Fabaceae (Caesalpinoideae)

©The World Botanical Associates Web Page
Prepared by Richard W. Spjut
December 2004

Caesalpinia placida
Near La Paz, BCS
May 1979



Trees and Shrubs of Kern County (Jan 2013)

*Caesalpinia gilliesii (Poinciana gilliesii Wallich ex Hooker 1830) D. Dietrich 1840. Bird-of-Paradise. Shrub or tree with leaves twice divided into small leaflets that have black dots near the margins on the lower surface; flowers conspicuous by the long exserted red stamens.  An introduced plant.  Type from Argentina: Prope Rio Quarto et Rio Quinto, et apud La Punta de San Luis.  CCH specimens are mainly from southern California. Kern Co.:  Occasional escape in the valley and the Temblor Range, especially about cities and towns (Twisselmann), also near Miracle Hot Springs along the Old Kern Canyon Rd, where likely planted along with other introductions such as Ailanthus.

Pharmacological References

Caesalpinia gillensii—a glycoprotein, cesalin, active in LL and SA, was isolated by Cole (Hartwell 1976).

Caesalpinia pulcherrima—a simple protein, active in SA, was reported by Cole as responsible for the activity in this species (Hartwell 1976).

Jiang R. W., S. C. Ma, Z. D. He, X. S. Huang, P. P. But, H. Wang, S. P. Chan, V. E. Ooi, H. X. Xu and T. C. Mak.  2002. Molecular structures and antiviral activities of naturally occurring and modified cassane furanoditerpenoids and friedelane triterpenoids from Caesalpinia minax. Bioorg. Med. Chem. 10(7): 2161–2170. “Further investigation of the active components of the chloroform fraction of the seeds of Caesalpinia minax led to the isolation of a new cassane furanoditerpenoid, caesalmin H (1), together with two known furanoditerpenoid lactones, caesalmin B (2) and bonducellpin D (3). Reduction of the naturally abundant caesalmin D (9), E (10) and F (11) resulted in three new furanoditerpenoid derivatives 4-6. Phytochemical study of the stem of the same plant and subsequent reduction afforded two friedelane triterpenoids (7-8), which were identified by spectroscopic methods. Compounds 1-2 and 4-8 were corroborated by single crystal X-ray analysis. The factors governing the reduction of cassane furanoditerpenoids and friedelane triterpenoids were investigated by correlating the crystallographic results with density functional theory. The inhibitory activities of 2-8 on the Para3 virus were evaluated by cytopathogenic effects (CPE) reduction assay

Kalauni S. K., S. Awale, Y. Tezuka, A. H. Banskota, T. Z. Linn, P. B. Asih, D. Syafruddin and S. Kadota.  2005. Antimalarial activity of cassane- and norcassane-type diterpenes from Caesalpinia crista and their structure-activity relationship. Biol. Pharm. Bull. 29(5):1050–1052.  “Malaria is one of the most life-threatening infectious diseases worldwide and claims millions of people's lives each year. The appearance of drug-resistance Plasmodium falciparum has made the treatment of malaria increasingly problematic, and thus, it is a dire need to search the new alternatives of current drugs. In the present study, 44 cassane- and norcassane-type diterpenes isolated from Caesalpinia crista of Myanmar and Indonesia were evaluated for their antimalarial activity against the malaria parasite Plasmodium falciparum FCR-3/A2 clone in vitro. Most of the tested diterpenes displayed antimalarial activity, and norcaesalpinin E (28) showed the most potent activity with an IC50 value of 0.090 microM, more potent than the clinically used drug chloroquine (IC50, 0.29 microM). Based on the observed results, a structure-activity relationship has been established.”

Kinoshita T., Y. Haga, S. Narimatsu, M. Shimada and Y. Goda.  2005. The isolation and structure elucidation of new cassane diterpene-acids from Caesalpinia crista L. (Fabaceae), and review on the nomenclature of some Caesalpinia species.  Chem. Pharm. Bull (Tokyo) 53(6): 717–720.  “New cassane diterpene-acids, neocaesalpins H and I, were isolated from the leaves of Caesalpinia crista (Fabaceae), and their structures were deduced on the basis of the spectroscopic and chemical basis. These compounds were characterized as having an alpha,beta-butenolide hemiacetal ring that is rare in nature. The lacking of 5-hydroxy group also distinguished neocaesalpins H and I from cassane diterpenes (caesalpins) occurring in other Caesalpinia species from the phytochemical viewpoint. The nomenclature of three Caesalpinia species was also reviewed, and it was found that some species belonging to the genus Caesalpinia are improperly named and should be changed to valid names.”

Montgomery R. and F. Yamauchi. 1977. Cesalin--an anti-neoplastic protein.  Lloydia 40(3): 269–274.  “An anti-neoplastic protein was isolated from the endosperm of the seeds of Caesalpinia gilliesii by extraction with water, dialysis and precipitation by ammonium sulfate or acidification. The precipitated protein mixture was separated by column chromatography into three principal proteins, one of which, termed cesalin, inhibited the growth of Walker 256 carcinosarcoma. There is an associated carbohydrate with the cesalin that can be largely removed by chromatography on hydroxyl apatite; the remaining carbohydrate (about 0.3%) is a hexosan. Cesalin, molecular weight 110,000, migrates as a single component by polyacrylamide gel electrophoresis at pH 8.3, but in a denaturing system containing sodium dodecyl sulfate three bands were observed. The correspond to protein sub-units of approximately 30,000 daltons. Anti-tumor tests in rats showed 70-80% inhibition of Walker 256 growth at a dose of 80 microgram/kg/day of cesalin.”

