Antiinflammatory and Wound Healing Effects of Caesalpinia sappan L.

Extracted compounds from Caesalpinia sappan L. were examined for the inhibitory activity against NO, PGE2 , and TNF-α productions and on associated transcription levels using RAW264.7 cells. They were also tested for their effects on wound healing using fibroblast L929 cells. Among the compounds tested, brazilin (8) was the most effective against lipopolysaccharide (LPS)-induced NO production in RAW264.7 cells with an IC50 value of 10.3 µM, followed by sappanchalcone (2, 31.0 µM). Brazilin (8) also inhibited PGE2 and TNF-α production with IC50 values of 12.6 and 87.2 µM, respectively. The antiinflammatory mechanism of brazilin involved down regulation of the mRNA expressions of the iNOS, COX-2, and TNF-α genes in a dose-dependent manner. An ethanol (EtOH) extract of C. sappan significantly increased fibroblast proliferation, fibroblast migration, and collagen production, whereas brazilin (8) only stimulated fibroblast migration. In addition, the EtOH extract showed no acute toxicity in mice, and it was therefore safe to make use of its potent antiinflammatory and wound healing activities. Brazilin was mainly responsible for its antiinflammatory effect through its ability to inhibit the production of NO, PGE2 , and TNF-α. This study supports the traditional use of C. sappan for treatment of inflammatory-related diseases.

Anti-HIV-1 Integrase Activity and Molecular Docking Study of Compounds from Caesalpinia sappan L.

Caesalpinia sappan L. (Caesalpiniaceae) has been traditionally used as blood tonic, expectorant, and astringent by boiling with water. Searching for HIV-1 integrase (IN) inhibitors from this plant is a promising approach. The EtOH extract of C. sappan and its isolated compounds were tested for their anti-HIV-1 IN effect using the multiplate integration assay, and the active compounds were determined for their mechanisms by molecular docking technique. Extraction from the heartwoods and roots of C. sappan led to the isolation of nine compounds. Among the compounds tested, sappanchalcone (2) displayed the strongest effect against HIV-1 IN with an IC50 value of 2.3 µM followed by protosappanin A (9, IC50 = 12.6 µM). Structure-activity relationships of compounds from C. sappan were found, in which the vicinal hydroxyl moiety were essential for anti-HIV-1 IN effect of compounds 2 and 9 by binding with the amino acid residues Gln148 and Thr66 in the core domain of the HIV- 1 IN enzyme, respectively.

Diterpenoids and triterpenoids with potential anti-inflammatory activity from the leaves of Aglaia odorata.

Chemical investigation of the leaves of the oriental medicinal plant Aglaia odorata resulted in the isolation of five compounds: two dolabellane diterpenoids, two dammarane triterpenoids and a protostane triterpenoid, along with twenty known compounds. Their structures were elucidated on the basis of extensive spectroscopic analysis and by comparison of their NMR spectroscopic data with those reported in the literature. The anti-inflammatory activities of all compounds were evaluated as inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Eleven compounds possessed potent nitric oxide inhibitory activity with IC(50) values ranging from 2.1 to 14.2 µM, these being better than that of the positive control, indomethacin (IC(50)=14.5 µM). In addition, three compounds exhibited significant activity against PGE(2) release with IC(50) values of 2.6, 16.1 and 23.0 µM.

Anti-inflammatory principles of Suregada multiflora against nitric oxide and prostaglandin E2 releases.

AIM OF THE STUDY: The stem bark of Suregada multiflora and the isolated compounds were carried out to investigate for anti-inflammatory activity. MATERIALS AND METHODS: The stem bark of Suregada multiflora and its isolated compounds were tested for their anti-inflammatory effects against lipopolysaccharide (LPS)-induced nitric oxide (NO) and prostraglandin E(2) (PGE(2)) releases in RAW264.7 cells as well as the anti-inflammatory mechanism on mRNA expression of the active compound (5, helioscopinolide A). RESULTS: The extract of Suregada multiflora possessed potent NO inhibitory effect with an IC(50) value of 8.6 µg/ml. Among the isolated compounds, helioscopinolide A (5) exhibited the highest activity against NO release with an IC(50) value of 9.1 µM, followed by helioscopinolide C (6) and suremulol D (2) with IC(50) values of 24.5 and 29.3 µM, respectively. The IC(50) value of 5 against PGE(2) production was found to be 46.3 µM. The mechanism in transcriptional level of compound 5 was found to inhibit iNOS and COX-2 mRNA expressions in dose-dependent manners. CONCLUSIONS: The present study may support the traditional use of Suregada multiflora stem bark for treatment of inflammatory-related diseases.

Potential anti-inflammatory diterpenoids from the roots of Caesalpinia mimosoides Lamk.

Anti-inflammatory assay-guided separation of extracts from the roots of Caesalpinia mimosoides Lamk. led to isolation of seven compounds: four diterpenes (1-4), a dimer (9), and two dibenzo[b,d]furans (10, 11) together with eleven known compounds. Their structures were elucidated by 1D- and 2D-NMR techniques as well as UV, IR, mass spectral data and comparison with literature values. The anti-inflammatory activities of all compounds were evaluated for inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Compounds 4, 6, 8, and 12-14 were also tested for the inhibitory effect on LPS-induced tumor necrosis factor-alpha (TNF-alpha) release in RAW264.7 cells. The results indicated that 4 possessed potent inhibitory activity for both tests with IC(50) values of 3.0 and 6.5 microM, respectively.

