Comparative X‐Ray and Conformational Analysis of a New Crystal of 13α,21-Dihydroeurycomanone with Eurycomanone from Eurycoma longifolia and Their Anti-Estrogenic Activity Using the Uterotrophic Assay

Abstract

13α,21-Dihydroeurycomanone (1), a known quassinoid of Eurycoma longifolia Jack was recrystallized from chloroform into a novel crystal structure in space group P2₁. Its X‐ray data were compared with those of eurycomanone (2). Following intraperioneal injections at similar doses of 2.44 µmol/kg/day for 3 consecutive days, 2 displayed comparable potency with tamoxifen but was more potent than 1 in the anti-estrogenic effect against 17α-ethynylestradiol (EE)-induced uterotrophy of immature rats.

Key words

Eurycoma longifolia - Simaroubaceae - 13α,21‐dihydroeurycomanone - eurycomanone - X‐ray - conformational analysis - anti‐uterotrophic activity

References

• 1 Chan K L, Choo C Y, Morita H, Itokawa H. High performance liquid chromatography in phytochemical analysis of Eurycoma longifolia.  Planta Med. 1998;  64 741-745
• 2 Teh C-H, Morita H, Shirota O, Chan K L. 2,3-Dehydro-4α-hydroxylongilactone, a novel quassinoid and two known phenyl propanoids from Eurycoma longifolia Jack.  Food Chem. 2010;  120 794-798
• 3 Lin L, Peng C, Wang H, Lee K, Wang P. Reinvestigation of the chemical constituents of Eurycoma longifolia.  Chin Pharm J. 2001;  53 97-106
• 4 Ang H-H, Chan K L, Wah Mak J. In vitro antimalarial activity of quassinoids from Eurycoma longifolia against Malaysian chloroquine-resistant Plasmodium falciparum isolates.  Planta Med. 1995;  61 177-178
• 5 Norhazlina A, Heriza A W N, Norfilza M, Moratv P. 423. Effects of Eurycoma longifolia Jack on spermatogenesis and sperm counts of male rats treated with oestradiol.  Reprod Fertil Dev. 2008;  20 103
• 6 Chan K L, Low B S, Teh C H, Das P K. The effect of Eurycoma longifolia on sperm quality of male rats.  Nat Prod Commun. 2009;  4 1331-1336
• 7 Tee T, Cheah Y, Hawariah L. F16, a fraction from Eurycoma longifolia Jack extract, induces apoptosis via a caspase-9-independent manner in MCF-7 cells.  Anticancer Res. 2007;  27 3425
• 8 Gimlette J D, Thomson H W. A Dictionary of Malayan Medicine. Kuala Lumpur; Oxford University Press 1977: 183
• 9 Ang H, Lee K. Effect of Eurycoma longifolia Jack on orientation activities in middle-aged male rats.  Fundam Clin Pharmacol. 2002;  16 479
• 10 Ang H, Lee K, Kiyoshi M. Eurycoma longifolia Jack enhances sexual motivation in middle-aged male mice.  J Basic Clin Physiol Pharmacol. 2003;  14 301
• 11 Ang H, Ngai T. Aphrodisiac evaluation in non-copulator male rats after chronic administration of Eurycoma longifolia Jack.  Fundam Clin Pharmacol. 2001;  15 265
• 12 Ang H, Sim M. Eurycoma longifolia Jack and orientation activities in sexually experienced male rats.  Biol Pharm Bull. 1998;  21 153-155
• 13 Ang H, Chan K, Gan E, Yuen K. Enhancement of sexual motivation in sexually naive male mice by Eurycoma longifolia.  Pharm Biol. 1997;  35 144-146
• 14 Abdul Rahman A, Ahmad Z, Naing L, Sulaiman S, Hamid A, Daud W, Krian K. The use of herbal medicines during pregnancy and perinatal mortality in Tumpat District, Kelantan, Malaysia.  Southeast Asian J Trop Med Public Health. 2007;  38 1150
• 15 Kuan C, Foo D, Tan R, Kumaresan S, Aziz R. Streamlined life cycle assessment of residue utilization options in Tongkat Ali (Eurycoma longifolia) water extract manufacturing process.  Clean Technol Environ Policy. 2007;  9 225-234
