mollissima215 is the first report of such compounds in which the carboxylic acid group of aristolochic acid forms an ester linkage with a sesqui- or diterpene (Table 6 and Fig. 2). It is interesting to note that eight sesquiterpene esters of aristolochic acids from the roots and stems of A. heterophylla216–217 and a diterpene ester of aristolochic acid from the roots and stems of A. elegans218were discovered by our group. Aristoloterpenates I 235 and III 237 are esters of aristolochic acid I with the sesquiterpenes, madolins M 93 and L 94, respectively, whereas aristoloterpenates II 234 and IV 236 are esters of aristolochic acid II with the same sesquiterpenes, madolins M 93 and L 94, respectively. In these four esters, C-11 of the aristolochic acid and C-4’ of the sesquiterpene were involved in the ester linkage.217The C-4’ stereochemistry of aristoloterpenates I–IV 234–237 was determined as R by circular dichroism studies.
Aristoloterpenates I–IV 234–237 showed cytotoxicity against hepatoma G2. 2. 2. 15 cell line.217 Aristophyllides A 239 and B 241 are aristolochic acid I esters of the rearranged ent-elemane type sesquiterpenes, aristophyllene and its stereoisomer, respectively.216 Aristophyllides C 238 and D 240 are aris-tolochic acid II esters of aristophyllene and its stereoisomer, respectively.216In these esters aristolochic acid and sesquiterpene were bound by an ester linkage between C-11 and C-12’. The absolute configurations of C-5’ and C-12’ of these four esters were determined by application of the circular dichroism exciton chirality method.219,220Aristophyllides A 239 and C 238 have R and S configurations at C-5’ and 12’ whereas aristophyllides B 241 and D 240 possessed the opposite stereochemistry S and R at the C-5’ and C-12’ centers. Aristolin 242 is the first example218 of an ester composed of aristolochic acid and a diterpenoid, in which the C-16 hydroxyl group of ent-kaurane-16,17-diol is involved in the ester linkage with the C-11 carboxylic acid group of aristolochic acid. Very recently, Lopes et al. have reported
Fig. 3 Structures of tri- and tetra-terpenoids from Aristolochia species.
the isolation of two more diterpene esters of aristolochic acids, aristoloins I 243 and II 244, together with aristolin from the tubercula of A. pubescens.221 In aristoloins I 243 and II 244, aristolochic acids I and II were bound to a kaurane diterpene, 16␣-hydroxy-ent-17-kaurane by an ester linkage through the C-11 and C-17’ centers. Thus, from these reports it appears that a general theme running through the chemistry of Aristolochia is the ability to form esters of aristolochic acids with a number of different types of secondary metabolites.
3.5 Triterpenoids
The triterpenoids constitute a large diverse group of natural products derived from squalene.222,223 The foliar epicuticular waxes of leaves of A. esperanzae224from Cerrado was analysed by Oliveira et al. and triterpenoids-amyrin 245, lupeol 246, epifriedelinol 247, and ursolic acid 249 were identified as major constituents (Fig. 3).222These triterpenoids clearly predominate over alkanes in the waxes from the Cerrado species. Another triterpenoid friedelin 248 was found in A. indica.225
3.6 Tetraterpenoids
Tetraterpenoids arise by head to head coupling of two geranyl-geranyl pyrophosphate molecules.226 Loliolide 250, an apoc-arotenoid was isolated as the sole tetraterpenoid from Aris-tolochia species, A. gehrtii.227 Apocarotenoids are carotenoids in which the carbon skeleton has been shortened by the formal removal of fragments from one or both ends.
4 References
1 L. Watson and M. J. Dallwitz, The Families of Flowering Plants, CSIRO Publications, Melbourne, 1992.
2 F. Gonzalez, A phylogenetic analysis of the Aristolochioideae (Aris-tolochiaceae), PhD thesis, The City University of New York, 1999.
3 J. Hutchinson, The Families of Flowering Plants, Clarendon Press, Oxford, 1973, 3rdedn., p. 510.
4 D. Hou, Flora of Taiwan, Editorial Committee of the Flora of Taiwan, Taipei, 1996, vol. 2, 2ndedn., p. 637.
5 T. S. Liu and M. J. Lai, Flora of Taiwan, Epoch, Taipei, 1976, vol.
2, p. 572.
