A new cassane diterpenoid lactone from the seed of Caesalpinia minax

A new cassane diterpenoid lactone was isolated from the seed of Caesalpinia minax.On the basis of spectral evidences,its structure was established as 12α-methoxyl,5α,14β-dihydroxy- 1α,6α,7β-triacetoxycass- 13(15)-en- 16,12-olide.     

Three new cassane diterpenes from the seeds of Caesalpinia minax Hance

Four fractions were prepared from the crude extract of Caesalpinia minax Hance and the inhibitory activity of nitric oxide (NO) production release of RAW 264.7 cells stimulated by lipopolysaccharide (LPS) was evaluated. The ethyl acetate (EtOAc) fraction showed obvious inhibitory effect. Bioassay-guided fractionation led to the isolation of three new cassane diterpenes, caesalmin X (1), caesalmin Y (2) and caesalmin Z (3), together with 19 known cassane diterpenoids (4–22). Their structures were mainly characterised on the basis of extensive spectroscopic analyses and comparison with reported data. Moreover, three compounds (20–22) which possessed furanditerpenoid 7,17-lactone structures, displayed moderate activities, with IC₅₀ value of 29.85, 27.38 and 25.40 μM, respectively.     

A new cassane diterpenoid lactone from the seed of Caesalptma minax

A new cassane diterpenoid lactone was isolated from the seed of Caesalpinia minax.On the basis of spectral evidences,its structure was established as 12α-methoxyl,5α,14β-dihydroxy-1α,6α,7β-triacetoxycass-13(15)-en-16,12-olide.     

Further Diterpenes from the Seeds of Caesalpinia minax Hance

Three 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.     

Antioxidative Cassane Diterpenoids from the Seeds of Caesalpinia minax

Five new cassane diterpenoids, caesalmins I–M ( 1 – 5 ), and 23 known analogs were isolated from the seeds of Caesalpinia minax. Their structures were elucidated by spectroscopic methods and comparison with reported data. The antioxidant properties of 1 – 28 were determined by the method of oxygen radical absorbance capacity of fluorescein (ORAC‐FL), and 14 compounds exhibited good antioxidant activities with ORAC‐FL values of 2.24–4.89 Trolox equivalents. The structure? activity relationship of the active compounds was also discussed.     

Simultaneous identification and analysis of cassane diterpenoids in Caesalpinia minax Hance 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 MS². 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.     

Three New Cassane‐Type Diterpenes from Caesalpinia minax

Three new cassane‐type diterpenes, 14‐dehydroxy‐12,16‐dihydrocaesaldekarin L ( 1 ), 1‐deacetyl‐12‐ethoxyneocaesalpin N ( 2 ), and 1‐deacetylneocaesalpin N ( 3 ), together with two known cassane‐type diterpenes, neocaesalpin A and neocaesalpin L, were isolated from the EtOH extract of the twigs and leaves of Caesalpinia minax. Their structures were elucidated by spectroscopic methods, as well as by comparison of their spectral data with those of related compounds.     

The new cassane-type diterpenes from Caesalpinia minax

Four new cassane-type diterpenes, Neocaesalpin S (1), Neocaesalpin T (2), Neocaesalpin U (3), and Neocaesalpin V (4) were isolated from Caesalpinia minax HANCE together with seven known compounds Neocaesalpin A (5), Neocaesalpin K (6), Neocaesalpin L (7), Neocaesalpin M (8), Neocaesalpin O (9), Neocaesalpin MP (10), and Magnicaesalpin (11). Their structures were elucidated on the basis of 1D- and 2D-NMR, MS, and circular dichroism (CD) analysis. Compounds 1-4 were tested against liver cancer (HepG-2) and breast cancer (MCF-7), and showed mild antiproliferative activity.     

Two new cassane diterpene lactams from the fruits of Caesalpinia mimosoides Lam

Two new cassane ditepenoid lactams, caesmimotam A (1) and B (2), along with eight known compounds (3–10) were isolated from the fruits of Caesalpinia mimosoides Lam. Their structures were identified by 1D and 2D NMR spectral data. Compounds 1 and 2 were evaluated for their cytotoxicity on HL-60, SMMC-7721, A-549, MCF-7 and SW-480 human cancer cell lines, but they were inactive.     

Cytotoxic cassane diterpenoids from the seeds of Caesalpinia sappan

Phytochemical investigation on the seeds of Caesalpinia sappan led to the isolation of five new cassanetype diterpenoids, named 11-oxo-phanginin A(1), caesalsappanins O–Q(2–4) and phanginin U(5),together with five known compounds. The structures of the new compounds were elucidated by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. All the new compounds showed moderate cytotoxic effects on human breast cancer MCF-7 and human colon cancer HCT116 cell lines.     

Rearranged diterpenoids from the seeds of Caesalpinia sappan

Two new rearranged diterpenoids, tomocinol C (1) and spirocaesalmin C (2) were isolated from the seeds of Caesalpinia sappan. Their structures were elucidated based on comprehensive analysis of spectroscopic data, and their absolute configurations were established by single crystal X-ray crystallography.     

