Chemistry of Sponges, IV. Spongian Diterpenes from Hyatella intestinalis

Cambie, R. C.; Craw, P. A.; Stone, Martin J.; Bergquist, Patricia R.

doi:10.1021/np50056a016

Cited by 29 publications

(51 citation statements)

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“…During this work the inhibition of DNA polymerase β lyase was demonstrated by compounds 15 (R= CO 2 Me, CO 2 H and CH 2 OAc), being ester 15 (R= CO 2 Me) the most active. In addition, compound 15 (R= Me) was also found in the sponge Hyatella intestinalis [41], as well as compound 15 (R= CO 2 H) has also been isolated from the sponges Spongia matamata [30] and Coscinoderma mathewsi [31].…”

Section: Intact Spongiane Skeletonmentioning

confidence: 99%

“…Compounds 16 and other acetate derivatives have been isolated from the nudibranch Casella atromarginata as well [43]. However, compounds 17 and 18 were found in the sponge Hyatella intestinalis [41]. The two epimers of compound 18 (R=H), 3α and 3β, named spongiadiol and epispongiadiol, respectively, were also isolated from Australian Spongia species [9], and together with the compound 17 (R=OH), named isospongiadiol and found in Caribbean Spongia species [44], are active against herpes simplex virus type 1 and P388 cancer cells.…”

Section: Intact Spongiane Skeletonmentioning

confidence: 99%

“…The studies of the constituents of the Mediterranean sponge Spongionella gracilis led to the structure elucidation by spectral analysis of gracilin A (39) and gracilin B ( 40), which represents the first bis-nor-diterpene observed from a marine sponge, together with two gracilin A derivatives (41)(42) and spongionellin (43) which possess a new carbocyclic skeleton (Fig.14) [70][71][72]. Gracilin A inactivates PLA 2 at 2µg/mL [55].…”

Section: Degraded or Rearranged Spongiane Skeletonmentioning

confidence: 99%

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Author Index To Volume 2

2007

CBC

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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: 99%

Section: Intact Spongiane Skeletonmentioning

confidence: 99%

Section: Degraded or Rearranged Spongiane Skeletonmentioning

confidence: 99%

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Author Index To Volume 2

2007

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“…The identity of the known metabolites 4 and 5 was readily established by comparison of their spectral properties with those reported [4,6,10,11]. 1 H and 13 C NMR chemical shifts of 5 previously unassigned [4] are reported here in Tables 1 and 2. Spectral analysis and comparison with literature data revealed that compound 1 is very closely related to isospongiadiol [7,12,13], previously isolated from marine sponges of the genus Spongia [7,14] and Hyatella [12]. Differences in the 1 H and 13 C NMR spectra between them being as a result of the absence Analysis of the 13 C NMR, 1 H-1 H-COSY ( Figure 2) and 1 H-13 C-HMBC spectrum of 2 confirmed it to possess identical connectivity and substitution pattern w.r.t.…”

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Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp

Gross

Wright

Reinscheid

et al. 2009

Natural Product Communications

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Chemical investigation of the marine sponge Spongia sp., collected from the Fiji Islands resulted in the isolation of three new furanoditerpenoids 1-3, along with the known compounds epispongiatriol (4) and 17,19-dihydroxyspongia-13(16),14-dien-2,3dione (5) While 1 is a new spongian diterpene with a modified oxidation pattern, compounds 2 and 3 represent two new ring A-contracted spongians, displaying a novel and unprecedented nor-spongian carbon skeleton. Despite their labile nature the structures could be established through a combined strategy including complete analysis of spectroscopic data (NMR, MS), molecular modeling and quantum-mechanical calculations.

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“…Spongian diterpenes were first reported in 1979 as unique metabolites of a sponge, 8) and since then a number of spongians have been reported. [9][10][11][12][13][14] Recent reports include new cyototoxic spongians 15) and rediscovery of spongiatriol (1) as a moderate apoptosis inducer and an inhibitor of nuclear factor-kappaB (NF-κB) activation. 16,17) In this report we describe the structures of three new spongians and their biological activities.…”

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Spongian Diterpenes from the Sponge <i>Hyattella</i> aff. <i>intestinalis</i>

Ahmadi

Haruyama²,

Kobayashi³

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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Extracts of the sponge Hyattella aff. intestinalis showed moderate inhibition against adenovirus. Chromatographic separation of the extracts followed by analysis of spectroscopic data allowed us to elucidate the structures of three new metabolites as 2α-hydroxyspongia-13(16),14-diene-3-one (4), 3β-hydroxyspongia-13(16), 14-diene-2-one (7), and 2α,3α-diacetoxy-17,19-dihydroxyspongia-13(16),14-diene (8) and to identify six known ones 1-3, 5, 6 and 9. Among the molecules, compounds 1 and 3 showed antiviral activity at IC 50 17.0 and 52.0 µM.

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Chemistry of Sponges, IV. Spongian Diterpenes from Hyatella intestinalis

Cited by 29 publications

References 1 publication

Author Index To Volume 2

Author Index To Volume 2

Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp

Spongian Diterpenes from the Sponge <i>Hyattella</i> aff. <i>intestinalis</i>

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