Globoidnan A

Globoidnan A
Names
Preferred IUPAC name
(2R)-3-(3,4-Dihydroxyphenyl)-2-{[4-(3,4-dihydroxyphenyl)-6,7-dihydroxynaphthalene-2-carbonyl]oxy}propanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
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).
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Infobox references

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

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.
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