The bark and leaf essential oils of Verbesina turbacensis were obtained by hydrodistillation and analyzed by GC-MS. The bark oil of the plant was composed mainly of monoterpene hydrocarbons (83.5-90.4%), predominately α-pinene, while the leaf oil was composed mainly of sesquiterpene hydrocarbons, dominated by germacrene-D (29.1-36.9%), and δ-elemene (21.7-22.1%). Three bornyl hydroxycinnamic esters isolated from the acetone bark extract were found to inhibit the cysteine protease, rhodesain. Molecular docking analysis to probe the inhibitory interactions of the esters was also carried out.
MabberleyDJ. (1997) The Plant-Book, 2nd Ed. Cambridge University Press, UK, 744;
2.
Bruno-ColmenárezJ, Amaro-LuisJM, RamírezI, Delgado-MéndezP, Díaz deDelgado G. (2010) Absolute configuration of two eudesmane derivatives from Verbesina turbacensis H.B.K. Journal of Chemical Crystallography, 40, 110–115;
3.
GargiulloMB, MagnusonBL, KimballLD. (2008) A Field Guide to Plants of Costa Rica.Oxford, New York. 163;
4.
GiovanniniP, HeinrichM. (2009) Xki yoma’ (our medicine) and xki tienda (patent medicine) – Interface between traditional and modern medicine among Mazatecs of Oaxaca, Mexico. Journal of Ethnopharmacology, 121, 383–399;
5.
LobitzGO, HeilmannJ, ZschockeS, Tamayo-CastilloG, BauerR, MerfortI. (1998) Bornyl cinnamate derivatives with antiinflammatory activity from Verbesina turbacensis. Pharmaceutical and Pharmacological Letters, 8, 115–118.
SteinbrecherT, HrennA, DormannKL, MerfortI, LabahnaA. (2008) Bornyl (3,4,5-trihydroxy)-cinnamate – An optimized human neutrophil elastase inhibitor designed by free energy calculations. Bioorganic & Medicinal Chemistry, 16, 2385–2390;
9.
SteinbrecherT, CaseDA, LabahnA. (2006) A multistep approach to structure-based drug design: Studying ligand binding at the human neutrophil elastase. Journal of Medicinal Chemistry, 49, 1837–1844.
10.
GualteriM, AraqueM, MoralesA, RondonM, RogasJ, AraujoL, VillaltaC. (2005) Chemical composition and antibacterial activity of the essential oil of Verbesina turbacensis Kunth, HBK. Revista Latinoamericana de Química, 33, 128–131;
11.
AlbuquerqueMRJR, CanutoKM, PessoaODL, NunesEP, NascimentoRF, SilveiraER. (2006) Essential oil composition of Verbesina diversifolia DC. Flavour and Fragrance Journal, 21, 634–636.
12.
PedroLG, SantosPAG, da SilvaJA, FigueiredoAC, BarrosoJG, DeansSG, LoomanA, SchefferJJC. (2001) Essential oils from Azorean Laurus azorica. Phytochemistry, 57, 245–250;
13.
VillegasLF, MarcaloA, MartinJ, FernándezID, MaldonadoH, VaisbergAJ, HammondGB. (2001) (+)-epi-α-Bisbolol is the wound-healing principle of Peperomia galioides: Investigation of the in vivo wound-healing activity of related terpenoids. Journal of Natural Products, 64, 1357–1359;
14.
PuratchikodyA, DeviCN, NagalakshmiG. (2006) Wound healing activity of Cyperus rotundus Linn. Indian Journal of Pharmaceutical Sciences, 68, 97–101;
15.
MartinsAP, SalgueiroLR, GonçalvesMJ, Proença da CunhaA, VilaR, CañigueralS. (2003) Essential oil composition and antimicrobial activity of Santiria trimera bark. Planta Medica, 69, 77–79.
16.
BakerJ. (1998) Essential oils: A complementary therapy in wound management. Journal of Wound Care, 7, 355–357;
17.
HartmanD, CoetzeeJC. (2002) Two US practitioner's experience of using essential oils for wound care. Journal of Wound Care, 11, 317–320;
18.
WoollardAC, TathamKC, BarkerS. (2007) The influence of essential oils on the process of wound healing: A review of the current evidence. Journal of Wound Care, 16, 255–257.
