Abstract
Bioassay-guided fractionation of the crude extract of Elaeocarpus hainanensis (Elaeocarpaceae), using the proliferation of non-small cell lung cancer A549/ATCC and human hepatocellular carcinoma BEL-7402 cells as a monitor, led to the isolation of ten cucurbitane-type triterpenoids, including three new compounds (1 – 3) and seven known compounds (4 – 10). Their structures were determined on the basis of spectroscopic analyses, chemical methods, and comparison with spectroscopic data in literature. The two known compounds, cucurbitacins D (5) and I (10) were found to exhibit the strongest cytotoxicity against A549/ATCC and BEL-7402 cells in vitro with IC50 values of less than 1 μM.
Key words
Elaeocarpus hainanensis
- Elaeocarpaceae - cucurbitane - triterpenoids - cytotoxicity
References
-
1
Newman D J, Cragg G M, Snader K M.
Natural products sources of new drugs over the period 1981 – 2002.
J Nat Prod.
2003;
66
1022-37
-
2 Hong Kong H erbarium, South China Botanical Garden C AS. Check list of Hong Kong plants. Hong Kong; Agriculture, Fisheries and Conservation Department 2001: 75
-
3
Ito A, Chai H B, Lee D, Kardono L BS, Riswan K, Farnsworth N R. et al .
Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii.
Phytochemistry.
2002;
61
171-4
-
4
Fang X D, Phoebe J RCH, Pezzuto J M, Fong H S, Farnsworth N R, Yellin B. et al .
Plant anticancer agents, XXXIV. cucurbitacins from Elaeocarpus dolichostylus.
J Nat Prod.
1984;
47
988-93
-
5
Carroll A R, Arumugan G, Quinn R J, Redburn J, Guymer G, Grimshaw P.
Grandisine A and B, novel indolizidine alkaloids with human δ-opioid receptor binding affinity from the leaves of the Australian rainforest tree Elaeocarpus grandis.
J Org Chem.
2005;
70
1889-92
-
6
Katavic P L, Venables D A, Forster P I, Guymer G, Carroll A R.
Grandisines C – G, indolizidine alkaloids from the Australian rainforest tree Elaeocarpus grandis.
J Nat Prod.
2006;
69
1295-9
-
7
Katavic P L, Venables D A, Rali T, Carroll A R.
Habbemines A and B, pyrrolidine alkaloids with human δ-opioid receptor binding affinity from the leaves of Elaeocarpus habbemensis.
J Nat Prod.
2007;
70
866-8
-
8
Katavic P L, Venables D A, Rali T, Carroll A R.
Indolizidine alkaloids with δ-opioid receptor binding affinity from the leaves of Elaeocarpus fuscoides.
J Nat Prod.
2007;
70
72-5
-
9
Elkhateeb A, Takahashi S K, Matsuura H, Yamasaki M, Yamato O, Maede Y. et al .
Anti-babesial ellagic acid rhamnosides from the bark of Elaeocarpus parvifolius.
Phytochemistry.
2005;
66
2577-80
-
10
Muňoz O, Delporte C, Backhouse N, Erazo S, Negrete R, Maldonado S. et al .
A new cucurbitacin glycosides from Kageneckia oblonga (Rosaceae).
Z Naturforsch.
2000;
55
141-5
-
11
Seger C, Sturm S, Haslinger E, Stuppner H.
NMR signal assignment of 22-deoxocucurbitacin D and cucurbitacin D from Ecballium elaterium L. (Cucurbitaceae).
Monatsheft Chem.
2005;
136
1645-9
-
12
Sarker S D, Whiting P, ik V, Dinan L.
Ecdysteroid antagonists (cucurbitacins) from Physocarpus opulifolius (Rosaceae).
Phytochemistry.
1999;
50
1123-8
-
13
Afifi M S, Ross S A, Elsohly M A, Naeem Z E, Halaweish F T.
Cucurbitacins of Cucumis prophetarum.
J Chem Ecol.
1999;
25
847-60
-
14
Fujita S, Kasai R, Ohtani K, Yamasaki K, Chiu M H, Nie R L. et al .
Dammarane glycosides from aerial parts of Neoalsomitra integrifoliola.
Phytochemistry.
1995;
38
465-72
-
15
Farias M R, Schenkel E P, Mayer R, Rücher G.
Cucurbitacins as constituents of Wilbrandia ebracteata.
Planta Med.
1993;
59
272-5
-
16
Velde V V, Lavie D.
13C-NMR spectroscopy of cucurbitacins.
Tetrahedron.
1983;
39
317-21
-
17
Chen C T, Fang X D, Phoebe J RCH, Kinghorn A D, Farnsworth N R, Yellin B. et al .
High-field 1H-NMR spectral analysis of some cucurbitacins.
J Nat Prod.
1985;
48
429-34
-
18
Schenkel E P, Farias M R, Mayer R, Breitmaier E, Rücher G.
Cucurbitacins from Wilbrandia ebracteata.
Phytochemistry.
1992;
31
1329-33
-
19
Chen J C, Chiu M H, Nie R L, Cordell G A, Qiu S X.
Cucurbitacins and cucurbitane glycosides: structures and biological activities.
Nat Prod Rep.
2005;
22
386-99
-
20
Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D. et al .
Feasibility of a high-flux anticancer drug screen utilizing a diverse panel of human tumor cell lines in culture.
J Natl Cancer Inst.
1991;
83
757-66
Prof. Dr. Weimin Zhao,
Liguang Lou
Shanghai Institute of Materia Medica
Shanghai Institutes for Biological Sciences
Chinese Academy of Sciences
555 Zu Chong Zhi Road
Zhangjiang Hi-Tech Park
Shanghai 201203
People’s Republic of China
Telefon: (WZ): +86/21/5080/6052
Telefon: (LL): +86/21/5080/6056
eMail: wmzhao@mail.shcnc.ac.cn
eMail: lglou@mail.shcnc.ac.cn