Genus Caesalpinia Research Articles

Structurally diverse diterpenoids from the seeds of Caesalpinia minax Hance and their bioactivities

Eight previously undescribed diterpenoids, caesamins A–H (1–8), were separated and identified from the seeds of Caesalpinia minax Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (1) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl. Caesamin F (6) represents the first example of cleistanthane diterpenoid from the genus Caesalpinia. Caesamins B (2) and F (6) exhibited inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values of 45.67 ± 0.92 and 42.99 ± 0.24 μM, comparable to positive control 43.69 ± 2.62 μM of NG-Monomethyl-L-arginine. Furthermore, the chemotaxonomic significance of the isolates was discussed.

Sexual Dimorphism in Caesalpinia platyloba Watson

Heterostyly and gynodioecism have been found in Caesalpinia platyloba Watson, and this is a new record for section Coulteria of the genus Caesalpinia L. The morphology and fertility of short-and long-style flower types are described and discussed their taxonomic significance.

Two new C-benzylated chalcones and one new mimosin-type homoisoflavonoid from the twigs and leaves of Caesalpinia digyna

Two new C-benzylated chalcones, 2′,4′-dihydroxy-3′-(2-hydroxylbenzyl) chalcone (1) and 2′,4′-dihydroxy-5′-(2-hydroxybenzyl) chalcone (2), one new and one known mimosin-type homoisoflavonoid, mimosol H (7) and mimosol G (8), together with four known chalcones (3‐6) and four known sappanin-type homoisoflavonoids (9–12), were isolated from the twigs and leaves of Caesalpinia digyna. Their structures were characterized by comprehensive spectroscopic analyses (including NMR and HRESIMS). Compounds 1, 2 and 8 exhibited moderate cytotoxicity against SMMC-7721, A-549 and/or MDA-MB-231 cell lines with IC50 values ranging from 11.41 ± 0.88 to 30.01 ± 1.56 μM. Notably, C-benzyl chalcones (1 and 2) were isolated from species of the genus Caesalpinia for the first time. Homoisoflavonoids 7 and 8 are the first examples of mimosin-type homoisoflavonoids reported in Caesalpinia digyna.

Chemical constituents from the leaves of Caesalpinia bonduc (L.) Roxb. and their chemotaxonomic significance

Caesalpinia bonduc (L.) Roxb. is an important herb in Ayurvedic medicines. In this study, five lignans (1–5), two phloroglucinols (6–7), five flavonoids (8–12) and four phenolics (13–16) were identified from the leaves of C. bonduc by comparison with spectroscopic data published in the literature. To the best of our knowledge, all of these identified phytochemicals were reported for the first time in this species. From the present investigation, compounds 1–4, 6–7, 11 and 13–14 were isolated from the genus Caesalpinia for the first time. Additionally, compounds 13 and 14 serve as valuable chemotaxonomic makers for C. bonduc in the Leguminosae family since there are no reports of isolation in Leguminosae.

Isolation and structure elucidation of two new cassane derivatives from the seed kernels of Caesalpinia sinensis

Two new cassane-type derivatives (1–2), together with three known compounds (3–5), were isolated from the seed kernels of Caesalpinia sinensis. Their structures were elucidated on the basis of interpretation of comprehensive spectroscopic data, including HRESIMS and 1D/2D NMR spectroscopy, and the absolute configuration were established by means of ECD calculation. Compound 2, possessing a 16-degradative cassane skeleton, was rarely encountered in cassane diterpenoids isolated from the genus Caesalpinia. All compounds were evaluated for their anti-inflammatory activities against the overproduction of NO in LPS-stimulated RAW 264.7 macrophages, and compounds 1–5 could inhibit production of NO at the concentration of 50 μM.

