The leaf oil of Siparuna grandiflora (Monimiaceae) has been obtained by hydrodistillation and analyzed by GC-MS. The major components were germacrone (66.9%), germacrene B (8.2%), δ-cadinene (2.5%), trans-β-elemenone (2.2%), and β-elemene (2.1%). The leaf oil exhibited notable in-vitro cytotoxic activity on MCF-7 cells, brine shrimp lethality, and limited antimicrobial activity. DFT calculations (B3LYP/6-31G*) indicate that germacrone is slightly more stable than its Cope rearrangement product trans-β-elemenone.
MortonJF. (1981) Atlas of Medicinal Plants of Middle America, Vol 1, Thomas Publisher, Springfield, Illinois, 230–231.
5.
CiccióJF, Gómez-LauritoJ. (2002) Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba, Costa Rica. Revista de Biología Tropical, 50, 963–967;
6.
FischerDCH, LimbergerRP, HenriquesAT, MorenoPRH. (2005) Essential oils from fruits and leaves of Siparuna guianensis (Aubl.) Tulasne from southeastern Brazil. Journal of Essential Oil Research, 17, 101–102;
7.
MachadoSMF, RibeiroVAFA, MilitaoJSLT, de MoraisSM, MachadoMIL. (1998) Seasonal variation of (E)-nerolidol in Siparuna guianensis Aublet and 13C-NMR spectral assignments of (E)- and (Z)-nerolidol. Journal of Essential Oil Research, 10, 708–710;
8.
VilaR, IglesiasJ, CañigueralS, SantanaAI, SolísPN, GuptaMP. (2002) Chemical composition and biological activity of the leaf oil of Siparuna thecaphora (Poepp. Et Endl.) A. DC. Journal of Essential Oil Research, 14, 66–67;
9.
ZoghbiMdGB, AndradeEHA, SantosAS, SilvaMHL, MaiaJGS. (1998) Essential oils of Siparuna guianensis Aubl. Journal of Essential Oil Research, 10, 543–546.
10.
OzakiY. (1990) Antiinflammatory effect of Curcuma xanthorrhiza Roxb, and its active principles. Chemical and Pharmaceutical Bulletin, 38, 1045–1048.
11.
MorikawaT, MatsudaH, NinomiyaK, YoshikawaM. (2002) Medicinal foodstuffs XXIX. Potent protective effects of sesquiterpenes and curcumin from Redoariae Rhizoma on liver injury induced by D-galactosamine/lipopolysaccharide or tumor necrosis factor-α. Biological and Pharmaceutical Bulletin, 25, 627–631.
12.
LoayzaI, AbujderD, ArandaR, JakupovicJ, CollinG, DeslauriersH, JeanFI. (1995) Essential oils of Baccharis salicifolia, B. latifolia and B. dracunculifolia. Phytochemistry, 38, 381–389;
13.
YangFQ, LiSP, ZhaoJ, LaoSC, WangYT. (2007) Optimization of GC-MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes. Journal of Pharmaceutical and Biomedical Analysis, 43, 73–82.
14.
MöllekenU, SinnwellV, KubeczkaKH. (1998) The essential oil composition of fruits from Smyrnium perfoliatum. Phytochemistry, 47, 1079–1083;
CaoJ, QiM, FangL, ZhouS, FuR, ZhangP. (2006) Solid-phase microextraction-gas chromatography-mass spectrometric analysis of volatile compounds from Curcuma wenyujin Y.H. Chen et C. Ling. Journal of Pharmaceutical and Biomedical Analysis, 40, 552–558;
17.
ZhouX, LiZ, LiangG, ZhuJ, WangD, CaiZ. (2007) Analysis of volatile components of Curcuma sichuanensis X.X. Chen by gas chromatography-mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis, 43, 440–444.
18.
NickersonGB, LikensST. (1966) Gas chromatography evidence for the occurrence of hop oil components in beer. Journal of Chromatography A, 21, 1–5. In the Likens-Nikerson apparatus, both the steam and chloroform vapors condense on the cold finger; when both liquids flow down, extraction takes place from aqueous phase into the chloroform. In the separation chamber, both phases demix, and by way of the connecting tubes, they flow back into their respective flasks. Thus, the volatile components are extracted from the sample by simultaneous hydrodistillation liquid-liquid extraction and concentrated in the chloroform.
19.
MoriarityDM, BansalA, ColeRA, TakakuS, HaberWA, SetzerWN. (2007) Selective cytotoxic activities of leaf essential oils from Monteverde, Costa Rica. Natural Product Communications, 2, 1263–1268.
20.
SetzerMC, WerkaJS, IrvineAK, JackesBR, SetzerWN. (2006) Biological activity of rainforest plant extracts from far north Queensland, Australia. In Biologically Active Natural Products for the Twenty-First Century. WilliamsLAD (Ed). Research Signpost, Trivandrum, India. 21–46.
21.
WerkaJS, BoehmeAK, SetzerWN. (2007) Biological activities of essential oils from Monteverde, Costa Rica. Natural Product Communications, 2, 1215–1219.
22.
SPARTAN ‘06 for Windows (2006) Wavefunction, Inc., Irvine, California.
23.
BeckeAD. (1993) Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648–5652;
24.
LeeC, YangW, ParrRG. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785–789.
25.
HehreWJ, RadomL, SchleyerPvR. (1986) Ab initio Molecular Orbital Theory.Wiley, New York.