Makaluvamine G, a cytotoxic pigment from an an Indonesian Sponge Histodermella sp.

Carney, John R.; Scheuer, Paul J.; Kelly‐Borges, Michelle

doi:10.1016/s0040-4020(01)96256-8

Cited by 87 publications

(99 citation statements)

References 12 publications

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“…Benzylation of 5 followed by condensation with ethyl all attempts to effect the final imine formation between the tryptamine nitrogen and the indoloquinone carbonyl in these types of intermediates (12a, b) were unsuccessful (Fig. An alternative approach (route b) in which phenolic coupling of the previously produced aminoindoloquinone imine (15) was employed in the final step accomplished the first total synthesis of discorhabdin C. The direct imine formation from the indoloquinone (13) was achieved by protection of the indoloquinone (9b) nitrogen with the tosyl group followed by an acidic dehydrative treatment. An alternative approach (route b) in which phenolic coupling of the previously produced aminoindoloquinone imine (15) was employed in the final step accomplished the first total synthesis of discorhabdin C. The direct imine formation from the indoloquinone (13) was achieved by protection of the indoloquinone (9b) nitrogen with the tosyl group followed by an acidic dehydrative treatment.…”

Section: Our Synthesis [3]mentioning

confidence: 99%

Pyrroloiminoquinone Alkaloids: Discorhabdins and Makaluvamines

Harayama¹,

Kita²

2005

COC

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The pyrroloiminoquinone alkaloid family consisting of discorhabdins and makaluvamines exhibits antitumor activities derived from their unique highly-fused structures. The total synthesis of them and the key reactions used in the total synthesis of these compounds are described. 3 (86%) 1 : R=H 2 : R=TMS Het 4 low yield Pyrroloiminoquinone Alkaloids Current Organic Chemistry, 2005, Vol. 9, No. 15 1569

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Section: Our Synthesis [3]mentioning

confidence: 99%

Pyrroloiminoquinone Alkaloids: Discorhabdins and Makaluvamines

Harayama¹,

Kita²

2005

COC

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“…Isolation of makaluvamine I (68) and damirone C (69) has previously been reported from a marine sponge Zyzzya fuliginosa or Histodermella sp. (Schmidt et al, 1995;Carney and Scheuer, 1993). Other related pyrroloiminoquinone pigments, makaluvamines A-N and damirones A-B, were also isolated from marine sponges Venables et al, 1997;Izawa et al, 1994).…”

Section: Alkaloidsmentioning

confidence: 96%

Secondary metabolites of slime molds (myxomycetes)

et al. 2005

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“…This series of alkaloids comprise of more than 60 metabolites including discorhabdins [35], epinardins [36], batzellines [37], isobatzellines [37], makaluvamines [33, 38-42], and veiutamine [43]. These alkaloids have shown a variety of biological activities such as inhibition of topoisomerase I [38] and II, [33] cytotoxicity against different tumor cell lines, [33, 44] antifungal [38] and antimicrobial activities [32]. …”

Section: Introductionmentioning

confidence: 99%

Recent advances in isolation, synthesis, and evaluation of bioactivities of bispyrroloquinone alkaloids of marine origin

Nijampatnam

Dutta

Velu

2015

Chinese Journal of Natural Medicines

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The ocean continues to provide a plethora of unique scaffolds capable of remarkable biological applications. A large number of pyrroloiminoquinone alkaloids, including discorhabdins, epinardins, batzellines, makaluvamines, and veiutamine have already been isolated from marine organisms. A class of pyrroloiminoquinone-related alkaloids known as bispyrroloquinones is the focus of this review. This family of marine alkaloids, which contain an aryl substituted bispyrroloquinone ring system, includes three subclasses of alkaloids namely, wakayin, tsitsikammamines A-B and zyzzyanones A-D. Both wakayin and the tsitsikammamines contain a tetracyclic fused bispyrroloiminoquinone ring system, while zyzzyanones contain a fused tricyclic bispyrroloquinone ring system. The unique chemical structures of these marine natural products and their diverse biological properties, including antifungal and antimicrobial activity, as well as the potent, albeit generally nonspecific and universal cytotoxicities, have attracted great interest of synthetic chemists over the past three decades. Tsitsikammamines, wakayin, and several of their analogues show inhibition of topoisomerases. One additional possible mechanism of anticancer activity of tsitsikammamines analogues that was discovered recently is through the inhibition of indoleamine 2,3-dioxygenase, an enzyme involved in tumoral immune resistance. This review discusses the isolation, synthesis, and bioactivities of bispyrroloquinone alkaloids and their analogues.

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Makaluvamine G, a cytotoxic pigment from an an Indonesian Sponge Histodermella sp.

Cited by 87 publications

References 12 publications

Pyrroloiminoquinone Alkaloids: Discorhabdins and Makaluvamines

Pyrroloiminoquinone Alkaloids: Discorhabdins and Makaluvamines

Secondary metabolites of slime molds (myxomycetes)

Recent advances in isolation, synthesis, and evaluation of bioactivities of bispyrroloquinone alkaloids of marine origin

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