New cassane- and norcassane-type diterpenoids from the seed kernels of Caesalpinia sinensis and their anti-inflammatory activity in vitro

The first investigation of phytochemistry on the seed kernels of Caesalpinia sinensis led to the isolation and characterization of six new compounds including three tricyclic-type cassane diterpenoids (1‐–3) and three norcassane-type diterpenoids (4–6), together with three know compounds (7–9). Compounds 1–9 represented the first discovery of cassane-type diterpenoids from C. sinensis. Their structures were elucidated by a combination of spectroscopic analysis, single-crystal X-ray diffraction experiment and ECD calculation. The characters for compounds 4 and 5 possessing the 15,16-degradative cassane skeleton were observed, which was extremely rare structural type in the genus Caesalpinia. The anti-inflammatory activities of all isolates were evaluated via examining their inhibitory effects against NO production in LPS-simulated RAW 264.7 cells. The results demonstrated that compound 1 exhibited the most significantly inhibitory efficacy with inhibition rate 67.3% at 10 μM. The iNOS enzyme activity assay further revealed that compound 1 showed potent NO inhibitory effect by reducing the enzymatic activity of iNOS.

A review of the genus Caesalpinia L.: emphasis on the cassane and norcassane compounds and cytotoxicity effects

A review of the genus Caesalpinia L.: emphasis on the cassane and norcassane compounds and cytotoxicity effects

A New Homoisoflavonoid from Caesalpinia bahamensis

Homoisoflavonoids constitute a rare subclass of flavonoids restricted to only some plant species, including members of the genus Caesalpinia. This research focused on homoisoflavonoids from Caesalpinia bahamensis Lam., Fabaceae, a medicinal plant used in Cuban traditional medicine and known as “brasilete.” An hydroalcoholic extract was prepared from the stem, followed by liquid-liquid partition and further chromatographic separations, resulting in the isolation and structure elucidation by nuclear magnetic resonance spectroscopy and mass spectrometry of an undescribed 3-(2-hydroxy-4-methoxybenzyl)chromane-4,7-diol, for which the name metasappanin was proposed.

Phanginin R Induces Cytoprotective Autophagy via JNK/c-Jun Signaling Pathway in Non-Small Cell Lung Cancer A549 Cells.

Cassane-type diterpenoids are widely distributed in the medical plants of genus Caesalpinia. To date, plenty of cassane diterpenoids have been isolated from the genus Caesalpinia, and some of them were documented to exhibit multiple biological activities. However, the effects of these compounds on autophagy have never been reported. To investigate the effects and mechanisms of the cassane diterpenoids including Phanginin R (PR) on autophagy in Non-Small Cell Lung Cancer (NSCLC) A549 cells. Western blot analysis and immunofluorescence assay were performed to investigate the effects of the compounds on autophagic flux in A549 cells. The pathway inhibitor and siRNA interference were used to investigate the mechanism of PR. MTT assay was performed to detect cell viability. PR treatment upregulated the expression of phosphatidylethanolamine-modified microtubule-associated protein Light-Chain 3 (LC3-II) in A549 cells. Immunofluorescence assay showed that PR treatment increased the production of red-fluorescent puncta in mRFP-GFP-LC3 plasmid-transfected cells, indicating PR promoted autophagic flux in A549 cells. PR treatment activated the c-Jun N-terminal Kinase (JNK) signaling pathway while it did not affect the classical Akt/mammalian Target of Rapamycin (mTOR) pathway. Pretreatment with the JNK inhibitor SP600125 or siRNA targeting JNK or c-Jun suppressed PR-induced autophagy. In addition, cotreatment with the autophagy inhibitor Chloroquine (CQ) or inhibition of the JNK/c-Jun signaling pathway increased PR-induced cytotoxicity. PR induced cytoprotective autophagy in NSCLC A549 cells via the JNK/c-Jun signaling pathway, and autophagy inhibition could further improve the anti-cancer potential of PR.

