Download PDF
Planta Med 2009; 75(12): 1331-1335
DOI: 10.1055/s-0029-1185546
Pharmacology
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

HIV-1-Inhibiting Activity of the Essential Oil of Ridolfia segetum and Oenanthe crocata

Carlo Bicchi1 , Patrizia Rubiolo1 , Mauro Ballero2 , Cinzia Sanna2 , Maura Matteodo1 , Francesca Esposito3 , Luca Zinzula3 , Enzo Tramontano3
  • 1Dipartimento di Scienza e Tecnologia del Farmaco University of Torino, Torino, Italy
  • 2Co.S.Me.Se., Department of Botanical Sciences, University of Cagliari, Cagliari, Italy
  • 3Department of Biomedical Science and Technology, University of Cagliari, Cagliari, Italy
Further Information

Publication History

received October 23, 2008 revised February 27, 2009

accepted March 4, 2009

Publication Date:
03 April 2009 (online)

    Permissions and Reprints

Abstract

The essential oils of Ridolfia segetum (L.) Moris and Oenanthe crocata L. (Apiaceae), collected in Sardinia (Italy), have been assayed for two enzyme-associated activities of the HIV-1 reverse transcriptase (RT): RNA-dependent DNA polymerase (RDDP) activity and ribonuclease H (RNase H) activity. In biochemical assays, the essential oils inhibited HIV-1 RT RDDP activity in a dose-dependent manner, while they were inactive towards RNase H activity. Furthermore, the oils were cytotoxic towards K562 cell replication. GC‐MS analysis of the essential oils obtained by steam distillation of the aerial parts showed that the main components of R. segetum were alpha-phellandrene, alpha-terpinolene, beta-phellandrene, and dillapiol and those of O. crocata were sabinene, trans-beta-ocimene, cis-beta-ocimene, and beta-pinene.

Key words

Ridolfia segetum - Oenanthe crocata - Apiaceae - essential oil - HIV‐1 reverse transcriptase inhibition - K562 cell - GC‐MS analysis

