C19H24O4, monoclinic, P2\ (no. 4), a = 9.231(2) Â, b = 16.318(3) k,c= 11.647(2) λ,β = 91.31(3)°, V = 1753.9 Â, Z = 4, Rgi(F) = 0.045, wR^F) = 0.124, 7=293 K. Source of material The ester 9-frans-p-coumaroyloxy-a-terpineol was isolated from a dichloromethane extract from the aerial parts of Haplopappus taeda Reiche (Asteraceae) [1] collected at the foothills in the Region del Maule (Chile). The compound was isolated and purified by usual chromatographic methods and its molecular structure was established by spectroscopic analysis [2]. Than it was dissolved in hexane at room temperature and colourless prismatic crystals suitable for X-ray diffraction studies grew over a period of one week when the solution was exposed to the air. Experimental details Η atoms attached C7, C8, CT and C8' were located in a difference Fourier map and refined. The rest of the hydrogen atoms were positioned geometrically, with C—Η distances constrained to 0.93 Â (aromatic CH), 0.96 Â (methyl CH3), 0.97 Â (methylene CH2) and 0.98 Â (methine CH) and refined in riding mode with t/iso(H) = xUeq(C), where χ = 1.5 for methyl Η atoms and χ = 1.2 for all other Η atoms. The hydroxyl hydrogen atoms were refined with a distance restraint of 0.82 Â, starting from the difference Fourier map coordinates and with t/iso(H) =1.5 Ueq(O). All problems of the crystal structure refinement of this compound are derived from the small size and bad quality of the crystals. In spite of collecting data of five crystals in four-circle diffractometer, we do not get sufficiently good quality. Nevertheless, we * Correspondence author (e-mail: sdrayosx@usal.es) think that the structural model is good enough from the chemical point of view. Discussion The spectroscopic data of this natural ester were compared with those of other previously isolated derivatives. The stereochemistry of C7'=C8* double bond was assigned by comparision with reported couplings (J = 16.0 Hz) of the olefinic protons in the NMR spectrum of 9-fra/w-cinnamoyloxy-a-terpineol [3,4] isolated from Haplopappus remyanus. The resinous leaves of Asteraceae are used in traditional medicine as digestive, as antiseptic, and also in relief of liver ailments or intestinal and urinary disorders. The scavenging activity [5] of the new ester was measured with DPPH and found to be IC50 75.5 μξ/πύ (quercetin as positive control: IC50 15.3 /<g/ml). The title compound was obtained as two symmetrically independent molecules in the crystal lattice with some difference in bond lengths, angles and torsion angles. For example, the hydroxyl group at atom C3 is coplanar with the benzene ring being the 01-C3-C4-C5 and 01'-C3'-C4'-C5' torsion angles of 179.6(5)° and -178.5(5)°, respectively. In the case of methyl group at C16 is also coplanar with the cyclohexene ring, being the values of the torsion angles C19-C16-C17-C18 and CI 9 ' C16'-C17'-C18' of 178.8(5)° and -177.8(5)°, respectively. The greatest dissimilarity is that C9-03-C10-C11 torsion angle is of 151.5 (5)° while the corresponding C9'-03'-C10'-CI 1' torsion angle is of 121.7(5)° in the other molecule. Due to their structural equivalence the discussion focuses only on the first molecule. All the bond lengths and angles are within the normal ranges. The C16=C17 bond length of 1.319(7) Â correspond to the value for a double bond. The 01—C3 and 04—C11 bond lengths are 1.378(6) Â and 1.461(5) Â, respectively. As ex-

Echinodorus macrophyllus leaf has been used in Brazilian folk medicine to treat inflammatory conditions and kidney dysfunctions. The present study evaluated the effects of leaf ethanolic extract from E. macrophyllus (EEEm) in acute and subchronic models of inflammation. The EEEm was found to cause significant and potent inhibition of carrageenan- and dextran-induced paw edema in rats and marked decreases in the exudate volume and leukocyte migration in rats with carrageenan-induced pleurisy, the vascular permeability increase induced by intraperitoneal acetic acid, and the croton oil-induced topical ear edema in mice. On the other hand, the EEEm was not active in the test model of cotton pellet-induced granuloma in rats. Phytochemical analysis with E. macrophyllus leaves revealed the presence of triterpenoids, steroids, flavones, flavonols, and xanthones. Two flavonoids were isolated from the ethyl acetate fraction and identified as isovitexin and vitexin. Our results support the traditional use of E. macrophyllus leaves in the treatment of acute inflammatory conditions.

