The constituents of marine sponges. I. The isolation from Aplysilla sulphurea (Dendroceratida) of (1R*, 1'S*, 1'R*,3R*)-1-Acetoxy-4-ethyl-5-(1,3,3-trimethylcyclohexyl)-1,3-dihydroisobenzofuran-1'(4),3-carbolactone and the determination of its crystal structure

Karuso, Peter; Skelton, B. W.; Taylor, WC; White, AH

doi:10.1071/ch9841081

Cited by 38 publications

(54 citation statements)

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“…Taylor and co-workers have also confirmed the absolute stereochemistry of 28 (R 1 = H, R 2 = OCOPr), except one stereocenter, by X-ray diffraction methods of the p-bromobenzoyl derivative [53]. Aplyroseol-1 (28, R 1 = H, R 2 = OCOPr) and aplyroseol-2 (28, R 1 = H, R 2 = OAc) have been found in the sponges Igernella notabilis [52], Aplysilla rosea [12] and Dendrilla rosea [13], and recently aplyroseol-2 (28, R 1 = H, R 2 = OAc) was isolated from the mollusk Chromodoris obsoleta showing cytotoxic activity (but no relevant anti-tumor activity in vivo) [17], as well as from Chromodoris inopinata [18].…”

Section: Intact Spongiane Skeletonmentioning

confidence: 57%

“…13) and a small amount of aplysulphuride whose structure was not elucidated. The structure 38 was confirmed by a single-crystal X-ray determination [13].…”

Section: Degraded or Rearranged Spongiane Skeletonmentioning

confidence: 80%

“…2). For example, aplyroseol-1 (4, R 1 = H, R 2 = Me, R 3 = OAc), was isolated from the dendroceratid sponges Aplysilla rosea [12,13], Dendrilla rosea [14] Aplysilla polyrhapis [15], and Chelonaplysilla violacea [16] and also from the nudibranches Chromodoris obsoleta [17] and Chromodoris inopinata [18]. Anti-tumor activity against the P388 mouse leukaemia cell line in vivo showed no significant activity.…”

Section: Intact Spongiane Skeletonmentioning

confidence: 99%

“…Compound 28 (R 1 = H, R 2 = OH) was also isolated from Igernella notabilis [52], and aplyroseol-3 ( OCOPr), aplyroseol-4 (28, R 1 = OAc, R 2 = OCOPr), aply-roseol-5 (28, R 1 = OCOPr, R 2 = OH) and aplyroseol-6 (28, R 1 = OCOPr, R 2 = OAc) were isolated from Aplysilla rosea [12] and also from Dendrilla rosea (except aplyroseol-4) [13], though the known aplyroseol-3 (28, R 1 = OH, R 2 = OCOPr) was isolated for the first time from Aplysilla sp. [54].…”

Section: Intact Spongiane Skeletonmentioning

confidence: 99%

“…In addition, aplyroseol-1 (28, R 1 = H, R 2 = OCOPr), aplyroseol-5 (28, R 1 = OCOPr, R 2 = OH), and aplyroseol-6 (28, R 1 = OCOPr, R 2 = OAc) are inhibitors of the enzyme phospholipase A 2 (PLA 2 ), an enzyme involved in inflammation processes [55]. Dendrillol-1 (28, R 1 = R 2 = H) and dendrillol-2 (28, R 1 = R 2 = OAc) were isolated from Dendrilla rosea [13], and the former was also found later in the mollusk identified as Ceratosoma brevicaudatum [19], along with compounds 29 (R 1 = OCOPr, R 2 = H, 17-β), 29 (R 1 = OAc, R 2 = H, 17-β), 29 (R 1 = OAc, R 2 = Ac, 17-α) and 29 (R 1 = OCOPr, R 2 = Ac, 17-α). The mollusk was ultimately identified to be Ceratosoma epicuria [20].…”

Section: Intact Spongiane Skeletonmentioning

confidence: 99%

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Author Index To Volume 2

2007

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In this review we cover the structures, occurrence, biological activities and synthesis of all the spongianes and rearranged spongianes since their discovery in 1974. We have given special attention to structure revisions and biological properties of these polycyclic terpenoids of exclusive marine origin. However, an important part of the review describes the synthetic efforts in the field. Thus, this part has been subdivided into syntheses from other natural products, syntheses by biomimetic approaches and other approaches including enantioselective total syntheses. Marine terpenoids are typical constituents of the secondary metabolite composition of marine flora and fauna. These isoprenoid-derived compounds are common in almost all marine phyla and show a wide range of novel structures. Although most of them are also present in terrestrial organisms, the occurrence of a few skeletons is restricted to certain marine species. In this review we focus our attention to diterpenoids characterized by polycyclic structures having either the spongiane (I, C 20 ) (Fig. 1) carbon framework or several degraded or rearranged spongiane-derived skeletons.Spongiane diterpenoids are bioactive natural products isolated exclusively from sponges and marine shell-less mollusks (nudibranchs), which are believed to be able of sequestering the spongian-derived metabolites from the sponges, soft corals, hydroids and other sessile marine invertebrates on which they feed. Most of these compounds play a key role as eco-physiological mediators and are of interest for potential applications as therapeutic agents.Spongianes having the characteristic carbon skeleton I (Fig. 1) have been reviewed up to 1990 and listed in the Dictionary of terpenoids [1]. During the last two decades, many new members of this family of natural products have been isolated and described in specific reviews on naturally occurring diterpenoids by Professor Hanson [2], and the excellent reviewing work on marine natural products by Professor Faulkner [3,4], now continued by the team of Professor Blunt [5,6], all of which have mainly covered the isolation and structural aspects of spongianes. A recent review on the chemistry of diterpenes isolated from marine opisthobranchs, has also included articles on isolation and structure determination of spongianes up to 1999 [7]. The latter also covered some synthetic studies of this class of substances. To the best of our knowledge, there is only one more report dealing with the initial studies towards the synthesis of spongianes [8]. We now provide full coverage of recent advances in the field including a comprehensive description of the synthetic approaches and syntheses reported in the literature on spongianes up to march 2006. STRUCTURE, OCCURRENCE AND BIOLOGICAL ACTIVITYThe semisystematic naming of this family of diterpenoids was introduced in 1979 following the isolation of the first members of

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Section: Intact Spongiane Skeletonmentioning

confidence: 57%

“…13) and a small amount of aplysulphuride whose structure was not elucidated. The structure 38 was confirmed by a single-crystal X-ray determination [13].…”

Section: Degraded or Rearranged Spongiane Skeletonmentioning

confidence: 80%