Prianicin A and B, nor-sesterterpenoid peroxide antibiotics from red sea sponges

Sokoloff, S.; Halevy, S.; Usieli, Varda; Colorni, A.; Sarel, Shalom

doi:10.1007/bf01949377

Cited by 26 publications

(19 citation statements)

References 3 publications

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“…29 The pallescensins are a group a sesquiterpene furans from Dysidea pallescens. 30 The synthesis of pallescensin-1 (191), pallescensin-2 (1 92), and pallescensin-A (193) allowed assignment of the absolute configurations. ' Pallescensin-E (1 94), pallescensin-F (1 9 9 , and pallescensin-G (1 96)' 33 have also been synthesized to confirm the structural assignments.…”

Section: Psummaplysilia P U R P ~R E a ~~mentioning

confidence: 99%

Marine natural products: metabolites of marine invertebrates

Faulkner¹

1984

Nat. Prod. Rep.

327

154

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Section: Psummaplysilia P U R P ~R E a ~~mentioning

confidence: 99%

Marine natural products: metabolites of marine invertebrates

Faulkner¹

1984

Nat. Prod. Rep.

327

154

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“…Several years later, in 1982, Solokoff et al [20] isolated from Red Sea sponges a norsesterterpenoid peroxide that was named as prianicin A, although it was identical to muqubilin (12). The antibiotic properties of 12 against gram-positive and gram-negative bacteria and against fungi were measured, proving to be four to ten times more effective than tetracycline against beta hemolytic Streptococcus but non-effective against the gramnegative bacteria assayed.…”

Section: Endoperoxide Norterpenes With a Monocyclic Carbon Skeletonmentioning

confidence: 99%

“…However, judging from the similar bioactivities of 15-17, the α,β-unsaturated ketone seems not to be essential [27]. One year later, the same authors [28] isolated, after esterification, ent-muqubilin benzyl ester (20). Its absolute configuration was determined by the Mosher's NMR methodology.…”

Section: Endoperoxide Norterpenes With a Monocyclic Carbon Skeletonmentioning

confidence: 99%

“…To a lesser extent, the anti-inflammatory activity has also been measured. Bacteria 1 [6], 3a [9], 4 [9] 12 [20] 57 [46], 58 [46], 61 [47], 67 [51], 68 [51], 79 [61] 80 [64], 81 [64], 84 [69], 86 [72] Yeasts 1 [6] 12 [20] 57 [46], 58 [46], 61 [47], 79 [61] Viruses 5 [11] 12 [11] 67 [51], 68 [51] Plasmodia 12 [24], 15 [24,28], 20 [24,28], 21 [39], 45 [39], 45a [39], 46 [39], 47 [39] 50 [23], 55 [28] 8 [24,28], 9 [15], 13 [39], 19 [24,28], 30 [39], 31 [15], 32 [15] Trypanosoma 10 [16], 11 [16] 22 [16] 50…”

Section: Biological Activity Overviewmentioning

confidence: 99%

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Marine Terpenic Endoperoxides

et al. 2021

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Organic extracts of marine invertebrates, mainly sponges, from seas all over the world are well known for their high in vitro anticancer and antibiotic activities which make them promising sources of compounds with potential use as pharmaceutical leads. Most of the structures discovered so far have a peculiar structural feature in common: a 1,2-dioxane ring. This is a highly reactive heterocycle that can be considered as an endoperoxide function. Together with other structural features, this group could be responsible for the strong biological activities of the substances present in the extracts. Numerous research programs have focused on their structural elucidation and total synthesis since the seventies. As a consequence, the number of established chiral centres and the similarity between different naturally occurring substances is increasingly higher. Most of these compounds have a terpenoid nature, mainly diterpene and sesterterpene, with several peculiar structural features, such as the loss of one carbon atom. Although there are many reviews dealing with the occurrence of marine peroxides, their activities, or potential pharmaceutical uses, no one has focused on those having a terpene origin and the endoperoxide function. We present here a comprehensive review of these compounds paying special attention to their structural features and their biological activity.

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“…The optical rotation and a complete listing of 13 C NMR signals for muqubilin were also made available for the first time. Through analyzing 1 H- 1 H coupling constants with the aid of empirical rule of 13 C NMR shifts for this family of cyclic peroxides and the information gained from chemical degradation, they reverted the relative configuration of (+)-muqubilin at the peroxy ring from cis (as assigned by Sarel) to trans (i.e., H-3 is trans to the methyl group at C-6). However, establishment of the stereochemistry at the C-2 was impossible.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis Muqubilin and Negombatoperoxides B and C/D

Wang

2021

J. Org. Chem.

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Muqubilin, negombatoperoxide B, and negombatoperoxide C/D were synthesized through enantioselective routes, with the quaternary center derived from a peroxy chiral building block of known absolute configuration. The C-2/C-3 stereogenic centers were introduced by asymmetric aldol condensation, and the 1,2-dioxane ring was constructed via an intramolecular alkylation of a hydroperoxide with a mesylate. The synthetic samples showed physical and spectroscopic data consistent with those reported in the literature and thus verified the configurations of the natural products. A potentially more expeditious enantioselective entry to the 1,2-dioxane-aldol moiety (C-1 to C-6) of such cyclic peroxides was also briefly explored, where the C-2/C-3 stereogenic centers were installed through a [2+2] cycloaddition and the 1,2-dioxane ring was closed via an intramolecular alkylation coupled with an alkyl-oxygen cleavage of a β-lactone.

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Prianicin A and B, nor-sesterterpenoid peroxide antibiotics from red sea sponges

Cited by 26 publications

References 3 publications

Marine natural products: metabolites of marine invertebrates

Marine natural products: metabolites of marine invertebrates

Marine Terpenic Endoperoxides

Enantioselective Synthesis Muqubilin and Negombatoperoxides B and C/D

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