Chemical and Biological Aspects of Marine Monoterpenes

Naylor, Stephen; Hanke, Frederick J.; Manes, L.; Crews, Phillip

doi:10.1007/978-3-7091-8714-2_3

Cited by 29 publications

(69 citation statements)

References 60 publications

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“…Marine terpenoids are also listed in the Dictionary of Terpenoids and can be found in annual reviews on the isolation of new C 10 (Grayson, 2000), C 15 (Fraga, 2005), C 20 (Hanson, 2005) and C 30 (Connolly and Hill, 2005) isoprenoids and sterols. Additionally, there exists a wealth of literature dealing predominantly with marine isoprenoids covering aspects of marine monoterpenoids (Naylor et al, 1983), marine diterpenoids (Fenical, 1978), algal sesquiterpenoids (Martin and Darias, 1978), marine sesterterpenes (Crews and Naylor, 1985) marine triterpenoid oligoglycosides (Minale et al, 1996) and marine sterols (Djerassi, 1981;Kerr and Baker, 1991;Sica and Musumeci, 2004). Other authors highlighted the presence and significance of terpenoids occurring in marine invertebrates (Faulkner, 1977;Pennock, 1977;Minale, 1978;Tursch et al, 1978;Andersen et al, 1990) or marine plants ( De Rosa, 1991;Kladi et al, 2004).…”

Section: Introductionmentioning

confidence: 95%

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

2006

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Marine organisms produce a wide array of fascinating terpenoid structures distinguished by characteristic structural features. Certain structural classes, e.g. cembrane, chamigrene, amphilectane skeletons, and unusual functional groups such as isonitrile, isothiocyanate, isocyanate, dichloroimine and halogenated functionalities occur predominantly in marine metabolites. Especially striking is the frequent occurrence of sesterterpenes in marine organisms, and sponges must be considered as one of the prime sources of these C 25 terpenoid compounds. In most cases however, these structural features are not strictly unique for marine natural products. The prominent biological activity of marine terpenes is evident in their ecological role in the marine environment, and makes them interesting as potential drugs. Several terpenoid compounds, e.g. eleutherobin, sarcodictyin, contignasterol derivatives, are in preclinical or clinical development. Despite the many structures known and their ecological and pharmacological importance, only a few biosynthetic studies on marine terpenoid compounds have been performed.

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Section: Introductionmentioning

confidence: 95%

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

2006

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“…Structures for myrcene, acyclic compounds A-C, and cyclic compound D with regiochemistry suggested by the citations discussed earlier are also provided in Figure 9. This working pathway has two parallel branches, one for acyclic halogenated monoterpenes, and another for cyclic halogenated monoterpenes, in accordance with the generic biogenic schemes for halogen addition proposed by Naylor et al (1983). All halogenated monoterpenes originate from a common precursor, myrcene.…”

Section: Patterns Of Halogenated Monoterpene Biosynthesismentioning

confidence: 67%

“…Biogenic schemes proposed by Naylor et al (1983) suggest that ocimene is the common monoterpene precursor to all the halogenated monoterpenes found in Plocamium, while myrcene is common precursor to all the halogenated monoterpenes found in Portieria, as shown below:…”

Section: Introductionmentioning

confidence: 98%

“…For example, macrophytic marine red algae or "red seaweeds" are a rich and diverse source of unique halogenated terpenoids (Fenical, 1975;Gribble, 1992). Halogenated monoterpenes have been reported from three genera of macrophytic red algae, including Plocamium, Portieria (formerly Chondrococcus) and Ochtodes (Naylor et al, 1983). In Ochtodes species, halogenated monoterpenes serve as chemical defense to herbivory (Paul et al, 1987).…”

Section: Introductionmentioning

confidence: 99%

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Halogenated monoterpene production by microplantlets of the marine red alga Ochtodes secundiramea within an airlift photobioreactor under nutrient medium perfusion

Polzin

Rorrer

2003

Biotech & Bioengineering

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Macrophytic marine red algae are a unique source of novel and bioactive terpenoids, including halogenated monoterpenes. Biomass and halogenated monoterpene production by regenerated microplantlet suspension cultures derived from the red alga Ochtodes secundiramea were studied within a perfusion airlift photobioreactor. Photobioreactor cultivations were carried out at 26 degrees C, 140 microE m(-2)s(-1) light intensity, 0.3 air L(-1) culture min(-1) aeration (3500 ppm CO(2)), and ESS/seawater medium perfusion rate of 0.2 L medium L(-1) culture d(-1). Macronutrient concentrations in the perfusion medium were adjusted to provide nitrate delivery rates of 0.0063, 0.077, and 0.74 mmol L(-1) d(-1) at a fixed N:P ratio of 19:1. Growth was maximized at the highest nutrient delivery rate, where 10 g dry biomass L(-1) culture was achieved after 30 days of cultivation. GC-MS analysis of dichloromethane extracts from cell biomass revealed that O. secundiramea microplantlets produced myrcene, three acyclic halogenated monoterpenes (10-bromomyrcene, 10-bromo-7-chloromyrcene, 3,10-dibromomyrcene), and one cyclic halogenated monoterpene (6-bromo-1,2,8-trichloro-3,4-ochtodene). 10E-bromomyrcene levels were much higher than those of its isomer 10Z-bromomyrcene, demonstrating stereoselective halogenation. Maximum yields of 10E-bromomyrcene and 6-bromo-1,2,8-trichloro-3,4-ochtodene were 15 and 13 micromol/g dry cell mass, respectively. Increasing the rate of nutrient delivery increased the accumulation of myrcene and 10-bromomyrcene during the first 14 days in culture. Furthermore, the yield selectivity toward higher halogenated monoterpenes increased as the rate of nutrient delivery decreased. From this data, a biogenic scheme was proposed where cyclic and acyclic halogenated monoterpenes are derived from sequential halogenation of myrcene, their common precursor.

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“…The red alga Plocamium cartilagineum (Dixon), of worldwide occurrence, has been shown to elaborate several structures of this type. Is a rich source of halogenated monoterpenes of cyclic, acyclic, and oxacyclic skeletons 1,2,3 . It is common in species of genus Plocamium to find metabolites with a high degree of halogen incorporation, usually up to 5 halogens, in a skeleton having only 10 carbon atoms.…”

Section: Introductionmentioning

confidence: 99%