A program for terpenoid skeleton prediction based on botanical information

Biochemical Systematics and Ecology

Volumn 31, Issue 1, 2003, Pages 25-43

  Ferreira, M J P ^a   Alvarenga, S A V ^b   Macari, P A T ^c   Rodrigues, G V ^d   Emerenciano, V P ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^c MACKENZIE PRESBYTERIAN UNIVERSITY   (Brazil)

^d FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Botanical information; Expert system; Natural products; Skeleton prediction; Terpenoids

Indexed keywords

STRUCTURAL ANALYSIS;

EID: 0037235332     PISSN: 03051978     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0305-1978(02)00066-2     Document Type: Article

References (104)

1. Ahmad, V.U., Zahid, M., Ali, M.S., Jassbi, A.R., Abbas, M., Ali, Z., Iqbal, M.Z., 1999. Bucharioside and buchariol from Salvia bucharica. Phytochemistry 52, 1319-1322.
2. Akihisa, T., Kimura, Y., Koike, K., Kokke, W.C.M.C., Ohkawa, T., Nikaido, T., 1999. (24R)- and (24S)-24-hydroxy-24-vinyllathosterols and other sterols from the aerial part of Bryonia dioica. Phytochemistry 52, 1601-1605.
3. Ali, M.S., Saleem, M., Akhtar, F., Jahangir, M., Parvez, M., Ahmad, V.U., 1999a. Three p-cymene derivatives from Zataria multiflora. Phytochemistry 52, 685-688.
4. Ali, M.S., Saleem, M., Ahmad, V.U., 1999b. Zatatriol: a new aromatic constituent from Zataria multiflora. Z. Naturforsch 54b, 807-813.
5. Ali, M.S., Saleem, M., Ali, Z., Ahmad, V.U., 2000. Chemistry of Zataria multiflora (Lamiaceae). Phytochemistry 55, 933-936.
6. Al-Musayeib, N.M., Abbas, F. A., Ahmad, M.S., Mossa, J.S., El-Feraly, F.S., 2000. Labdane diterpenes from Otostegia fruticosa. Phytochemistry 54, 771-775.
7. Alvarenga, S.A.V., Rodrigues, G.V., Gastmans, J.P., Emerenciano, V.P., 1995. Natural product substitution pattern and skeletal recognition method. Nat. Prod. Lett. 7, 133-140.
8. Alvarenga, S.A.V., Gastmans, J.P., Rodrigues, G.V., Emerenciano, V.P., 1997. Ditregra - an auxiliary program for structural determination of diterpens. Spectroscopy 13, 227-249.
9. Alvarenga, S.A.V., Ferreira, M.J.P., Emerenciano, V.P., Cabrol-Bass, D., 2001a. Chemosystematic studies of natural compounds isolated from Asteraceae: characterization of tribes by principal component analysis. Chemom. Intell. Lab. Syst. 56, 27-37.
10. Alvarenga, S.A.V., Gastmans, J.P., Rodrigues, G.V., Moreno, P.R.H., Emerenciano, V.P., 2001b. A computer-assisted approach for chemotaxonomic studies - diterpenes in Lamiaceae. Phytochemistry 56, 583-595.
11. Attias, R., 1983. DARC substructure search system: a new approach to chemical information. J. Chem. Inf. Comp. Sci. 23, 102-108.
12. Atta-ur-Rahman, Shabbir, M., Yousaf, M., Qureshi, S., e-Shahwar, D., Naz, A., Choudhary, M.I., 1999. Three withanolides from Withania coagulans. Phytochemistry 52, 1361-1364.
13. Badertscher, M., Korytko, A., Schulz, K.P., Madison, M., Munk, M.E., Portmann, P., Junghans, M., Fontana, P., Pretsch, E., 2000. Assemble 2.0: a structure generator. Chemometr. Intell. Lab. Syst. 2, 73-79.
14. Bedir, E., Calis, I., Khan, I.A., 2000. Macrophyllosaponin E: a novel compound from the roots of Astragalus oleifolius. Chem. Pharm. Bull. 48, 1081-1083.
15. Ben Jannet, H., Chaari, A., Mighri, Z., Martin, M.T., Loukaci, A., 1999. Neo-clerodane diterpenoids from Ajuga pseudoiva leaves. Phytochemistry 52, 1541-1545.
