Lupane Triterpenoids and a Diarylheptanoid from Clematoclethra actinidioides

Abstract

Three new compounds, actinidione (1), 3β,29-dihydroxylup-20(30)-en-28-al (2) and 3β-O-trans-caffeoyl-29-hydroxybetulin (3), along with twenty known compounds (4 - 23), were isolated from the leaves and twigs of Clematoclethra actinidioides Maxim. Their structures were determined by analysis of spectral data or comparison with authentic samples. Compounds 1, 2 and 3 exhibited cytotoxicity against Lu-06, N-04 and Bre-04 cell lines with GI₅₀ values of 15.02 - 41.64 μg/mL.

References

• 1 Zhang H Y, Zhang Z H. Handbook of Chinese Traditional Medicine Resources. Beijing; Academic Press 1994: p 234
• 2 Zhang X R, Ding L S, Peng S L, Wang M K. Chemical constituents from Clematoclethra scandens .  Tianran Chanwu Yanjiu Yu Kaifa. 2000;  12 38-41
• 3 Zhang X R, Peng S L, Wang M K, Ding L S. Triterpenoids from Clematoclethra scandens .  Yaoxue Xuebao. 2001;  36 910-2
• 4 Sinha N K, Seth K K, Pandey V B. Flavonoids from the flowers of Clerodendron infortunatum .  Planta Med. 1981;  42 296-8
• 5 Patra A, Chaudhuri S K, Panda S K. Betulin-3-caffeate from Quercus suber.¹³C-NMR spectra of some lupenes.  J Nat Prod. 1988;  51 217-20
• 6 Lee Y J, Wu T D. Total synthesis of kaempferol and methylated kaempferol derivatives.  J Chin Chem Soc. 2001;  48 201-6
• 7 Rancona S, Chabouda A, Darboura N, Comteb G, Barronb D, Raynauda J. et al . A new C-glycosylxanthone isolated from Davallia solida .  Phytochemistry. 1999;  52 1677-9
• 8 Shen C C, Chang Y S, Ho L K. Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids.  Phytochemistry. 1993;  34 843-5
• 9 Zhang Z Z, Sohly H N, Li X C, Khan S I, Broede S E, Raulli R E. et al . Phenolic compounds from Nymphaea odorata .  J Nat Prod. 2003;  66 548-50
• 10 Kazuma K, Noda N, Suzuki M. Malonylated flavonol glycosides from the petals of Clitoria ternatea .  Phytochemistry. 2003;  62 229-37
• 11 Tarpley A R, Goldstein J H. Carbon-13 nuclear magnetic resonance spectra of uracil, thymine, and the 5-halouracils.  J Am Chem Soc. 1971;  93 3573-8
• 12 Sun I C, Wang H K, Kashiwada Y, Shen J K, Cosentino L M, Chen C H. et al . Anti-AIDS agents 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents.  J Med Chem. 1998;  41 4648-57
• 13 Skehan P, Storing R, Scudiero D, Monk A, McMahon J, Visica D. New colorimetric cytotoxity assay for anticancer-drug-screen.  J Natl Cancer Inst. 1990;  82 1107-12
• 14 Rubinstein L V, Shoemaker R H, Paul K D, Tosini S, Skehan P, Scudiero D A. et al . Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines.  J Natl Cancer Inst. 1990;  82 1113-8
• 15 Ma Z Z, Yoshio H, Qiu F, Chen Y J, Taro N. Determination of the absolute stereochemistry of lupane triterpenoids by fucofuranoside method and ORD spectrum.  Tetrahedron Lett. 2004;  45 3261-3
• 16 Huang L, Yu D Q. Application of UV Spectrum in Organic Chemistry. Beijing; Academic Press 2000: p 291