Planta Med 2008; 74(1): 80-83
DOI: 10.1055/s-2007-993781
Natural Product Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Anthocleistenolide, A New Rearranged Nor-Secoiridoid Derivative from the Stem Bark of Anthocleista vogelii

Mathieu Tene1 , Pierre Tane1 , Jules-Roger Kuiate2 , Jean de Dieu Tamokou2 , Joseph D. Connolly3
  • 1Chemistry Department, University of Dschang, Dschang, Cameroon
  • 2Biochemistry Department, University of Dschang, Dschang, Cameroon
  • 3Chemistry Department, University of Glasgow, Glasgow, Scotland, U.K.
Further Information

Publication History

Received: September 20, 2007 Revised: November 14, 2007

Accepted: November 23, 2007

Publication Date:
18 January 2008 (online)

Abstract

A new rearranged nor-secoiridoid, anthocleistenolide (1), along with the known 1-hydroxy-3,7-dimethoxyxanthone (2), 1-hydroxy-3,7,8-trimethoxyxanthone (3), 7α-hydroxysitosterol (4) and sitosterol 3-O-β-D-glucopyranoside (5), were isolated from the stem bark of Anthocleista vogelii. Their structures were elucidated on the basis of spectral studies and comparison with published data. Compounds 1 - 3 and 5 were evaluated for their antibacterial and antifungal activities. Relatively low anti-staphylococcal (MIC = 200 μg/mL against Staphylococcus aureus) and anti-enterococcal (MIC = 100 μg/mL against Enterococcus faecalis) activities were observed for 1, while compounds 2 and 3 were active against Candida parapsilosis (MIC = 200 μg/mL for 2 and 25 μg/mL for 3). Compound 5 was inactive against all the bacterial and fungal species used.

References

  • 1 Meszaros S, Jan de L aet, Smets E. Phylogeny of temperate Gentianaceae: a morphological approach.  Syst Bot. 1996;  21 153-68
  • 2 Leeuwenberg A JM. Loganiacées. In: Aubreville A, Leroy J-F, editors Flore du Cameroun. vol. 12 Paris; Muséum National d’Histoire Naturelle 1972: 3-22
  • 3 Okorie D A. A new phthalide and xanthones from Anthocleista djalonensis and Anthocleista vogelii. .  Phytochemistry. 1976;  15 1799-800
  • 4 Igoli J O, Ogaji O G, Tor-Anyiin T A, Igoli N P. Traditional medicine practice amongst the Igede people of Nigeria. Part II.  Afr J Trad CAM. 2005;  2 134-52
  • 5 Chapelle J P. Constituants chimiques des feuilles d’Anthocleista vogelii. .  Planta Med. 1974;  26 301-4
  • 6 Chapelle J P. Vogeloside et acide sécologanique, glucosides sécoiridoïdes d’Anthocleista vogelii. .  Planta Med. 1976;  29 268-74
  • 7 Chapelle J P. Grandifloroside et méthylgrandifloroside, glucosides iridoïdes nouveaux d’Anthocleista grandiflora. .  Phytochemistry. 1976;  15 1305-7
  • 8 Eloff J N. Which extractant should be used for the screening and isolation of antimicrobial components from plants?.  J Ethnopharmacol. 1998;  60 1-8
  • 9 Tene M, Tane P, Sondengam B L, Connolly J D. Clerodane diterpenoids from Microglossa angolensis. .  Tetrahedron. 2005;  61 2655-8
  • 10 Morota T, Sasaki H, Sugama K, Nishimura H, Chin M, Mitsuhashi H. Two non-glycosidic iridoids from Rehmannia glutinosa. .  Phytochemistry. 1990;  29 523-6
  • 11 Sampaio-Santos M I, Kaplan M AC. Biosynthesis significance of iridoids in chemosystematics.  J Braz Chem Soc. 2001;  12 144-53
  • 12 Monte F JQ, Soares F P, Braz-Filho R. A xanthone from Shultesia guianensis. .  Fitoterapia. 2001;  72 715-6
  • 13 Valantao P, Andrade P B, Silva E, Vicente A, Santos H, Bastos M L. et al . Methoxylated xanthones in the quality control of small centaury (Centaurium erythaea) flowering tops.  J Agric Food Chem. 2002;  50 460-3
  • 14 Guerriero A, D’Ambrosio M, Pietra F, Debitus C, Ribes O. Pteridines, sterols, and indole derivatives from the lithistid Corallistes undulatus of the coral sea.  J Nat Prod. 1993;  56 1962-70
  • 15 Kojima H, Sato N, Hatano A, Ogura H. Sterol glucosides from Prunella vulgaris. .  Phytochemistry. 1990;  29 2351-5
  • 16 Gulluce M, Sokmen M, Daferera D, Agar G, Ozkan H, Kartal N. et al . The in vitro antibacterial, antifungal and antioxidant activities of the essential oil and methanol extracts of herbal parts and callus cultures of Satureja hortensis L.  J Agric Food Chem. 2003;  51 3958-65

Dr. Mathieu Tene

Department of Chemistry

University of Dschang

P. O. Box 67

Dschang

Cameroon

Phone: +237-7780-8420

Fax: +237-3345-1735

Email: mtene2001@yahoo.fr