C19H24O4, monoclinic, P2(1) (no. 4), a = 9.231(2) angstrom, b = 16.318(3) angstrom, c = 11.647(2) angstrom, beta = 91.31(3)degrees, V = 1753.9 angstrom(3), Z = 4, R-gt(F) = 0.045, wR(ref)(F-2) = 0.124, T = 293 K.

Piper solmsianum C. DC. var. solmsianum (Piperaceae) is a shrub commonly found in areas with wet tropical soils. Other Piper species have been used in folk medicine as antitumoral and antiseptic agents. We studied the crude methanolic extract, some organic fractions and compounds isolated from this plant for possible antimicrobial activity against Grampositive and Gram-negative bacteria. The bioautographic assays disclosed three inhibition zones. The minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) were determined showing excellent activity, particularly against the Gram-positive bacteria (Bacillus cereus, Staphylococcus aureus, Staphylococcus saprophyticus and Streptococcus agalactiae). It appears that the antimicrobial activity of Piper solmsianum is related mainly to the presence of conocarpan and eupomatenoid-5 (neolignans). However another, as yet unidentified, active compound could also be extracted from the plant.

Two new phenolic esters 9-trans-p-coumaroyloxy-alpha-terpineol (1) and 7-trans-p-coumaroyloxy-taedol (2), both endowed with free radical scavenger activity and cleroda-3,13 (E)-dien-15,18-diol (3) for which a cis stereochemistry at the decalin junction was found, were isolated from the resinous exudate from Haplopappus taeda upper parts.

Iridoids are naturally occurring oxygenated monoterpenes with wide range of pharmacological activities. Scrophulariaceae Juss. is a family of flowering plants with 74 genera and 1533 species well known as rich sources of iridoids.The aim of this review is to describe the phytochemistry and structural diversity of iridoids isolated from various genera of the family. Also, their reported activities and pharmacokinetics are highlighted to provide an overall overview of iridoids in Scrophulariaceae as a fundament for further studies on this important class of compounds.A literature survey was performed by searching for relevant information through different scientific databases as SciFinder, ScienceDirect, PubMed, Google Scholar and The World Flora Online.More than 190 scientific works of literature were consulted from 1980 to 2022. Nearly 250 compounds belonging to iridoid glycosides, seco-iridoids glycosides and non-glycosidic iridoids are reported herein from 102 species. They are isolated from polar alcoholic or aqueous alcoholic extracts of the plant. These compounds exhibit anti-inflammatory, antiprotozoal, neuroprotective, cardioprotective, antioxidant and anticancer activities. Pharmacokinetic studies reported differences in their behaviour due to structural variations. However, most of these iridoids showed low oral bioavailability.The collected data indicates that more than 70% of iridoids of the family were isolated and identified from Scrophularia, Verbascum and Buddleja genera. Moreover, glycosides of C9 iridoids are the major class representing more than 80% of the total iridoids and third of the identified compounds show activity against inflammation. Further future investigations are recommended regarding the molecular mechanism of action of iridoids, their structure activity relationship, effective doses, toxicity and clinical effects, in order to promote the use of iridoids from Scrophulariaceae as source of new therapeutic medications.

From the resinous exudate of Heliotropium sinuatum (family Boraginaceae), a new compound: 4-(3',5'-dihydroxynonadecyl)phenol 1, together with eight previously described flavonoids, were isolated and their antioxidant activities were assessed by quenching measurements with ABTS and DPPH cation radicals.

From the resinous exudate of twigs end leaves of Larrea nitida, two lignans nor isoguaiacine 1 and meso-nor-dihydroguaiaretic acid 2 and ferulic acid 3 were isolated. The antioxidant activities of resin and pure compounds were assesed by bleaching of the ABTS derived radical-cation.

From the resinous exudate of leaves of Haplopappus multifolius two new coumarins were isolated and assigned the structures 6-hydroxy-7-(5′-hydroxy-3′,7′-dimethylocta-2′,6′-dien)-oxycoumarin (1) and 6-hydroxy-7-(7′-hydroxy-3′,7′-dimethylocta-2′,5′-dien)-oxy coumarin (2).

