New Alkaloids from the Papua New Guinean Sponge <i>Agelas nakamurai</i>

Iwagawa, Tetsuo; Kaneko, Masakatsu; Okamura, Hiroaki; Nakatani, Munehiro; Soest, R.W.M. van

doi:10.1021/np980173q

Cited by 63 publications

(46 citation statements)

References 9 publications

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“…Given that many of these compounds probably result from rearrangements 47 of anominine (22), we first decided to focus our attention on the synthesis of this product first. We also hoped that the more straightforward derivatives such as thelepogine (26), 48 Agelas compound 27, 49 and aignopsanoic acid (28) 50 would not only be accessible through the same methodology, but that their simpler structures might prove a fruitful training ground to develop our strategy for the more structurally challenging Aspergillus natural products. Our initial synthetic endeavors were directed by the availability of compound 29, proceeding from our total syntheses of xylarenal A (30) 51 (Scheme 3).…”

Section: Background To Developing a New Wmk Synthesismentioning

confidence: 99%

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

Bradshaw¹,

Bonjoch²

2011

Synlett

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The Hajos-Parrish-Eder-Sauer-Wiechert reaction can be considered as the origin of asymmetric organocatalysis, giving rise to the Wieland-Miescher ketone 1 (WMK), a versatile building block. Although 40 years have passed since its discovery, a highly enantioselective and scalable synthesis of the WMK has remained elusive. This account details a solution to that problem that came about in the development of methodology towards C-8a WMK analogues as part of the total synthesis of complex diterpene natural products. The work has been placed in the context of the historical background and reactivity of this important building block, highlighting the challenges faced by organocatalysis in large-scale reactions.

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Section: Background To Developing a New Wmk Synthesismentioning

confidence: 99%

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

Bradshaw¹,

Bonjoch²

2011

Synlett

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“…Agelasine J, K and L [47] and agelasimine A and B [48,49] were isolated from the Solomon Islands orange marine sponge Agelas mauritiana . An agelasine 1 with an unusual thelepogane skeleton in the terpene moiety was isolated from the sponge Agelas nakamurai Hoshino collected in the Fly Islands, Papua, New Guinea [66]. Another new agelasine derivative has recently been isolated from the Caribbean sponge Agelas clathrodes [67], this compound has been called agelasidine J, even though it is described as a new 9-methyladeninium derivative.…”

Section: Sources Of Agelasines Asmarines and Related Compoundsmentioning

confidence: 99%

Terpenyl-Purines from the Sea

Gordaliza

2009

Marine Drugs

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Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity against a variety of species, including Mycobacterium tuberculosis, and also an important cytotoxic activity against several cancer cell lines, including multidrug-resistant ones. Of particular interest in this context are the asmarines (tetrahydro[1,4]diazepino[1,2,3-g,h]purines), which have shown potent antiproliferative activity against several types of human cancer cell lines. This review summarizes the sources of isolation, chemistry and bioactivity of marine alkylpurines and their bioactive derivatives.

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“…1), and named brevicompanine D. The MOM group is a common protective group for amines, 6) alcohols, 7) and phenols 8) in organic synthesis but the MOM ether or MOM amine groups are quite rare in natural products. 9,10) Compound 4, named brevicompanine E, was obtained as a colorless powder. The molecular formula of 4 was established as C 25 were observed in 4 instead.…”

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confidence: 99%

Diketopiperazine Alkaloids from a Deep Ocean Sediment Derived Fungus Penicillium sp.

Xia

Zhu

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Five new diketopiperazine alkaloids, brevicompanines D-H (3-7), together with two known analogs, allobrevicompanine B (1) and fructigenine B (2), were isolated from a deep ocean sediment derived fungus Penicillium sp. Their structures were established by spectroscopic methods including 2D NMR and chiral HPLC analysis. Compounds 4 and 7 inhibited lipopolysaccharide (LPS)-induced nitric oxide production in BV2 microglial cells.

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New Alkaloids from the Papua New Guinean Sponge Agelas nakamurai

Abstract: Two new bromopyrroles and a new diterpene possessing a 9-methyladenium moiety have been isolated from the Papua New Guinean sponge Agelas nakamurai Hoshino.

Cited by 63 publications

References 9 publications

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

Terpenyl-Purines from the Sea

Diketopiperazine Alkaloids from a Deep Ocean Sediment Derived Fungus Penicillium sp.

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