New combinations in Guilandina (Leguminosae: Caesalpinioideae)

SummaryThe Caesalpinia Group (Leguminosae: Caesalpinioideae) and the genus Caesalpinia sensu lato were recently reclassified resulting in a reduction in the number of species in Caesalpinia sensu stricto to nine. Of the genera now accepted as distinct from Caesalpinia, the pantropical genus Guilandina lacks any recent global taxonomic account and estimates of the number of species in the genus range from seven to as many as 20. Seven putative species are currently known only under Caesalpinia binomials and have no published combination in Guilandina. This inconvenience is rectified here. Putting these binomials into the correct genus will ensure that they are not overlooked in any future revision of Guilandina, a genus of taxonomic complexity and including some nomenclatural conundrums.

In Silico Exploration of the Molecular Mechanism of Cassane Diterpenoids on Anti-inflammatory and Immunomodulatory Activity.

Cassane diterpenoids (CAs), recognized as main constituents of many medical plants of the genus Caesalpinia, exhibit diverse bioactivities, including anti-inflammatory and immunomodulatory activity, and also showed a therapeutic effect on rheumatoid arthritis (RA) according to previous work, including ours. In this study, 102 CA compounds were selected to explore the possible molecular mechanism of this class of natural products on anti-inflammatory and immunomodulatory activity using RA as a disease model through a series of in silico methods: chemical-similarity-based target prediction, molecular docking, and molecular dynamics (MD) simulation. As a consequence, four signaling pathways (TCR signaling pathway, TLR signaling pathway, VEGF signaling pathway, and osteoclast differentiation pathway) by which CAs exert their effect on inflammation and immunomodulation were identified. Furthermore, the binding modes of CAs complexing with several crucial targets, which were picked out by credible docking results and took part in these signaling pathways, were explored by MD simulations. This is the first time that the molecular mechanism of the anti-RA activity of natural CAs has been investigated with in silico methods, and these findings might explain the activity of CAs on anti-inflammation and immunomodulation, which could supply a valuable reference for drug design research on CAs.

Genotoxic evaluation of sibipiruna extract (Caesalpinia peltophoroides Benth) in vivo

Caesalpinia peltophoroides Benth, popularly known as sibipiruna or false brazilwood, is an ornamental species with wood potential and with great distribution in Brazil. The genus Caesalpinia has more than five hundred species, most of which have not yet been studied for their pharmacological potential. Several species of the genus are known for their antioxidant and anti-inflammatory activities. The aim of the present study was to evaluate the effect of sibipiruna leaf and flower extract on Cyclophosphamide (CP) induced DNA damage in male Swiss mice using the micronucleus test. The animals (6 animals/group) were treated for 15 consecutive days with ethanolic extract (via gavage) and on day 15 received intraperitoneally NaCl (0.9%) or CP (25 mg/Kg), being sacrificed 24 hours after treatment to evaluate the frequency of micronucleated polychromatic erythrocytes (MNPCEs). The results showed that pretreatment with the ethanolic flower extract and sibipiruna leaf, under the conditions tested, did not reduce the frequency of MNPCEs induced by CP when compared to the positive control group. However, the groups treated only with the ethanolic extract of sibipiruna flowers and leaves significantly increased the frequency of micronuclei in polychromatic erythrocytes of bone marrow when compared to the negative control group, thus demonstrating a possible mutagenic effect. Therefore, it was possible to verify that sibipiruna did not present antimutagenic activity, but a plant with possible mutagenic action in the concentrations used.

Germination capacity and viability of stored pollen in two ornamentals species of the genus Caesalpinia L. (Caesalpini Oideae-Fabaceae) and their maintenance

Germination capacity and viability of stored pollen in two ornamentals species of the genus Caesalpinia L. (Caesalpini Oideae-Fabaceae) and their maintenance

Beneficial effects of Caesalpinia digyna extract against acid aspiration-Induced acute lung injury in mice

