Two new Kalihinenes from the Marine Sponge<i>Acanthella Cavernosa</i>

Braekman, Jean‐Claude; Daloze, Désiré; Gregoire, F.; Попов, Симеон; Soest, R.W.M. van

doi:10.1002/bscb.19941030504

Cited by 15 publications

(6 citation statements)

References 25 publications

(5 reference statements)

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“…Owing to their chloro‐oxepane ring, kalihioxepanes A—G ( 1 — 7 ) are the first members of the large kalihinene diterpenoid family to differ from the reported tetrahydropyran or tetrahydrofuran kalihinols, [ 1‐4,8‐13 ] thus enriching the structural diversity of this compound family. Furthermore, only kalihioxepanes A ( 1 ) and B ( 2 ) showed significant cytotoxicities, indicating that the isocyano substituent was important for cytotoxicity.…”

Section: Discussionmentioning

confidence: 99%

“…[ 5‐6 ] Kalihinene diterpenoids are highly functionalized tricyclic derivatives that are further divided into two main groups, namely, tetrahydropyran and tetrahydrofuran kalihinols. [ 1‐4,7‐13 ] Biflorane diterpenoids have linear C 8 side‐chains. [ 6 ] Both groups are cyclization products of geranylgeranyl pyrophosphate and the trans ‐ or cis ‐form of the biflorane skeleton.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Kalihioxepanes A—G: Seven Kalihinene Diterpenoids from Marine Sponge Acanthella cavernosa Collected off the South China Sea

et al. 2022

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Seven new kalihinene diterpenoids, kalihioxepanes A-G (1-7) bearing a rare oxepane ring, were isolated from sponge Acanthella cavernosa collected from the South China Sea. The structures and absolute configurations were elucidated by comprehensive spectroscopic analysis, single crystal X-ray diffraction, and quantum chemical calculation methods. Kalihioxepane A (1) displayed strong cytotoxicity against H69 and K562 tumor cells, while kalihioxepane B (2) showed moderate cytotoxicity against K562 cells.

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Section: Discussionmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Kalihioxepanes A—G: Seven Kalihinene Diterpenoids from Marine Sponge Acanthella cavernosa Collected off the South China Sea

et al. 2022

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“…Unlike the other chemically analysed Phyllidiidae, P. rudmani possesses kalihinol-type diterpenes (see Figs. 16, S4a, S9h) that are known from the sponges Acanthella cavernosa Dendy, 1922 and A. pulcherrima Ridley & Dendy, 1886 (Braekman et al, 1994;Chang et al, 1984;Hirota et al, 1996;Patra et al, 1984;Rodriguez et al, 1994;Wolf & Schmitz, 1998). Whilst none of our specimens was photographed on Acanthella, there are a number of photographs on iNaturalist illustrating P. rudmani on cf.…”

Section: Phyllidiella Rudmanimentioning

confidence: 92%

Phyllidiidae (Nudibranchia, Heterobranchia, Gastropoda): an integrative taxonomic approach including chemical analyses

et al. 2022

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Members of the widely distributed and common nudibranch family Phyllidiidae are often easily spotted in the marine environment because of their conspicuous colours and obvious presence on the reef. They are interesting with regard to their defensive chemical compounds that may lead to new drug discoveries. Despite their abundance, the family is also well known for its taxonomic problems and the difficulties in species identification due to very similarly coloured species and lack of morphological characters. In this study, phyllidiid species were analysed using an integrative approach. Molecular analysis of the mitochondrial genes 16S and CO1 was utilised, running phylogenetic analyses, species delimitation tests, and haplotype network analyses. Additionally, for the first time, external morphological characters were analysed, museum material was re-analysed, and chemical profiles were applied for characterising species. The analyses are based on sequences of 598 specimens collected in Indonesia by the team, with the addition of published sequences available on GenBank. This study comprises 11 species of Phyllidia, seven species of Phyllidiopsis, and at least 14 species of Phyllidiella. Moreover, 11 species belonging to these three genera are probably new to science, Phyllidiopsis pipeki is synonymised with P. krempfi, and Phyllidiella albonigra is resurrected. Some of the external colouration previously used for species identification is shown to not be valid, but alternative characters are provided for most species. Chemical analyses led to species characterisation in a few examples, indicating that these species use particular sponge species as food; however, many species show a broad array of compounds and are therefore characterised more by their composition or profile than by distinct or unique compounds.

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“…From this moment on, numerous isocyanides were isolated and characterized from said sponge and many others ( Halichondria , Pseudaxinella , Acanthella , Bubaris , Cribochalina , Cymbastela , Amphimedon , Ciocalypta , Geodia , Phakellia , and Svenzea ) and evaluated for their biological activity whenever possible, with an emphasis on their cytotoxicity against cancer cell lines and their antimalarial activity. For the sake of simplicity, we are grouping those isolated isocyanides as shown in the figures, and for each represented group we report their published biological activities. ,,− …”

Section: Isocyano Group In Natural Productsmentioning

confidence: 99%

Medicinal Chemistry of Isocyanides

et al. 2021

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In eons of evolution, isocyanides carved out a niche in the ecological systems probably thanks to their metal coordinating properties. In 1859 the first isocyanide was synthesized by humans and in 1950 the first natural isocyanide was discovered. Now, at the beginning of XXI century, hundreds of isocyanides have been isolated both in prokaryotes and eukaryotes and thousands have been synthesized in the laboratory. For some of them their ecological role is known, and their potent biological activity as antibacterial, antifungal, antimalarial, antifouling, and antitumoral compounds has been described. Notwithstanding, the isocyanides have not gained a good reputation among medicinal chemists who have erroneously considered them either too reactive or metabolically unstable, and this has restricted their main use to technical applications as ligands in coordination chemistry. The aim of this review is therefore to show the richness in biological activity of the isocyanidecontaining molecules, to support the idea of using the isocyanide functional group as an unconventional pharmacophore especially useful as a metal coordinating warhead. The unhidden hope is to convince the skeptical medicinal chemists of the isocyanide potential in many areas of drug discovery and considering them in the design of future drugs.

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Two new Kalihinenes from the Marine SpongeAcanthella Cavernosa

Cited by 15 publications

References 25 publications

Kalihioxepanes A—G: Seven Kalihinene Diterpenoids from Marine Sponge Acanthella cavernosa Collected off the South China Sea

Kalihioxepanes A—G: Seven Kalihinene Diterpenoids from Marine Sponge Acanthella cavernosa Collected off the South China Sea

Phyllidiidae (Nudibranchia, Heterobranchia, Gastropoda): an integrative taxonomic approach including chemical analyses

Medicinal Chemistry of Isocyanides

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