Palmerolide macrolides from the Antarctic tunicate Synoicum adareanum

Noguez, Jaime H.; Diyabalanage, Thushara; Miyata, Yoshinari; Xie, Xiao Song; Valeriote, Frederick A.; Amsler, Charles D.; McClintock, James B.; Baker, Bill J.

doi:10.1016/j.bmc.2011.06.004

Cited by 50 publications

(27 citation statements)

References 12 publications

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“…[15]; the unusual antibacterial polyketide, lindgomycin ( 46 ) from the culture broth of a Lindgomycetaceae strain [36]; the antioxidant compound ramalin ( 104 ) from the Antarctic lichen Ramalina terebrata [61]; the new antiparasitic tricyclic sesquiterpenoids, shagenes A ( 130 ) and B ( 131 ) from an undescribed Antarctic soft coral [76]; and the new macrolides, palmerolide A ( 205 ) and D–G ( 206 – 209 ) with potent V-ATPase inhibitory and sub-micromolar activity against melanoma from the Antarctic tunicate Synoicum adareanum [111,112]. …”

Section: Discussionmentioning

confidence: 99%

“…Further chemical investigation of the same Antarctic tunicate S. adareanum yielded five new bioactive macrolides, palmerolide A ( 205 ) and D–G ( 206 – 209 ) (Figure 19). Most of these palmerolides were potent V-ATPase inhibitors and had sub-micromolar activity against melanoma [111,112]. Especially, palmerolide A remained the most potent of this series of natural products against melanoma cells.…”

Section: Tunicatesmentioning

confidence: 99%

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Secondary Metabolites from Polar Organisms

Tian

Zhao

2017

Marine Drugs

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Polar organisms have been found to develop unique defences against the extreme environment environment, leading to the biosynthesis of novel molecules with diverse bioactivities. This review covers the 219 novel natural products described since 2001, from the Arctic and the Antarctic microoganisms, lichen, moss and marine faunas. The structures of the new compounds and details of the source organism, along with any relevant biological activities are presented. Where reported, synthetic and biosynthetic studies on the polar metabolites have also been included.

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Section: Discussionmentioning

confidence: 99%

Section: Tunicatesmentioning

confidence: 99%

Secondary Metabolites from Polar Organisms

Tian

Zhao

2017

Marine Drugs

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“…Palmerolide A Palmerolide A (25) ( Figure 13) is a macrocyclic polyketide isolated from the ascidian Synoicum adareanum. Palmerolide A displays selective cytotoxicity toward melanoma by inhibiting V-ATPase [74]. As a promising compound, palmerolide A was chemically synthesized by enantio-selective methods [75], by which a large amount of palmerolide A and its analogs could be made for the Most of the peptides discovered from ascidian-associated microbes contain circular sequences and exhibit antibiotic or antitumor activities.…”

Section: Polyketides From Ascidiansmentioning

confidence: 99%

Origins and Bioactivities of Natural Compounds Derived from Marine Ascidians and Their Symbionts

Dou

Dong

2019

Marine Drugs

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Marine ascidians are becoming important drug sources that provide abundant secondary metabolites with novel structures and high bioactivities. As one of the most chemically prolific marine animals, more than 1200 inspirational natural products, such as alkaloids, peptides, and polyketides, with intricate and novel chemical structures have been identified from ascidians. Some of them have been successfully developed as lead compounds or highly efficient drugs. Although numerous compounds that exist in ascidians have been structurally and functionally identified, their origins are not clear. Interestingly, growing evidence has shown that these natural products not only come from ascidians, but they also originate from symbiotic microbes. This review classifies the identified natural products from ascidians and the associated symbionts. Then, we discuss the diversity of ascidian symbiotic microbe communities, which synthesize diverse natural products that are beneficial for the hosts. Identification of the complex interactions between the symbiont and the host is a useful approach to discovering ways that direct the biosynthesis of novel bioactive compounds with pharmaceutical potentials.

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“…Isolation : The palmerolides (Figure 1) were isolated by Baker and co‐workers from the tunicate Synoicum adareanum encountered in the cold shallow waters off Antarctica near Anvers Island 1. 2 These compounds, like many Antarctic marine natural products, offer exciting opportunities for drug discovery. Antarctica is isolated from the other continents by large distances, deep waters, and circumpolar marine currents 3.…”

Section: Introductionmentioning

confidence: 99%

“…V-ATPase inhibition versus cytotoxicity among the palmerolides. [2] Palm A Palm D Palm E Palm F Palm G V-ATPase [a] 0.002 0.025 > 10.000 0.063 0.007 UACC-62 [b] 0.024 0.002 > 5.000 0.758 1.207…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cytotoxic Palmerolides

Lisboa

Dudley

2013

Chemistry A European J

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The chemical synthesis of the palmerolides is the subject of this review. The palmerolides are a family of Antarctic marine natural products, many of which display potent and selective cytotoxicity against melanoma cells. The confluence of promising bioactivities, limited natural supplies, and complex structures makes the palmerolides exciting targets for chemical synthesis. To date, several approaches have been reported, and a consensus strategy based on convergent fragment assembly has emerged. Collective wisdom from myriad approaches reviewed here may enable hybrid strategies capable of delivering larger amounts of synthetic palmerolides to support continued biological studies. Considering the relative lack of options for melanoma chemotherapy and the intriguing activity profile of the palmerolides, efforts aimed at developing an efficient, gram-scale synthesis of palmerolide A and congeneric structures should be given a high priority.

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Palmerolide macrolides from the Antarctic tunicate Synoicum adareanum

Cited by 50 publications

References 12 publications

Secondary Metabolites from Polar Organisms

Secondary Metabolites from Polar Organisms

Origins and Bioactivities of Natural Compounds Derived from Marine Ascidians and Their Symbionts

Synthesis of Cytotoxic Palmerolides

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