Objective: Caesalpinia digyna belongs to the genus Caesalpinia, which is known since ancient times for its medicinal properties. The present work was designed to evaluate the beneficial potential of hydroalcoholic extract of the roots of C. dignea against hydrochloric acid (HCl)-induced acute lung injury in mice. Materials and Methods: Ethanolic extract of C. dignea roots at a dose of 50, 100, or 200 mg/kg boy weight was given once orally 90 min before HCl administration. Mice were then analyzed for infiltration of inflammatory cells in bronchoalveolar lavage fluid (BALF) and oxidative stress markers in the lung tissue. Further, the effects of the extract were compared with bergenin isolated from the extract. Results: Our results showed that an oral administration of the extract 90 min before HCl instillation reduced the infiltration of neutrophils in the lungs in a dose-dependent manner. Reduction in lung inflammation was associated with decline in pulmonary edema as the total protein content in the BALF was found to be decreased substantially. The drug also restored the redox balance in the lungs toward normal on HCl treatment as assessed by measuring the levels of reactive oxygen species (ROS), malondialdehyde (MDA), glutathione (GSH), and catalase activity. Bergenin, isolated from the plant, was able to suppress the neutrophils but increased the macrophage number in BALF when administered before HCl instillation, suggesting immunoregulatory properties of the key constituent of the extract. Conclusion: Our data suggest that hydroalcoholic extract of Caesalpinia digyna roots constitute the phytochemicals that can protect against HCl-induced acute lung injury in mice. Abbreviations Used: ALI: Acute lung injury, BALF: Bronchoalveolar lavage fluid, MDA: Malondialdehyde, ROS: Reactive oxygen species, DCF-DA: 2' 7'-dichlorofluorescein diacetate

Phytochemical Screening and Content Determination of Different Species of Genus Caesalpinia belonging to Different Origin with Antidiabetic Activity

Aim: The main aim of the study is to investigate the phytochemical screening of C. decapetala along with the content determination of different species of genus Caesalpinia with respect to their antidiabetic activity and identification of most bioactive species belonging to different origins. Methods: To achieve our goal different species of genus Caesalpinia collected from China and Pakistan were subjected to open column chromatography, High Pressure Liquid Chromatography (HPLC), antioxidant, and antidiabetic assays for evaluation. Results: From η-BuOH fraction of C. decapetala extract, eight compounds were isolated using open column chromatography and identified as apigenin-7-rhamnoside (1), 4-O-methylepisappanol (2), caesalpinol (3), daucosterol (4), astragalin (5), kaempferol (6), quercitrin (7), and naringin (8) using Nuclear Magnetic Resonance (NMR) spectroscopy. HPLC analysis of different species of genus Caesalpinia showed that the most active antidiabetic compound ‘quercitrin’ was present more in C. pulcherrima followed by decreasing order in C. sappan, C.decapetala, and C. bonduc. Conclusion: The results indicated that quercitrin is the most bioactive content and C. pulcherrima is most bioactive specie of China origin from genus Caesalpinia.

Cassane-type diterpenes from Caesalpinia minax induce apoptosis in pituitary adenoma: structure–activity relationship, ER stress and Wnt/β-catenin pathways

Plant-derived natural products have been the highly significant sources of novel antitumor agents. The cassane-type diterpenes of genus Caesalpinia have been reported to bear antiproliferative activities toward different types of cancer cells. In this study, we evaluated the antineoplasmic activities of 16 natural origin cassane-type diterpenes isolated from the CHCl3 extract of the seeds of C. minax in pituitary adenomas cells and identified caesalpin G (CAG) showed the strongest cytotoxicity. Moreover, we further investigated the structure–activity relationship and molecular mechanism of these derivatives systematically. The results confirmed the unsaturated lactone-type ring, hydroxyl at C-7, and alkenyl at C-11 or C-14 functionality as critical for anticancer activity in this family of natural products. In addition, the mechanism experiments also demonstrated unfolded protein response and ER stress and Wnt/β-catenin pathway were involved in the CAG-induced apoptosis.

Enhanced Cutaneous Wound Healing In Vivo by Standardized Crude Extract of Poincianella pluviosa.