6 A. Balbach, Flora Nacional na Medicina Domestica, Edel, Sao Paulo, 1979, 11thedn., pp. 45, 458, 573, 739, 840.
7 Farmacopeia Homeopatica Brasileira, ed. Andrei, Sao Paulo, 1977.
8 C. M. O. Simoes, L. A. Mentz, E. P. Schenkel, B. E. Iragang and J. R. Stehmann, Plantas da Medicina Popular no Rio Grande do Sul, UFRGS, Porto Alegre, 1986, p. 50.
9 M. P. Correa, Dicionario das Plantas Uteis do Brasil e das Exoticas Cultivadas, Imprensa Nacional, Rio de Janeiro, 1978, vols. I–II, pp. 1926–1978.
10 J. A. Duke, CRC Handbook of Medicinal Herbs, CRC Press, Boca Raton, FL, 1985, p. 63.
11 J. A. Duke and E. S. Ayensu, Medicinal Plants of China, Reference Publications Inc., Algonac, MI, 1985, vol. I, p. 131.
12 Jiangsu New Medicine College, Encyclopedia of Chinese Materia Medica, Shanghai Science and Technology Press, Shanghai, 1977, vol. 1, p. 294.
13 Pharmacopeia of China, Peoples Press, Beijing, 1985, vol. 1, pp. 36–
38.
14 S. Z. Li, Ban Tso Gan Mo, 1595, Peoples Health Press, Beijing, 1977.
15 D. Bensky, A. Gamble, T. Kaptchuk and L. L. Bensky, Chinese Herbal Medicine: Materia Medica, revised edn., Eastland Press:, Seattle, 1993, p. 136.
16 W. Tang and G. Eisenbrand, Chinese Drugs of Plant Origin:
Chemistry, Pharmacology and Use in Traditional and Modern Medicine, Springer-Verlag, Berlin, 1992, p. 145.
17 L. M. X. Lopes, I. R. Nascimento and T. Da. Silva, Phytochemistry of the Aristolochiaceae family, in Research Advances in Phytochem-istry, ed. R. M. M. Mohan, Global Research Network, Kerala, 2001, vol. 2, pp. 19–108.
18 J. Metzger and L. M. Perry, Medicinal Plants of East and Southeast Asia, MIT press, Cambridge, p. 1980.
19 R. N. Chopra, S. L. Nayer and I. C. Chopra, Glossary of Indian Medicinal Plants, Council of Scientific and Industrial Research, New Delhi, 1956, p. 24.
20 K. R. Kirtikar and B. D. Basu, Indian Medicinal Plants III, ed.
L. M. Basu, Periodical Experts, Allahabad, 1935, p. 2123.
21 K. P. Biswas and A. Ghosh, Bharatiya Bonousadhi IV, Calcutta University, India, 1973, p. 385.
22 B. Mukerji, The Indian Pharmaceutical Codex Vol. 1–Indigenous Drugs, Council of Scientific and Industrial Research, New Delhi, India, 1953, p. 21.
23 F. R. Irvine, Woody Plants of Ghana with Special Reference to their Uses, Oxford University Press, London, 1961, p. 878.
24 J. M. Daiziel, The Useful Plants of West Tropical Africa, Crown Agents for the Colony, London, 1937, vol. 6, p. 612.
25 J. M. Watt and M. G. Breyer-Brandwijk, Medicinal and Poisonous Plants of Southern and Eastern Africa, E. and S. Livingstone Ltd, Edinburgh, 1962, 2ndedn., p. 118.
26 J. Hieronymus, Plantae diaphoricae florae argentinae, Bolet´ın de la Academia Nacional de Ciencias, C ´ordoba, 1882, vol. 4, pp. 199–
598.
27 J. A. Dominguez, Contribuciones a la Materia Medica Argentina, Peuser, Buenos Aires, 1928.
28 M. Martinez, Las Plantas Medicinales de M´exico, D. F. M´exico, Botas, 1991, 6thedn., p. 270.
29 L. E. Navas, Flora de la Cuenca de Santiago de Chile, Universidad de Chile, Santiago de Chile, vol. 2, 1976.
30 A. Murillo, Memoria sobre plantas medicinales de Chile y el uso que de ellas se hace en el pais, Imprentadel Ferrocarril, Santiago de Chile, 1861.
31 L. Hong, Y. Sakagami, S. Marumo and C. Xinmin, Phytochemistry, 1994, 37, 237.
32 J. Velasco, Historia del Rein de Quito, La Historia Natura, Empresa Editoria EI Comercio: Quito, Ecuador, 1946, vol. 1.
