Supplementary Materialsmolecules-22-01690-s001. of displayed cytotoxicity to Vero cells [22], the icetexane derivatives isolated from your chloroform draw out of the same varieties showed cytotoxic activity, with 19-deoxyicetexone [23] becoming the most active compound against the HeLa cervical malignancy cell collection [21]. In turn, 19-deoxyicetexone showed anti-diarrheal activity inside a rodent model [24], the essential oil of the aerial parts of the flower exhibited insecticide activity against Walker (Lepidoptera, Noctuidae) [25], and the chloroform draw out of the aerial parts showed insecticide and insectistatic activities against the same insect [26]. In continuation of our studies on Mexican spp. in search of antiproliferative diterpenoids [11], we analyzed a populace of collected from your municipality of Linares, State of Nuevo Leon (Mexico). Aside from the previously known anastomosine (6) [27], 7,20-dihydroanastomosine (7) [23], icetexone (8) [15], the icetexane diterpenoid 9, isolated from [28], conacytone (10) [15], and 7-acetoxy-19-hydroxyroyleanone (11) [29], we isolated four fresh icetexanes, 1C4, and a new abietane, 5. The structure and absolute construction of the new compounds were established primarily by spectroscopic means and, when possible, by solitary crystal X-ray diffraction analysis and vibrational circular dichroism (VCD). Diterpenoids 3, 4, 6C8 and 10 were tested for antiproliferative activity, in addition to anti-inflammatory and antioxidant activities. While 3, 4, 6C8 showed interesting antiproliferative activity in the sulforhodamine B assay [30], 3 and 10 showed significant reduction of edema in the 12-afforded, after considerable chromatographic purification, eleven diterpenoids: the icetexanes 1C4, 6C9, and the abietanes 5, 10, 11 (Number 1). While icetexanes 1, 2, 7 and 9 are related to anastomosine (6), metabolites 3 and 4 are considered as icetexone (8) derivatives. Diterpenoids 6C11 are known natural products and have been recognized by spectroscopic methods, primarily high field (700 MHz) NMR, and comparisons with the literature; icetexone (8) and conacytone (10) were explained originally as constituents of the aerial parts of [15], as well as of additional spp. [28,33]; anastomosine (6) was from [27]; 7,20-dihydroanastomosine (7) was from [23]; compound 9 was from [28]; and 7-acetoxy-19-hydroxyroyleanone (11) was from [29]. The complete assignments of the NMR data of 6, 7, 9, and 11 are included in this paper, since some discrepancies have been found among the literature assignments. It is noteworthy that although icetexone (8), the 1st 9(1020)-[15] 41 years ago, and have since then been from several spp., they lacked total 1H- and 13C-NMR projects, and complete construction determinations which were recently accomplished by solitary crystal X-ray and VCD determinations [34]. Compounds 1C5 are fresh diterpenoids whose constructions were established based on the following considerations. Open in a separate window Number 1 Chemical constructions of 1C11. Compound 1 was isolated like a yellow oil which showed IR bands due to hydroxyl organizations (3597 and 3412 cm?1), -lactone (1778 cm?1), quinone carbonyl organizations (1654 and 1621 cm?1), and conjugated two times bonds (1583 cm?1). The UV spectrum showed P7C3-A20 price bands at 213, 243, and 332 nm, indicating the presence of an = 7.1 Hz), and H 1.26 P7C3-A20 price (6H, d, = 7.1 Hz). These signals were ascribed to H-15 P7C3-A20 price and the C-16/C-17 methyl organizations, respectively. The presence of an isopropyl group in the C-13 position is definitely a common feature in all diterpenoids isolated RASGRP1 from this populace of = 10.3 and 2.3 Hz), the large value indicated a orientation for H-6. In the COSY spectrum, H-6 correlated to a doublet at H 3.41 (= 10.2) that has been ascribed to H-5, and also with a broad singlet at H 5.53 (H-7) assigned to the geminal hydrogen atom of a hydroxyl group, which must be attached to C-7. The adjacent quinone ring influences the chemical shift of H-7, therefore explaining the lower chemical shift of H-7 in comparison to H-6, which is definitely geminal to.