16. Beutler, J.A., McCall, K.L., Herbert, K., Johnson, T., Shoemaker, R.H., Boyd, M.R., 2000. Cytotoxic clerodane diterpene esters from Laetia corymbosa. Phytochemistry 55, 233-236.
17. Bremser, W., Fachinger, W., 1985. Multidimensional spectroscopy. Magn. Reson. Chem. 23, 1056-1071.
18. Bremser, W., Grzonka, M., 1991. Speclnfo - a multidimensional spectroscopic interpretation system. Mikrochim. Acta 11, 483-491.
19. Chhabra, B.R., Kohli, J.C., Dhillon, R.S., 1999. Three ambrosanolides from Parthenium hysterophorus. Phytochemistry 52, 1331-1334.
20. Connolly, J.D., Hill, R.A., 1991. Dictionary of Terpenoids. , 1a. Chapman and Hall, London.
21. Djerassi, C., Smith, D.H., Crandell, C.W., Gray, N.A.B., Nourse, J.G., Lindley, M.R., 1982. The DENDRAL project: computational aid to natural products structure elucidation. Pure Appl. Chem. 54, 2425-2442.
22. Duan, H., Takaishi, Y., 1999. Sesquiterpene evoninate alkaloids from Tripterygium hypoglaucum. Phytochemistry 52, 1735-1738.
23. 13C NMR spectroscopy of sesquiterpene skeletal types. Spectroscopy 11, 95-115.
24. Emerenciano, V.P., Rodrigues, G.V., Gastmans, J.P., 1993b. Um método de codificação semi-automático assistido por computador para o SISTEMAT. Química Nova 16, 431-434.
25. Emerenciano, V.P., Rodrigues, G.V., Macari, P.A.T., Vestri, S.A., Borges, J.H.G., Gastmans, J.P., Fromanteau, D.L.G., 1994. Applications d'intelligence artificielle dans la chimie organique, XVII. Nouveaux programmes du projet SISTEMAT. Spectroscopy 12, 91-98.
26. Faini, F., Labbé, C., Torres, R., Delle Monache, F., Delle Monache, G., 1999. Diterpenes from Haplopappus chrysanthemifolius. Phytochemistry 52, 1547-1550.
27. Flagg, M.L., Valcic, S., Montenegro, G., Gomez, M., Timmermann, B.N., 1999. Pentacyclic triterpenes from Chuquiraga ulicina. Phytochemistry 52, 1345-1350.
28. 13C NMR spectroscopy of monoterpenoids. Prog. Nucl. Mag. Reson. Spec. 33, 153-206.
29. 13C NMR data disfunctionalization. Anal. Chim. Acta 429, 151-170.
30. Ferreira, M.J.P., Rodrigues, G.V., Brant, A.J.C., Emerenciano, V.P., 2001b. REGRAS: an auxiliary program for pattern recognition and substructure elucidation of monoterpenes. Spectroscopy 15, 65-98.
31. Gao, K., Wang, W., Jia, Z., 1998. Coniferyl and sinapyl alcohol derivatives from Ligularia duciformis. Phytochemistry 47, 269-272.
32. Garg, S.N., Mehta, V.K., 1998. Acyclic monoterpenes from the essential oil of Tagetes minuta flowers. Phytochemistry 48, 395-396.
33. Gastmans, J.P., Furlan, M., Lopes, M.N., Borges, J.H.G., Emerenciano, V.P., 1990. A inteligância artificial aplicada à química de produtos naturais, O programa SISTEMAT. Parte I - Bases teóricas. Química Nova 13, 10-16.
34. González-Romero, M.A., Villaescusa-Castillo, L., Díaz-Lanza, A.M., 2000. Sesquiterpene lactones from Inula montana L. Z. Naturforsch 55c, 697-700.
35. Gottlieb, O.R., 1982. Micromolecular Evolution. An Essay into a Novel Botanical Discipline. Springer, Heidelberg.
36. Helal, A.M., Nakamura, N., El-Askary, H., Hattori, M., 2000. Sesquiterpene lactone glucosides from Sonchus asper. Phytochemistry 53, 473-477.
37. Hoberg, E., Orjala, J., Meier, B., Sticher, O., 1999. Diterpenoids from the fruits of Vitex agnus-castus. Phytochemistry 52, 1555-1558.
38. Hüther, J., Passreiter, C.M., Wray, V., Willuhn, G., 1999. Acylated 2-hydroxythymol 3-O-diglycosides from Melampodium divaricatum. Phytochemistry 51, 979-986.
