Triterpenoids from Tillandsia fasciculata Zulema Cantillo-Ciau, † Wendy Brito-Loeza, † and Leovigildo Quijano* ,‡ Departamento de Quı ´mica Orga ´ nica, Facultad de Quı ´mica, Universidad Auto ´ noma de Yucata ´ n, Calle 41 No. 421, Col. Industrial, C.P. 97150, Me ´ rida, Yucata ´ n, Me ´ xico, and Instituto de Quı ´mica, Universidad Nacional Auto ´ noma de Me ´ xico, Circuito Exterior, Ciudad Universitaria, Me ´ xico, D.F., Me ´ xico Received February 13, 2001 The leaves of Tillandsia fasciculata afforded four tetracyclic triterpenoids of the cycloartane type, two new compounds identified as cyclolaudenyl formate (2) and the (24S)-24-isopropenyl cycloartanone, which we named tillandsinone (1), and the known cyclolaudenone (3) and cyclolaudenol (4). The genus Tillandsia is an interesting group of epiphytic plants with about 500 species, which belong to the subfam- ily Tillandsioideae of the family Bromeliaceae. There are about 175 species recorded in Me ´xico, 20 of which can be found in the state of Yucatan. 1,2 A search of the literature showed very few Tillandsia species chemically studied. Tillandsia usneoides, commonly known as “Spanish moss”, is the most extensively studied, followed by Tillandsia recurvata. The studied species contain cycloartane triter- penoids, pentacyclic triterpenes, sterols, 3,4 and flavonoids. 5,6 As part of our search for biologically active compounds of plants from the ecological reserve “El Eden” located in the state of Quintana Roo in Mexico, we have undertaken the phytochemical study of Tillandsia fasciculata Swarts (Bromeliaceae), which is one of the more abundant species in the area. Column chromatography of the hexane and dichloromethane extracts of dried leaves of T. fasciculata afforded four cycloartane triterpenoids (1-4). The 1 H NMR spectra of compounds 1-4 (Table 1) indicated the presence of a cycloartane type skeleton with the typical high-field AB doublets due to the nonequivalent hydrogens (H-19) of the 9,19 cyclopropane ring. 3 Compound 1 gave a molecular ion peak (HRMS) corre- sponding to the molecular formula C 33 H 54 O. Chemical * To whom correspondence should be addressed. Tel: 52(5)6224411. Fax: 52(5)6162217. E-mail: quijano@servidor.unam.mx. † Universidad Auto ´noma de Yucata ´n. ‡ Universidad Nacional Auto ´noma de Me ´xico. Table 1. 1 H NMR (500 MHz) and 13 C NMR (75 MHz) Spectral Data for Tillandsinone (1) and Cyclolaudenyl Formate (2) in CDCl3 1 2 position δH (ppm), J (Hz) δC (ppm) δH (ppm), J (Hz) δC (ppm) 1R 1.85 tdd (13.5, 4.5, 1.0) 33.4 t 1.60 m 31.5 t 1 1.54 m a 1.25 m 2R 2.30 ddd (14, 4.5, 3.0) 37.5 t 1.75 m 26.9 t 2 2.71 td (14.0, 5.0, 7.0) 1.60 m 3 216.6 s 4.57 dd (11.5, 4.5) 80.3 d 4 50.3 s 39.4 s 5 1.71 dd (12.5, 4.5) 48.5 d 1.40 m 47.2 d 6R,6 1.55 m, 0.94 m 21.5 t 1.60 m, 0.80 m 20.9 t 7R,7 1.28 m, 1.90 m 28.1 t 1.27 m, 1.86 m 28.0 t 8 1.58 m 47.9 d 1.50 m 47.8 d 9 21.1 s 20.1 s 10 25.9 s 25.8 s 11R,11 2.03 m, 1.17 m 26.8 t 1.98 m, 1.11 m 26.5 t 12 1.65 m (2H) 32.8 t 1.60 m (2H) 32.8 t 13 48.7 s 48.8 s 14 45.3 s 45.2 s 15 1.28 m (2H) 35.6 t 1.27 m (2H) 35.5 t 16 1.38 m, 1.14 m 25.9 t 1.32 m, 1.12 m 25.8 t 17 1.60 m 52.2 d 1.57 m 52.2 d 18 0.98 s 18.0 q 0.96 s 17.9 q 19R 0.57 d (4.5) 29.6 t 0.35 d (4.4) 29.7 t 19 0.79 d (4.0) 0.59 d (4.4) 20 1.32 m 36.7 d 1.35 m 36.0 d 21 0.88 d (7.0) 18.7 q 0.86 d (6.5) 18.3 q 22 0.80 m, 1.37 m 34.5 t 0.93 m, 1.32 m 33.9 t 23 1.03 m, 1.62 m 26.8 t 1.14 m, 1.45 m 31.6 t 24 1.53 m 55.5 d 2.09 m b 41.6 d 25 147.4 s 150.2 s 26a 4.61 da (2.5) 111.9 t 4.66 m 109.3 t 26b 4.75 dq (2.5, 1.5) 4.67 m 27 1.58 s (br) 19.0 q 1.69 s (br) 18.6 q 28 1.05 s 22.2 q 0.89 s 25.3 q 29 1.10 s 20.8 q 0.91 s 15.1 q 30 0.90 s 19.3q 0.89 s 19.3 q 31 1.52 30.3 d 1.00 d (6.9) 20.1 q 32 0.92 d (6.0) 20.8 q 33 0.81 d (6.0) 21.5 q H-COO- 8.12 s 161.1 d a Assignments and chemical shifts of overlapped 1 H multiplets are based on COSY, NOESY, and HMQC experiments; 13 C assignments confirmed by DEPT, HMQC, and HMBC experi- ments. b Pseudo-sextet (J ≈ 7.0 Hz). 953 J. Nat. Prod. 2001, 64, 953-955 10.1021/np0100744 CCC: $20.00 © 2001 American Chemical Society and American Society of Pharmacognosy Published on Web 06/08/2001