AgiusBR, VoglerB, StokesSL, SetzerWN, CaffreyCR, HansellE, McKerrowJH. (2007) Inhibition of cruzain by triterpenoids isolated from a Salacia species from Monteverde, Costa Rica. Natural Product Communications, 2, 1083–1084.
21.
SajidM, MckerrowJH. (2002) Cysteine proteases of parasitic organisms. Molecular and Biochemical Parasitology, 120, 1–21;
22.
MackeyZB, O'BrienTC, GreenbaumDC, BlankRB, McKerrowJH. (2004) A Cathepsin B-like protease is required for host protein degradation in Trypanosoma brucei. Journal of Biological Chemistry, 279, 48426–48433;
23.
GonzálezFV, IzquierdoJ, RodríguezS, McKerrowJH, HansellE. (2007) Dipeptidyl-α,β-epoxyesters as potent irreversible inhibitors of the cysteine proteases cruzain and rhodesain. Bioorganic and Medicinal Chemistry Letters, 17, 6697–6700.
24.
VermelhoAB, De SimoneSG, d'Avila-LevyCM, Souza doSantos AL, Nogueira deMelo AC, SilvaFP, Pinto da SilvaBon E, BranquinhaMH. (2007) Trypanosomatidae peptidases: A target for drugs development. Current Enzyme Inhibition, 3, 19–48.
SetzerWN, SetzerMC, BatesRB, NakkiewP, JackesBR, ChenL, McFerrinMB, MeehanEJ. (1999) Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia. The crystal and molecular structure of (+)-bornyl coumarate. Planta Medica, 65, 747–748.
27.
ChenYC, LiaoCH, ChenIS. (2007). Lignans, an amide and anti-platelet activities from Piper philippinum. Phytochemistry, 68, 2101–2111;
28.
MongelliE, MartianezJ, AnayaJ., GrandeC, GrandeM, TorresP, PomilioAB. (2003) Bolax gummifera: Toxicity against Artemia sp. of bornyl and iso-bornyl esters. Molecular Medicinal Chemistry, 1, 26–29;
29.
RubioBK, TenneyK, AngKH, AbdullaM, ArkinM, McKerrowJH, CrewsP. (2009) The marine sponge Diacarnus bismarckensis as a source of peroxiterpene inhibitors of Trypanosoma brucei, the causative agent of sleeping sickness. Journal of Natural Products, 72, 218–222.
30.
FreiburghausF, SteckA, PfanderH, BrunR. (1998) Bioassay-guided isolation of a diastereoisomer of kolavenol from Entada abyssinica active on Trypanosoma brucei rhodesiense. Journal of Ethnopharmacology, 61, 179–183;
31.
LikensST, NickersonGB. (1964) Determination of certain hop oil constituents in brewing products. Proceedings of the American Society of Brewing Chemists, 5–13;
32.
SetzerWN. (2008) Essential oil composition of Dendropanax gonatopodus from Monteverde, Costa Rica. An ab initio examination of aromadendrane sesquiterpenoids. Natural Product Communications, 3, 1557–1561.
33.
AdamsRP. (2007) Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry, 4th Ed. Allured Publishing Co. Carol Stream, Illinois.
34.
HernándezVM, MirandaR, MartínezM, Joseph-NathanP. (1986) Presence of bornyl p-coumarate in the roots of Eupatorium deltoideum. Journal of Natural Products, 49, 1173–1174;
35.
MaldonadoE, Ramírez ApanMT, Pérez-CastorenaAL. (1998) Anti-inflamatory activity of phenyl propanoids from Coreopsis mutica var mutica. Planta Medica, 64, 660–661.
36.
CaffreyCR, HansellE, LucasKD, BrinenLS, HernandezAA, ChengJ, GwaltneySLII, RoushWR, StierhofYD, BogyoM, SteverdingD, McKerrowJH. (2001) Active site mapping, biochemical properties and subcellular localization of rhodesain, the major cysteine protease of Trypanosoma brucei rhodesiense. Molecular & Biochemical Parasitology, 118, 61–73;
37.
BarrettAJ, KembhaviAA, BrownMA, KirschkeH, KnightCG, TamaiM, HanadaK. (1982) L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L. Biochemical Journal, 201, 189–198;
38.
Molegro Virtual Docker v. 4.0 (2009) Molegro ApS. Aarhus, Denmark;
39.
ThomsenR, ChristensenMH. (2006) MolDock: A new technique for high-accuracy molecular docking. Journal of Medicinal Chemistry, 49, 3315–3321.
