Diterpenoid feeding-deterrents from Laurencia saitoi

Kurata, K.; Taniguchi, Koki; Agatsuma, Yukio; Suzuki, Minoru

doi:10.1016/s0031-9422(97)00461-5

Cited by 77 publications

(46 citation statements)

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“…-The marine red algal species of the genus Laurencia (order Ceramiales, family Rhodomelaceae) have been extensively investigated and were found to be rich sources of halogenated sesquiterpenes, diterpenes, triterpenes, and nonterpenoid C 15 -acetogenins [1]. However, only one article describing chemical constituents of L. saitoi has been published, revealing the presence of halogenated and nonhalogenated diterpenes of parguerane, isoparguerane, and deoxyparguerane types [2].In our continuing investigations on the chemical constituents of Chinese marine red algal species of the Rhodomelaceae family [3 -12], we examined the chemical constituents of L. saitoi that was collected off the coast of northern Shandong Province, P. R. China. These efforts resulted in the isolation and identification of four new halogenated sesquiterpenes including 10-bromo-3-chloro-2,7-epoxychamigr-9-en-8a-ol (1), 2,10b-dibromochamigra-2,7-dien-9a-ol (2), (9S)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (3), and (9R)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (4).…”

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Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae)

et al. 2009

Helvetica Chimica Acta

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Four new halogenated sesquiterpenes, 10-bromo-3-chloro-2,7-epoxychamigr-9-en-8a-ol (1), 2,10b-dibromochamigra-2,7-dien-9a-ol (2), (9S)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (3), and (9R)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (4), were characterized from the marine red alga Laurencia saitoi. In addition, two known halosesquiterpenes, 2,10-dibromo-3-chlorochamigr-7-en9a-ol (5) and isolaurenisol (6), were also isolated and identified. Their structures were established on the basis of extensive analysis of spectroscopic data.Introduction. -The marine red algal species of the genus Laurencia (order Ceramiales, family Rhodomelaceae) have been extensively investigated and were found to be rich sources of halogenated sesquiterpenes, diterpenes, triterpenes, and nonterpenoid C 15 -acetogenins [1]. However, only one article describing chemical constituents of L. saitoi has been published, revealing the presence of halogenated and nonhalogenated diterpenes of parguerane, isoparguerane, and deoxyparguerane types [2].In our continuing investigations on the chemical constituents of Chinese marine red algal species of the Rhodomelaceae family [3 -12], we examined the chemical constituents of L. saitoi that was collected off the coast of northern Shandong Province, P. R. China. These efforts resulted in the isolation and identification of four new halogenated sesquiterpenes including 10-bromo-3-chloro-2,7-epoxychamigr-9-en-8a-ol (1), 2,10b-dibromochamigra-2,7-dien-9a-ol (2), (9S)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (3), and (9R)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (4). Additionally, two known sesquiterpenes, 2,10-dibromo-3-chlorochamigr-7-en9a-ol (5) [13] and isolaurenisol (6) [14], were also identified. This article describes the isolation and structure determination of compounds 1 -6.

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Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae)

et al. 2009

Helvetica Chimica Acta

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“…A rearing experiment also demonstrated that the volume of this alga consumed by M. nudus was insignificant and the growth rate was extremely low. Since fish, sea urchin and abalone are deterred from feeding on Laurencia because of its production of halogenated terpene or diterpenes (Hay et al 1987(Hay et al , 1988Kurata et al 1998), the growth and gonad production are also likely to be reduced. Thus, it is possible that the magnitude of the growth at the late sere stage is reduced in potential food species of algae with feeding deterrent chemicals.…”

Section: -1e Somatic Growth and Seaweed Successionmentioning

confidence: 99%

Population Dynamics of Edible Sea Urchins Associated with Variability of Seaweed Beds in Northern Japan

Agatsuma¹

2014

Aqua-BioSci. Monogr. (ABSM)

