Synergistic Combination of NAPROC-13 and NMR 13C DFT Calculations: A Powerful Approach for Revising the Structure of Natural Products.

This article describes the structure revision of nine triterpenoids that have been reported corresponding to the same 13C NMR data set. In addition, 13C NMR calculation shows that some chemical shift assignments must be swapped. Our analysis improves the fit between the experimental and calculated data. Correcting misassigned structures and correctly assigning each signal is essential for elucidating new structurally related compounds. Furthermore, the ambiguity of several compounds, the structure of which differs in the literature and the Sci-Finder database, has been eliminated. Misassigned structures were found by chemical shift searches in NAPROC-13, and the results provide two or more different compounds with the same 13C NMR data. The process to determine the correct, most likely structural proposal in agreement with the experimental 13C NMR data was carried out by DFT calculations.

Computational Structural Revision of Elaeophorbate and Other Triterpenoids with the Help of NAPROC-13. A New Strategy for Structural Revision of Natural Products.

A considerable number of natural products have been published in recent years with misassigned structure, even though they had been correctly elucidated in the past. The availability of databases containing revised structures can prevent the amplification of errors in structural elucidation. NAPROC-13, a dereplication tool based on the 13C chemical shift, has been used to search for substances that, possessing the same chemical shifts, have been described with different structures. The correct structure of these different structural proposals is verified by computational chemistry. This paper reports the structural revision of nine triterpenoids following this methodology.

Antileishmanial Activity and In Silico Molecular Docking Studies of Malachra alceifolia Jacq. Fractions against Leishmania mexicana Amastigotes.

Malachra alceifolia Jacq. (family Malvaceae), known as "malva," is a medicinal plant used as a traditional therapy in many regions of America, Africa and Asia. Traditionally, this plant is used in the form of extracts, powder and paste by populations for treating fever, stomachache, inflammation, and parasites. However, the ethnopharmacological validation of M. alceifolia has been scarcely researched. This study showed that the chloroform fraction (MA-IC) and subfraction (MA-24F) of the leaves of M. alceifolia exhibited a potential antileishmanial activity against axenic amastigotes of Leishmania mexicana pifanoi (MHOM/VE/60/Ltrod) and had high and moderate cytotoxic effects on the viability and morphology of macrophages RAW 264.7. This study reports, for the first time, possible terpenoid metabolites and derivatives present in M. alceifolia with activity against some biosynthetic pathways in L. mexicana amastigotes. The compounds from the subfractions MA-24F were highly active and were analyzed by gas chromatography-mass spectrometry (GC-MS) and by a molecular docking study in L. mexicana target protein. This study demonstrates the potential modes of interaction and the theoretical affinity energy of the metabolites episwertenol, α-amyrin and methyl commate A, which are present in the active fraction MA-24F, at allosteric sites of the pyruvate kinase, glyceraldehyde-3-phosphate dehydrogenase, triose phosphate isomerase, aldolase, phosphoglucose isomerase, transketolase, arginase and cysteine peptidases A, target proteins in some vital biosynthetic pathways were responsible for the survival of L. mexicana. Some phytoconstituents of M. alceifolia can be used for the search for potential new drugs and molecular targets for treating leishmaniases and infectious diseases. Furthermore, contributions to research and the validation and conservation of traditional knowledge of medicinal plants are needed globally.

An Overview of Genus Malachra L.-Ethnobotany, Phytochemistry, and Pharmacological Activity.

The genus Malachra L. belongs to the family Malvaceae. It includes herbs or subshrubs of nine accepted species with approximately thirty synonyms, and it has been widely used in community folk medicine to treat health problems including inflammation, nasal obstruction, leishmaniasis, malaria, childbirth, kidney disorders, fever, respiratory tract diseases, among others. From the genus Malachra L., flavonoids, steroids, triterpenes, anthocyanins, leucoanthocyanins, saponins, carbohydrates, phenols, glycosides, and alkaloids have been isolated and identified. Some pharmacological reports have indicated that the genus has antidiarrheal, antiepileptic, antiulcerogenic, antioxidant, anticonvulsant, antiviral, anticancer, antibacterial, anthelmintic, and hepatoprotective properties. However, there have been limited studies of bioactive molecules with pharmacological and biological activities associated with Malachra alceifolia Jacq., Malachra capitata (L.) L., Malachra fasciata Jacq., Malachra radiata (L.) L., Malachra ruderalis Gürke., Malachra rudis Benth., Malachra helodes Mart., Malachra urens Poit. ex Ledeb. & Alderstam., and Malachra officinalis Klotzsch. In this review, we consider the conservation of these species to save the ancestral knowledge of their traditional use in populations, and their pharmacological potential for future studies in search of alternatives for solutions to diseases in humans and animals and tools for the design and search of potential bioactive compounds against infectious and non-infectious agents.