33 L. C. Branch and M. F. Do Silva, Acta Amazonica, 1983, 13, 737.
34 M. Montes and T. Wilkcomirsky, Medicina Traditional Chilena, Editorial de la Universidad de Concepci ´on, Chile, 1985, pp. 15, 23, 52.
35 J. L. Diaz, Usos de las Plantas Medicinales de M´exico, Monografias Cientificas II, Instituto Mexicano para el Estudio de las Plantas Medicinales, D. F. M´exico, M´exico, 1976, p. 11.
36 S. Del Amo, Plantas Medicinales del Estado de Veracruz, Instituto Nacional de Investigationes sobre Recursos Bioticos, Xalapa, M´exico, 1979, p. 15.
37 Jiangsu New Medical College, Encyclopedia of Chinese Materia
Medica, Shanghai Science and Technology Press: Shanghai, 1977, vol. 1, p. 976.
38 J. Parker, Mil plantas medicinales, Bilblioteca Nueva, Buenos Aires, 1949, p. 170.
39 E. L. Ratera and M. O. Ratera, Plantas de la flora argentina empleadas en Medicina Popular, Hemisferio Sur, Buenos Aires, 1980, pp. 57–190.
40 M. Toursarkissian, Plantas medicinales de la Argentina: sus nombres bot´anicos, vulgares, usos y disribucio´an geogr´afica, Hemisferio Sur, Buenos Aires, 1980, pp. 1–178.
41 Q. Boelcke, Plantas vasculares de la Argentina, Fundaci ´on para la educaci ´on, la ciencia y la cultura (FECIC), Buenos Aires, 1981, p. 201.
42 Compilation of Chinese Herb Medicine, Peoples Publishing House, Beijing, 1978, vol. 2, p. 43.
43 The Great Lexicon of Chinese Medicinal Plants, Scientific and Technical Press, Shanghai, 1978, vol. 2, p. 1557.
44 M. E. Vand der Berg, Plantas Medicinais da Amazˆonia. Contribuic˜ao ao Seu Conhecimento Sistem´atico, Pr/MCT/CNPq, Bel´em, 2nd edn., 1993.
45 H. Achenbach and A. Fischer, Planta Med., 1997, 63, 387.
46 H. Achenbach and A. Fischer, Planta Med., 1997, 63, 679.
47 R. Braga, Plantas do Nordeste, Especialmente do Cear´a, Imprensa Oficial, Fortaleza, Cear´a, Brasil, 2ndedn., 1960.
48 L. M. Conserava, M. S. D. Silva and R. B. Filho, Phytochemistry, 1990, 29, 257.
49 H. Achenbach, R. Waibel and M. Zwanzger, J. Nat. Prod., 1992, 55, 918.
50 A. Y. Tsuruta, M. D. Bomm, M. N. Lopes and M. X. Lucia, Ecl´etica Quim., 2002, 27, 103.
51 D. Kostalova, V. Hrochova and N. Pronayova, Chem. Pap., 1991, 45, 713.
52 H. S. Lee and D. S. Han, Saengyak Hakhoechi, 1993, 24, 32.
53 T. S. Wu, Y. L. Leu and Y. Y. Chan, Chem. Pharm. Bull., 1999, 47, 571.
54 R. Martinez-Crovetto, Las Plantas Utilizadas en Medicina Popular en el Noroeste de Corrientes (Republica Argentina), Miscel´anea No.
69, Fundaci ´on Miguel Lillo, Tucum´an, Rep ´ublica Argentina, 1981, pp. 34–40.
55 F. C. Hoehne, Plantas e Subst´ancias Vegetais T´oxicas e Medicinais, Dto. de Botanica de Estado de S´ao Paulo, S´ao Paulo, 1939.
56 L. M. X. Lopes, J. A. Martins and R. M. Piasentin, Ecl´etica Quim., 1991, 16, 63.
57 N. Y. Chiu and K. H. Chang, The illustrated Medicinal Plants of Taiwan, Southern Materials Center, Inc., Taipei, 1987, vol. 1, p. 22.