• 16 Teh C H, Teoh S C, Yeap C S, Chan K L, Fun H-K. 4,5,7,8,17-Pentahydroxy-14,18-dimethyl-6-methylene-3,10-dioxapentacyclo[9.8.0.0^1,7.0^4,19.0^13,18]nonadec-14-ene-9,16-dione methanol solvate dihydrate.  Acta Crystallogr E. 2009;  65 o898-o899
• 17 Kang K, Kim H, Ryu D, Che J, Lee Y. Immature uterotrophic assay is more sensitive than ovariectomized uterotrophic assay for the detection of estrogenicity of p-nonylphenol in Sprague–Dawley rats.  Toxicol Lett. 2000;  118 109-115
• 18 Morita H, Kishi E, Takeya K, Itokawa H, Tanaka O. New quassinoids from the roots of Eurycoma longifolia.  Chem Lett. 1990;  19 749-752
• 19 Odum J, Lefevre P, Tittensor S, Paton D, Routledge E, Beresford N, Sumpter J, Ashby J. The rodent uterotrophic assay: critical protocol features, studies with nonyl phenols, and comparison with a yeast estrogenicity assay.  Regul Toxicol Pharmacol. 1997;  25 176-188
• 20 Vieira I J C, Braz-Filho R. Quassinoids: structural diversity, biological activity and synthetic studies.  Stud Nat Prod Chem. 2006;  33 433-492
• 21 Polonsky J. Chemistry and biogenesis of the quassinoids (simaroubolides).  Recent Adv Phytochemistry. 1973;  6 31-64
• 22 Bucourt R. The torsion angle concept in conformational analysis. Eliel EL, Allinger NL Topics in stereochemistry, Vol. 8. New York; Interscience 1974: 159
• 23 Bhatnagar S, Polonsky J, Prange T, Pascard C. New toxic quassinoid glucosides from Simarouba glauca. X-ray analysis.  Tetrahedron Lett. 1984;  25 299-302
• 24 Greico P A, Moher E D, Seya M, Huffman J C, Grieco H J. A quassinoid (peninsularinone) and a steroid from Castela peninsularis.  Phytochemistry. 1994;  37 1451-1454
• 25 Grieco P A, Haddad J, Pineiro-Nunez M M, Huffman J C. Quassinoids from the twigs and thorns of Castela polyandra.  Phytochemistry. 1999;  50 637-645
• 26 Wani M C, Taylor H L, Thompson J B, Wall M E, McPhail A T, Onan K D. Plant antitumour agents-XV: Isolation and x-ray crystal structure of a new antileukaemic quassinoid undulatone from Hannoa undulata.  Tetrahedron. 1979;  35 17-24
• 27 Jacobs H, Lewis D E, Sawyer J F, McLean S. Cedronin and 7-epicedronin: x-ray crystal structure analysis.  J Nat Prod. 1987;  50 700-705
• 28 Bucourt R. The torsion angle concept in conformational analysis. Eliel EL, Allinger NL Topics in stereochemistry. New York; John Wiley & Sons, Inc. 1974 8: 159-224
• 29 Low B S, Ng B H, Choy W P, Yuen K H, Chan K L. Bioavailability and pharmacokinetic studies of eurycomanone from Eurycoma longifolia.  Planta Med. 2005;  71 803-807
• 30 Zhu J X, Wang Y, Kong L D, Yang C, Zhang X. Effects of Biota orientalis extract and its flavonoid constituents, quercetin and rutin on serum uric acid levels in oxonate-induced mice and xanthine dehydrogenase and xanthine oxidase activities in mouse liver.  J Ethnopharmacol. 2004;  93 133-140
• 31 Sekihashi K, Sasaki T, Yamamoto A, Kawamura K, Ikka T, Tsuda S, Sasaki Y F. A comparison of intraperitoneal and oral gavage administration in comet assay in mouse eight organs.  Mutat Res. 2001;  493 39-54
• 32 Clode S A. Assessment of in vivo assays for endocrine disruption.  Best Pract Res Clin Endocrinol Metab. 2006;  20 35-43
• 33 Tee T T, Azimahtol H L. Induction of apoptosis by Eurycoma longifolia Jack extracts.  Anticancer Res. 2005;  25 2205-2213
• 34 Kim H S, Shin J H, Moon H J, Kim T S, Kang I H, Seok J H, Kim I Y, Park K L, Han S Y. Evaluation of the 20-day pubertal female assay in Sprague-Dawley rats treated with DES, tamoxifen, testosterone, and flutamide.  Toxicol Sci. 2002;  67 52-62
• 35 Harper M J, Walpole A L. A new derivative of triphenylethylene: effect on implantation and mode of action in rats.  J Reprod Fertil. 1967;  13 101-119