Pyrroloiminoquinone and related metabolites from marine sponges

Antunes, Edith; Copp, Brent R.; Davies‐Coleman, Michael T.; Samaai, Toufiek

doi:10.1039/b407299p

Cited by 183 publications

(172 citation statements)

References 74 publications

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“…[9] However, the presence of a variety of such alkaloids in M. rosea, [3] M. sanguinolenta [4] and in M. haematopus confirms that the occurrence of pyrroloquinoline alkaloids is not restricted to marine sources, but they also appear to be common, in the very least, in some Mycena species.…”

Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 70%

“…Until recently, pyrroloquinoline alkaloids were considered to be rare in terrestrial sources, [9] whereas many representatives are known from the marine environment. [9] However, the presence of a variety of such alkaloids in M. rosea, [3] M. sanguinolenta [4] and in M. haematopus confirms that the occurrence of pyrroloquinoline alkaloids is not restricted to marine sources, but they also appear to be common, in the very least, in some Mycena species.…”

Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 99%

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Red Pyrroloquinoline Alkaloids from the Mushroom Mycena haematopus

Peters¹,

Jaeger²,

Spiteller³

2007

Eur J Org Chem

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Four so far unknown red alkaloid pigments, haematopodin B (1) and the mycenarubins D (3), E (5) and F (6), were isolated from fruiting bodies of Mycena haematopus. The structures of these pyrroloquinoline alkaloids were established by 2D NMR spectroscopic and MS (ESI) methods. Their absolute configurations were determined by comparison of their CD spectra with that of haematopodin (2) or mycenarubin A (4).

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Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 70%

Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 99%

Red Pyrroloquinoline Alkaloids from the Mushroom Mycena haematopus

Peters¹,

Jaeger²,

Spiteller³

2007

Eur J Org Chem

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“…The taxonomy and systematics of the family Latrunculiidae has been complex and controversial [18,51,52], and the arrangements in the family are still being refined [19]. However, L. biformis is easily recognisable due to the possession of an additional form of anisodiscorhabd with a long apical spine, and it has been described from different sites around Antarctica and the Shetland islands [17,53].…”

Section: Discussionmentioning

confidence: 99%

Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity

Janussen

Peifer

et al. 2018

Marine Drugs

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The Antarctic deep-sea sponge Latrunculia (Latrunculia) biformis Kirkpatrick, 1908 (Class Demospongiae Sollas, Order Poecilosclerida Topsent, Latrunculiidae Topsent) was selected for chemical analyses due to its potent anticancer activity. Metabolomic analysis of its crude extract by HRMS/MS-based molecular networking showed the presence of several clusters of pyrroloiminoquinone alkaloids, i.e., discorhabdin and epinardin-type brominated pyridopyrroloquinolines and tsitsikammamines, the non-brominated bis-pyrroloiminoquinones. Molecular networking approach combined with a bioactivity-guided isolation led to the targeted isolation of the known pyrroloiminoquinone tsitsikammamine A (1) and its new analog 16,17-dehydrotsitsikammamine A (2). The chemical structures of the compounds 1 and 2 were elucidated by spectroscopic analysis (one-dimensional (1D) and two-dimensional (2D) NMR, HR-ESIMS). Due to minute amounts, molecular modeling and docking was used to assess potential affinities to potential targets of the isolated compounds, including DNA intercalation, topoisomerase I-II, and indoleamine 2,3-dioxygenase enzymes. Tsitsikammamines represent a small class of pyrroloiminoquinone alkaloids that have only previously been reported from the South African sponge genus Tsitsikamma Samaai & Kelly and an Australian species of the sponge genus Zyzzya de Laubenfels. This is the first report of tsitsikammamines from the genus Latrunculia du Bocage and the successful application of molecular networking in the identification of comprehensive chemical inventory of L. biformis followed by targeted isolation of new molecules. This study highlights the high productivity of secondary metabolites of Latrunculia sponges and may shed new light on their biosynthetic origin and chemotaxonomy.

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“…A prime example of this latter group of marine metabolites are ammosamides A (1) and B (2), whose first total synthesis was reported very recently by Hughes and Fenical. [3] The research group of Fenical is also to be credited with the discovery of 1 and 2, which were obtained from the marine streptomyces strain CNR-698 that was isolated from oceanic bottom sediments collected at a depth of more than 1600 m. [4] Ammosamides belong to the pyrroloiminoquinone class of natural products, [5] and it is worth noting that ammosamide A (1) is the first natural product ever isolated to contain a thiog-lactam ring. [4,6] Although the structures of 1 and 2 are less complex than what one generally tends to associate with marine natural products, they still pose a formidable challenge for total synthesis, because of the dense functionalization of the aromatic core, and also because of their very poor solubility in organic solvents.…”

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confidence: 98%