58 M. Mizuno, M. Oka, M. Iinuma and T. Tanaka, J. Nat. Prod., 1990, 53, 179.
59 J. De, P. Teresa, J. G. Urones and A. Fernandez, Phytochemistry, 1983, 22, 2745.
60 P. F. Quer, Plantas Medicinales, Labor, Barcelona, 1973.
61 T. Nakanishi, K. Iwasak, M. Nasu, I. Miura and K. Yoneda, Phytochemistry, 1982, 21, 1759.
62 S. J. Lee, Korean Folk Medicine, S. 47, Seoul National University, Seoul, 1966.
63 China’s Pharmacopoeia Part one, Traditional Chinese Medicine, Pharmacopoeia Commission, China, 1978, p. 242.
64 I. C. Th. Uphof, Dictionary of economic plants, Verlag J. Gramer, New York and Lehre, 1968, pp. 48–49.
65 A. Kery, A. A. Askari and K. A. Sharefi, Int. J. Crude Drug Res., 1983, 21, 141.
66 J. Bellakhdar, La Pharmacop´ee Marocaine Traditionnelle, Ibis Press, Paris, 1997, p. 764.
67 A. Merzouki, F. Ed-Derfoufi, A. El-Allali and J. Molero-Mesa, Fitoterapia, 1997, 68, 444.
68 C. A. Gadhi, M. Weber, F. Mory, A. Benharref, C. Lion, M. Jana and A. Lozniewski, J. Ethnopharmacol., 1999, 67, 87.
69 L. Pistelli, E. Nieri, A. R. Bilia, A. Marsili and I. Morelli, Int. J. Pharmacogn., 1995, 33, 366.
70 M. P. Corr´ea, Dicion´ario das Plantas ´Uteis do Brasil e das Ex´oticas Cultivadas, Imprensa Nacional, Rio de Janeiro, 1984, vol. IV, pp. 452, 454, 477.
71 Z. Dayuan, W. Baode, H. Baoshan, X. RenSheng, Q. Yunping and C. Xiuzhen, Heterocycles, 1982, 17, 345.
72 D. Bensky, A. Gamble, T. Kaptchuk and L. L. Bensky, Chinese Herbal Medicine: Materia Medica, revised edn., Eastland Press, Washington, 1993, p. 204.
73 C. H. Hong, S. K. Hur, O. J. Oh, S. S. Kim, K. A. Nam and S. K.
Lee, J. Ethnopharmacol., 2002, 83, 153.
74 R. Otero, V. N ´u ˜nez, J. Barona, R. Fonnegra, S. L. Jim´enez, R. G.
Osorio, M. Saldarriaga and A. Diaz, J. Ethnopharmacol., 2000, 73, 233.
75 D. M. Secoy and A. E. Smith, Econ. Bot., 1983, 37, 28.
76 I. M. A. Zarroug, A. D. Nuggud, A. K. Bashir and A. A. Mageed, Int. J. Crude Drug Res., 1988, 26, 77.
77 P. M. Shafi, M. K. Rosamma, J. Kaiser and P. S. Reddy, Fitoterapia, 2002, 73, 439.
78 S. M. Kupchan and R. W. Doskotsch, J. Med. Pharm. Chem., 1962, 45, 657.
79 A. Pakrashi, B. Chakrabarty and A. Dasgupta, Experientia, 1976, 32, 394.
80 A. Pakrashi and B. Chakrabarty, Experientia, 1978, 34, 1377.
81 A. Pakrashi and C. Shaha, Experientia, 1978, 34, 1192.
82 A. Pakrashi and C. Shaha, Experientia, 1977, 33, 1498.
83 A. Pakrashi and P. L. Pakrashi, Indian J. Exp. Biol., 1977, 15, 256.
84 A. Pakrashi and P. L. Pakrashi, Indian J. Exp. Biol., 1977, 15, 428.
85 C. T. Che, M. S. Ahmed, S. S. Kang, D. P. Waller, A. S. Bingel, A. Martin, P. Rajamahendran, N. Bunyapraphatsara, D.C. Lankin, G. A. Cordell, D. D. Soejarto, R. O. B. Wijesekera and H. H. S.
Fong, J. Nat. Prod., 1984, 47, 331.
86 M. J. Ruffa, G. Ferraro, M. L. Wagner, M. L. Calcagno, R. H.
Campos and L. Cavallaro, J. Ethnopharmacol., 2002, 79, 335.
87 C. A. Gadhi, R. Hatier, F. Mory, L. Marchal, M. Weber, A.
Benharref, M. Jana and A. Lozniewski, J. Ethnopharmacol., 2001, 75, 207.
88 E. Mongelli, S. Pampuro, J. Coussio, H. Salomon and G. Ciccia, J. Ethnopharmacol., 2000, 71, 145.
89 A. Camporese, M. J. Balick, R. Arvigo, R. G. Esposito, N.
Morsellino, F. De Simone and A. Tubaro, J. Ethnopharmacol., 2003, 87, 103.
