Five new flavonoid derivatives, cajavolubones A-E (1-5), along with six known analogues (6-11) were isolated from Cajanus volubilis, and their structures were elucidated by spectroscopic analysis and quantum chemical calculations. Cajavolubones A and B (1 and 2) were identified as two geranylated chalcones. Cajavolubone C (3) was a prenylated flavone, while cajavolubones D and E (4 and 5) were two prenylated isoflavanones. Compounds 3, 8, 9 and 11 displayed cytotoxicity against HCT-116 cancer cell line.
Flavonoids/chemistry* ; Cajanus ; Molecular Structure ; Chalcones/chemistry*

OBJECTIVETo establish quality control criteria for medicinal herb Cajanus cajan based on the determination of longistylin A and longistylin C, two bioactive and specific stilbenes of the plant.

METHODLongistylin A and longistylin C were obtained from the leaves of C. cajan by silica gel column chromatography and identified as marker compounds of this plant by spectroscopic analysis. A RP-HPLC method was established to determine the two compounds.

RESULTLongistylin A and longistylin C were well separated on a Thermo BDS Hypersil C18 column (4.6 mm x 250 mm, 5 microm) with a mobile phase methanol-water (8:2), and showed good linearity in the range of 0.00288 - 0.0576 microg and 0.0112 - 0.224 microg, respectively. The average recoveries were 98.9% and 97.2% with RSD of 2.4% and 2.2% for these two compounds, respectively.

CONCLUSIONThe established analysis method is simple and accurate, whicn can be used for quality control of C. cajan.

Cajanus ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Diethylstilbestrol ; analysis ; isolation & purification ; Drugs, Chinese Herbal ; analysis ; isolation & purification ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry

This study is to investigate the protective effect of longistyline A against corticosterone-induced neurotoxicity in PC12 cells. While PC12 cells were exposed to 100 micromol x L(-1) corticosterone for 48 h, cell survival rate was reduced and lactate dehydrogenase (LDH) release increased. In parallel, corticosterone caused significant elevations of DNA fragmentation, [Ca2+]i and caspase-3 activity. However, when the PC12 cells were incubated with longistyline A (4.0, 8.0 and 16.0 micromol x L(-1)) in the presence of 100 micromol x L(-1) corticosterone for 48 h, the effects were evidently alleviated, but dose-dependent manner was not obvious. In summary, longistyline A could generate a neuroprotective effect against corticosterone-induced neurotoxicity in PC12 cells possibly by decreasing [Ca2+]i and caspase-3 activity.
Animals ; Cajanus ; chemistry ; Calcium ; metabolism ; Caspase 3 ; metabolism ; Cell Survival ; drug effects ; Corticosterone ; toxicity ; DNA Fragmentation ; drug effects ; L-Lactate Dehydrogenase ; metabolism ; Molecular Structure ; Neuroprotective Agents ; isolation & purification ; pharmacology ; PC12 Cells ; Phenols ; isolation & purification ; pharmacology ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Rats

The Cajanus cajan L. is a natural plant, which contains lots of potential active components. The effects of the stilbene extracts from Cajanus cajan L. (sECC) on ovariectomy (OVX)-induced bone loss in rats were identified. All experimental female rats were divided into 6 groups, i. e. sham-operated rats, OVX rats, 17beta-estradiol (E2)-treated rats, sECC-treated rats with three dosages, 50, 100, and 200 mg x kg(-1), separately. Two weeks after the operation, different dosage of sECC, E2 or deionized water were given to the 6 groups of rats, respectively for another 8 weeks through stomach. Then, all rats were killed. The body weight and uterus wet weight were measured. Contents of serum E2, follicle stimulating hormone (FSH), and luteinizing hormone (LH) were measured by radioimmunoassay. Femoral morphology was observed by HE stain. The results showed that there were no changes of the uterine weight and serum E2 concentration in sECC-treated rats compared with OVX rats. However, the serum FSH and LH concentrations reduced by 11.5% and 15.2% (P < 0.05), respectively. By HE staining, it is found that the 60% of the femur structure had been significantly improved in OVX rats treated with 200 mg x kg(-1) of sECC. The trabeculae were thicker and larger than that of OVX rats. It is clear that sECC improved femoral morphological structure and decreased FSH and LH contents without affecting serum E2 level and uterine weight in OVX rats. The results suggested that sECC had potential action in treatment of postmenopausal osteoporosis.
Animals ; Body Weight ; drug effects ; Cajanus ; chemistry ; Drugs, Chinese Herbal ; isolation & purification ; pharmacology ; Estradiol ; blood ; Female ; Femur ; pathology ; Follicle Stimulating Hormone ; blood ; Luteinizing Hormone ; blood ; Organ Size ; drug effects ; Osteoporosis ; blood ; pathology ; Ovariectomy ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Rats ; Rats, Wistar ; Uterus ; pathology

