*4.2. Extraction and Isolation of Triterpenoids and Polyprenylated Benzophenones*

Two hundred grams of BRP were extracted with aqueous ethanol 70% (Vetec Química, Rio de Janeiro, Brazil) for three times, 1:10 sample/solvent ratio, and g/mL furnishing 140 g of crude extract. The extract was then mixed with 200 g of microcrystalline cellulose (Sigma Aldrich, St. Louis, MO, USA) and submitted to solid-liquid partition with hexanes (Vetec Química, Rio de Janeiro, Brazil), three times of 500 mL, furnishing 23.8 g of hexane crude fraction. The hexane fraction was then submitted to vacuum liquid chromatography (VLC) by using 150 g of silica gel (Sigma Aldrich, St. Louis, MO, USA), 40–63 μm particle size, as the stationary phase and mixtures of increasing polarity of hexanes:ethyl acetate (100:0→30:70) as the mobile phase. The eluted fractions were monitored by thin layer chromatography (TLC) and pooled by similarity, generating four fractions: F1 (6 g), F2 (9.26 g), F3 (2.27), and F4 (1.1 g). TLC was carried out on precoated glass TLC silica gel 60F254 plates (Merck, Darmstadt, Germany), with detection accomplished by visualization with a UV lamp at 254 and 360 nm, followed by spraying with a 1% solution of 2-aminoethyl diphenylborinate in methanol (w/v). A portion of fraction F2 (500 mg) was submitted to centrifugal thin-layer chromatography on a Chromatotron device (Harrison Research, USA) by using a 1-mm disk of silica gel (10–40 μm particle size) as the stationary phase, and mixtures of increasing polarity of hexanes:ethyl acetate (100:0→30:70) as the mobile phase, affording compounds **8** (70 mg) and **9** (30 mg). A portion of fraction F1 (500 mg) was submitted to flash chromatography on an Isolera One equipment (Biotage, Sweden) by using a 10-g cartridge of silica gel (40 μm particle size) and mixtures of increasing polarity of hexanes:ethyl acetate (100:0→50:50) as the mobile phase, affording compounds **10** (30 mg) and **11** (40 mg). A portion of the *S. globulifera* resin (100 g) was also submitted to the procedures as describe above furnishing the same compounds **8**–**11**.

One-dimensional and 2-D NMR spectra of compounds **8**–**11** were acquired in a Brucker DRX500 NMR spectrometer (Brucker, Santa Barbara, CA, USA) operating at a frequency of 500 MHz for 1H and 125 MHz for 13C by using CDCl3 and CD3OD + 0.1% TFA as deuterated solvents (Sigma Aldrich, St. Louis, MO, USA). High-resolution mass spectrometry data of compounds **8** and **9** were obtained by direct infusion in negative ionization mode on an orbitrap mass spectrometer (Thermo Scientific, San Jose, CA, USA).

*Guttiferone E* (**8**): yellow amorphous powder; UV (HPLC-online) λ*max*: 249.6, 354.4 nm; 1H and 13C NMR data as reported by Gustafson et al., 1992 [10]. HRESIMS negative mode *m*/*z* 601.3546 [M - H]− (calcd. for C38H50O6, 601.3529), 525.3232, 183.0116, 109.0284.

*Oblongifolin B* (**9**): yellow amorphous powder; UV (HPLC-online) λ*max*: 244.9, 350.9 nm; 1H and 13C NMR data as reported by Hamed et al., 2006 [12]. HRESIMS negative mode *m*/*z* 601.3546 [M - H]− (calcd. for C38H50O6, 601.3529), 525.3232, 333.1349, 183.0116, 109.0284.

β*-Amyrin* (**10**): white needles; 1H and 13C NMR data as reported by Lima et al., 2004 [13].