90 S. Sosa, M. J. Balick, R. Arvigo, R. G. Esposito, C. Pizza, G. Altinier and A. Tubaro, J. Ethnopharmacol., 2002, 81, 211.
91 L. Lajide, P. Escoubas and J. Mizutani, J. Agric. Food Chem., 1993, 41, 669.
92 P. Escoubas, L. Lajide and J. Mizutani, ACS Symp. Ser., 1994, 551, 162.
93 A. K. Haruna and M. K. Choudhury, Phytother. Res., 1997, 11, 527.
94 A. M. Broussalis, G. E. Ferraro, V. S. Martino, R. Pinzon, J. D.
Coussio and J. C. Alvarez, J. Ethnopharmacol., 1999, 67, 219.
95 G. O. Gutkind, V. Martino, N. Gra ˜na, J. D. Coussio and R. A. de Torres, Fitoterapia, 1981, 52, 213.
96 K. R. Alagawadi, P. M. Ronad, R. D. Hunshal, T. M. Shah and A. K. Ashif, J. Oil Technol. Assoc. India, 2000, 32, 3.
97 N. I. Dirdiri, S. E. Barakat and S. E. Adam, Vet. Hum. Toxicol., 1987, 29, 133.
98 A. El-Tahir, G. M. Satti and S. A. Khalid, Phytother. Res., 1999, 13, 474.
99 L. Rastrelli, A. Capasso, C. Pizza and N. D. Tommasi, J. Nat. Prod., 1997, 60, 1065.
100 K. Imamura, T. Okajima, K. Suzuki and F. Urushizaki, Jpn. Kokai Tokyo Koho JP07215887, 1995, p. 4.
101 Y. Seibu, K. Wakamatsu, K. Tanaka and T. Tsuda, Jpn. Kokai Tokyo Koho JP 2002363089, 2002, p. 27.
102 Y. Seibu, K. Wakamatsu, K. Tanaka and T. Tsuda, Jpn. Kokai Tokyo Koho JP 2002363057, 2002, p. 27.
103 C. Barnard, Aust. J. Sci., 1949, 12, 30.
104 D. A. Berghe, M. Ieven, F. Mertens and J. Vlietinck, J. Nat. Prod., 1978, 41, 463.
105 H. J. Lee and J. H. Ryu, Saengyak Hakhoechi, 2000, 31, 273.
106 V. P. Bulgakov, Y. N. Zhuravlev, S. V. Radchenko, S. A. Fedoreyev, V. A. Denisenko, M. Veselova, N. I. Kulesh and E. K. Alshevskaya, Fitoterapia, 1996, 67, 238.
107 X. Zhang, J. Zhang, X. Liu, Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1077339 A, 20 Oct 1993, p. 12.
108 M. Niikawa, A. F. Wu, T. Sato, H. Nagase and H. Kito, Nat. Med., 1995, 49, 329.
109 J. Guo, Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1093913 A, 26 Oct 1994, p. 5.
110 M. Primorac, D. Sekulovic and S. Antonic, Pharmazie, 1985, 40, 585.
111 R. Joseph, G. M. Rosa, A. V. Martha, G. Gilberto, V. Otto and B. J.
Hans, Z. Naturforsch., C: J. Biosci., 2001, 56, 575.
112 V. S. Lemos, Thomas G and J. M. Barbosa Filho, J. Ethnopharma-col., 1993, 40, 141.
113 C. A. Gadhi, A. Benharref, M. Jana and A. Lozniewski, J. Ethnopharmacol., 2001, 75, 203.
114 C. A. Gadhi, A. Benharref, M. Jana, A. M. Basile, N. Contet-Audonneau and F. Fortier, Phytother. Res., 2001, 15, 79.
115 F. Abe, S. Nagauji, T. Yamauchi, H. Okabe, J. Maki, H. Higo, H.
Akahane, A. Aguilar, M. Jimenez-Estrada and R. Reyes-Chilpa, Biol. Pharm. Bull., 2002, 25, 1188.
116 J. B. Schvartzman, D. B. Krimer and R. M. Azorero, Experientia,
1977, 33, 663. A. L. Bandoni, Phytochemistry, 2003, 63, 221.
120 H. A. Priestap, J. D. Bonafede and E. A. Ruveda, Phytochemistry, 1977, 16, 1579.
121 A. L. Waechter, M. E. Ferreira, A. Fournet, A. Rojas de Arias, H.
Nakayama, S. Torres, R. Hocqemiller and A. Cave, Planta Med., 1997, 53, 433.