39. Jaspars, M., 1999. Computer assisted structure elucidation of natural products using two-dimensional NMR spectroscopy. Nat. Prod. Rep. 16, 241-247.
40. Kakuda, R., Imai, M., Yaiota, Y., Machida, K., Kikuchi, M., 2000. Secoiridoid glycosides from the flower buds of Lonicera japonica. Phytochemistry 55, 879-881.
41. Kamel, M.S., Ohtani, K., Hasanain, H.A., Mohamed, M.H., Kasai, R., Yamasaki, K., 2000a. Monoterpene and pregnane glucosides from Solenostemma argel. Phytochemistry 53, 937-940.
42. Kamel, M.S., Mohamed, K.M., Hassanean, H.A., Ohtani, K., Kasai, R., Yamasaki, K., 2000b. Iridoid and megastigmane glycosides from Phlomis aurea. Phytochemistry 55, 353-357.
43. Kisiel, W., Barszcz, B., Szneler, E., 2000. A new lupane-type triterpenoid from Taraxacum officinale. Polish J. Chem. 74, 281-283.
44. Koul, S., Razdan, T.K., Andotra, C.S., Kalla, A.K., Koul, S., Taneja, S.C., Dhar, K.L., 2000. Koelpinin-A, B and C - three triterpenoids from Koelpinia linearis. Phytochemistry 53, 305-309.
45. Krishna, V., Singh, P., 1999. A clerodane derivative from Grangea maderaspatana. Phytochemistry 52, 1341-1343.
46. Kumar, S., Sati, O.P., Semwal, V.D., Nautiyal, M., Sati, S., Takeda, Y., 2000. Iridoid glycosides from Lonicera quinquelocularis. Phytochemistry 53, 499-501.
47. Li, B.L., Chen, S.N., Shi, Z.X., Chen, Y.Z., 2000. ent-Kaurene diterpenoids from Isodon rubescens. Phytochemistry 53, 855-859.
48. Lin, Y., Ou, J., Chrn, C., Kuo, Y., 1998. Eremophilanes from Petasites formosanus Kitamura. Chem. Pharm. Bull. 46, 1807-1809.
49. Lindsay, R.K., Buchanan, B.G., Fergenbaum, E.A., Lederberg, J., 1980. Applications of Artificial Intelligence for Organic Chemistry: The DENDRAL Project. McGraw-Hill, New York.
50. Macari, P.A.T., Gastmans, J.P., Rodrigues, G.V., Emerenciano, V.P., 1994. An expert system for structure elucidation of triterpenes. Spectroscopy 12, 139-166.
51. Macías, F.A., Oliva, R.M., Varela, R.M., Torres, A., Molinillo, J.M.G., 1999. Allelochemicals from sunflower leaves cv. Peredovick. Phytochemistry 52, 613-621.
52. Magiatis, P., Melliou, E., Tsitsa, E., Charvala, C., Mitaku, S., 2000. Two new acylated iridoid glycosides from Verbascum undulatum. Z. Naturforsch 55c, 667-669.
53. Munk, M.E., 1998. Computer-based structure determination: Then and now. J. Chem. Inf. Comp. Sci. 38, 997-1009.
54. Murakami, R., Shi, Q.-W., Oritani, T., 1999. A taxoid from the needles of the Japanese yew, Taxus cuspidata. Phytochemistry 52, 1577-1580.
55. Nawaz, H.R., Malik, A., Khan, P.M., Ahmed, S., 1999. Ajugin E and F: two withanolides from Ajuga parviflora. Phytochemistry 52, 1357-1360.
56. Ngounou, F.N., Atta-ur-Rahman, Choudhary, M.I., Malik, S., Zareen, S., Ali, R., Lontsi, D., Sondengam, B.L., 1999. Two saponins from Pteleopsis hylodendron. Phytochemistry 52, 917-921.
57. Nieto, M., García, E.E., Giordano, O.S., Tonn, C.E., 2000. Icetaxane and abietane diterpenoids from Salvia gilliessi. Phytochemistry 52, 911-915.
58. 13C NMR spectroscopy of eudesmane sesquiterpenes. Prog. Nucl. Magn. Reson. Spec. 35, 1-45.
59. Ono, M., Masuoka, C., Odake, Y., Ito, Y., Nohara, T., 2000. Eudesmane derivatives from Tessaria integrifolia. Phytochemistry 53, 479-484.
60. Osorio, C., Duque, C., Fujimoto, Y., 2000. Oxygenated monoterpenoids from badea (Passiflora quadrangularis) fruit pulp. Phytochemistry 53, 97-101.
61. Passreiter, C.M., Matthiesen, U., Willuhn, G., 1998. 10-Acetoxy-9-Chloro-8,9-dehydrothymol and further thymol derivatives from Arnica sachalinensis. Phytochemistry 49, 777-781.