A biologically monitored fractionation of the resinous exudate extract of Haplopappus foliosus DC. is reported. Purification of the two active fractions yielded 2-alpha-hydroxy- cis-cleroda-3,13(Z),8(17)-trien-15-oic acid (1) and 2-alpha-acetoxy- cis-cleroda-3,13(Z),8(17)-trien-15-oic acid (2), two new clerodane diterpenes.

Del exudado resinoso de Diplostephium cinereum, se han aislado dos benzodihidrofuranos. Sus estructuras fueron determinadas por espectroscopia de alta resolucion como: 13-(2-metilpropanoiloxi)toxol (2) y 13[(R)-3-hidroxi-3-fenilpropanoiloxi]toxol (3)

Ganoderma P. Karst. (Ganodermatales, Basidiomycetes) is a cosmopolitan genus of wood decaying polypore mushrooms. In the Orient, Ganoderma species are used in folk medicine for treating several diseases, and some strains are commercially cultivated for medicinal use. The pharmacological effects of the Ganoderma species are attributable mainly to polysaccharides and triterpenoids. G. australe is a common species on the Santa Catarina Island (southern Brazil). Literature is scarce on the chemical composition of this species and also on studies relating substances produced by G. australe and their biological activity. A methanol extract from the basidioma of this species was obtained, which was partitioned successively with hexane, chloroform, and ethyl acetate. These extracts were fractionated using silica gel column chromatography. The fractions obtained in each column were grouped by analysis in thin layer chromatography. On the basis of thin-layer chromatography and antibacterial activity assay, some of the fractions were purified. Of these fractions, the following sterols were identified: 5α-ergost-7-en-3β-ol; 5α-ergost-7,22-dien-3β-ol; 5,8-epidioxi-5α,8α-ergost-6,22-dien-3β-ol; and the triterpenes applanoxidic acids A, C, F, and G. A preliminary study on the antibacterial activity of the extracts and chromatographic fractions obtained was carried out by the agar diffusion method. The extracts and some fractions were active mainly against the Gram-positive bacteria Bacillus cereus and Staphylococcus aureus.

A new triterpenoid, (17α, 20R) -dammara-12, 24-dien-3β-ol, was isolated (as the acetate) from the fruits of Clusia guaviarensis and was identified by spectroscopic and chemical methods. This is the first example of a naturally occurring triterpenoid with a (17α, 20R) -dammarane skeleton.

Fruit body of Ganoderma applanatum (Pers.) Pat. FLOR 11.470 was dried, milled, and extracted with methanol. Starting with this extract, successive extractions with hexane, chloroform, and ethyl acetate were performed. From the final extracts different compounds were isolated by column chromatography (silica gel) using the following eluents with increasing polarity: Bz/EtOAc (9/1 to 7/3), CHCl3/MeOH (98/2 to 9/1), CHCl3/MeOH/ H20 (65/28/6.5). Among them, three sterols: 5α-ergost-7en-3β-ol, 5α-ergost-7,22-dien-3β-ol, and 5,8-epidioxy-5α,8α-ergost-6,22-dien-3β-ol, as well as a novel lanostanoid were obtained. The antibacterial activity of these compounds was determined by minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC). The following bacterial species were used to test the antimicrobial activity: Bacillus cereus MIP 96016, Corynebacterium diphtheriae MIP 96048, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus ATCC 25923, Staphylococcus saprophyticus MIP 97018, and Streptococcus pyogenes MIP 83111. Among the seven bacterial species tested, the Gram-positives were more sensitive (MICs of 0.003 to 2.0 mg/ml; MBCs of 0.06 to 4.0 mg/ml) than the Gram-negatives (MICs of 1.0 to 4.0 mg/ml; MBCs of 2.0 to > 4.0 mg/ml). The values obtained for MIC and MBC were close to one another. These results point to broad-spectrum substances with bactericidal effect.

Three new styrenes have been isolated from Dorstenia barnimiana (Moraceae) and were assigned the structures 6-methoxy-5-vinylbenzofuran, 4,6-dimethoxy-5-vinylbenzofuran and 2,4-dimethoxystyrene.