Two new 11α,12α-epoxy-ursan-28,13β-olides and other triterpenes from Cecropia catharinensis

Natural Product Research

Volumn 22, Issue 15, 2008, Pages 1310-1316

  Machado, E C ^a   Yunes, R A ^a   Malheiros, A ^b   Gomez, E C ^c   Delle Monache, F ^d  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^b UNIVERSIDADE DO VALE DO ITAJAÍ   (Brazil)

^c FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^d SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

2 acetoxy 3 ,19 dihydroxy 11 , 12 epoxy ursan 28,13 olide; 2 o acetyl euscaphic acid; 3 acetoxy 2 , 19 dihydroxy 11 ,12 epoxy ursan 28,13 olide; Catharinensis; Cecropia; Cecropiaceae; Triterpenes

Indexed keywords

2 O ACETYL EUSCAPHIC ACID; 2 O ACETYL TORMENTIC ACID; 2ALPHA ACETOXY 3ALPHA,19ALPHA DIHYDROXY 11ALPHA,12ALPHA EPOXYURSAN,28,13BETA OLIDE; 2ALPHA ACETOXY 3BETA,19ALPHA DIHYDROXY 11ALPHA,12ALPHA EPOXYURSAN 28,13BETA OLIDE; 3BETA ACETOXY 2ALPHA,19ALPHA DIHYDROXY 11ALPHA,12ALPHA EPOXYURSAN 28,13BETA OLIDE; 3BETA O(6' O N ACYL BETA DEXTRO GLUCOPYRANOSYL)SITOSTEROL; GLUCOSIDE; ISOORIENTIN; ISOVITEXIN; ORIENTIN; PLANT EXTRACT; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG; VITEXIN; 2 ACETOXY 3BETA,19 DIHYDROXY 11,12 EPOXY URSAN 28,13BETA OLIDE; 2-ACETOXY-3BETA,19-DIHYDROXY-11,12-EPOXY-URSAN-28,13BETA-OLIDE; 2-O-ACETYL-EUSCAPHIC ACID; 3BETA ACETOXY 2,19 DIHYDROXY 11,12 EPOXY URSAN 28,13BETA OLIDE; 3BETA-ACETOXY-2,19-DIHYDROXY-11,12-EPOXY-URSAN-28,13BETA-OLIDE; TRITERPENE;

ARTICLE; CECROPIA; CECROPIA CATHARINENSIS; CONTROLLED STUDY; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PLANT LEAF; PLANT ROOT; PLANT STEM; STRUCTURE ANALYSIS; BRAZIL; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; MEDICINAL PLANT; STEREOISOMERISM;

CECROPIA; URTICACEAE;

BRAZIL; CECROPIA PLANT; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT LEAVES; PLANT ROOTS; PLANTS, MEDICINAL; STEREOISOMERISM; TRITERPENES;

EID: 57049131975     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786410701766406     Document Type: Article

References (23)

1. Begun, S., Adil, Q., Siddiqui, B. and Siddiqui, BS (1993) Triterpenoids from the leaves of Thevethia neriifolia. Journal of Natural Products, 56, pp. 613-617.
2. Brummit, RK (1992) Vascular plant families and Genera, Royal Botanic Gardens, Kew
3. Castellano, E., de Corea, RS, Martinez, E. and Calderon, JS (2002) Oleanane triterpenoids from Cedrela montana (Meliaceae). Zeitschrift Fur Naturforschung C, 57, pp. 575-578.
4. Chanmasathien, W., Li, Y., Satake, M. and Oshima, Y. (2004) Flavonoids C-glycosides from Cecropia adenopus. Nature Medicine (Tokyo, Japan), 58, p. 46.
5. Fang, J-M, Wang, KC and Cheng, Y-S (1991) Steroids and terpenoids from Rosa laevigada. Phytochemistry, 30, pp. 3383-3387.
6. Geng, P-W, Fukuyama, Y., Rei, W., Jinxian, B. and Nakagawa, K. (1988) An acylated sitosterol glucoside from Alisma plantago-aquatica. Phytochemistry, 27, pp. 1895-1896.
7. Hikawczuk, VJ, Saad, JR, Guardia, T., Juarez, AO and Giordano, OS (1998) Anti-inflammatory activity of compounds isolated from Cecropia pachystachia. Anales de la Asociacion Quimica Argentina, 86, pp. 167-170.
8. Ikuta, A., Kamiya, K., Satake, T. and Saiki, Y. (1995) Triterpenoids from the callus tissue cultures of Paeonia species. Phytochemistry, 38, pp. 1203-1207.
9. Ikuta, A. and Morikawa, A. (1992) Triterpenes from Stauntonia hexaphylla. Journal of Natural Products, 55, pp. 1230-1233.
10. Jayasinghe, GL, Wannigama, P. and Macleod, JK (1993) Triterpenoids from Anaminta cocculus. Phytochemistry, 34, pp. 1111-1116.
11. Kakuno, T., Yoshikawa, K. and Arihara, S. (1992) Triterpenes saponins from Ilex. Phytochemistry, 31, pp. 3553-3357.
12. Kojima, K. and Ogura, H. (1986) 2,3-Dihydroxy-ol-12-en-28-oic acid. Phytochemistry, 25, pp. 729-733.
13. Leitao, SG and Delle Monache, F (1998) 2′-O-Cafeoylorientin from Vitex polygama. Phytochemistry, 49, pp. 2167-2169.
14. Lontsi, D., Sondengam, BL, Martin, MT and Bodo, B. (1998) Cecropioic acid, a pentacyclic triterpene from Musanga cecropioides. Phytochemistry, 48, pp. 171-174.
15. Majunder, PL and Chakraborty, M. (1979) Reinvestigation of the action of hydrogen peroxide on ursolic acid acetate. Tetrahedron, 35, pp. 2397-2403.
16. Neidlein, R. and Koch, E. (1980) Isolierung and Struktur der Inhalstoffe von Ceropia adenopus Martius, 1. Mitt. Archiv der Pharmazie, 313, pp. 498-508.
17. Oliveira, RR, Moraes, MCC, Castilho, RO, Valente, AP, Carauta, JR Lopes, D. et al. (2003) High-speed counter-current chromatography as a evaluablr tool to isolate C-glycosylflavones from Cecropia lyratiloba Miguel. Phytochemical Analysis, 14, pp. 96-99.
18. Penso, G. (1980) Inventory of medicinal plants used in the different countries, World Health Organization DPM/80.3, Rome
19. Rizzini, C. (1968) Flora Illustrada Catarinense
20. Seo, S., Tomita, Y. and Tori, K. (1975) Carbon-13 NMR spectra of urs-12-enes and application to structural assignments of components of Isodon japonicas tissue cultures. Tetrahedron Letters, pp. 7-10.
21. Syamasundar, KV, Wannigama, P. and Macleod, JK (1995) Two titerpenoid lactones from the resin of Bursera delpechiana. Phytochemistry, 40, pp. 337-339.
22. Velasquez, J. (1971) Contribucion al conocimiento de las especies del genero Cecropia (Moraceae). "Yagrumos" de Venezuela. Acta Botanica Venezuelica, 6, pp. 25-64.
23. Yang, M-H, Blunden, G., O'Neil, MJ and Lewis, JA (1992) Triterpenes from Myrianthus arboreus. Planta Medica, 58, pp. 227-230.