ABSTRACT
Plant tissue culture has emerged as an important tool to produce bioactive compounds from various plant species, including the sustainable production of limonoids that are receiving considerable attention due to the benefits associated with human health such as anticancer activities. The purpose of the present study was to evaluate the capacity of limonoids aglycone production from callus culture from sweet orange cv. Pera (Citrus sinensis) seeds and identify the compounds produced in this cell line. Callus induction occurred in Murashige and Skoog medium supplemented with 2,4-dichlorophenoxyacetic (2,4-D), malt extract, agar and coconut water. For the analysis and identification of the limonoids, CG-MS-EI ion-positive mode and UPLC-QTOF-ESI were used operating in positive and negative mode. An intense peak corresponding to limonin appeared in the callus extracts at a retention time of 58.1 min. in CG-MS-EI and four major limonoids aglycone by positive ion mode UPLC-QTOF-ESI: limonin, nomilin, deacetylnomilin, and nomilinic acid. The culture medium was efficient at the bioproduction of limonoids aglycone in callus cultures of C. sinensis seeds. Therefore, data obtained from UPLC-QTOF-ESI proved its importance at identifying new compounds that benefit human health, and may assist future work in the identification of known or new limonoids in Citrus species and related genera.
Subject(s)
Biotechnology , Citrus sinensis/chemistry , Phytochemicals , Limonins/classificationABSTRACT
Six new tirucallane protolimonoids, toonapubesins A-F (1-6), one new rearranged tirucallane protolimonoid, toonapubesin G (7), and two new 21,22,23-trinorapotirucallane limonoids, toonapubesic acids A (8) and B (9), possessing an unprecedented carbon skeleton, along with five known tirucallane protolimonoids (10-14) and one known apotirucallane limonoid (15), were isolated from the stem bark of Toona ciliata var. pubescens. Their structures and relative configurations were determined by detailed spectroscopic analysis and by chemical methods. The proposed structures of 8 and 11 were confirmed by X-ray diffraction analysis of their respective derivatives (8a and 11a). The absolute configuration of 8 was determined by a novel solid-state TDDFT ECD approach on its derivative 8a while the absolute configuration of 10 was determined by the modified Mosher's method. In addition, the structures of dyvariabilin H (10c) proposed by Sticher et al. and cneorin-NP(36) (11b) by Mondon et al. were corrected as 10 and 11, respectively. Toonapubesin G (7) showed promising inhibitory activity against CDC25B with an IC(50) value of 2.1 µM, while compound 8a showed significant cell protecting activity against H(2)O(2)-induced SH-SY5Y cell damage with 11.5% increase in cell viability.
Subject(s)
Chemistry, Pharmaceutical/methods , Drugs, Chinese Herbal/chemistry , Limonins/chemistry , Meliaceae/chemistry , cdc25 Phosphatases/antagonists & inhibitors , Cell Line, Tumor , Cell Survival/drug effects , Crystallography, X-Ray , Drugs, Chinese Herbal/pharmacology , Humans , Hydrogen Peroxide/adverse effects , Limonins/classification , Limonins/isolation & purification , Limonins/pharmacology , Molecular Structure , Neuroblastoma/drug therapy , Neuroblastoma/pathology , Nuclear Magnetic Resonance, Biomolecular , Oxidative Stress/drug effects , Plant Bark/chemistry , Plant Stems/chemistry , cdc25 Phosphatases/metabolismSubject(s)
Coumarins/pharmacology , Esters/pharmacology , Limonins/pharmacology , Plants/chemistry , Steroids/pharmacology , Animals , Cell Line, Tumor , Coumarins/chemical synthesis , Coumarins/chemistry , Coumarins/classification , Esters/chemical synthesis , Esters/chemistry , Esters/classification , Humans , Limonins/chemical synthesis , Limonins/classification , Mice , Plants, Medicinal , Steroids/chemical synthesis , Steroids/chemistry , Steroids/classificationABSTRACT
Species of Swietenia elaborate limonoid chemistry along only one route, which leads to the mexicanolide type in most species and the phragmalin type in S. mahogani. A hexane extract from leaves of S. macrophylla afforded six new phragmalins with a 8,9,30-ortho-ester unit, namely, 6-O-acetylswietephragmin E (1), 3beta-O-destigloyl-3beta-O-benzoyl-6-O-acetylswietephragmin E (2), 12alpha-acetoxyswietephragmin C (3), 3beta-O-destigloyl-3beta-O-benzoyl-12alpha-acetoxyswietephragmin C (4), 12alpha-acetoxyswietephragmin D (5), and 3beta-O-destigloyl-3beta-O-benzoyl-12alpha-acetoxyswietephragmin D (6). This appears to be the first record of phragamalins from S. macrophylla, and this study shows the potential of tricyclic [3.3.1(2,10).1(1,4)]-decane limonoids as taxonomically useful chemical markers in the Meliaceae.
Subject(s)
Limonins/chemistry , Limonins/isolation & purification , Meliaceae/chemistry , Brazil , Limonins/classification , Meliaceae/genetics , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistryABSTRACT
Seven phragmalin limonoids of swietephragmins A-G, and two other different types of 2-hydroxy-3-O-tigloylswietenolide and deacetylsecomahoganin, were isolated along with three known limonoids from the leaves of Swietenia mahogani (Meliaceae). Their structures were determined by spectroscopic methods.
