[en] Phytochemical investigation of the ethanol extract of the stem bark of Hypericum lanceolatum Lam. (Guttifereae)
afforded eight known compounds including 2,2ʹ,5,6ʹ-tetrahydroxybenzophenone (1), 5-hydroxy-3-methoxyxanthone
(2), 3-hydroxy-5-methoxyxanthone (3), betulinic acid (4), hydroquinone (5) 6,7-dihydroxy-1,3-dimethoxyxanthone
(6), calophyllumin A (7), and 1,3,5,6-tetrahydroxy-4-prenylxanthone (8). Compound 1 was submitted to acetylation
reaction to give 5-acetoxy-2,2ʹ,6ʹ-trihydroxybenzophenone (9), a new hemisynthetic derivative. Compounds 5 and
8 were isolated for the first time from this plant. The structures were established by extensive analysis of their mass
spectrometry and nuclear magnetic resonance (NMR) spectroscopic data and comparison with those from the literature.
The isolated compounds (1, 2, 4, 5, and 8) and the derivative of benzophenone (9) were tested for their antipromastigote
and cytotoxic activities against visceral leishmaniasis parasite Leishmania donovani and macrophage RAW 264.7 cell
line, respectively. Compound 9 was the most active with an IC50 value of 6.1 μg/ml, while compounds 1, 2, 4, and 8
were moderately active with IC50 values ranging from 11.4 to 34.8 μg/ml against L. donovani and were not cytotoxic
except compound 5 that was very toxic and not active. The findings of the present study suggested that compounds 1,
2, 4, and 8 could be considered as a potential source of therapeutic medicine for the treatment of leishmaniasis.
Research center :
CIRM - Centre Interdisciplinaire de Recherche sur le Médicament - ULiège
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Kowa, Théodora; Institute of Medical Research and Medicinal PlantsStudies, Yaounde
Tchokouaha, Lauve; Institute of Medical Research and Medicinal PlantsStudies, Yaounde
Nyemb, Jean-Noël; University of Ngaoundere
Wabo, Hippolyte; University of Dschang
Tchinda, Alembert; Institute of Medical Research and Medicinal PlantsStudies, Yaounde
Appiah-Opong, Regina; University of Ghana
Agbor, Gabriel
Tane, Pierre
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Language :
English
Title :
Antipromastigote and cytotoxic activities of some chemical constituents of Hypericum lanceolatum Lam.
Alves LV, Do Canto-Cavalheiro MM, Cysne-Finkelstein L, Leon L. In vitro antiproliferative effects of several diaryl derivatives on Leishmania spp. Biol Pharm Bull, 2003; 26:453-6.
Azebaze AGB, Ouahouo BMW, Vardamides JC, Valentin A, Kuete V, Acebey L, Beng VP, Nkengfack AE, Meyer M. Antimicrobial and antileishmanial xanthones from the stem bark of Allanblackia gabonensis. Chem Nat Compd, 2008; 44:582-7.
Bahmani M, Saki K, Ezatpour BSS, Eftekhari Z, Jelodari M, Mahmoud R-K, Reza S. Leishmaniosis phytotherapy: review of plants used in Iranian traditional medicine on leishmaniasis. Asian Pac J Trop Biomed, 2015; 5:695-701.
Bruneton J. Pharmacognosie, Phytochimie, Plantes medicinales, 3eme edition, Technique et Documentation Lavoisier, Paris, pp 235-669, 1999.
Chan-Bacab MJ, Balanza E, Deharo E, Munoz V, Duran R, Pena-Rodriguez LM. Variation of leishmanicidal activity in four populations of Urechites andreuxii. J Ethnopharmacol, 2003; 86:243-7.
Den Boer M, Argaw D, Jannin J, Alvar J. Leishmaniasis impact and treatment access. Clin Microbiol Infect, 2011; 17:1471-7.
Duthie MS, Raman VS, Piazza FM, Reed SG. The development and clinical evaluation of second-generation leishmaniasis vaccines. Vaccine, 2012; 30:134-41.
Einzhammer DA, Xu ZQ. Betulinic acid: a promising anticancer candidate. IDrugs, 2004; 4:359-73.
Ejazi SA, Ali N. Developments in diagnosis and treatment of visceral leishmaniasis during the last decade and future prospect. Exp Rev Anti-Infect Ther, 2013; 11:79-98.
Essid R, Rahali FZ., Msaada K, Sghair I, Hammami M, Bouratbine A, Aoun K, Limam F. Antileishmanial and cytotoxic potential of essential oils from medicinal plants in Northern Tunisia. Ind Crops Prod, 2015; 77:795-802.
Evangelos T, Sjef B, Vassiliki E, Anatassios N, Troganis J. Vervoort J, Loannis P, Gerothanassis P. Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochem, 2007; 68:383-93.
Fobofou SAT, Franke K, Porzel A, Brandt W, Wessjohann LA. Tricyclic acylphlorolucinols from Hypericum lanceolatum and regioselective synthesis of selancins A and B. J Nat Prod, 2016; 79:743-53.
Focho DA, Nkeng EAP, Lucha CF, Ndam WT, Afegenui A. Ethnobotanical survey of plants used to treat diseases of the reproductive system and preliminary phytochemical screening of some species of Malvaceae in Ndop Central Sub-Division, Cameroon. J Med Plan Res, 2009; 3:301-14.
