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Isolation, structural elucidation, and absolute stereochemistry of enigmazole A, a cytotoxic phosphomacrolide from the Papua New Guinea marine sponge Cinachyrella enigmatica.

Enigmazole A (1), a novel phosphate-containing macrolide, was isolated from a Papua New Guinea collection of the marine sponge Cinachyrella enigmatica. The structure of 1, including the absolute stereochemistry at all eight chiral centers, was determined by a combination of spectroscopic analyses an... Full description

Journal Title: Journal of the American Chemical Society August 4, 2010, Vol.132(30), pp.10278-10285
Main Author: Oku, Naoya
Other Authors: Takada, Kentaro , Fuller, Richard W , Wilson, Jennifer A , Peach, Megan L , Pannell, Lewis K , Mcmahon, James B , Gustafson, Kirk R
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; DOI: 10.1021/ja1016766
Link: http://search.proquest.com/docview/748929941/?pq-origsite=primo
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title: Isolation, structural elucidation, and absolute stereochemistry of enigmazole A, a cytotoxic phosphomacrolide from the Papua New Guinea marine sponge Cinachyrella enigmatica.
format: Article
creator:
  • Oku, Naoya
  • Takada, Kentaro
  • Fuller, Richard W
  • Wilson, Jennifer A
  • Peach, Megan L
  • Pannell, Lewis K
  • Mcmahon, James B
  • Gustafson, Kirk R
subjects:
  • Animals–Chemistry
  • Antineoplastic Agents–Isolation & Purification
  • Drug Screening Assays, Antitumor–Pharmacology
  • Humans–Chemistry
  • Macrolides–Isolation & Purification
  • Models, Molecular–Pharmacology
  • Molecular Structure–Drug Therapy
  • Neoplasms–Chemistry
  • Organophosphorus Compounds–Isolation & Purification
  • Oxazoles–Pharmacology
  • Papua New Guinea–Chemistry
  • Porifera–Isolation & Purification
  • Porifera–Pharmacology
  • Porifera–Chemistry
  • Antineoplastic Agents
  • Macrolides
  • Organophosphorus Compounds
  • Oxazoles
  • Enigmazole A
ispartof: Journal of the American Chemical Society, August 4, 2010, Vol.132(30), pp.10278-10285
description: Enigmazole A (1), a novel phosphate-containing macrolide, was isolated from a Papua New Guinea collection of the marine sponge Cinachyrella enigmatica. The structure of 1, including the absolute stereochemistry at all eight chiral centers, was determined by a combination of spectroscopic analyses and a series of microscale chemical derivatization studies. Compound 1 is comprised of an 18-membered phosphomacrolide that contains an embedded exomethylene-substituted tetrahydropyran ring and an acyclic portion that spans an embedded oxazole moiety. Two additional analogues, 15-O-methylenigmazole A and 13-hydroxy-15-O-methylenigmazole A, were also isolated and assigned. The enigmazoles are the first phosphomacrolides from a marine source and 1 exhibited significant cytotoxicity in the NCI 60-cell line antitumor screen, with a mean GI(50) of 1.7 microM.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; DOI: 10.1021/ja1016766
fulltext: no_fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleIsolation, structural elucidation, and absolute stereochemistry of enigmazole A, a cytotoxic phosphomacrolide from the Papua New Guinea marine sponge Cinachyrella enigmatica.
creatorOku, Naoya ; Takada, Kentaro ; Fuller, Richard W ; Wilson, Jennifer A ; Peach, Megan L ; Pannell, Lewis K ; Mcmahon, James B ; Gustafson, Kirk R
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identifierE-ISSN: 1520-5126 ; DOI: 10.1021/ja1016766
subjectAnimals–Chemistry ; Antineoplastic Agents–Isolation & Purification ; Drug Screening Assays, Antitumor–Pharmacology ; Humans–Chemistry ; Macrolides–Isolation & Purification ; Models, Molecular–Pharmacology ; Molecular Structure–Drug Therapy ; Neoplasms–Chemistry ; Organophosphorus Compounds–Isolation & Purification ; Oxazoles–Pharmacology ; Papua New Guinea–Chemistry ; Porifera–Isolation & Purification ; Porifera–Pharmacology ; Porifera–Chemistry ; Antineoplastic Agents ; Macrolides ; Organophosphorus Compounds ; Oxazoles ; Enigmazole A
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descriptionEnigmazole A (1), a novel phosphate-containing macrolide, was isolated from a Papua New Guinea collection of the marine sponge Cinachyrella enigmatica. The structure of 1, including the absolute stereochemistry at all eight chiral centers, was determined by a combination of spectroscopic analyses and a series of microscale chemical derivatization studies. Compound 1 is comprised of an 18-membered phosphomacrolide that contains an embedded exomethylene-substituted tetrahydropyran ring and an acyclic portion that spans an embedded oxazole moiety. Two additional analogues, 15-O-methylenigmazole A and 13-hydroxy-15-O-methylenigmazole A, were also isolated and assigned. The enigmazoles are the first phosphomacrolides from a marine source and 1 exhibited significant cytotoxicity in the NCI 60-cell line antitumor screen, with a mean GI(50) of 1.7 microM.
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titleIsolation, structural elucidation, and absolute stereochemistry of enigmazole A, a cytotoxic phosphomacrolide from the Papua New Guinea marine sponge Cinachyrella enigmatica.
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titleIsolation, structural elucidation, and absolute stereochemistry of enigmazole A, a cytotoxic phosphomacrolide from the Papua New Guinea marine sponge Cinachyrella enigmatica.
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