentioning

confidence: 99%

Baculiferins A–O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera

Fan

Shen

et al. 2010

Bioorganic & Medicinal Chemistry

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“…The purple active component was obtained from a hydrolyzed fraction of the ethanolic extract. It was therefore speculated to originate from precursors which were either sugar or protein conjugates (Chan et al, 1993). Our investigations on Iotrochota obtained from South China Sea also resulted in purpurone as a natural product.…”

Section: Resultsmentioning

confidence: 70%

“…Studies on the marine sponge Iotrochota sp. resulted in the bromoindole methyl (E)-3-(6-bromoindol-3-yl) prop-2-enoate (Dellar et al, 1981) and the aromatic pyrrole derivative purpurone (1) (Chan et al, 1993). Three halogenated tyrosine derivatives (Costantino et al, 1994), five ecdysteroids (Costantino et al, 2000), and five sterols with a nucleus skeleton of 6-hydroxy-4-en-3-one (Li et al, 2005) have been isolated from Iotrocbota birotulata.…”

Section: Introductionmentioning

confidence: 99%

“…Compound 1 was identified by comparison of its spectral data with those of purpurone, which was isolated from the same genus. Purpu-0939Ð5075/2008/0900Ð0636 $ 06.00 " 2008 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D rone inhibited ATP-citrate lyase in a dose-dependent manner and had an IC 50 value of 7 μm (Chan et al, 1993).…”

Section: Introductionmentioning

confidence: 99%

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