Complete Assignments of ¹H and 13C-NMR Spectra of the 3,4-seco-Triterpene Canaric Acid isolated from Rudgea jasminoides

Abstract

O ácido canárico 1 foi isolado das folhas de Rudgea jasminoides. A substância isolada é um derivado triterpênico do tipo seco-lupano e teve sua estrutura elucidada com base nos dados espectrais, principalmente em experimentos de RMN a 1D e 2D. O sitosterol, o estigmasterol e os ácidos ursólico e oleanólico também foram isolados. The canaric acid 1 was isolated from the leaves of Rudgea jasminoides. Compound 1 is a seco-lupane derivative and its structure was established on the basis of spectral data, mainly by 1D and 2D NMR experiments. Sitosterol, stigmasterol and ursolic and oleanolic acids were also isolated.

A New 3,4-seco-Lupane Derivative from Lasianthus gardneri

“…From these data compound 1 was characterized as 3,4- seco -lupa-4(23),20(29)-dien-3-ol. Among natural compounds with a seco -lupane structure, canaric acid ( 3 ) shows spectroscopic properties very similar to compound 1 , apart from the presence in 1 of a hydroxymethyl group in position C-3 instead of a carboxylic function. The relative configuration of 1 was assigned on the basis of NOESY data.…”

Complete NMR assignment of 3, 4‐seco‐lup‐20(29)‐en‐3‐oic acid from Decatropis bicolor

“…Finally, at the characteristic chemical shift for an α ‐methylene group joined to a carboxyl group of δ H 2.16 (ddd, J = 2.8, 5.2, 8.8 Hz), resonance signals from two hydrogens were observed ( vide supra ). All spectroscopic characteristics define this natural product as a 3,4‐ seco ‐lupane‐type triterpene that contains a carboxyl group on C‐2 and an isopropyl group on C‐5, establishing the structure as 3,4‐ seco ‐lup‐20(29)‐ en ‐3‐oic acid ( 1 ). Accordingly, 30 signals were observable in 13 C NMR spectrum.…”

Biological Activities of Compounds Isolated from Loxostylis alata (Anacardiaceae) Leaf Extract

“…This confirmed the isolated compound to be a 24-steroid derivative. Comparison of the carbon spectral data for compound 2 with previously compiled data [26][27][28] led to the proposed structure of the compound to be β-sitosterol (Figure 2b). Mass spectroscopy with molecular ion of 414 and prominent peaks at 396 and 105 served to confirmed the compound to be β-sitosterol with a molecular formula C 30 H 50 O [26][27][28].…”