Lituarines A, B, and C: a new class of macrocyclic lactones from the New Caledonian sea pen Lituaria australasiae

Vidal, J.; Escale, R.; Girard, Jean Pierre; Rossi, Jean‐Claude; Chantraine, J.; Aumelas, André

doi:10.1021/jo00048a017

Cited by 47 publications

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“…A similar blocking action at the G1 phase was also noticed for dichlorolissoclimide (101a) and chlorolissoclimide (101b), which are labdane diterpenes isolated from Lissoclinum voeltzkowi [103d]. Lituarines A ± C (73a ± 73c), which are macrolides isolated from a pennatulacean coral, Lituaria australasiae, proved cytotoxic at the ppb level [82]. At the same dosage level, a family of macrolides from deeper-water lithistid sponges, sphinxolides 14a ± 14i, proved cytotoxic toward several human cancer cell lines, 14b being the most active, causing depolymerization of microfilaments, similar to the cyanobacterial macrolides scytophycins [17f] and tolytoxin [17g], which they structurally resemble.…”

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confidence: 60%

“…Another New Caledonian pennatulacean, Lituaria australasiae (Gray, 1970), digresses sharply from its taxonomic group due to the production of macrolides 73a ± 73c [82]. As an isolated example from pennatulaceans, the polyether nature of these macrolides suggests bacterial biosynthesis.…”

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confidence: 99%

“…Pennatulacea, Veretillidae, Lituaria australasiae (Gray, 1970)/SW lagoon Lituarines A ± C (73a ± 73c) (ct KB 3.7 ± 5 ¥ 10 À3 , 1 ± 2 ¥ 10 À3 , 5 ± 6 ¥ 10 À3 , resp. )/polyether macrolides [82] Unique examples of macrolides from pennatulacean corals. (ct P388,and HT29 10 and 20 resp.…”

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confidence: 99%

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Natural‐Product Diversity of the New Caledonian Marine Ecosystem Compared to Other Ecosystems: A Pharmacologically Oriented View

Laurent

Pietra²

2004

Chemistry & Biodiversity

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In comparison with other ecosystems, biodiversity and natural-product diversity of the New Caledonian marine ecosystem, comprising lagoons, barrier reefs, and deep waters in seamount regions, are described here phylogenetically with the aid of molecular drawings and tabulation of data. Admittedly, since the inception of these studies in 1977, the comparison is biased by selection of New Caledonian organisms on the basis of positive pharmacologically oriented bioassays. However, we show that these and other distortions must be accepted to draw any comparison on a regional basis, which, nonetheless, turn out to be useful for the progress of knowledge, particularly in directing future explorations of biodiversity in the search for new pharmacologically active metabolites.

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confidence: 99%

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Natural‐Product Diversity of the New Caledonian Marine Ecosystem Compared to Other Ecosystems: A Pharmacologically Oriented View

Laurent

Pietra²

2004

Chemistry & Biodiversity

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“…In an authoritative taxonomic guide, this genus does not appear, while Plexauroides is listed [2fl. Except for Lituaria [6], briaranes were reported for representative species of all the above genera of pennatulacean corals, including some in the primitive suborder Sessiliflorae (Cavernulina [3fl, Renilla [3d], Veretillum [l] and, here, Funiculina). Therefore, briarane diterpenes must be an ancient acquisition by pennatulaceans.…”

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confidence: 99%

“…cynomorium. It would be interesting to know if species of the sessilifloran Lituaria [6] contain briaranes. Table 2).…”

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Bis‐allylic Reactivity of the Funicolides, 5,8(17)‐diunsaturated briarane diterpenes of the sea pen Funiculina quadrangularis from the tuscan archipelago, leading to 16‐nortaxane derivatives

Guerriero¹,

D’Ambrosio²,

Pietra³

1995

Helvetica Chimica Acta

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(19.1V.95) Funicolides A C (1-3), D (5), and E (7) and 7-epifunicolide A (4), new 5,8(17)-diunsaturated briarane diterpenes, as well as the known analogue brianthein W (6), were isolated from the pennatulacean coral Funiculina quadrangularis (PALLAS, 1766) collected in the Tuscan archipelago. Easy degradation under oxidative and/or basic conditions served to assign the ester groups at C(2) or C(14), while revealing bis-allylic reactivity at C(7) with formation of 16-nortaxane derivatives.1. Introduction. -Briarane diterpenes, which conceivably arise biogenetically via C(3)-C(8) cyclization of cembranoid precursors [I], were first isolated from the gorgonacean coral Briareum asbestinum (PALLAS) (

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Preparation of N ‐Formylamides by Oxidative Cleavage of N ‐Acylaminoacids

Kilenyi¹

2023

Organic Syntheses

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N ‐Formylamides are versatile intermediates for the preparation of pharmacologically‐preferred 1,2,4‐triazole ring system by the Einhorn‐Brunner reaction. They are also important as starting materials for the rather inaccessible enamide and dienamide functional groups, which are found in several highly biologically‐active natural products. This chapter describes the procedure for preparation of N‐formylamides by oxidative cleavage of N ‐acylaminoacids. It presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. The chapter also describes the hazards associated with working with chemicals and the ways to deal with these hazards.

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Lituarines A, B, and C: a new class of macrocyclic lactones from the New Caledonian sea pen Lituaria australasiae

Cited by 47 publications

References 0 publications

Natural‐Product Diversity of the New Caledonian Marine Ecosystem Compared to Other Ecosystems: A Pharmacologically Oriented View

Natural‐Product Diversity of the New Caledonian Marine Ecosystem Compared to Other Ecosystems: A Pharmacologically Oriented View

Bis‐allylic Reactivity of the Funicolides, 5,8(17)‐diunsaturated briarane diterpenes of the sea pen Funiculina quadrangularis from the tuscan archipelago, leading to 16‐nortaxane derivatives

Preparation of N ‐Formylamides by Oxidative Cleavage of N ‐Acylaminoacids

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