Lupeol Rodrigo S. Corre ˆa, a,c * Carla P. Coelho, b Marcelo H. dos Santos, b Javier Ellena a and Anto ˆnio C. Doriguetto c a Instituto de Fı ´sica de Sa ˜o Carlos, Universidade de Sa ˜o Paulo, 13560-970, Sa ˜o Carlos, SP, Brazil, b Laborato ´ rio de Fitoquı ´mica e Quı ´mica Medicinal, Departamento de Cie ˆncias Exatas, Universidade Federal de Alfenas, Unifal, MG, Brazil, and c Laborato ´ rio de Cristalografia, Departamento de Cie ˆncias Exatas, Universidade Federal de Alfenas, Unifal, MG, Rua Gabriel Monteiro da Silva, 714, CEP 37130-000, Alfenas, MG, Brazil Correspondence e-mail: rodrigocorrea@ursa.ifsc.usp.br Received 10 October 2008 Accepted 10 February 2009 Online 21 February 2009 The title compound [systematic name: 3-lup-20(29)-en-3-ol], C 30 H 50 O, was isolated from the leaves of Garcinia brasiliensis (common name: bacupari; a member of the Guttiferae family) and has been shown to have many useful medicinal and biological properties. The lupeol molecule consists of four six- membered rings (adopting chair conformations) and one five- membered ring (with an envelope conformation), all fused in trans fashion. Lupeol is isomorphic with the pentacyclic triterpene 3,30-dihydroxylup-20(29)-ene, which differs from lupeol due to the presence of an additional hydroxy group. The crystal packing is stabilized by van der Waals interactions and intermolecular O—HO hydrogen bonds, giving rise to an infinite helical chain along the c axis. Comment As part of our ongoing studies on the chemical constituents of Brazilian medicinal plants (Da Cruz et al., 2008; Derogis et al. , 2008; Martins et al. , 2007; Doriguetto et al. , 2006, 2001; Soares et al., 2006; Lemos et al. , 2006), we have studied lupeol, (I), a natural pentacyclic triterpene isolated from the leaves of Garcinia brasiliensis, known popularly as bacupari (Corre ˆa, 1978). From Garcinia genus (Guttiferae family), biflavonoids, xanthones, proanthocyanins, poliprenilated benzophenones, sesquiterpenes and pentacyclic triterpenes (PCTT) have been isolated (Derogis et al. , 2008; Dos Santos et al. , 2007; Delle Monache et al. , 1983). In particular, (I) has shown many interesting biological properties, such as inhibition of cardio- toxicity induced by cyclosphosphamide (Sudharsan et al., 2006), and hepatoprotective (Sahdeo et al. , 2007), anticancer (Laszczyk et al., 2006) and cytotoxic activities (Gauthier et al., 2006). Previous studies have also shown that (I) is a potential anti-inflammatory agent, preventing the production of some pro-inflammatory mediators (Ferna ´ ndez et al., 2001). Other biological targets of (I) are microorganisms such as bacteria and fungi (Shai et al., 2008). In spite of its biological importance, up until now, (I) has been characterized only by spectroscopic and spectrometric analysis (S ´ liwowski & Kasprzyk, 1974; Shamma et al., 1962). Therefore, in the present paper, we report for the first time the crystal structure of (I) (Fig. 1). The anomalous scattering was not large enough to permit the determination of the enan- tiomer present and therefore distinguish between the enan- tiomorphous space groups P4 1 and P4 3 (Flack, 2003). However, P4 3 was chosen because this space group is consis- tent with the stereochemistry specified by biosynthesis (S ´ liwowski & Kasprzyk, 1974). Thus, the chiral atoms present the following configurations: C3(S), C5(R), C8(R), C9(S), C10(R), C13(R), C14(R), C17(R), C19(R). Interestingly, another PCTT recently determined by us, namely 3,30-di- hydroxylup-20(29)-ene, (II) (Pimenta et al., 2006), which differs chemically from (I) due to the hydroxy group present at C30, was reported in the enantiomorphous P4 1 (or P4 3 ) space group [a = 19.038 (1) A ˚ and c = 7.2290 (4) A ˚ ]. It is also important to mention that space groups P4 3 and P4 1 are rare for organic and organometallic compounds. Currently, in the Cambridge Structural Database (Version 5.29, updated in August 2008; Allen, 2002), there are only 341 and 454 struc- tures deposited with space groups P4 3 and P4 1 , respectively. Indeed, (I) is the first PCTT determined in P4 3 on the basis of X-ray diffraction analysis and biosynthesis arguments (S ´ liwowski & Kasprzyk, 1974). Fig. 1 shows that (I) contains five rings, all trans-fused, where all of the six-membered rings (A, B, C and D) adopt chair conformations, while the five-membered ring (E) adopts an envelope conformation with atom C17 in the flap position. organic compounds Acta Cryst. (2009). C65, o97–o99 doi:10.1107/S0108270109004910 # 2009 International Union of Crystallography o97 Acta Crystallographica Section C Crystal Structure Communications ISSN 0108-2701 Figure 1 The structure of lupeol, showing the atom-numbering scheme. Displace- ment ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.