Anti-HIV-1 Constituents from Leaves and Twigs of Cratoxylum arborescens

Abstract

Two new xanthones, 1,3,8-trihydroxy-2,4-dimethoxyxanthone (1) and 1,7-dihydroxy-2,8-dimethoxyxanthone (2), along with twelve known compounds 3 - 14 were isolated from leaves and twigs of Cratoxylum arborescens. Compound 1, euxanthone (4), betulinic acid (8), lup-20(29)-ene-3β,30-diol (9), 3β-hydroxylup-20(29)-en-30-oic acid (10) and 3,4-dihydroxybenzoic acid (11) displayed anti-HIV-1 activities in the syncytium assay using ^{Δ Tat/Rev}MC99 virus and the 1A2 cell line system (EC₅₀ values between 3.9 and 32.2 μg/mL with TI ranging from 1.5 to 11.7), while 1,3,7-trihydroxy-6-methoxy-4,5-diisoprenylxanthone (3), 4, and 8 - 10 inhibited HIV-1 reverse transcriptase with IC₅₀ values between 8.7 and 84.9 μg/mL.

References

• 1 Pattanaprateeb P, Ruangrungsi N, Cordell G A. Cytotoxic constituents from Cratoxylum arborescens .  Planta Med. 2005;  71 181-3
• 2 Seo E -K, Kim N -C, Wani M C, Wall M E, Navarro H A, Burgess J P. et al . Cytotoxic prenylated xanthones and the unusual compounds anthraquinobenzophenones from Cratoxylum sumatranum .  J Nat Prod. 2002;  65 299-305
• 3 Fujita T, Liu D Y, Ueda S, Takeda Y. Xanthones from Polygala tenuifolia .  Phytochemistry. 1992;  31 3997-4000
• 4 Gunatilaka A AL, Nanayakkara N PD, Sultanbawa M US, Balasubramaniam S. Friedelin D: a-friedo-olean-3,21-dione and 21α-hydroxy-D:A-friedo-olean-3-one from Kokoona zeylanica .  Phytochemistry. 1982;  21 2061-3
• 5 Salazar G CM, Silva G DF, Duarte L P, Vieira Filho S A, Lula I S. Two epimeric friedelane triterpenes isolated from Maytenus truncata Reiss: ¹H and ¹³C chemical shift assignments.  Magn Reson Chem. 2000;  38 977-80
• 6 Meselhy M R. Constituents from Moghat, the roots of Glossostemon bruguieri (Desf.)  Molecules. 2003;  8 614-21
• 7 Fujioka T, Kashiwada Y. Anti-AIDS agents, 11. Betulinic acid and platonic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids.  J Nat Prod. 1994;  57 243-7
• 8 Abdel-Mogib M. A lupane triterpenoid from Maerua oblongifolia .  Phytochemistry. 1999;  51 445-8
• 9 Ullah N, Ahmed Z, Ahmed S, Muhammad P, Malik A. A pentacyclic triterpene from Daphne oleoides .  Phytochemistry. 1999;  50 839-41
• 10 Ruth M, Maria T S, Sagrario B, José L C. Solubility of some phenolic compounds contained in grape seeds in supercritical carbon dioxide.  J Supercrit Fluids. 2002;  23 113-21
• 11 Tschesche R, Delhvi S, Sepulveda S, Breitmaier E. Eucryphin, a new chromone rhamnoside from the bark of Eucryphia cordifolia .  Phytochemistry. 1979;  18 867-9
• 12 Kasai R, Hirono S, Chou W -H, Tanaka O, Chen F -H. Sweet dihydroflavonol rhamnoside from leaves of Engelhardtia chrysolepis, a Chinese folk medicine, Hung-qi.  Chem Pharm Bull. 1988;  36 4167-70
• 13 Gaffield W. Absolute configurations of the cis-dihydroquercetin-3-O-β-L-rhamnosides isoastilbin and neoisoastilbin.  Chem Pharm Bull. 1996;  44 1102-3
• 14 Akihisa T, Ogihara J, Kato J, Yasukawa K, Ukiya M, Yamanouchi S. et al . Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase.  Lipids. 2001;  36 507-12
• 15 Park J G, Park J C, Hur J M, Park S J, Choi D R, Shin D Y. et al . Phenolic compounds from Orostachys japonicus having anti-HIV-1 protease activity.  Nat Prod Sci. 2000;  6 117-21
• 16 Wolfender J L, Hamburger M, Msonthi J D, Hostettmann K. Xanthones from Chironia krebsii .  Phytochemistry. 1991;  30 3625-9
• 17 Tan G T, Pezzuto J M, Kinghorn A D. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.  J Nat Prod. 1991;  54 143-54
• 18 Kiser R, Makovsky S, Terpening S J, Laing N, Clanton D J. Assessment of a cytoprotection assay for the discovery and evaluation of anti-human immunodeficiency virus compounds utilizing a genetically-impaired virus.  J Virol Methods. 1996;  58 99-109
• 19 Nara P L, Hatch W C, Dunlop N M, Robey W G, Arthur L O, Gonda M A. et al . Simple, rapid, quantitative, syncytium forming microassay for the detection of human immunodeficiency virus neutralizing antibody.  AIDS Res Hum Retroviruses. 1987;  3 283-302