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Keyword Clements Tsukidate 1992). Sargassum beds trap nutrients and contribute to high rates of primary production (e.g. Wanders 1976). The highest annual production of 8.25 kg dry/m 2 was recorded in Sargassum macrocarpum in Iida Bay, Ishikawa in the Sea of Japan (Taniguchi and Yamada 1978).Edible sea urchins are primary consumers in coastal rocky-bottom ecosystems and their main diet is marine algae (De Ridder and Lawrence 1982). About 20 species of sea urchins are consumed in the world. Most sea urchins belong to the order Echinoida. All the species inhabit shallow waters (Lawrence 2001). Since Abstract Effects of variability of seaweed beds on population dynamics of sea urchins have not been studied in detail. The present study documents that population dynamics of edible sea urchins is closely associated with variability of seaweed beds in subtidal rocky regions in northern Japan, from larval settlement, gonad production, somatic growth, recruitment and seasonal migration of the sea urchins Mesocentrotus nudus, Strongylocentrotus intermedius and Hemicentrotus pulcherrimus. Dibromomethane (DBM), which is produced abundantly by crustose coralline algae, induced larval metamorphosis of more than 80% of individuals of M. nudus and S. intermedius in the presence of 34-61 ppm within 24 h, indicating its instantaneous effect on a high success of metamorphosis. Conversely, 2,4-dibromophenol (DBP) and 2,4,6-tribromophenol (TBP), which are released from kelps Eisenia bicyclis and Ecklonia kurome, killed all eightarmed larvae of M. nudus and S. intermedius in the presence of 20-50 ppm. The larval metamorphosis were significantly reduced in the presence of 1-10 ppm. These suggest that the population size of these sea urchins is enhanced on coralline barrens and reduced in kelp forests. Population size of M. nudus was enhanced by episodic recruitment of juveniles on crustose coralline barrens affected by large-scale oceanographic processes. Growth and gonad production of M. nudus and H. pulcherrimus is greatly affected by the amount and the kind of seaweed beds, which alter the states of crustose coralline flats and large perennial kelp or fucoid forests in the course of algal succession through oceanographic condition. The sea urchins migrate to seaweed beds to increase in gonad size toward maturation and spawning in the species-specific reproductive cycles to succeed in reproduction. Release of hatchery-raised seeds of S. intermedius into the wild and aquaculture of wild or hatchery-raised sea urchins fed on surplus or low-priced sea foods for humans enabled the sea urchins to increase the population size and improve the gonad production and somatic growth.

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“…From Chinese L. karlae, a novel diterpene 106 featuring a ring system of a cycloheptane trans-fused to a transdecalin was identified (Su et al 1995), and its hydroxyl group was revised to be a-oriented from the original b orientation by chemical synthesis via the free-radical reaction (Justicia et al 2005). Three diterpenes possessing isoparguerane (107) and parguerane (108 and 109) backbones along with their possible biogenic precursor 110, originally identified from Australian L. filiformis, were isolated from Japanese L. saitoi, which exhibited moderate feeding-deterrent activity against young abalone Haliotis discus hannai with electivity indexes ranging from 0.42 to 0.63 (Kurata et al 1998;Rochfort and Capon 1996). Overall, 16 nonhalogenated diterpenes (95-110) with nine skeletons were characterized from eight Laurencia species, which accounted for almost one-fifth of the total Laurencia-derived diterpenes.…”

Section: Nonhalogenated Diterpenesmentioning

confidence: 99%

Nonhalogenated organic molecules from Laurencia algae

Wang

2013

Phytochem Rev

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The marine red algae of the genus Laurencia have produced more 700 secondary metabolites and exhibited high molecular diversity and intriguing bioactivity. Since the halogenated structures have been comprehensively reviewed previously, this review, covering up to the end of 2012, mainly focuses on the source, structure elucidation, and bioactivity of nonhalogenated organic molecules from Laurencia spp. as well as the relationship between nonhalogenated and halogenated products. Overall, 173 new or new naturally occurring compounds with 58 skeletons, mainly including sesquiterpenes, diterpenes, triterpenes, and C 15 -acetogenins, are described.

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Diterpenoid feeding-deterrents from Laurencia saitoi

Cited by 77 publications

References 9 publications

Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae)

Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae)

Population Dynamics of Edible Sea Urchins Associated with Variability of Seaweed Beds in Northern Japan

Nonhalogenated organic molecules from Laurencia algae

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