Rogioldiol A, a new obtusane diterpene, and rogiolal, a degraded derivative, of the red seaweed <i>Laurencia microcladia</i> from II rogiolo along the coast of tuscany: A Synergism in Structural Elucidation

Guella, Graziano; Pietra, Francesco; Marchetti, Fabio

doi:10.1002/hlca.19970800306

Cited by 12 publications

(22 citation statements)

References 27 publications

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“…Three diterpenes featuring the bicyclic obtusane skeleton (608-610) and three 15,14-friedoobtusanes (611-613), resulting from a 1,2-methyl migration to C-14, have been reported so far. Obtusadiol (608), the first diterpene featuring the bicyclic obtusane skeleton, was originally isolated from L. obtusa collected from the Greek shores near Athens [320] and later from L. microcladia from Il Rogiolo, Italy [518]. The latter population afforded also two related degraded C 11 derivatives, namely, rogiolal (614) and isorogiolal (615) [518].…”

Section: Dactylomelanesmentioning

confidence: 99%

“…Obtusadiol (608), the first diterpene featuring the bicyclic obtusane skeleton, was originally isolated from L. obtusa collected from the Greek shores near Athens [320] and later from L. microcladia from Il Rogiolo, Italy [518]. The latter population afforded also two related degraded C 11 derivatives, namely, rogiolal (614) and isorogiolal (615) [518]. Most of the metabolites belonging to this group are characterized by a cis-1,2-bromohydrin functionality, with the exception of compound 609 and laurenditerpenol (613 …”

Section: Dactylomelanesmentioning

confidence: 99%

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The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

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Nature, the most prolific source of biological and chemical diversity, has provided mankind with treatments for health problems since ancient times and continues to be the most promising reservoir of bioactive chemicals for the development of modern drugs. In addition to the terrestrial organisms that still remain a promising source of new bioactive metabolites, the marine environment, covering approximately 70% of the Earth's surface and containing a largely unexplored biodiversity, offers an enormous resource for the discovery of novel compounds. According to the MarinLit database, more than 27,000 metabolites from marine macro- and microorganisms have been isolated to date providing material and key structures for the development of new products in the pharmaceutical, food, cosmeceutical, chemical, and agrochemical sectors. Algae, which thrive in the euphotic zone, were among the first marine organisms that were investigated as sources of food, nutritional supplements, soil fertilizers, and bioactive metabolites.Red algae of the genus Laurencia are accepted unanimously as one of the richest sources of new secondary metabolites. Their cosmopolitan distribution, along with the chemical variation influenced to a significant degree by environmental and genetic factors, have resulted in an endless parade of metabolites, often featuring multiple halogenation sites.The present contribution, covering the literature until August 2015, offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. Since mollusks feeding on Laurencia are, in many cases, bioaccumulating, and utilize algal metabolites as chemical weaponry against natural enemies, metabolites of postulated dietary origin of sea hares that feed on Laurencia species are also included in the present review. Altogether, 1047 secondary metabolites, often featuring new carbocyclic skeletons, have been included.The chapter addresses: (1) the "Laurencia complex", the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; (2) the secondary metabolites, which are organized according to their chemical structures and are classified into sesquiterpenes, diterpenes, triterpenes, acetogenins, indoles, aromatic compounds, steroids, and miscellaneous compounds, as well as their sources of isolation which are depicted in tabulated form, and (3) the biological activity organized according to the biological target and the ecological functions of Laurencia metabolites.

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Section: Dactylomelanesmentioning

confidence: 99%

Section: Dactylomelanesmentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

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“…Three diterpenes featuring the bicyclic obtusane skeleton (608-610) and three 15,14-friedoobtusanes (611-613), resulting from a 1,2-methyl migration to C-14, have been reported so far. The latter population afforded also two related degraded C 11 derivatives, namely, rogiolal (614) and isorogiolal (615) [518]. The latter population afforded also two related degraded C 11 derivatives, namely, rogiolal (614) and isorogiolal (615) [518].…”

Section: Obtusanes 1514-friedoobtusanes and Related Diterpenesmentioning

confidence: 98%

Progress in the Chemistry of Organic Natural Products 102

Kinghorn¹,

Falk²,

Gibbons³

et al. 2016

Progress in the Chemistry of Organic Natural Products

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“…± An atypical form of a red seaweed, Laurencia microcladia KÏtzning (Ceramiales), which has colonized a short tract of the Tuscany coast called Il Rogiolo [1], is known as a prolific source of a variety of secondary metabolites. These include uniquely branched C 15 acetogenins [1], novel chamigrane sesquiterpenes [2], obtusane diterpenes like rogioldiol A (1) [3], and 15,14-friedoobtusane diterpenes like rogioldiol B (2) and rogioldiol C (3) [4], besides rogiolal (4), which may be viewed as a degradation product of these diterpenes [3].…”

mentioning

confidence: 99%

A New-Skeleton Diterpenoid, New Prenylbisabolanes, and Their Putative Biogenetic Precursor, from the Red SeaweedLaurencia microcladia from Il Rogiolo: Assigning the Absolute Configuration when Two Chiral Halves are Connected By Single Bonds

Guella¹,

Pietra²

2000

HCA

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We report here a new-skeleton tricyclic diterpenoid, neorogioldiol (8), along with new prenylbisabolanes, rogioldiol D (6) and O 11 , 15-cyclo-14-bromo-14,15-dihydrorogiol-3,11-diol (5), and their putative biogenetic precursor, (À)-geranyllinalool (7), isolated from the red seaweed Laurencia microcladia, which has colonized a small tract of the Tuscany coast called Il Rogiolo. In a case study of the assignment of the absolute configuration for molecules composed of chiral halves that are connected by single bonds, the absolute configuration of neorogioldiol (8) was based on a) the assumption of the identity of the cyclohexane moiety with co-occurring (2S,3R,6S)-rogiolal (4) and b) NMR-derived relative configurations for the bicyclic moiety, and c) the combination of these two pieces of information by molecular-mechanics-aided conformational analysis, in agreement with NOE data.

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Rogioldiol A, a new obtusane diterpene, and rogiolal, a degraded derivative, of the red seaweed Laurencia microcladia from II rogiolo along the coast of tuscany: A Synergism in Structural Elucidation

Cited by 12 publications

References 27 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Progress in the Chemistry of Organic Natural Products 102

A New-Skeleton Diterpenoid, New Prenylbisabolanes, and Their Putative Biogenetic Precursor, from the Red SeaweedLaurencia microcladia from Il Rogiolo: Assigning the Absolute Configuration when Two Chiral Halves are Connected By Single Bonds

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