Isolation of 10-Hydroxycoronaridine from Tabernaemontana penduliflora and its Estrogen-Like Activity

Abstract

The methanol extract of Tabernaemontana penduliflora was found to appreciably inhibit [³ H]-estradiol binding to estrogen receptors. Activity-guided fractionation led to the isolation of two known alkaloids, 10-hydroxycoronaridine (1) and its 10-O-methyl ether, voacangine (2). These alkaloids together with other related alkaloids were tested for their estrogenic activities. Among these molecules, 1 was found to be the most potent estrogen agonist and is distinctly more active than genistein.

References

• 1 Ichikawa  K,, Kitaoka  M,, Taki  M,, Takaishi  S,, Iijima  Y,, Boriboon  M,, Akiyama  T.. .  Planta Med.. 1997;;  63 540-3
• 2 Kitaoka  M,, Kadokawa  H,, Sugano  M,, Ichikawa  K,, Taki  M,, Takaishi  S,, Iijima  Y,, Tsutsumi  S,, Boriboon  M,, Akiyama  T.. .  Planta Med.. 1998;;  64 511-5
• 3 Miyamoto  M,, Matsushita  Y,, Kiyokawa  A,, Fukuda  C,, Iijima  Y,, Sugano  M,, Akiyama  T.. .  Planta Med.. 1998;;  64 516-9
• 4 Minami  E,, Taki  M,, Takaishi  S,, Iijima  Y,, Tsutsumi  S,, Akiyama  T.. .  Chem. Pharm. Bull.. in press; 
• 5 Rizzoli  R,, Bonjour  J-P.. .  Lancet. 1997;;  349 s120-3
• 6 Hutchinson  J,, Dalziel  J M.. Flora of West Tropical Africa,. Vol. 2. Crown Agents, London; 1963
• 7 van Beek  T A,, van Gessel  M AJT.. Alkaloids,. (Pelletier SW, eds.) Vol. 6: 75-226, John Wiley & Sons, New York; 1988
• 8 Gunasekera  S P,, Cordell  G A,, Farnsworth  N R.. .  Phytochemistry. 1980;;  19 1213-8
• 9 Okuyama  E,, Gao  L-H,, Yamazaki  M.. .  Chem. Pharm. Bull.. 1992;;  40 2075-9
• 10 Takayama  H,, Suda  S,, Chen  I,, Kitajima  M,, Aimi  N,, Sakai  S.. .  Chem. Pharm. Bull.. 1994;;  42 280-4
• 11 Keydar  I,, Chen  L,, Karby  S,, Weiss  F R,, Delarea  J,, Radu  M,, Chaitcik  S,, Brenner  H J.. .  Eur. J. Cancer. 1979;;  15 659-70
• 12 Reddel  R R,, Sutherland  R L.. .  Eur. J. Cancer Clin. Oncol.. 1984;;  20 1419-24
• 13 Wakeling  A E,, Bowler  J.. .  J. Steroid Biochem.. 1988;;  31 645-53
• 14 Meyer  W E,, Coppola  J A,, Goldman  L.. .  J. Pharm. Sci.. 1973;;  62 1199-201
• 15 Mehrotra  P K,, Kamboj  V P.. .  Planta Med.. 1978;;  33 345-9
• 16 Nulamba  T,, Delaude  C,, Le Men-Olivier  L,, Levy  J.. .  J. Nat. Prod.. 1981;;  44 184-9
• 17 Kitajima  M,, Sakai  S,, Santiarworn  S,, Liawruangrath  B,, Aimi  N.. .  Natural Medicines. 1998;;  52 289
• 18 Polz  L,, Stöckigt  J,, Takayama  H,, Uchida  N,, Aimi  N,, Sakai  S.. .  Tetrahedron Letters. 1990;;  31 6693-6
• 19 Endress  S,, Suda  S,, Takayama  H,, Kitajima  M,, Aimi  N,, Sakai  S,, Stöckigt  J.. .  Phytochemistry. 1993;;  32 725-30
• 20 Ponglux  D,, Wongseripipatana  S,, Subhadhirasakul  S,, Takayama  H,, Yokota  M,, Ogata  K,, Phisalaphong  C,, Aimi  N,, Sakai  S.. .  Tetrahedron. 1988;;  44 5075-94
• 21 Ponglux  D,, Wongseripipatana  S,, Takayama  H,, Kikuchi  M,, Kurihara  M,, Kitajima  M,, Aimi  N,, Sakai  S.. .  Planta Med.. 1994;;  60 580-1
• 22 Aimi  N,, Sakai  S,, Ban  Y.. The Alkaloids,. (Brossi A, eds.) Vol. 36: 1-68, Academic Press, San Diego; 1989
• 23 Sakai  S,, Aimi  N,, Takahashi  K,, Kitagawa  M,, Yamaguchi  K,, Haginiwa  J.. .  Yakugaku Zasshi. 1974;;  94 1274-80