A novel diarylheptanoid bearing flavonol moiety from the rhizomes of Alpinia officinarum Hance

<正>A novel diarylheptanoid bearing flavonol moiety,named officinin A(1),along with two known compounds galangin and kaempferide were isolated from the rhizomes of Alpina officinarum Hance.The structure elucidation was accomplished by HRESI -MS,1D and 2D NMR methods.     

Cassane‐Type Diterpenoids from the Seeds of Caesalpinia magnifoliolata

Two novel cassane‐type diterpenes, named magnicaesalpin ( 1 ) and neocaesalpin O ( 2 ), together with three known compounds, caesalmin D ( 3 ), caesalmin E ( 4 ), and neocaesalpin L ( 5 ), were isolated from the MeOH extract of seeds of Caesalpinia magnifoliolata Metc . Their structures were determined by spectroscopic methods, (1D‐ and 2D‐NMR, HR‐EI‐MS) and X‐ray analysis, as well as by comparison of their spectral data with those of related compounds.     

微波场协同提取紫背天葵色素的研究

研究了微波提取紫背天葵(Begonia fimbristipula Hance)色素的新工艺,并确定了最佳工艺条件：提取剂为φ(C2H5OH)=60％的乙醇,提取剂与原料用量比为1：60,微波功率为648W,提取时间为200s,提取次数为2次。最佳工艺条件下的色素提取率为96．8％,产率为9．98％,色价E(1％,526m)为10．5,产品pH值为6．5。与溶剂浸提法相比,微波法提取紫背天葵色素的每次提取时间由24h减少到200s,提取率从95．9％增加到96．8％。     

Cassane‐Type Diterpenes from the Seeds of Caesalpinia crista

A new dimer 1 and two new cassane‐type diterpenes 2 and 3 , designated taepeenin J–L, were isolated from the seeds of Caesalpinia crista L. Compound 1 possesses a dimeric vouacapane skeleton. Their structures were elucidated on the basis of spectroscopic analysis.     

Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.

A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C₄₆H₇₄O₁₇, [M]⁺ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results.     

A New Flavonol Glycoside from Anaphalis sinica Hance

ＩｎｔｒｏｄｕｃｔｉｏｎＳｅｖｅｒａｌｐｌａｎｔｓｏｆｇｅｎｕｓＡｎａｐｈａｌｉｓ(Ｃｏｍｐｏｓｉｔａｅ)ｈａｖｅｂｅｅｎｐｈｙｔｏｃｈｅｍｉｃａｌｌｙｓｔｕｄｉｅｄ ,ｆｒｏｍｗｈｉｃｈｆｌａｖａｎｏｉｄｓ[1,2 ] ,ｈｅｌｉｐｙｒｏｎｅ[3] ,ｃｈｌｏｒｏａｃｅｔｙｌｅｎｉｃｃｏｍｐｏｕｎｄｓｗｉｔｈａｄｉｈｙｄｒｏｐｙｒａｎｏｒｆｕｒａｎｒｉｎｇ[4] ａｎｄｐｈｔｈａｌｉｄｅｓｈａｖｅｂｅｅｎｒｅｐｏｒｔｅｄ[5 ] .Ａ .ｓｉｎｉｃａＨａｎｃｅ ,ｄｉｓｔｒｉｂｕｔｅｄｉｎＣｈｉｎａａｎｄａｌｓｏｆｏｕｎｄ…     

Bioactive Eudesmane sesquiterpenes from Artabotrys hongkongensis Hance

Abstract

A new naturally occurring trinoreudesmane sesquiterpene, artahongkongol A (1), together with seven known eudesmane sesquiterpenes (2?8), was isolated from the stems and leaves of Artabotrys hongkongensis Hance. Among them, 1 is a rare trinoreudesmane sesquiterpene containing 12 carbon atoms on the carbon skeleton. All known compounds (2?8) were isolated from the genus Artabotrys for the first time. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1?8 showed significant inhibitory effects against various human cancer cell lines with IC₅₀ values ranging from 0.57 to 15.68?μM.     

Caesaljaponins A and B: New Cassane‐Type Furanoditerpenoids from the Seeds of Caesalpinia decapetala var. japonica

Two new cassane‐type furanoditerpenoids, designated caesaljaponin A and caesaljaponin B ( 1 and 2 , resp.), were isolated from seeds of Caesalpinia decapetala var. japonica. The structures were elucidated by spectroscopic data, and the absolute configuration of 1 was determined by X‐ray crystallographic analysis using the anomalous scattering of CuK_α radiation.     

A new furanoid diterpene from Caesalpinia pulcherrima

A new cassane-type diterpene isovouacapenol E (1) was isolated from the leaves of Caesalpinia pulcherrima, together with the known compounds caesaldekarin A (3), spathulenol (4), caryophyllene oxide (5), phytol, and sitosterol. The structure of 1 was elucidated by spectral data interpretation.