62. Pauli, G.F., Matthiesen, U., Fronczek, F.R., 1999. Sulfates as novel steroid metabolites in higher plants. Phytochemistry 52, 1075-1084.
63. Riehl, C.A.S., Pinto, A.C., 2000. A cleistanthane diterpene lactone from Vellozia compacta. Phytochemistry 53, 917-919.
64. Riscala, E.C., Turbay, S., Catalán, C.A.N., Hernández, L.R., Joseph-Nathan, P., 2000. A glycosidic eudesmanolide from Hyaloseris salicifolia. Phytochemistry 53, 873-876.
65. Roengsumran, S., Limsuwankesorn, S., Ngamrojnavanich, N., Petsom, A., Chaichantipyuth, C., Ishikawa, T., 2000. Cassane diterpenoid from Caesalpinia major. Phytochemistry 53, 841-844.
66. Rösecke, J., König, W.A., 1999. Steroids from the fungus Fomitopsis pinicola. Phytochemistry 52, 1621-1627.
67. Sánchez-Arreola, E., Cerda-García-Rojas, C.M., Román, L.U., Hernández, J.D., Joseph-Nathan, P., 1999. Longipinene derivatives from Stevia porphyrea. Phytochemistry 52, 473-477.
68. Sánchez-Contreras, S., Díaz-Lanza, A.M., Bartolomé, C., Bernabé, M., 2000. Minor sulfated saikosaponins from the aerial parts of Bupleurum rigidum L. Phytochemistry 54, 783-789.
69. Sánchez-Martínez, R., Villaescusa-Castillo, L., Bernabé, M., Díaz-Lanza, A.M., 2000. Two new eudesmane alcohols from Jasonia glutinosa. Z Naturforsch 55c, 693-696.
70. Sang, S., Lao, A., Wang, H., Chen, Z., 1999. Furostanol saponins from Allium tuberosum. Phytochemistry 52, 1611-1615.
71. Shen, Y.-C., Chen, Y.-J., Chen, C.-Y., 1999. Taxane diterpenoids from the seeds of Chinese yew Taxus chinensis. Phytochemistry 52, 1565-1569.
72. Shi, Q.-W., Oritani, T., Sugiyawa, T., 1999a. Three rearranged, 2(3→20) abeotaxanes from the bark of Taxus mairei, Phytochemistry 2 (3), 1559-1563.
73. Shi, Q.-W., Oritani, T., Sugiyawa, T., Yamada, T., 1999b. Two novel pseudoalkaloid taxanes from the Chinese yew, Taxus chinesis var. mairei. Phytochemistry 52, 1571-1575.
74. Shi, Q.-W., Oritani, T., Kiyota, H., Zhao, D., 2000. Taxane diterpenoids from Taxus yunnanensis and Taxus cuspidata. Phytochemistry 54, 829-834.
75. Siddiqui, B.S., Firdous, Begum, S., 1999. Two triterpenoids from the leaves of Plumeria obtusa. Phytochemistry 52, 1111-1115.
76. Siddiqui, B.S., Sultana, I., Begum, S., 2000. Triterpenoidal constituents from Eucalyptus camaldulensis var. obtusa leaves. Phytochemistry 54, 861-865.
77. Sigler, P., Saksena, R., Deepak, D., Khare, A., 2000. C21 steroidal glycosides from Hemidesmus indicus. Phytochemistry 54, 983-987.
78. Spring, O., Zipper, R., Klaiber, I., Reeb, S., Vogler, B., 2000. Sesquiterpene lactones in Viguiera eriophora and Viguiera puruana (Heliantheae; Asteraceae). Phytochemistry 53, 255-261.
79. Sudo, H., Takushi, A., Hirata, E., Ide, T., Otsuka, H., Takeda, Y., 1999. Premnaodorosides D-G: acyclic monoterpenediols iridoid glucoside diesters from leaves of Premna subscandens. Phytochemistry 52, 1495-1499.
80. Suksamram, A., Promrangsan, N., Jintasirikul, A., 2000. Highly oxygenated ecdysteroids from Vitex canescens root bark. Phytochemistry 53, 921-924.
81. Takeda, Y., Matsumura, H., Masuda, T., Honda, G., Otsuka, H., Takaishi, Y., Sezik, E., Yesilada, E., 2000. Phlorigidosides A-C, iridoid glucosides from Phlomis rigida. Phytochemistry 53, 931-935.
82. Takenaka, Y., Tanahashi, T., Shintaku, M., Sakai, T., Nagakura, N., Parida, 2000. Secoiridoid glucosides from Fraxinus americana. Phytochemistry 55, 275-284.
