Globoidnan A

Globoidnan A is a lignan found in Eucalyptus globoidea, a tree native to Australia.

Globoidnan A

Names
IUPAC name (2R)-(3,4-dihydroxyphenyl)-2-{[4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-naphthoyl]oxy}propanoic acid
Identifiers
CAS Number	827322-48-5^Y
3D model (JSmol)	Interactive image
ChemSpider	26333277^N
PubChem CID	3013628
CompTox Dashboard (EPA)	DTXSID60895853
InChI InChI=1S/C26H20O10/c27-18-3-1-12(5-20(18)29)6-24(25(33)34)36-26(35)15-7-14-10-22(31)23(32)11-17(14)16(8-15)13-2-4-19(28)21(30)9-13/h1-5,7-11,24,27-32H,6H2,(H,33,34)/t24-/m1/s1^N Key: DHZIDIIBBCIIEG-XMMPIXPASA-N^N InChI=1/C26H20O10/c27-18-3-1-12(5-20(18)29)6-24(25(33)34)36-26(35)15-7-14-10-22(31)23(32)11-17(14)16(8-15)13-2-4-19(28)21(30)9-13/h1-5,7-11,24,27-32H,6H2,(H,33,34)/t24-/m1/s1 Key: DHZIDIIBBCIIEG-XMMPIXPABS
SMILES c1cc(c(cc1C[C@H](C(=O)O)OC(=O)c2cc3cc(c(cc3c(c2)c4ccc(c(c4)O)O)O)O)O)O
Properties
Chemical formula	C26H20O10
Molar mass	492.436 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

The molecule has been found to weakly inhibit the action of HIV integrase (IC₅₀ = 0.64 μM) in vitro.[1] HIV integrase is an enzyme which is responsible for the introduction of HIV viral DNA into a host's cellular DNA. It is not known that globoidnan A inhibits the action of other retroviral integrases.

References

1. Ovenden SP, Yu J, Wan SS, et al. (2004). "Globoidnan A: a lignan from Eucalyptus globoidea inhibits HIV integrase". Phytochemistry. 65 (24): 3255–59. doi:10.1016/j.phytochem.2004.10.006. PMID 15561191.