Avarol

Specifications / Handling

More Information
Product Details
Synonyms	NSC 306951
Product Type	Chemical
Properties
Formula	C₂₁H₃₀O₂
MW	314.5
CAS	55303-98-5
Source/Host Chemicals	Isolated from sponge Dysidea avara.
Purity Chemicals	≥95% (HPLC)
Appearance	Off-white solid.
Solubility	Soluble in ethanol or DMSO.
Identity	Determined by ¹H-NMR.
InChi Key	JSPUCPNQXKTYRO-LWILDLIXSA-N
Smiles	[H][C@@]12CCC=C(C)[C@@]1(C)CC[C@H](C)[C@@]2(C)CC1=CC(O)=CC=C1O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Antibacterial against selected Gram-positive strains, antifungal [1, 6].
Anticancer compound [2].
Antileukemic [4, 5, 8, 9].
Antimitotic agent [3].
Antiviral compound [7, 8, 14].
Inhibits HIV activity [7, 8, 14].
Anti-inflammatory [10, 12].
Synovial phospholipase A2, cyclooxygenase and lipoxygenase inhibitor [10, 12].
Modulator of superoxide dismutase and glutathione peroxidase [11].
Platelet aggregation inhibitor [13].
Anti-psoriatic [15, 17], mediated by inhibition of TNF-α generation and NF-κB activation [18, 19].
Reviews [16, 20].

Product References

Antimicrobial activity of avarol, a sesquiterpenoid hydroquinone from the marine sponge, Dysidea avara: L. Cariello, et al.; Comp. Biochem. Physiol. B. 71, 281 (1982)
Avarol, a cytostatically active compound from the marine sponge Dysidea avara: W.E. Müller, et al.; Comp. Biochem. Physiol. C. 80, 47 (1985)
Inhibition of mitosis by avarol, a natural product isolated from the sponge Dysidea avara: W.E. Müller, et al.; Basic Appl. Histochem. 29, 321 (1985)
Potent antileukemic activity of the novel cytostatic agent avarone and its analogues in vitro and in vivo: W.E. Müller, et al.; Cancer Res. 45, 4822 (1985)
Antimutagenic activity of the novel antileukemic agents, avarone and avarol: B. Kurelec, et al.; Mutat. Res. 144, 63 (1985)
Antibacterial and antifungal activity of Avarone and Avarol: G. Seibert, et al.; Zentralbl. Bakteriol. Mikrobiol. Hyg. A. 260, 379 (1985)
Inhibition of replication of the etiologic agent of acquired immune deficiency syndrome (human T-lymphotropic retrovirus/lymphadenopathy-associated virus) by avarol and avarone: P.S. Sarin, et al.; J. Natl. Cancer Inst. 78, 663 (1987)
Influence of the antileukemic and anti-human immunodeficiency virus agent avarol on selected immune responses in vitro and in vivo: W.E. Müller, et al.; Biochem. Pharmacol. 36, 1489 (1987)
Avarol-induced DNA strand breakage in vitro and in Friend erythroleukemia cells: W.E. Müller, et al.; Cancer Res. 47, 6565 (1987)
Induction of gamma-interferon by avarol in human peripheral blood lymphocytes: R. Voth, et al.; Jpn. J. Cancer Res. 79, 647 (1988)
Action of the antileukemic and anti-HTLV-III (anti-HIV) agent avarol on the levels of superoxide dismutases and glutathione peroxidase activities in L5178y mouse lymphoma cells: E. Batke, et al.; Cell Biochem. Funct. 6, 123 (1988)
Avarol and avarone, two new anti-inflammatory agents of marine origin: M.L. Ferrandiz, et al.; Eur. J. Pharmacol. 253, 75 (1994)
In vitro effect of avarone and avarol, a quinone/hydroquinone couple of marine origin, on platelet aggregation: M.A. Belisario, et al.; Pharmacol. Toxicol. 79, 300 (1996)
Natural products with anti-HIV activity from marine organisms: L.A. Tziveleka, et al.; Curr. Top. Med. Chem. 3, 1512 (2003) (Review)
Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line: M. Amigo, et al.; J. Nat. Prod. 67, 1459 (2004)
Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida: D. Sladic & M.J. Gasic; Molecules 11, 1 (2006)
Identification of avarol derivatives as potential antipsoriatic drugs using an in vitro model for keratinocyte growth and differentiation: M. Amigó, et al.; Life Sci. 79, 2395 (2006)
Antipsoriatic effects of avarol-3'-thiosalicylate are mediated by inhibition of TNF-alpha generation and NF-kappaB activation in mouse skin: M Amigó, et al.; Br. J. Pharmacol. 152, 353 (2007)
Avarol inhibits TNF-alpha generation and NF-kappaB activation in human cells and in animal models: M. Amigó, et al.; Life Sci. 82, 256 (2008)
Cytotoxic terpene quinones from marine sponges: M. Gordaliza; Mar. Drugs 8, 2849 (2010)
Avarol induces apoptosis in pancreatic ductal adenocarcinoma cells by activating PERK–eIF2α–CHOP signaling: T. Namba & R. Kodama; Mar. Drugs 13, 2376 (2015)

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