Wound healing is a complex process that involves several biological events, and a delay in this process may cause economic and social problems for the patient. The search continues for new alternative treatments to aid healing, including the use of herbal medicines. Members of the genus Caesalpinia are used in traditional medicine to treat wounds. The related species Poincianella pluviosa (DC.) L.P. Queiroz increases the cell viability of keratinocytes and fibroblasts and stimulates the proliferation of keratinocytes in vitro. The crude extract (CE) from bark of P. pluviosa was evaluated in the wound-healing process in vivo, to validate the traditional use and the in vitro activity. Standardized CE was incorporated into a gel and applied on cutaneous wounds (TCEG) and compared with the formulation without CE (Control) for 4, 7, 10, or 14 days of treatment. The effects of the CE on wound re-epithelialization; cell proliferation; permeation, using photoacoustic spectroscopy (PAS); and proteins, including vascular endothelial growth factor (VEGF), superoxide dismutase 2 (SOD-2) and cyclooxygenase 2 (COX-2) were evaluated. The TCEG stimulated the migration of keratinocytes at day 4 and proliferation on the following days, with a high concentration of cells in metaphase at 7 days. Type I collagen formed more rapidly in the TCEG. PAS showed that the CE had permeated through the skin. TCEG stimulated VEGF at day 4 and SOD-2 and COX-2 at day 7. The results suggest that the CE promoted the regulation of proteins and helped to accelerate the processes involved in healing, promoting early angiogenesis. This led to an increase in the re-epithelialized surface, with significant mitotic activity. Maturation of collagen fibers was also enhanced, which may affect the resistance of the extracellular matrix. PAS indicated a correlation between the rate of diffusion and biological events during the healing process. The CE from P. pluviosa appears promising as an aid in healing.

Simultaneous identification and analysis of cassane diterpenoids inCaesalpinia minaxHance by high-performance liquid chromatography with quadrupole time-of-flight mass spectrometry

Cassane diterpenoids were successfully and simultaneously identified in Caesalpinia minax Hance by high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. A total of 59 peaks were detected, and among them 51 compounds, including 41 furanocassane diterpenoids, 10 furanolactone cassane diterpenoids were simultaneously identified and characterized on the basis of the protonated molecule, retention behavior, and fragments in MS(2) . Ten compounds, including seven novel compounds, were identified or tentatively identified for the first time in C. minax. In a positive ion mode, the fragmentation pathways of cassane diterpenoids were also analyzed for the first time. The relative amounts of the five main diterpenoids (caesalpinin L, caesalpinin F2 , bondcellpin C, caesalpinin E, and ξ-caesalmin) were simultaneously quantified by high-performance liquid chromatography. Results showed that the newly discovered and known components of C. minax can be used to determine the material basis of bioactivity; this method can also be applied to analyze cassane diterpenoids in herbal medicines from the genus Caesalpinia belonging to the family Fabaceae.

Further Diterpenes from the Seeds of Caesalpinia minaxHance

AbstractThree new cassane‐type diterpenes, neocaesalpin AF (1), neocaesalpin AG (2), and neocaesalpin AH (3), were isolated from the seeds of Caesalpinia minax Hance. Their structures were elucidated on the basis of extensive spectroscopic analyses. The partially hydrogenated lactone unit in a tetracyclic cassane diterpene in 2 is rarely encountered in the cassane diterpenes isolated from the genus Caesalpinia. All compounds were evaluated for their in vitro cytotoxic activities against HCT‐8 and MCF‐7 human cancer cell lines.

Caesappin A and B, two novel protosappanins from Caesalpinia sappan L.

Two novel protosappanins, named Caesappin A (1) and B (2), along with three known protosappanins were isolated from Caesalpinia sappan L. Caesappin A is a new type protosappanin with a seven-membered ring fusing an acetal-type section. Compound 4 was isolated from the genus Caesalpinia for the first time. The structures were elucidated on the basis of spectral analysis and the absolute configuration was determined by the ECD experiment coupled with calculated ECD spectra. Their cytotoxic activities were evaluated using MTT assay.