Novel Bioactive Dammarane Caffeoyl Esters from Celastrus rosthornianus

Abstract

Three new dammar-type triterpenoid caffeates (1 - 3) were isolated from the stalks of Celastrus rosthornianus Loes. Their structures were established through various spectral studies as 3β,20(S),24(S)-trihydroxyldammar-25-ene 3-caffeate (1), 3β,20(S),24(R)-trihydroxyldammar-25-ene 3-caffeate (2) and 3β,20(S),25-trihydroxyldammar-23(Z)-ene 3-caffeate (3), respectively. The three new compounds (1 - 3) showed strong antitumor activity against the human cervical squamous carcinoma cell line with IC₅₀ values of 6.4, 5.3 and 6.5 μg/mL, respectively. The biological analyses of 1 - 3 and their hydrolysates 1a - 3a indicated that the caffeoyl group could increase the bioactivity.

References

• 1 State Administration of Traditional Chinese M edicine. Zhong Hua Ben Cao editorial board, Zhong Hua Ben Cao. Shanghai; Shanghai Science and Technology Publisher 1999 Vol 5: pp 175-6
• 2 Chen B, Duan H Q, Takaishi Y. Triterpene caffeoyl esters and diterpenes from Celastrus stephanotifolius .  Phytochemistry. 1999;  51 683-7
• 3 Laphookhieo S, Karalai C, Ponglimanont C, Chantrapromma K. Pentacyclic triterpenoid esters from the fruits of Bruguiera cylindrica .  J Nat Prod. 2004;  67 886-8
• 4 Asakawa J, Kasai R, Yamasaki K, Tanaka O. ¹³C NMR study of ginseng sapogenins and their related dammarane type triterpenes.  Tetrahedron. 1977;  33 1935-9
• 5 Wang D Q, Fan J, Feng B S, Li S R, Wang X B, Yang C R. et al . Studies on saponins from the leaves of Panax japonicus var. bipinnatifidus (Seem.) Wu et Feng.  Acta Pharm Sin. 1989;  24 593-9
• 6 Placente S, Pizza C. New dammarane-type glycosides from Gynostemma pentaphyllum.  J Nat Prod. 1995;  58 512-9
• 7 Banskota A H, Tezuka Y, Tran K Q, Tanaka K, Saik I, Kadota S. Thirteen novel cycloartane-type triterpenes from Combretum quadrangulare .  J Nat Prod. 2000;  63 57-64
• 8 Ohtani I, Kasumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids.  J Am Chem Soc. 1991;  113 4092-6
• 9 Wang D Q, Feng B S, Wang X B, Yang C R, Zhou J. Further study on dammarane saponins of leaves of Panax japonicus var. major collected in Qinling Mountains China.  Acta Pharm Sin. 1989;  24 633-8
• 10 Butruille D, Dominguez X A. Fouquierol et isofouquierol: deux nouveaux triterpenes de la série du dammarane. Tetrahedron Let 1974: 639-42
• 11 Wang K W, Sun H X, Wu B, Pan Y J. Two novel oleane triterpenoids from Celastrus hypoleucus .  Helv Chim Acta. 2005;  88 990-5