Dysidea arenaria
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| Dysidea arenaria | ||||||||||||
| PR Bergquist , 1965 |
Dysidea arenaria is a sponge from the order of the horny sponges (Dictyoceratida).
habitat
The first specimen was classified near the Palau Islands . According to today's knowledge, their habitat is the South China Sea and the Western Pacific .
Secondary metabolites
In the past few years, Dysidea arenaria has been analyzed several times in order to find potentially useful secondary metabolites .
Extraction and use
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Countless sesquiterpenes and hydroquinones have been isolated from marine sponges. Of interest is the potential bioactivity as the cytotoxicity , the antibacterial and insecticidal effect, and the phospholipase A2 - inhibitor (PLA2 inhibitor) and the anti-HIV activity.
9α, 11α-epoxycholest-7-ene-3β, 5α, 6α, 19-tetrol-6-acetate (ECTA)
Is the first natural maritime product containing the fluconazole resistance , which by Candida albicans MDR - efflux pump mediated, cancels.
It was isolated from the lipophilic extract of an Australian collection of Dysidea arenaria cf. Bergquist .
The compound was discovered in 1983 by Gunasekera and Schmitz from a sample of a Dysidea sp. isolated from Guam .
19-hydroxypolyfibrospongol
After extraction and subsequent fractionation , a previously unknown sesquiterpene hydroquinone, which is secondarily metabolically active, could be isolated. In addition to the 19-hydroxypolyfibrospongol, another five known components could be deposited.
The newly discovered 19-hydroxypolyfibrospongol B could be isolated as a white, amorphous solid. The determination of the molecular composition by means of mass spectrometry gave a C 24 H 34 O 6 molecule. The phenol group can be detected using infrared and ultraviolet spectroscopy. The other components of 19-hydroxypolyfibrospongol B were also determined spectroscopically. The anti-HIV effect was checked by inhibiting HIV-1 reverse transcriptases (RT). The substances isosemnonorthoquinone, ilimachinone, smenospongin and smenotronic acid showed very weak inhibitory effects. No activity could be determined for the components 19-hydroxypolyfibrospongol B and polyfibrospongol B. These different responses to the HIV-1 RT can be explained by the presence and absence of the free quinoid ring.
9-Hydroxylfurodysinine O-lactone
A freeze-dried sample of Dysidea arenaria was extracted with dilute ethanol. Furodysinin-O-ethyllactone was isolated in the light petroleum fraction and polyhydroxylated sterol, the sesquiterpene furodysinin lactone and the previously unknown component, 9-hydroxylfurodysinin-O-lactone, in the dichloromethane fraction. The 9-hydroxylfurodysinine-O-lactone is described with a molecular composition of C 17 H 24 O 4 .
Cryptophycin
Cryptophycin's bioactivity was originally used as an antifungal agent. However, the molecule was not pursued because it was considered too toxic to humans. Based on recent research, it was found that cryptophycin-1 is an inhibitor of tubulin binding . The binding is believed to occur on the peptide binding side, similar to what is believed to be the case with dolastatin 10 and hemiasterlin derivative HTI-286. Cryptophycin-24 (arenastatin A) from D. arenari is considered a potent cytotoxin. The inhibitory concentration is 5 pg / mL (IC 50 ).
literature
- PR Bergquist: The Sponges of Micronesia, Part I. The Palau Archipelago. In: Pacific Science. 19 ( 2 ), 1965, pp. 123-204. ( PDF; 42.1 MB )
Web links
- Dysidea arenaria at World Porifera Database
- Dysidea arenaria at sealifbase.org (English)
credentials
- ^ PR Bergquist: The Sponges of Micronesia, Part I. The Palau Archipelago , pp. 144-145.
- ↑ JNA Hooper, JA Kennedy, RWM van Soest: Annotated checklist of sponges (Porifera) of the South China Sea region ( Memento of the original from December 26, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. . In: The Raffles Bulletin of Zoology. 8, 2000, pp. 125-207.
- ↑ a b M. R. Jacob u. a .: Reversal of Fluconazole Resistance in Multidrug Efflux-Resistant Fungi by the Dysidea arenaria Sponge Sterol 9α, 11α-Epoxycholest-7-ene-3β, 5α, 6α, 19-tetrol 6-Acetate. In: J. Nat. Prod. 2003, 66, pp. 1618-1622. doi: 10.1021 / np030317n
- ↑ S. Gunasekera, F. Schmitz In: J. Org. Chem. 1983, Volume 48, pp. 885-886. doi: 10.1021 / jo00154a029
- ^ Y. Qiu, XM Wang: A new sesquiterpenoid hydroquinone from the marine sponge Dysidea arenaria . In: Molecules . June 6, 2008, pp. 1275-1281. doi: 10.3390 / molecules13061275
- ↑ AM Piggot, P. Karuso: 9-Hydroxyfurodysinin-O-ethyl Lactone: A new Sesquiterpene isolated from the tropical marine sponge Dysidea arenaria . In: Molecules. October 31, 2005, pp. 1292-1297. doi: 10.3390 / 10101292
- ↑ Naoyuki Kotoku, Fuminori Narumi, Tomoya Kato, Miho Yamaguchi, Motomasa Kobayashi: Stereoselective total synthesis of arenastatin A, a spongean cytotoxic depsipeptide . In: Tetrahedron Letters . tape 48 , no. 40 , October 2007, p. 7147-7150 , doi : 10.1016 / j.tetlet.2007.07.193 .
