Six sesquiterpenoids with unprecedented macrocyclic humulene-type structures, namely, dolichocarpols A-E (1− 5) with ether-bridged bicyclic rings between C-10 and C-2, C-10 and C-7, C-10 and C-6 (×2), and C-6 and C-3 and dolichocarpol F (6) cyclized between C-7 and C-2 and with an ether bridge between C-10 and C-3, were isolated from Anaxagorea dolichocarpa roots. The structures of the compounds were elucidated by NMR, MS, and IR data. Absolute configurations of compounds 1−3 and 6 were established on the basis of data from electronic circular dichroism, whereas relative configurations of compounds 4 and 5 were suggested by the NOESY spectrum. In addition, a putative biosynthetic pathway of the compounds is proposed. Furthermore, the cytotoxicity of 3, 4, and 6 against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) was evaluated.
Nordine was reported to be an unusual
humulene-type macrocyclic
sesquiterpenoid that contains an ether-bridged bicyclic ring between
C-10 and C-6 with a hydroxy group at position 2. Here, we report the
structure revision of nordine based on incongruities found for carbon
chemical shifts in the originally proposed structure, in addition
to formation of a diacetylated derivative. As expected, a single-crystal
X-ray diffraction analysis unambiguously confirmed our proposal that
the nordine (1) structure contains an ether-bridged bicyclic
ring between C-10 and C-7 and hydroxy groups at C-2 and C-6. Furthermore,
the absolute configuration was determined by ECD spectroscopic analysis.
Wissadula periplocifolia (L.) C. Presl. is a medicinal plant widely distributed in USA, but it has not yet been investigated extensively. Some pharmacochemical studies were performed at the Federal University of Paraiba, and the components of the crude ethanolic extract were identified; one of them was a tiliroside, which has already been shown to have excellent anti-inflammatory activity that can inhibit the arachidonic acid cascade and can inhibit the release of prostaglandins, prostacyclins, and leukotrienes from leukocytes and neutrophils. This study aimed to verify the possible long-term toxicity of this plant. Chronic toxicity tests were performed, including all recommended parameters; Wistar rats of both sexes were treated with 3 doses of the ethanolic extract of W. periplocifolia (L.) C. Presl leaves, and 2 satellite groups and a control group were set. The platelet and white blood cell counts for all treated males were higher than those in the controls. The anatomopathological tests did not reveal any alterations which were consistent with those obtained from the biochemical tests.
TWO NEW AZAPHENANTHRENE ALKALOIDS FROM Anaxagorea dolichocarpa Sprague & Sandwith. A chemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith, a member of Annonaceae family, was carried out. The ethanolic extract from the roots of this plant led, by chromatography tecniches, to isolation of the new azaphenanthrene alkaloids dolichocarpine (1) and 9-methoxyeupolauramine (2), besides the known alkaloids eupolauramine (3), 3-methoxyeupolauridine (4), eupolauramine (5) and 4-methylsampangine (6). The structures of isolated compounds were established by 1D and 2D NMR, HRESIMS, tandem MS n and IR data. The cytotoxicity of compounds 1-5 was evaluated against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) cell lines.
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