Nakamura E. S., F. Kurosaki, M. Arisawa, T. Mukainaka, J. Takayasu, M. Okuda, H. Tokuda, H. Nishino and F. Pastore.  2002. Cancer chemopreventive effects of a Brazilian folk medicine, Juca, on in vivo two-stage skin carcinogenesis. J. Ethnopharmacol. 81(1): 135–137.  Gallic acid (1) and methyl gallate (2) were isolated from Juca, a Brazilian folk medicine, fruits of Caesalpinia ferrea Mart. (Leguminosae), decreased significantly the average number of papillomas per mouse in the experiment of the promoting effects of 12-O-tetra- decanoylphorbol-13-acetate (TPA) on skin tumor formation in mice initiated with 7,12-dimethylbenz[a]anthracene (DMBA).

Promsawan N., P. Kittakoop, S. Boonphong and P. Nongkunsarn.  2003. Antitubercular cassane furanoditerpenoids from the roots of Caesalpinia pulcherrima.  Planta Med. 69(8): 776–777. “Activity-guided fractionation of a root extract of Caesalpinia pulcherrima led to the isolation of two cassane-furanoditerpenoids, 6 beta-benzoyl-7 beta-hydroxyvouacapen-5 alpha-ol (1) and 6 beta-cinnamoyl-7beta-hydroxyvouacapen-5 alpha-ol (2). Compound 2 showed strong antitubercular activity with a minimum inhibitory concentration (MIC) of 6.25 microg/mL, whereas the benzoyl analogue (1) was less active (MIC 25 microg/mL). Both compounds expressed moderate cytotoxic activity towards KB (human oral carcinonoid cancer), BC (human breast cancer) and NCl-H187 (small cell lung cancer) cell lines

Rao Y. K., S. H. Fang and Y. M. Tzeng.  2005. Anti-inflammatory activities of flavonoids isolated from Caesalpinia pulcherrima.  J. Ethnopharmacol. 100(3): 249–253.  “The anti-inflammatory activities of five flavonoids, namely 5,7-dimethoxyflavanone (1), 5,7-dimethoxy-3',4'-methylenedioxyflavanone (2), isobonducellin (3), 2'-hydroxy-2,3,4',6'-tetramethoxychalcone (4) and bonducellin (5), all of them isolated from Caesalpinia pulcherrima L. was studied in lipopolysaccharide (LPS) and interferon (IFN)-gamma activated murine peritoneal macrophages. These five compounds significantly and dose-dependently inhibited the inflammatory mediators; nitric oxide (NO), and cytokines [tumor necrosis factor (TNF)-alpha and interleukin (IL)-12]. According to their inhibitory results, the order of anti-inflammatory potency was compounds 3>5>4>2>1. Furthermore, peritoneal macrophages were pre-activated with LPS/IFN-gamma for 24h, and determined the inhibitory effects of the above-mentioned isolates on the production of NO after a further 24h. The present study supports the use of Caesalpinia pulcherrima for the treatment of inflammatory diseases in traditional medicine. This is the first study on compounds 1-5 about their anti-inflammatory activities

Woldemichael G. M., M. P. Singh, W. M. Maiese and B. N. Timmermann.  2003. Constituents of antibacterial extract of Caesalpinia paraguariensis Burk. Z. Naturforsch [C]. 58(1-2): 70–75.  “The Argentinean legume Caesalpinia paraguariensis Burk. (Fabaceae) was selected for further fractionation work based on the strong antimicrobial activity of its CH2Cl2-MeOH (1:1 v/v) extract against a host of clinically significant microorganisms, including antibiotic resistant strains. 1D and 2D NMR enabled the identification of the novel benzoxecin derivative caesalpinol along with the known compounds bilobetin, stigma-5-en-3-O-beta-6'-stearoylglucopyranoside, stigma-5-en-3-beta-6'-palmitoylglucopyranoside, stigma-5-en-3-beta-glucopyranoside, oleanolic acid, 3-O-(E)-hydroxycinnamoyl oleanolic acid, betulinic acid, 3-O-(E)-hydroxycinnamoyl betulinic acid, and lupeol from the active fractions. Oleanolic acid was found active against Bacillus subtilis and both methicillin-sensitive and -resistant Staphylococcus aureus with MICs of 8 (17.5 microM), 8 and 64 (140 microM) microg/ml, respectively. The rest of the compounds, however, did not show activity.”

Ye M., W. D. Xie, F. Lei, Z. Meng, Y. N. Zhao, H. Su and L. J. Du.  2006. Brazilein, an important immunosuppressive component from Caesalpinia sappan L.  Int. Immunopharmacol.  6(3): 426–432. “Caesalpinia sappan has been shown to have interesting immunosuppressive properties. Its heartwood has long been used in Chinese medicines for treating a variety of immune-mediated pathology and inflammatory disease. The purpose of this work was to evaluate the immunocompetence effects of brazilein on mice lymphocytes in vitro and in vivo. The results showed that brazilein and Caesalpinia sappan ethanol extract (SME) could distinctly inhibit the proliferation of T lymphocyte stimulated by Concanavalin A (Con A) and the proliferation of B lymphocyte stimulated by lipopolysaccharides (LPS), and brazilein could suppress mice humoral immune response by plaque forming cell (PFC) test. In addition, immune organs (thymus and spleen) in mice treated with brazilein were notably atrophied and weight loss in vivo (intraperitoneal injection, i.p.). In attempting to investigate the mechanisms of the immunosuppressive activity of brazilein, we discovered that brazilein can induce apoptosis in mice spleen lymphocytes by flow cytometry analysis and DNA fragmentation assay, which may be one of the pathways that brazilein inhibited immunocompetence of mice lymphocytes.”