Absolute configuration of isovouacapenol C.

The title compound, C(27)H(34)O(5) {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihy-droxy-4,4,7,11b-tetra-methyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodeca-hydro-phenanthro[3,2-b]furan-5-yl benzoate}, is a cassane furan-oditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The three cyclo-hexane rings are trans fused: two of these are in chair conformations with the third in a twisted half-chair conformation, whereas the furan ring is almost planar (r.m.s. deviation = 0.003 Å). An intra-molecular C-H⋯O inter-action generates an S(6) ring. The absolute configurations of the stereogenic centres at positions 4a, 5, 6, 6a, 7, 11a and 11b are R, R, R, S, R, S and R, respectively. In the crystal, mol-ecules are linked into infinite chains along [010] by O-H⋯O hydrogen bonds. C⋯O [3.306 (2)-3.347 (2) Å] short contacts and C-H⋯π inter-actions also occur.

Absolute configuration of vouaca-pen-5α-ol.

The title compound, C(20)H(30)O(2), {systematic name: (4aR,6aS,7R,11aS,11bR)-4,4,7,11b-tetra-methyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodeca-hydro-phenanthro[3,2-b]furan-4a-ol}, is a cas-sane furan-oditerpene which was isolated from the roots of Caesalpinia pulcherrima. The absolute configurations at positions 4a, 6a, 7, 11a and 11b are R, S, R, S and R, respectively. The mol-ecule has four-fused rings consisting of three cyclo-hexane rings and one furan ring. The three cyclo-hexane rings are trans-fused. Two cyclo-hexane rings are in chair conformations, while the third is in an envelope conformation. In the crystal structure, the mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds into a zigzag chain along the a axis. A short O⋯O contact [3.0398 (14) Å] is also present.

Absolute configuration of odorine.

The title compound, known as odorine or roxburghiline {systematic name: (S)-N-[(R)-1-cinnamoylpyrrolidin-2-yl]-2-methyl-butanamide}, C(18)H(24)N(2)O(2), is a nitro-genous compound isolated from the leaves of Aglaia odorata. The absolute configuration was determined by refinement of the Flack parameter with data collected using Cu Kα radiation showing positions 2 and 2' to be S and R, respectively. The pyrrolidine ring adopts an envelope conformation. In the crystal, mol-ecules are linked into chains along [010] by inter-molecular N-H⋯O hydrogen bonds.

Anti-allergic activity of principles from the roots and heartwood of Caesalpinia sappan on antigen-induced beta-hexosaminidase release.

The dichloromethane extract of the roots and heartwood of Caesalpinia sappan exhibited potent inhibitory activity against beta-hexosaminidase release as marker of degranulation in rat basophilic leukemic (RBL-2H3) cells, with inhibition of 98.7% and 87.5% at concentration of 100 microg/ml, respectively. These extracts were further separated by chromatographic techniques to give two chalcones and seven homoisoflavones. Among the compounds tested, sappanchalcone (2) possessed the most potent effect against allergic reaction in RBL-2H3 cells with an inhibitory concentration (IC50) value of 7.6 microM, followed by 3-deoxysappanchalcone (1, IC50 = 15.3 microM), whereas other compounds showed moderate and mild effects. The results suggested the following structural requirements of chalcones (1 and 2) and homoisoflavones (3-9) for anti-allergic activity: (i) chalcone exhibited higher activity than homoisoflavone (ii) vicinal hydroxylation at B-ring of chalcone conferred higher activity than one hydroxylation; and (iii) for homoisoflavone, the hydroxyl groups at C-3 and C-4 positions decreased the activity. This is the first report of C. sappan for anti-allergic activity.

Phanginin A-K, diterpenoids from the seeds of Caesalpinia sappan Linn.

The first chemical study on the seeds of Caesalpinia sappan Linn. led to isolation of 11 cassane-type diterpenes, named phanginin A-K (1-11). The skeleton present in compounds 1-8 is rather unusual, consisting of a cassane-type diterpene with an ether bridge between C-19/C-20 in compounds 1-6 and C-11/C-20 in compounds 7 and 8. Their structures were elucidated on the basis of spectroscopic techniques. In addition, the X-ray structure of phanginin A (1) is reported. Only phanginin I (9) exhibited cytotoxic effect against KB cell line with IC50 value of 4.4 microg/ml.

Potential anti-allergic ent-kaurene diterpenes from the bark of Suregada multiflora.

Two ent-kaurene diterpenes, ent-16-kaurene-3beta,15beta,18-triol (1) and ent-3-oxo-16-kaurene-15beta,18-diol (2), were isolated from a dichloromethane extract of the bark of Suregada multiflora along with five known diterpenes:ent-16-kaurene-3beta,15beta-diol (3), abbeokutone (4), helioscopinolide A (5), helioscopinolide C (6) and helioscopinolide I (7). Their structures were elucidated on the basis of spectroscopic analysis. Compounds 1-7 possessed appreciable anti-allergic activities in RBL-2H3 cells model with IC50 values ranging from 22.5 to 42.2 microM.