122 M. Matsuda, Y. Endo, S. Fushiya, T. Endo and S. Nozoe, Heterocycles, 1994, 38, 1229.
123 J. de Pascual Teresa, J. G. Urones and A. Fernandez, Phytochem-istry, 1983, 22, 2753.
124 N. Hayashi, Y. Sugiyama and H. Komae, J. Nat. Prod., 1987, 50, 769.
125 S. F. Palmeira Jr, L. M. Conserva, E. H. de A. Andrade and G. M. S.
P. Guilhon, Flavour Fragrance J., 2001, 16, 85.
126 R. Vila, M. Mundina, L. Muschietti, H. A. Priestap, A. L. Bandoni, T. Adzet and S. Canigueral, Phytochemistry, 1997, 46, 1127.
127 H. A. Priestap, C. M. van Baren, P. D. L. Lira, H. J. Prado, M.
Neugebauer, R. Mayer and A. L. Bandoni, Flavour Fragrance J., 2002, 17, 69.
128 G. G. Leitao, D. Lopes, F. de S. Menezes, M. A. C. Kaplan, A. A.
Craveiro and J. W. Aledcar, J. Essent. Oil Res., 1991, 3, 403.
129 L. Sagrero-Nieves, J. P. Bartley, B. G. Espinosa, X. A. Dominguez and S. J. Verde, Flavour Fragrance J., 1997, 12, 401.
130 S. N. Lorenzo, G. R. Waller and R. P. Sgaramella, Flavour Fragrance J., 1993, 8, 11.
131 M. Mizuno, M. Oka, T. Tanaka, H. Yamamoto, M. Iinuma and H.
Murata, Chem. Pharm. Bull., 1991, 39, 1310.
132 L. Jirovetz, G. Buchbauer, C. Puschmma, W. Fleischhacker, P. M.
Shafi and M. K. Rosamma, Sci. Pharm., 2000, 86, 309.
133 J. E. Larrahondo and C. Acevedo, An. Asoc. Quim. Argent., 1990, 78, 355.
134 G. R. Waller, S. N. Lorenzo and R. P. Sgaramella, Flavour Fragrance J., 1989, 11, 79.
135 J. B. Stenlake and W. D. Williams, J. Pharm. Pharmacol., 1954, 6, 1005.
136 P. J. Dumont, Pharm. Belg., 1957, 12, 475.
137 T. S. Wu, Y. Y. Chan and Y. L. Leu, Chem. Pharm. Bull., 2000, 48, 357.
138 T. S. Wu, Y. Y. Chan and Y. L. Leu, J. Chin. Chem. Soc., 2000, 47, 957.
139 W. Parker, Quart. Rev. Chem. Soc., 1967, 21, 331.
140 G. A. Cordell, Chem. Rev., 1976, 76, 425.
141 D. E. Cane, Biosynthesis of Isoprenoid Compounds, ed. J. W. Porter et al., Wiley, New York, 1981, vol. 1, p. 283.
142 M. A. Urzua and A. R. Rodriguez, Bol. Soc. Chil. Quim., 1992, 37, 183.
143 Y. L. Leu, Studies on the Constituents of Formosan Arsitolochia Plants and Pachliopta aristolochiae interpositus, PhD Thesis, Na-tional Cheng Kung University, Tainan, Taiwan, 1999.
144 Y. Y. Chan, Studies on the Constituents and Biological Activity of Aristolochia Plants and the Synthesis of Protosappanin A, PhD Thesis, National Cheng Kung University, Tainan, Taiwan, 1999.
145 T. S. Wu, Y. Y. Chan and Y. L. Leu, J. Nat. Prod., 1998, 61, 511.
152 J. B. Stenlake and W. D. Williams, J. Pharm. Pharmacol., 1954, 6, 1005.
153 J. W. Steele, J. B. Stenlake and W. D. Williams, J. Chem. Soc., 1959, 3289.
154 M. Martin-Smith, P. de Nayo, S. J. Smith, J. B. Stenlake and W. D.
Williams, Tetrahedron Lett., 1964, 5, 2391.
155 L. X. He, J. Zhang and H. Z. Xue, Acta Bot. Sin., 1987, 29, 197.
156 J. Zhang and L. X. He, Chin. Chem. Lett., 1990, 1, 223.
157 J. Zhang, L. X. He, H. Z. Xue, R. Feng and Q. L. Pu, Acta Pharm.
Sin., 1991, 26, 846.