Hutchinson J, Dalziel JM. Pour les Verbenaceae. In: Hepper FN (ed.). Flora of West Tropical Africa. 2nd edition, vol. 2, pp 383-6, 1963.
Iinuma M, Tosa H, Tanaka T, Ito T, Yonemori S, Chelladurai V, Aquil M, Takahashi Y, Naganawa H. Occurrence of xantholignoids in Guttiferous plants. Heterocycles, 1996; 43:1521-7.
Kedzierski L. Leishmaniasis. Human Vaccine, 2011; 7:1204-14.
Kopa TK, Tchinda AT, Tala MF, Zofou D, Jumbam R, Wabo HK, Titanji VPK, Frederich M, Tan N-H, Tane P. Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae). Phytochem Lett, 2014; 8:41-6.
Lewis, LW. Medical botany. John Wiley and Sons, Inc., Hoboken, NJ, p 654, 2003.
Meseguer AS, Sanmartin I. Paleobiology of the genus Hypericum (Hyperi-caceae): a survey of the fossil record and its palaeogeographic implications. Anal Jard Bot Madrid, 2012; 69:97-106.
Ming-Jaw D, Yeh-Jeng H, Ray-Ling H, Yun-Lian L. New phenolics principles from Hypericum sampsonii. Chem pharm Bull, 2004; 52:866-9.
Muhammad K, Abdul LK, Liaqat A, Javid H, Muhammad W, Ahmed A-H, Qari MI, Yoon-Ha K, Sang-Mo K B-W Y, In-Jung L. Hydroquinone a novel bioactive compound from plant-derived smoke can cue seed germination of Lettucein. Front Chem, 2017; 30:1-9.
Rodriguez KAF, Amorim LV, Dias CN, Moraes DFC, Carneiro SMP, Carvalho FAA. Syzygium cumini (L) skeels essential oil and its major constituent α-pinene exhibit anti-leishmania activity through immunomodulation in vitro. J Ethnopharmacol, 2015; 160:32-40.
Seabra RM, Vascongelos MH, Cruz Costa MA, Alves AC. Phenolic compounds from Hypericum perforatum and Hypericum undulatum. Fitoterapia, 1992; 68:473-4.
Shah NA, Khan MR, Nadhman A. Antileishmanial, toxicity and phytochemical evaluation of medicinal plants collected from Pakistan. Biomed Res Int, 2014; article ID 384204, 1-7.
Suzgec-Selcuk S, Mericli AH, Guven KC, Kaiser M, Casey RS, Hingley SW, Lalvani A, Tasdemir D. Evaluation of Turkish seaweeds for antiprotozoal, antimycobacterial and cytotoxic activities. Phytother Res, 2011; 5:778-83.
Tanaka N, Takaishi Y, Yasuhiro S, Yuka N, Kenneth BN, Lee K, Honda G, Takeda Y, Olimjon K, Ozodbek A. Prenylated benzophenones and xanthones from Hypericum scabrum. J Nat Prod, 2004; 67:1870-5.
Tanaka N, Takaishi Y. Xanthones from Hypericum chinense. Phytochem, 2006; 67(19):2146-51.
Tchakam PD, Lunga PK, Kowa TK, Wabo HK, Tapondjou AL, Tane P, Kuiate JR. Antimicrobial and antioxidant activities of the extracts and compounds from the leaves of Psorospermum aurantiacum Engl. and Hypericum lanceolatum Lam. BMC Complement Alternat Med, 2012; 12:1-8.
Vera RR, Chane-Ming J, Fraise DJ. Essential oil of Hypericum lanceolatum Lam. from Reunion. Rivista Italiana. EPPOS, 1996; 7:639-44.
Wabo HK, Kowa TK, Lonfouo AHN, Tchinda AT, Tane P, Kikuchi H, Frederich M, Oshima Y. Phenolic Compounds and Terpenoids from Hypericum lanceolatum. Rec Nat Prod, 2012; 6:94-100.
WHO. World Organization Health. Weekly Epidemiology Record, 2016; 91:441-60.
Wong IL, Chan KF, Chen YF, Lun ZR, Chan TH, Chow LM. In vitro and in vivo efficacy of novel flavonoid dimers against cutaneous leishmaniasis. Antimicrob Agents Chemother, 2014; 48:3379-88.
Wu Q-L, Wang S-P, Du L-J, Yang J-S, Xiao P-G. Xanthones from Hypericum japonicum and Hypericum Henryi. Phytochem, 1998; 49:1395-402.
Yogeeswari P, Sriram D. Betulinic acid and its derivatives: a review on their biological properties. Curr Med Chem, 2005; 12:657-66.
Yu MO. Research of biologically active substances of Hypericum L. species. Farmatsevtichnii Zhurnal, 1998; 5:38-44.
Zofou D, Kowa TK, Wabo HK, Ngemenya MN, Tane P, Titanji VPK. Hypericum lanceolatum (Hypericaceae) as a potential source of new anti-malarial agents: a bioassay-guided fractionation of the stem bark. Malaria J, 2011; 10:1-7.