References

  • 1 Moore J P, Stevenson M. New targets for inhibitors of HIV‐1 replication.  Nat Rev Mol Cell Biol. 2000;  1 40-49
    PubMedGoogle Scholar
  • 2 Klarmann G J, Hawkins M E, Le Grice S F. Uncovering the complexities of retroviral ribonuclease H reveals its potential as a therapeutic target.  AIDS Rev. 2002;  4 183-189
    PubMedGoogle Scholar
  • 3 Turpin J A. The next generation of HIV/AIDS drugs: novel and developmental anti-HIV drugs and targets.  Expert Rev Anti-Infect Ther. 2003;  1 97-128
    PubMedGoogle Scholar
  • 4 Tramontano E. HIV‐1 RNase H: recent progress in an exciting, yet little explored, drug target.  Mini-Rev Med Chem. 2006;  6 727-737
    PubMedGoogle Scholar
  • 5 Cos P, Maes L, Vlietinck A, Pieters L. Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection: an update (1998–2007).  Planta Med. 2008;  74 1323-1337
    Article in Thieme ConnectPubMedGoogle Scholar
  • 6 Yu D, Morris-Natschke S L, Lee K H. New developments in natural products-based anti-AIDS research.  Med Res Rev. 2007;  27 108-132
    CrossrefPubMedGoogle Scholar
  • 7 Chen K, Shi Q, Kashiwada Y, Zhang D C, Hu C Q, Jin J Q, Nozaki H, Tramontano E, Cheng Y C, McPhail D R, McPhail A T, Lee K H. Anti-AIDS agents, 6. Salaspermic acid, an anti-HIV principle from Tripterygium wilfordii, and the structure-activity correlation with its related compounds.  J Nat Prod. 1992;  55 340-346
    CrossrefPubMedGoogle Scholar
  • 8 Ballero M, Bruni A, Sacchetti G, Mossa L, Poli F. Indagine etnofarmacobotanica del territorio di Arzana (Sardegna orientale).  Ann Bot LII. 1995;  II 489-500
    PubMedGoogle Scholar
  • 9 Ballero M, Santus M, Poli F. Plants used in folk medicine of Monteleone (Northern Sardinia).  Fitoterapia. 1998;  LXIX 52-64
    PubMedGoogle Scholar
  • 10 Paulis G. I nomi popolari delle piante in Sardegna. Sassari; Delfino Editore 1992
    Google Scholar
  • 11 Clarks E G, Kidder D E, Robertson W D. The isolation of the toxic principle of Oenanthe crocata.  J Pharm Pharmacol. 1949;  1 377-381
    PubMedGoogle Scholar
  • 12 Janot M M, Robineau C, Le Men J. Crocatone, the non-toxic crystalline principle from Oenanthe crocata L. (Umbelliferae).  Bull Soc Chim Biol. 1955;  37 (2–3) 361-364
    PubMedGoogle Scholar
  • 13 King L A, Lewis M J, Parry D, Twitchett P J, Kilner E A. Identification of oenanthotoxin and related compounds in hemlock water dropwort poisoning.  Hum Toxicol. 1985;  4 355-364
    CrossrefPubMedGoogle Scholar
  • 14 Kite G C, Stoneham C A, Veitch N C, Stein B K, Whitwell K E. Application of liquid chromatography-mass spectrometry to the investigation of poisoning by Oenanthe crocata.  J Chromatogr B Analyt Technol Biomed Life Sci. 2006;  838 63-70
    PubMedGoogle Scholar
  • 15 Durand M F, Pommier P, Chazalette A, de Haro L. Child poisoning after ingestion of a wild Apiaceae: a case report.  Arch Pediatrie. 2008;  15 139-141
    PubMedGoogle Scholar
  • 16 Jaspersen-Schib R, Theus L, Guirguis-Oeschger M, Gossweiler B, Meier-Abt P J. Serious plant poisonings in Switzerland 1966–1994.  Schweiz Med Wochenschr. 1996;  126 1085-1098
    PubMedGoogle Scholar
  • 17 Martínez-Honduvilla M P, Aramburu E, Bahlsen C, G-Serranillos F M. Toxicity of the fruit of Oenanthe crocata L.  Arch Farmacol Toxicol. 1981;  7 197-200
    PubMedGoogle Scholar
  • 18 Anger J P, Anger F, Chauvel Y, Girre R L, Curtes N, Curtes J P. Fatal poisoning by water dropwort (Oenanthe crocata).  Eur J Toxicol Environ Hyg. 1976;  9 119-125
    PubMedGoogle Scholar
  • 19 Bicchi C, Liberto E, Matteodo M, Sgorbini B, Mondello L, d'Acampora Zellner B, Costa R, Rubiolo P. Quantitative analysis of essential oils: a complex task.  Flavour Frag J. 2008;  23 382-391
    CrossrefPubMedGoogle Scholar
  • 20 Adams R P. Identification of essential oil components by gas chromatography/mass spectrometry, 4th edition. Carol Stream, IL; Allured 2007
    Google Scholar
  • 21 Tramontano E, Cheng Y C. HIV‐1 reverse transcriptase inhibition by a dipyridodiazepinone derivative: BI‐RG‐587.  Biochem Pharmacol. 1992;  43 1371-1376
    CrossrefPubMedGoogle Scholar
  • 22 Tramontano E, Esposito F, Badas R, Di Santo R, Costi R, La Colla P. 6-[1-(4-Fluorophenyl)methyl-1H-pyrrol-2-yl)]-2–4-dioxo-5-hexenoic acid ethyl ester a novel diketo acid derivative which selectively inhibits the HIV‐1 viral replication in cell culture and the ribonuclease H activity in vitro.  Antivir Res. 2005;  65 117-124
    CrossrefPubMedGoogle Scholar
  • 23 Bolognese A, Correale G, Manfra M, Lavecchia A, Mazzoni O, Novellino E, Barone V, Pani A, Tramontano E, La Colla P, Murgioni C, Serra I, Setzu G, Loddo R. Antitumor agents. 1. Synthesis, biological evaluation, and molecular modeling of 5H-pyrido[3,2-a]phenoxazin-5-one, a compound with potent antiproliferative activity.  J Med Chem. 2002;  45 5205-5216
    CrossrefPubMedGoogle Scholar
  • 24 Bonsignore L, Casu L, Loy G, Deidda D, Genco F. Analysis of the essential oil of Oenanthe crocata L. and its biological activity.  J Essent Oil Res. 2004;  16 266-269
    PubMedGoogle Scholar
  • 25 Gattefosse J, Igolen G. Contribution à l'étude de la flore aromatique du Maroc. L'essence de fenouil des Moissons (Ridolfia segetum).  Bull Soc Chim. 1946;  361-363
    PubMedGoogle Scholar
  • 26 Gattefosse J, Igolen G. Essential oil of Ridolfia segetum.  Industrie Parfum. 1951;  6 305-307
    PubMedGoogle Scholar
  • 27 Fleisher Z, Fleisher A. Volatiles of leaves and flowers of Ridolfia segetum (L.) Moris. Aromatic plants of the Holy Land and the Sinai. Pan XII.  J Essent Oil Res. 1996;  8 189-191
    PubMedGoogle Scholar
  • 28 Pala-Paul J, Velasco-Negueruela A, Perez-Alonso M J, Ramos-Vazquez P. Volatile constituents of Ridolfia segetum (L.) Moris gathered in Spain, Andalucia Province.  J Essent Oil Res. 2002;  14 206-209
    PubMedGoogle Scholar
  • 29 Ben Jannet H, Mighri Z. Hydrodistillation kinetic and antibacterial effect studies of the flower essential oil from the Tunisian Ridolfia segetum (L.).  J Essent Oil Res. 2007;  19 258-261
    PubMedGoogle Scholar
  • 30 Marongiu B, Piras A, Porcedda S, Tuveri E, Maxia A. Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.  Nat Prod Res. 2007;  21 412-417
    CrossrefPubMedGoogle Scholar

Prof. Mauro Ballero

Co.S.Me.Se.
Department of Botanical Sciences
University of Cagliari

viale Sant'Ignazio 13

09123 Cagliari

Italy

Phone: + 39 07 06 75 35 06

Fax: + 39 07 06 75 35 03

Email: ballero@unica.it

      >