83. Taketa, A.T.C., Schmittmann-Schlager, T., Guillaume, D., Gosmann, G., Schenkel, E.P., 2000. Triterpenoid glycosides and a triterpene from Ilex brevicuspis. Phytochemistry 53, 901-904.
84. Thuy, T.T., Ripperger, H., Porzel, A., Sung, T.V., Adam, G., 1999. Coumarins, limonoids and an alkaloid from Clausena excavata. Phytochemistry 52, 511-516.
85. Todorova, M.N., Tsankova, E.T., 1999. New sesquiterpenoids from Achillea clypeolata. Phytochemistry 52, 1515-1518.
86. Tojo, E., Rial, M.E., Urzua, A., Mendoza, L., 1999. Clerodane diterpenes from Haplopappus deserticola. Phytochemistry 52, 1531-1533.
87. Tori, M., Katto, A., Sono, M., 1999. Nine new clerodane diterpenoids from rhizomes of Solidago altissima. Phytochemistry 52, 487-493.
88. Tori, M., Takeichi, Y., Kuga, H., Nakashima, K., Sono, M., 2000. Two new chlorine-containing germacranolides, eupaglehnins E and F from Eupatorium glehni. Heterocycles 52, 1075-1078.
89. Torres, P., Ayala, J., Grande, C., Anaya, J., Grande, M., 1999. Furanoeremophilane derivatives from Senecio flavus. Phytochemistry 52, 1507-1513.
90. Ulubelen, A., Öksüz, S., Kolak, U., Tan, N., Bozok-Johansson, C., Çelik, C., Kohlbau, H.-J., Voetler, W., 1999. Diterpenoids from the roots of Salvia bracteata. Phytochemistry 52, 1455-1459.
91. Vajs, V., Todorovic, N., Ristic, M., Tesevic, V., Todorovic, B., Janackovic, P., Marin, P., Milosavljevic, S., 1999. Guaianolides from Centaurea nicolai: antifungal activity. Phytochemistry 52, 383-386.
92. Villaescusa-Castillo, L., Díaz-Lanza, A.M., Gasquet, M., Delmas, F., Ollivier, E., Bernabé, M., Faure, R., Elias, R., Balausard, G., 2000. Antiprotozoal activity of sesquiterpenes from Jasonia glutinosa. Pharm. Biol. 38, 176-180.
93. Warashina, T., Noro, T., 2000. Steroidal glycosides from the aerial part of Asclepias incarnata. Phytochemistry 53, 485-498.
94. Waterman, P.G., Gray, A.I., 1987. Chemical systematics. Nat. Prod. Rep. 4, 175-203.
95. Waterman, P.G., 1998. Chemosystematics-Current status. Phytochemistry 49, 1175-1178.
96. Wei, X.M., Xhu, Q.X., Chen, J.C., Cheng, D.L., 2000. Two new iridoid glucosides from Clerodendrum serratum. Chin. Chem. Lett. 11, 415-416.
97. Will, M., Fachinger, W., Richert, J.R., 1996. Fully automated structure elucidation-A spectroscopist's dream comes true. J. Chem. Inf. Comp. Sci. 36, 221-227.
98. Wu, T., Kao, M., Wu, P., Lin, F., Shi, L., Liou, M., Li, C., 1999a. The bakkenolides from the root of Petasites formosanus and their cytotoxicity. Chem. Pharm. Bull. 47, 375-382.
99. Wu, T., Kao, M., Wu, P., Lin, F., Shi, L., Teng, C., 1999b. Antiplatelet principles from the root of Petasites formosanus. Phytochemistry 52, 901-905.
100. Xiang, T., Tezuka, Y., Wu, L., Banskota, A.H., Kadota, S., 2000. Saponins from Lonicera bournei. Phytochemistry 54, 795-799.
101. Yang, H., Jiang, B., Na, Z., Guo, Y.P., Sun, H.D., 2000. Two new iridoid glucosides from Clerodendrum serratum. Chin. Chem. Lett. 11, 231-234.
102. Ye, W., Zhang, Q.-W., Liu, X., Che, C.-T., Zhao, S.-X., 2000. Oleanane saponins from Gymnema sylvestre. Phytochemistry 53, 893-899.
103. Zani, C.L., Alves, T.M.A., Queiróz, R., Fontes, E.S., Shin, Y.G., Cordell, G.A., 2000. A cytotoxic diterpene from Alomia myriadenia. Phytochemistry 53, 877-880.
104. Zhang, Z., Koike, K., Jia, Z., Nikaido, T., Guo, D., Zheng, J., 1999. Triterpenoidal saponins from Gleditsia sinensis. Phytochemistry 52, 715-722.