Tetrahedron Letters 46 (2005) 1341–1344
An anti-herpes simplex virus-type 1 agent from
Xylaria mellisii (BCC 1005)
Pattama Pittayakhajonwut,a,* Rapheephat Suvannakad,a Surang Thienhirun,b
Samran Prabpai,c Palangpon Kongsaereec and Morakot Tanticharoena
aNational Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development
Agency (NSTDA), 113, Paholyothin Rd., Klong 1, Klong Luang, Pathum Thani 12120, Thailand
bRoyal Forest Department, Bangkok 10900, Thailand
cDepartment of Chemistry and Center for Protein Structure and Function, Faculty of Science, Mahidol University,
Rama VI Road, Bangkok 10400, Thailand
Received 30 October 2004; revised 16 December 2004; accepted 21 December 2004
Available online 12 January 2005
Abstract—A structurally unique polyketide, mellisol (1) and 1,8-dihydroxynaphthol 1-O-a-glucopyranoside (3), were isolated from
the fungus Xylaria mellisii (BCC 1005). The relative stereostructure of 1 was determined on the basis of X-ray crystallographic data.
Compounds 1 and 3 exhibited activity against herpes simplex virus-type 1 with IC50 values of 10.50 and 8.40 lg/mL, respectively.
They also showed cytotoxic activity against vero cells at the concentration of 40–50 lg/mL.
2004 Elsevier Ltd. All rights reserved.
Fungi of the genus Xylaria have been shown to be po-
tential sources of novel secondary metabolites and many
of these possess very useful biological activities.1–4 For
example, the antifungal xylarin and multiplolides were
isolated from X. longipes2 and X. multiplex, respec-
tively,3 and acetylcholine esterase inhibitors, xyloketals
A–E, from Xylaria sp. collected from the South China
Sea coast.4 The structural diversity of chemical constit-
uents within the genus Xylaria should also be noted5–7
and in many cases, due to the difficulty and confusion
regarding the identity of Xylaria species, these metabo-
lite mixtures were used as markers for their taxonomic
identification.7 Herein we report another example of a