Structural Characterization and Anti-infective Activity of 9,10-Seco-29-norcycloartane Glycosides Isolated from the Flowers of the Peruvian Medicinal Plant Cordia lutea

Abstract

Six new secocycloartane glycosides (1−6) were isolated from the ethanol extract of the flowers of Cordia lutea Lam. on the basis of bioassay-guided fractionation. Their structures were determined by the application of NMR and MS data analyses together with X-ray crystallographic analyses for compounds 1 and 2. Compounds 1−6 represent the first examples of 9,10-seco-29-norcycloartane glycosides. These compounds showed significant in vitro anti-Helicobacter pylori activity, and no activity against either Escherichia coli or Pseudomonas aeruginosa. Significant activity was observed for 5 and 6 against Staphylococcus aureus. All compounds displayed weak cytotoxicity against RAW 264.7 cells. The in vitro antileishmanial and antiplasmodial activities of 1−6 were also evaluated.

Cordiasecosides G-J, 9,10-Seco-29-norcycloartane glycosides isolated from Cordia lutea and their antibacterial activities

“…Nine hundred grams of dry flowers of C. lutea were proceeded as previously described to afford a methanolic extract (6 g) [1]. This extract was processed by successive MPLC on silica gel as described in supplementary material.…”

“…Fraction 5 was pooled with other fractions of similar TLC profiles obtained during the purification of fraction 4. This fraction (528 mg) was submitted to successive MPLC on silica gel to give a mixture (41.8 mg), which was further separated by successive injections of 3 mg on semi-preparative HPLC eluted with H2O-CH3CN at 3 mL/min and the gradient as follows: 0 min 30 H2O/70 CH3OH, 10-15 min 0 H2O/100 CH3OH, 25 min 30 H2O/70 CH3OH to isolate as white, amorphous solids Cordiasecoside I (compound 3, 5.1 mg) whose purity was estimated at 89% on 1 Antibacterial activity and cytotoxicity evaluation on RAW cells 264.7 were assessed as previously described [1]. Briefly, the Helicobacter pylori strain (CIP 103995) was obtained from Pr.…”

“…In the course of our investigation on traditional Peruvian medicine, we have already described Cordiasecosides A-F, six 9,10-Seco-29-norcycloartanes isolated from an ethanolic extract of the dried flowers of Cordia lutea Lam. (Boraginaceae), together with their antibacterial activity [1]. These flowers are sold on traditional medicinal plant markets in Peru and are a highly valued remedy against liver and digestive disfunctions [2].…”

Reproducibility challenges in the search for antibacterial compounds from nature

“…These studies report on plant species, parts, nature of the extract, and bacteria species on which antibacterial activity was observed. In the case of a positive outcome, the follow-up studies typically aim at isolating, characterizing, and even optimizing the active compounds towards a lead compound, which is suitable for pre-clinical studies [6][7][8].…”

Cytotoxic Activities of 9,10-seco-Cycloartane-Type Triterpenoids from the Chinese Liverwort Lepidozia reptans

“…Triterpenes are biosynthesized via the mevalonic acid (MVA) pathway, while their huge structural diversity is attributed to the evolutionary malleability of the biosynthetic pathway composed of diverse enzyme functions. , Cycloartanes, a major constituent of triterpenoids, are widely distributed in the species of Actaea and Cimicifuga (Ranunculaceae) and Astragalus (Leguminosae). − The liverworts, transitional plants of aquatic to terrestrial environments, also produce cycloartanes from various genera, such as Herbertus , Plagiochila , , Mastigophora , and Dendromastigophora . 9,10- seco -Cycloartanes, a small group of cycloartane triterpenoids featuring a seven-membered B ring, comprise about 20 representatives found in plants of the families Buxaceae, Ranunculaceae, Boraginaceae, and Leguminosae. − However, no related compounds have been reported from liverworts so far.…”