A Complex Pyrrolo‐oxazinone and Its Iodo Derivative Isolated from a Tunicate

Yoshida, Wesley Y.; Lee, Kit K.; Carroll, Anthony Richard; Scheuer, Paul J.

doi:10.1002/hlca.19920750525

Cited by 86 publications

(57 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pyrrole-derived alkaloids related to lamellarin include lukianols ( 224–225 ), isolated from an unidentified Pacific tunicate [ 145 ], polycitones ( 226–227 ) and polycitrins ( 228–229 ), from Polycitor species [ 146 , 147 ], and ningalins ( 230–233 ), from Didemnum sp. ( Figure 25 ) [ 148 ].…”

Section: Tyrosine- and Phenylalanine-derived Alkaloidsmentioning

confidence: 99%

“…The structures of the lukianols A and B contained a pyrrolooxazinone moiety; they appear to arise by the same biogenetic pathways leading to lamellarin O and P isolated from the marine sponge Dendrilla cactos [ 135 ]. Lukianol A ( 224 ) inhibited DNA synthesis in L1210 lymphocytic leukemia cell lines with less effect on RNA and protein synthesis, demonstrating a therapeutic profile very similar to current clinically used anticancer agents [ 145 ]. Ningalins A–D ( 230–233 ) are condensed aromatic systems with the unifying theme that all appear derived from the condensation of two, three, four, and five DOPA precursors, respectively.…”

Section: Tyrosine- and Phenylalanine-derived Alkaloidsmentioning

confidence: 99%

See 1 more Smart Citation

Alkaloids from Marine Ascidians

2011

View full text Add to dashboard Cite

show abstract

Section: Tyrosine- and Phenylalanine-derived Alkaloidsmentioning

confidence: 99%

Section: Tyrosine- and Phenylalanine-derived Alkaloidsmentioning

confidence: 99%

Alkaloids from Marine Ascidians

2011

View full text Add to dashboard Cite

show abstract

“…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

View full text Add to dashboard Cite

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).

show abstract

“…19 As part of our interest in the chemical diversity of Chinese marine sponges, the species Iotrochota baculifera, which is indigenous to the reef Bay of Hainan Island, was collected. From this material, 15 new purpurone related alkaloids were isolated and characterized, mostly sulfated pyrrole alkaloids, named baculiferins A-O (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16), together with purpurone (1) and ningalin A (17). 0968 …”

Section: Introductionmentioning

confidence: 99%