The cajanine (longistylin A-2-carboxylic acid) is isolated and identified from extracts of Cajanus cajan L. (ECC) , which structure is similar to diethylstilbestrol. The regulation properties of the cajanine and other four extracts of Cajanus cajan L. (32-1, 35-1, 35-2, and 35-3) were tested in human osteoblast-like (HOS) TE85 cells and marrow-derived osteoclast-like cells. By using MTT assay to test the change of cell proliferation, 3H-proline incorporation to investigate the formation of collagen, and by measuring alkaline phosphatase (ALP) activity, bone formation in HOS TE85 cell was evaluated after pretreated for 48 hours. Bone marrow cells were cultured to examine the derivation of osteoclast cells (OLCs), which were stained with tartrate-resistant acid phosphatase (TRAP). The long term effect (pretreated for 18 days) on promoting mineralized bone-like tissue formation was tested by Alizarin red S staining in HOS TE85 cells. After the treatment with cajanine (1 x 10(-8) g x mL(-1)) for 48 hours, cell number increased significantly (57.7%). 3H-Proline incorporation also statistically increased (98.5%) in those cells. Significant change of ALP activity was also found (P < 0.01) in 35-1 and 35-3 treated cells (they were 66.2% and 82.4% in the concentration of 1 x 10(-8) g x mL(-1), respectively). The long term (18 days) effects of 32-1 and 35-3 on promoting mineralized bone-like tissue formation in HOS TE85 cell were obvious. There were much more red blots over the field of vision compared with that of control group. After the treatment of cajanine, derived-osteoclast cells appeared later and much less compared with control. The inhibition of cajanine was 22.8% while it was 37.9% in 32-1 treated cells in the dose of 1 x 10(-7) g x mL(-1). It is obvious that cajanine and ECCs promoted the osteoblast cells proliferation and mineralized bone-like tissue formation in HOS TE85 cells, while inhibited derivation of osteoclast cells. All of these suggested that cajanine has the estrogen-like action on osteoblast and osteoclast, which could be developed as anti-osteoporosis drugs.
Alkaline Phosphatase ; metabolism ; Animals ; Bone Marrow Cells ; cytology ; Bone Neoplasms ; metabolism ; pathology ; Cajanus ; chemistry ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Cells, Cultured ; Collagen ; biosynthesis ; Diethylstilbestrol ; analogs & derivatives ; isolation & purification ; pharmacology ; Drugs, Chinese Herbal ; isolation & purification ; pharmacology ; Humans ; Osteoblasts ; drug effects ; Osteoclasts ; cytology ; metabolism ; Osteogenesis ; drug effects ; Osteosarcoma ; enzymology ; pathology ; Phytoestrogens ; isolation & purification ; pharmacology ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Rats ; Rats, Wistar

Cajanus cajan L. is a natural plant, which contains a lot of potential active components. In the present study, we identified the effects of the stilbene extract from Cajanus cajan L. (sECC) on hepatic cholesterol metabolism in diet-induced (for 4 weeks) hyperlipidemic Kunming mice. All experimental mice were divided into 5 groups: control group, high lipid model group, sECC-treated with 200 or 100 mg kg(-1), and simvastatin (Sim, 12 mg kg(-1)) treated group. The mice were fed with fat and cholesterol-enriched chow except control mice that were fed with standard diet. The effects of sECC were investigated by monitoring serum and liver lipid profile (i. e. cholesterol homeostasis) in mice. To further explore the mechanism of sECC, hepatic cholesterol 7alpha-hydroxylase (CYP7A1) and low density lipoprotein (LDL) receptor expressions in cholesterol homeostasis were analyzed by reverse transcription PCR. After 4 weeks pretreatment, the mice in the high lipid model group showed markedly higher serum and hepatic lipid contents than control group (P< 0.01). Compared with high lipid model group, the increased serum and hepatic lipid contents were markedly attenuated by sECC (200 mg kg(-1)), the serum and hepatic total cholesterol were reduced by 31.5% and 22.7% (P<0.05), respectively. The triglyceride contents of serum and liver were also lowered by 23.0% and 14.4%, respectively. At the same times, serum LDL cholesterol decreased by 53.0% (P<0.01). The mRNA expressions of hepatic CYP7A1 and LDL-receptor were significantly enhanced in the mice administered with sECC (200 mg kg(-1)), whereas those expressions were suppressed by the fat and cholesterol-enriched diet. These data indicate that sECC reduces the atherogenic properties of dietary cholesterol in mice. It is indicated that expression enhancement of hepatic LDL-receptor and cholesterol 7alpha-hydroxylase may be responsible for the hypercholesterolemic effect.
Animals ; Anticholesteremic Agents ; isolation & purification ; pharmacology ; Body Weight ; drug effects ; Cajanus ; chemistry ; Cholesterol ; blood ; metabolism ; Cholesterol 7-alpha-Hydroxylase ; biosynthesis ; genetics ; Cholesterol, LDL ; blood ; Drugs, Chinese Herbal ; isolation & purification ; pharmacology ; Gene Expression Regulation ; Hypercholesterolemia ; blood ; genetics ; metabolism ; pathology ; Liver ; metabolism ; pathology ; Male ; Mice ; Organ Size ; drug effects ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; RNA, Messenger ; metabolism ; Receptors, LDL ; biosynthesis ; genetics ; Stilbenes ; isolation & purification ; pharmacology ; Triglycerides ; blood ; metabolism