Abstract
The hemolytic activity of the epoxydammarane triterpenoids isolated from the Far-East species of the genus Betula and their semi-synthetic derivatives was investigated. Comparative studies of epoxydammarane triterpenoid activities at pH 5.5 and 5.0 and at 37 and 42 °C showed that 3-oxo, 3,11-dioxo, 3- and 11-acetoxy, as well as 3,11-diacetoxy derivatives had hemolytic potencies lower than the corresponding polyols; triterpenoids with a 3α-OH group were stronger than their analogues with a 3β-OH group; epoxydammaranetriols were somewhat more potent than epoxydammaranediols. Triterpenoids esterified with malonic acid at C-3 possessed the strongest hemolytic activity among the tested compounds.
References
1
Atopkina L N, Malinovskaya G V, Elyakov G B, Uvarova N I, Woerdenbag H J, Koulman A.
et al. Cytotoxicity of natural ginseng glycosides and semisynthetic analogues.
Planta Med.
1999;
65
30-4
2 Lee H Y, Kim S I, Lee S K, Chung H Y, Kim K W. Differentiation mechanism of ginsenosides in cultured murine F9 teratocarcinoma stem cells. Proc. of the 6th Intl. Ginseng Symposium. Korea; 1993: pp 127-31
3
Osaka Y K.
Antitumor protopanaxadiols and protopanaxatriols. 1983, Patent. 58 131 999. Jp. 30.01.82; 06.08.83.
Chem Abstr.
1983;
99
200492t
4
Rickling B, Glombitza K W.
Saponins in the leaves of birch? Hemolytic dammarane triterpenoids esters of Betula pendula
.
Planta Med.
1993;
59
76-9
5
Prokof’eva N G, Likhatskaya G N, Volkova O V, Anisimov M M, Kiseleva M I, Ilyin S G. et al .
Effect of betulafolienetetraol on the erythrocyte and model membranes.
Biol Membranes.
1992;
9
954-60
6
Prokof’eva N G, Anisimov M M, Rebachuk N M, Kiseleva M I, Pokhilo N D.
Cytotoxic effects of the dammarane triterpenes from leaves of the Betula
.
Izv Akad Nauk Ser Biol.
2002;
6
645-9
7
Ma L Y, Xaio P G, Liang F Q, Chi M G, Dong S J.
Effects of saponins of Panax notoginseng on synaptosomal Ca-45 uptake.
Acta Pharmacologica Sinica.
1997;
18
213-5
8
Prokof’eva N G, Shentsova E B, Stekhova S I, Anisimov M M, Pokhilo N D, Uvarova N I.
A comparative study of the hemolytic potency of dammarane-type triterpene polyols.
Izv Akad Nauk Ser Biol.
1999;
3
493-6
9
Pokhilo N D, Malinovskaya G V, Makhankov V V, Anufriev V Ph, Uvarova N I.
Triterpenoids from Betula lanata leaves.
Khim Prir Soedin.
1980;
4
513-8; Chem Abstr 1980; 93 : 200 981
10
Ohmoto T, Nikaido T, Ikuse M.
Constituents of pollen. V. Constituents of Betula platyphylla var. japonica
.
Chem Pharm Bull.
1978;
26
1437-42
11
Pokhilo N D, Denisenko V A, Uvarova N I.
Triterpenoids and flavonoids from the amenta of Betula exilis
.
Khim Prir Soedin.
1985;
1
124-5; Chem Abstr 1985; 102 : 201 173
12
Pokhilo N D, Malinovskaya G V, Makhankov V V, Denisenko V A, Uvarova N I.
Triterpenoids from the leaves of Siberian birch species Betula nana and Betula exilis
.
Khim Prir Soedin.
1985;
3
352-6; Chem Abstr 985; 103 : 102 019
13
Novikov V L, Malinovskaya G V, Pokhilo N D, Uvarova N I.
Refinement of the structure of triterpenes from Betula ermanii leaves.
Khim Prir Soedin.
1980;
1
50-3; Chem Abstr 1980; 93 : 46 878
14
Aminin D L, Agafonova I G, Gnedoi S N, Strigina L I, Anisimov M M.
The effect of pH on biological activity of plant cytotoxin cauloside C.
Comp Biochem Physiol Part A.
1999;
122
45-51
15 Kalinin V I, Anisimov M M, Prokofieva N G, Avilov S A, Afiyatullov S hSh, Stonik V A. Biological activities and biological role of triterpene glycosides from holothuroids (Echinodermata). In: Jangoux MJ, Lawrence M, editors Echinoderm Studies . A. A. Balkema Rotterdam, Brookfield; 1996: pp 139-81
16
Bader G, Plohmann B, Hiller K, Franz G.
Cytotoxicity of triterpenoid saponins. 1. Activities against tumor cells in vitro and hemolytical index.
Pharmazie.
1996;
51
414-7
17
Wachsberger P R, Burd R, Wahl M L, Leeper D B.
Betulinic acid sensitization of low pH adapted human melanoma cells to hyperthermia.
Int J Hyperthermia.
2002;
18
153-64
M. M. Anisimov
Pacific Institute of Bioorganic Chemistry
Far East Branch of the Russian Academy of Sciences
pr. 100 let Vladivostoku, 159
690022 Vladivostok
Russian Federation
Fax: +7-4232-31-40-50
Email: anisimov@piboc.dvo.ru