158 J. Zhang and L. X. He, Acta Pharm. Sin., 1986, 21, 273.
159 H. Z. Xue, J. Zhang, L. X. He, C. H. He, Q. T. Zheng and R. Feng, Acta Pharm. Sin., 1989, 24, 917.
160 G. R ¨ucker, R. Mayer, H. Wiedenfeld, B. S. Chung and A. G ¨ullmann, Phytochemistry, 1987, 26, 1529.
161 A. Matsu, H. Nozaki, N. Kubota, S. Uto and M. Nakayama, J. Chem. Soc., Perkin Trans. 1, 1984, 203.
162 G. R ¨ucker, W. M. Chen, R. Mayer, G. Will and A. G ¨ullmann, Phytochemistry, 1990, 29, 983.
163 P. L. Wu, G. C. Su and T. S. Wu, J. Nat. Prod., 2003, 66, 996.
164 O. Kazuhito, J. Zhao, M. Higa and S. Yogi, Bull. Coll. Sci., 1992, 54, 17. Pharm. Sin., 1992, 27, 37.
168 Y. Z. Chen, Q. J. Wu, B. J. Xu, F. C. Lou and L. S. Ding, Youji Huaxue, 1992, 12, 54.
169 X. H. Wang and G. Q. Han, Acta Bot. Yunnanica, 1993, 15, 306.
170 C. W. Ming, R. Mayer, H. Zimermann and G. R ¨ucker, Phytochem-istry, 1989, 28, 3233.
171 T. R. Govindachari, P. A. Mohamed and P. C. Parthasarathy, Tetrahedron, 1969, 26, 615.
172 G. Ourisson, S. Munavalli and C. Ehret, International Tables of Selected Constants, 15, Data Relative to Sesquiterpenoids, Pergamon Press, New York, 1966.
173 T. R. Govindachari, P. C. Parthasarathy, H. K. Desai and P. A.
Mohamed, Indian J. Chem., 1973, 11, 971.
174 J. B. Bream, D. C. Eaton and H. B. Henbest, J. Chem. Soc., 1971, 9, 1310.
175 T. Kariyone and S. Naito, Yakugaku Zasshi, 1955, 75, 1511.
176 S. Furukawa and N. Soma, Yakugaku Zasshi, 1961, 81, 559.
177 S. Furukawa, K. Oyamada and N. Soma, Yakugaku Zasshi, 1961, 81, 565.
178 S. Furukawa, Yakugaku Zasshi, 1961, 81, 570.
179 J. Kˇrepinsky, G. Jommi, Z. Samek and F. Sorm, Collect. Czech.
Chem. Commun., 1970, 35, 745.
180 G. B ¨uchi, F. Greuter and T. Tokoroyama, Tetrahedron Lett., 1962, 3, 827.
181 R. Nishida and Z. Kumazawa, Agric. Biol. Chem., 1973, 37, 341.
182 G. R ¨ucker, R. Mayer, E. Breitmaier, G. Will, A. Kirfel and M. E.
Kordy, Phytochemistry, 1984, 23, 1647.
183 B. Rodriguez, M. C. de la Torre, F. Simoes, O. Batista, J. Nascimento, A. Duarte and R. Mayer, Phytochemistry, 1995, 38, 905.
184 A. K. Ganguly, K. W. Gopinath, T. R. Govindachari, K. Nagarajan, B. R. Pai and P. C. Parthasarathy, Tetrahedron Lett., 1969, 10, 133.
185 T. R. Govindachari, K. Nagarajan and P. C. Parthasarathy, Chem.
Commun., 1969, 823.
186 T. R. Govindachari and P. C. Parthasarathy, Indian J. Chem., 1971, 9, 1310.
187 S. C. Pakrashi, P. P. Ghosh Dastidar, S. Basu and B. Achari, Phytochemistry, 1977, 16, 1103.
188 S. C. Pakrashi, P. P. Ghosh Dastidar, S. Chakrabarty and B. Achari, J. Org. Chem., 1980, 45, 4765.
189 T. S. Wu, Y. L. Leu, Y. L. Tsai, F. W. Lin, Y. Y. Chan and C. Y.
Chiang, J. Chin. Chem. Soc., 2001, 48, 109.
190 A. p. F. da Silva, S. F. P. J ´unior, L. M. Conserva and G. M. S. P.
Guilhon, J. Braz. Chem. Soc., 1999, 10, 122.
