A new ent-clerodane diterpenoid from Crassocephalum bauchiense Huch. (Asteraceae).

[en] A phytochemical investigation of the whole plant of Crassocephalum bauchiense Huch. resulted in the isolation of a new clerodane diterpenoid, ent-2beta,18,19-trihydroxycleroda-3,13-dien-16,15-olide (1), together with two known flavonoids 3',5-dihydroxy-4',5',6,7,8-pentamethoxyflavone (2) and 4',5-dihydroxy-3',5',6,7,8-pentamethoxyflavone (3). The compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. Compound 2 showed weak activity (IC50 = 10.1 g/mL) whilst compounds 1 and 3 were inactive. The structures of the compounds were elucidated by using detailed spectral analyses, especially 1H and 13C NMR, 1H-1H COSY, NOESY, HMBC and HR-ESI-MS.

Disciplines :

Pharmacy, pharmacology & toxicology

Author, co-author :

Tchinda, Alembert T.

Mouokeu, Simplice R.

Ngono, Rosalie A. N.

Ebelle, Madeleine R. E.

Mokale, Aristide L. K.

Nono, Diane K.

Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie

Language :

English

Title :

A new ent-clerodane diterpenoid from Crassocephalum bauchiense Huch. (Asteraceae).

Publication date :

2015

Journal title :

Natural Product Research

ISSN :

1478-6419

eISSN :

1478-6427

Publisher :

Taylor & Francis, United Kingdom

Volume :

Issue :

Pages :

1990-1994

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 26 March 2015

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Bibliography

Arbonnier M. 2000. Arbres, arbustes et lianes des zones sèches d'Afrique de l'Ouest (Trees, shrubs and liana of dried zones of west Africa). Montpellier: CIRAD.
Das B, Ramu R, Venkateswarlu K, Rao YK, Reddy MR, Ramakrishna KVS, Harakishore K, Murty US. 2006. New clerodane diterpenoids from the aerial parts of Pulicaria wightiana. Chem Biodiv. 3: 175-179.
Esquivel R, Hernandez LM, Cardenas J, Ramamoorthy TP, Rodriguez-Hahn L. 1989. Further ent -clerodane diterpenoids from Salvia melissodora. Phytochemistry. 28: 561-566.
Frederich M, Jacquier MJ, Thepenier P, De Mol P, Tits M, Philippe G, Delaude C, Angenot L, Zeches-Hanrot M. 2002. Antiplasmodial activity of alkaloids from various Strychnos species. J Nat Prod. 65: 1381-1386.
Fushiya S, Kishi Y, Hattori K, Batkhuu J, Takano F, Singab AN, Okuyama T. 1999. Flavonoids from Cleome droserifolia suppress NO production in activated macrophages in vitro. Planta Med. 65: 404-407.
Gu J, Cheng G-G, Qian S-Y, Li Y, Liu P-P, Luo X-D. 2014. Dysoxydensins A-G, seven new clerodane diterpenoids from Dysoxylum densiflorum. Planta Med. 80: 1017-1022.
Hutchinson JJ, Dalziel JM. 1963. Flora of West Tropical Africa. 2 Revised by FN Hepper. London: Crown Agents.
Kenmogne M, Prost E, Harakat D, Jacquier MJ, Frederich M, Sondengam LB, Zeches M, Waffo-Teguo P. 2006. Five labdane diterpenoids from the seeds of Aframomum zambesiacum. Phytochemistry. 67: 433-438.
Merrit AT, Ley SV. 1992. Clerodane diterpenoids. Nat Prod Rep. 9: 243-287.
Mouokeu RS, Ngono RAN, Lunga PK, Koanga MM, Tchinda AT, Njateng GSS, Tamokou JDD, Kuiate JR. 2011. Antibacterial and dermal toxicological profiles of ethyl acetate extract from Crassocephalum bauchiense (Hutch.) Milne-Redh (Asteraceae). BMC Compl Altern Med. 11: 43. doi: 10.1186/1472-6882-11-43.
Mouokeu RS, Ngono RAN, Njateng GSS, Kamtchueng MO, Kuiate JR. 2014. Antifungal and antioxidant activity of Crassocephalum bauchiense (Hutch.) Milne-Redh ethyl acetate extract and fractions (Asteraceae). BMC Res Notes. 7: 1-7.
Mouokeu RS, Ngono RAN, Tume C, Kamtchueng MO, Njateng GSS, Dzoyem JP, Tamokou JDD, Kuiate J-R. 2013. Immunomodulatory activity of ethyl acetate extract and fractions from leaves of Crassocephalum bauchiense (Asteraceae). Pharmacologia. 4: 38-47. doi: 10.5567/pharmacologia.2013.38.47.
Pink R, Hudson A, Mouries MA, Bendig M. 2005. Opportunities and challenges in antiparasitic drug discovery. Nat Rev Drug Disc. 4: 727-740.
Sujata P, Sreekanth G, Khasim S, Rao BVA, Kumar BR, Rao AVNA. 2013. Flavonoids of Dikamali: A phytochemical reinvestigation. Nat Prod Res. 27: 1930-1932.
Taiwe GS, Ngo Bum E, Talla E, Dimo T, Neteydji S, Dawe A, Nguimbou RM, Djomeni DP D, De Waard M. 2012. Evaluation of antinociceptive effects of Crassocephalum bauchiense Hutch. (Asteraceae) leaf extract in rodents. J Ethnopharmacol. 141: 234-241.
Tchinda AT, Jansen O, Nyemb J-N, Tits M, Dive G, Angenot L, Frédérich M. 2014. Strychnobaillonine, an unsymmetrical bisindole alkaloid with an unprecedented skeleton from Strychnos icaja Baill. roots. J Nat Prod. 77: 1078-1082.
Tchinda AT, Ngono ARN, Tamze V, Jonville M-C, Cao M, Angenot L, Frédérich M. 2012. Antiplasmodial alkaloids from the stem bark of Strychnos malacoclados. Planta Med. 78: 377-382.
Tchinda AT, Tamze V, Ngono ARN, Ayimele GA, Cao M, Angenot L, Frédérich M. 2012. Alkaloids from the stem bark of Strychnos icaja. Phytochem Lett. 5: 108-113.