Heterocyclic terpenes: linear furano- and pyrroloterpenoids

Liu, Yonghong; Zhang, Si; Abreu, Pedro

doi:10.1039/b604586c

Cited by 84 publications

(53 citation statements)

References 207 publications

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“…Glaciapyrrols A (1), B (2), and C (3) are a family of pyrrolosesquiterpenoids that have been purified from culture extracts of a marine Streptomyces sp. (NPS008187) isolated from a sediment collected in Alaska.…”

Section: Introductionmentioning

confidence: 99%

The Absolute Configuration of the Pyrrolosesquiterpenoid Glaciapyrrol A

Riclea

Dickschat

2011

Chemistry A European J

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The total syntheses of the structurally unique and moderately cytotoxic pyrrolosesquiterpenoid glaciapyrrol A that has been isolated from a marine streptomycete by Macherla et al. and of seven of its stereoisomers have been performed from geraniol or nerol, respectively, using a known diastereoselective Ru-catalysed approach for the synthesis of tetrahydrofurans previously reported by Stark and co-workers. Comparison of (1)H and (13)C NMR data unambiguously clarified the relative configuration of natural glaciapyrrol A that was previously only partly solved from the available NMR data. An enantioselective synthesis was carried out resulting in the unnatural enantiomer (11S,12R,15R)-(-)-glaciapyrrol A. These data establish the absolute configuration of the natural product as (11R,12S,15S)-(+)-glaciapyrrol A.

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Section: Introductionmentioning

confidence: 99%

The Absolute Configuration of the Pyrrolosesquiterpenoid Glaciapyrrol A

Riclea

Dickschat

2011

Chemistry A European J

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“…Marine sponges of the order Dictyoceratida have frequently provided a large number of linear sesterterpenoids (Blunt et al, 2006;Faulkner, 2002;Liu et al, 2006a). Sponges of the genus Sarcotragus were reported to contain compounds such as variabilin (Perry et al, 1987), (7E,12E,20E)-variabilin, (7E,12Z,20Z)-variabilin, 8-hydroxy-(12E,20Z)-variabilin, 14-furan-3-yl-3,7,11-trimethyl-tetradeca-7,11-dienoic acid (Barrow et al, 1988), sarcochromenol sulfates AÐC and sarcohydroquinone sulfates AÐC (Stonik et al, 1992), octa-and nonaprenylhydroquinone sulfates (Wakimoto et al, 1999), geranylfarnesylacetone (Ponomarenko et al, 1998), and sarcotragins A and B (Shin et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

“…Sponges of the order Dictyoceratida have yielded a wide range of new sesterterpenes, many 0939Ð5075/2007/0700Ð0473 $ 06.00 " 2007 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D of which contain both furan and tetronic acid functional groups (Liu et al, 2006a). Typical for these furanosesterterpene tetronic acids is variabilin, which was first isolated from the sponge Ircinia variabilis (Faulkner, 1973).…”

Section: Introductionmentioning

confidence: 99%

Variabilin, a Chemotaxonomic Marker for the Family Irciniidae

Liu

Zhang

Jung

et al. 2007

Zeitschrift Für Naturforschung C

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“…The possible role of chemical repellents such as the sesquiterpenes detected in U. nana (Liu et al, 2006) in biotic interactions with herbivores and other predators is unknown. In Namibia (Burke, 1997) U. nana is found in meadows where herbivores habitually graze, but this activity is not a factor in Falset.…”

Section: Predation By Ants: a Possible Biological Control Of The Invamentioning

confidence: 99%

“…5C). In this phase the outer epidermis of the corolla lobes secrete small golden, refringent, terpenic drops (Liu et al, 2006) which can act as an olfactory reward for possible pollinators.…”

Section: Flower Maturation Protandry and Geitonogamymentioning

confidence: 99%

<i>Ursinia nana</i> (Anthemideae, Asteraceae), an adventive from South Africa which is becoming naturalized in the NE Iberian Peninsula. Observations about its reproductive biology and fruit dispersal mechanisms

Briones¹

2009

Collect. Bot

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The presence of Ursinia nana, an Anthemideae of South-African origin which has been introduced into the NE Iberian Peninsula, is reported for the fi rst time in Europe. The data offered cover its precise location, morphology, chromosome number, ecology and a population census, as well as its life cycle, fl oral structure, reproductive biology and fruit dispersal mechanisms. Of special note are the clear predominance of autogamy (geitonogamy) over xenogamy as a reproductive system and the large number of fruits produced with high and immediate germinative capacity. These characteristics permit rapid colonization by the introduced species, which can become invasive. However, fruit predation by the ant Messor barbarus points to a natural mechanism that helps regulate population growth and makes biological control possible. Finally its possibilities of expansion in the colonized area and of naturalization in the NE Iberian Peninsula are assessed.Key words: annuals; autogamy; Catalonia; fl oral structure; fruit predation; geitonogamy; Messor barbarus; naturalization process; pollination ecology; Spain; Ursinia. ResumenUrsinia nana (Anthemideae, Asteraceae), una adventicia de Sudáfrica en proceso de naturalización en el noreste de la península Ibérica. Observaciones sobre su biología reproductiva y sus mecanismos de dispersión de los frutos.-Se indica por primera vez para el continente europeo la presencia de Ursinia nana, una Anthemideae de origen sudafricano introducida en el NE de la Península Ibérica. Además de su localización precisa, morfología, número cromosómico, ecología y de un censo de sus poblaciones, se ofrecen datos sobre el ciclo vital, estructura fl oral, biología reproductiva y dispersión de los frutos. Son remarcables el claro dominio de la autogamia (geitonogamia) sobre la xenogamia como sistema reproductivo y la alta producción de frutos con elevada e inmediata capacidad germinativa, características que permiten una colonización rápida de esta especie introducida que pudiera devenir invasora. No obstante la predación de sus frutos por la hormiga Messor barbarus evidencian un mecanismo natural que interviene en la regulación del crecimiento de sus poblaciones, lo que puede permitir su control biológico. Finalmente se analizan las posibilidades de expansión en el área colonizada y de su posible naturalización en el NE de la Península Ibérica.Palabras clave: autogamia; Cataluña; depredación de los frutos; España; especies anuales; estructura fl oral; geitonogamia; polinización; Messor barbarus; proceso de naturalización; Ursinia. Resum Ursinia nana (Anthemideae, Asteraceae), una adventícia d'Àfrica del sud en procés de naturalització al nord-est de la península Ibèrica. Observacions sobre la seva biologia reproductiva i els seus mecanismes de dispersió dels fruits.-La presència d'Ursinia nana, una Anthemideae d'origen sud-africà introduïda al NE de la Península Ibèrica, s'assenyala per primera vegada al continent europeu. A més de la seva precisa localització, morfologia, nombre cromosòmic, ec...

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Heterocyclic terpenes: linear furano- and pyrroloterpenoids

Cited by 84 publications

References 207 publications

The Absolute Configuration of the Pyrrolosesquiterpenoid Glaciapyrrol A

The Absolute Configuration of the Pyrrolosesquiterpenoid Glaciapyrrol A

Variabilin, a Chemotaxonomic Marker for the Family Irciniidae

<i>Ursinia nana</i> (Anthemideae, Asteraceae), an adventive from South Africa which is becoming naturalized in the NE Iberian Peninsula. Observations about its reproductive biology and fruit dispersal mechanisms

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