191 S. N. Lorenzo, J. Essent. Oil Res., 1996, 8, 573.
192 A. Usubillaga, N. Khouri and L. B. Rojas, J. Essent. Oil Res., 2001, 13, 128.
193 L. Muschietti, H. A. Priestap, A. L. Bandoni, R. Vila, M. Mundina and T. Adzet, J. Essent. Oil Res., 1997, 9, 83.
194 M. D. Bomm, J. Zukerman-Schpector and L. M. X. Lopes, Phytochemistry, 1999, 50, 455.
195 I. R. Nascimento and L. M. X. Lopes, Phytochemistry, 1999, 52, 345.
196 L. Y. Watanabe and L. M. X. Lopes, Phytochemistry, 1995, 40, 991.
197 H. Tan and Y. Liu, Zhongguo Zhongyao Zazhi, 1994, 19, 677.
198 J. R. Hanson, Prog. Chem. Org. Nat. Prod., 1971, 29, 395.
199 J. R. Hanson, Chemistry of Terpenes and Terpenoids, ed. A. A.
Newman, Academic Press, London, 1972, p. 155.
200 C. A. West, Biosynthesis of Isoprenoid Compounds, ed. J. W. Porter et al., Wiley, New York, 1981, vol. 1, p. 375.
201 G. Snatzke, Tetrahedron, 1965, 21, 413.
202 F. Bohlmann, P. Singh, R. K. Singh, K. C. Joshi and J. Jakupovic, Phytochemistry, 1985, 24, 1114.
203 L. M. X. Lopes, V. da S. Bolzani and L. M. V. Trevisan, Phytochemistry, 1987, 26, 2781.
204 P. K. Grant, L. R. Hanton and S. F. Tsai, Aust. J. Chem., 1985, 38, 1461.
205 F. S. El-Feraly and D. A. Benigni, J. Chem. Soc., Perkin Trans. 1, 1983, 355.
206 L. M. X. Lopes and V. da S. Bolzani, Phytochemistry, 1988, 27, 2265.
207 G.G. Leit˜ao, M. A. C. Kaplan and C. Galeffi, Phytochemistry, 1992, 31, 3277.
208 M. K. Choudhury, A. K. Haruna, E. C. Johnson and P. J. Houghton, Indian J. Pharm. Sci., 1997, 59, 34.
209 A. K. Haruna and M. K. Choudhury, Indian J. Pharm. Sci., 1995, 57, 222.
210 G. R ¨ucker, B. Langmann and N. S. de Siqueira, Planta Med., 1981, 41, 143.
211 L. M. X. Lopes, V. da S. Bolzani, L. M. V. Trevisan and T. M.
Grigolli, Phytochemistry, 1990, 29, 660.
212 M. S. Correa, G. M. S. P. Guhhon and L. M. Conserva, Fitoterapia, 1998, 69, 277.
213 Y. L. Tsai, Constituents from the roots and stems of Aristolochia elegans, MSc Thesis, National Cheng Kung University, Tainan, Taiwan, 1994.
214 V. Luiz, V. da S. Bolzani, L. M. V. Trevisan and L. M. X. Lopes, Quim. Nova, 1990, 13, 250.
215 G. P. Peng, F. C. Lou, Y. Wang, S. X. Zhao and D. J. Chen, Acta Pharm. Sin., 1996, 31, 446.
216 T. S. Wu, Y. Y. Chan, Y. L. Leu, P. L. Wu, C. Y. Li and Y. Mori,
219 M. Koreeda, G. Weiss and K. Nakanishi, J. Am. Chem. Soc., 1973, 95, 239.
220 N. Harada and K. Nakanishi, Circular Dichroism Spectroscopy-Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, CA, 1983.
221 I. R. Nascimento and L. M. X. Lopes, Phytochemistry, 2003, 63, 953.
222 J. D. Connolly, Chemistry of Terpenes and Terpenoids, ed. A. A.
Newman, Academic Press, London, 1972, p. 207.
223 T. W. Goodwin, Biosynthesis of Isoprenoid Compounds, ed. J. W.
Porter et al., Wiley, New York, 1981, vol. 1, p. 443.
224 A. F. M. Oliveira and A. Salatino, Z. Naturforsch. C: J. Biosci., 2000, 55, 688.
225 V. K. Mahesh and H. L. Bhaumik, Indian J. Chem., Sect. B, 1987, 26, 86.
226 S. L. Spurgeon, Biosynthesis of Isoprenoid Compounds, ed. J. W.
Porter et al., Wiley, New York, 1981, vol. 2, p. 1.
227 H. M. D. Navickiene and L. M. X. Lopes, J. Braz. Chem. Soc., 2001, 12, 467.