Sabinyl Acetate,the Main Component of Juniperus sabina L'Hérit. Essential Oil,is Responsible for Antiimplantation Effect

The essential oil of Juniperus sabina , containing 50% sabinyl acetate, was administered s.c. to mice at doses of 15, 45 and 135 mg/kg either on days 0–4 of pregnancy (implantation period) or on days 8–11 (organogenesis) to investigate its mechanism of action. The mice were killed on days 9 and 17 respectively. Subsequently to the previous assays, sabinyl acetate was injected s.c. at a dose of 70 mg/kg, corresponding to the higher dose of essential oil, on days 0–4, the mice being killed on day 9. The number of prominent corpora lutea and implantation sites were recorded for mice killed on day 9. The uterine content of those killed on day 17 were examined and the fetuses removed and examined for malformations. Treatment with the oil on days 0–4 prevented pregnancy in half the mice treated with the two higher doses. The same pattern was observed with sabinyl acetate (70 mg/kg). In contrast, treatment with the oil on days 8–11 did not impair fertility, nor did it increase the incidence of malformations compared with the results obtained for the control group. This result indicates that the abortifacient effect of Juniperus sabina essential oil is related to an implantation inhibiting effect, induced by sabinyl acetate, the mechanism of which is being investigated.     

A bioactivity guided study on the antidiabetic activity of Juniperus oxycedrus subsp. oxycedrus L. leaves

Ethnopharmacological relevance

Juniperus (Cupressaceae) species are widely used as folk medicine in spreading countries. Decoction of Juniperus oxycedrus subsp. oxycedrus L. leaves is used internally to lower blood glucose levels in Turkey.

Aim of the study

To determine hypoglycaemic and antidiabetic activities of Juniperus oxycedrus subsp. oxycedrus leaves and to identify active compounds through bioactivity guided isolation technique.

Materials and methods

Ethanol and water extracts of Juniperus oxycedrus subsp. oxycedrus (Joso), leaves on oral administration were studied using in vivo models in normal, glucose-hyperglycemic and streptozotocin-induced diabetic rats. Through in vivo bioactivity-guided fractionation processes, a nonpolar fraction was separated from the n-hexane subextract by silica gel column chromatography as the main active fraction. Subfractions of this fraction was found to possess antidiabetic activity and their chemical composition was investigated by GC-FID and GC–MS, simultaneously.

Results

This is the first report on the antidiabetic constituents of Joso leaves. Fatty acids, such as palmitic, linoleic and linolenic acid were found as the major compounds in subfractions.

Conclusion

Results indicated that Joso leaf extract and its active constituents might be beneficial for diabetes mellitus.     

沙地柏多酚的纯化及其抗氧化活性测定

目的：提高沙地柏多酚的纯化程度并考察其抗氧化活性。方法：采用Folin-Ciocalteu法测定沙地柏的多酚含量,经筛选用HPD-700大孔树脂纯化沙地柏多酚。通过对沙地柏多酚,1,1-二苯基-2-三硝基苯肼(DPPH)自由基、超氧阴离子、羟自由基的清除能力、总抗氧化能力及三价铁离子（Fe³⁺）还原能力的测定来评价其抗氧化能力。结果：经纯化后,沙地柏多酚纯度由0.53‰提高到9.95‰。抗氧化活性测定结果表明,沙地柏多酚对DPPH自由基的抑制率和Fe³⁺还原能力的维生素C当量质量浓度分别为9.4 μg/ml、30.09 μg/ml,对超氧阴离子和羟自由基的清除能力分别为151.83 U/ml、204.59 U/ml,总抗氧化能力为72.68 U/ml。结论：沙地柏多酚具有较强的抗氧化活性,值得进一步研究其药理作用。     

巨柏茎叶的萜类成分（英文）

目的：对巨柏（Cupressus gigantea）茎叶的化学成分进行研究。方法：采用硅胶和 Sephadex LH-20 柱色谱的方法分离和纯化化合物, 通过 NMR, MS 及理化性质鉴定化合物结构。结果：从巨柏茎叶分离得到 15 个 labdane-type二萜, 其中一个为新化合物, 分别为：15-methoxy-18-hydroxylabda-8（17）,13-diene （1）, 13-epitoruolsol （2）, labd-8（17）,14-dien-13-ol （3）, 13-epi-cupressic acid （4）, cis-communic acid （5）, trans-communic acid （6）, labd-15-aceoxy-8（17）,13E-dien （7）, labd-8（17）,13E-dien-15-ol （8）, isocupressic acid （9）, acetylisocupressic acid （10）, isoabienol （11）, 13-oxo-14,15-dinor-labd-8（17）-en-19-oic acid （12）, pimarenic acid （13）, sandaracopimaric acid （14）, and pimarol （15） 此外还有两个已知倍半萜 ent-oplopanone （16） 和 （＋）-T-Cadinol （17）。结论：化合物（1）为新的倍半萜, 所有化合物均为首次从该植物中分得。     

Cloning and expression of a major allergen from Cupressus arizonica pollen, Cup a 3, a PR-5 protein expressed under polluted environment

BACKGROUND: This paper describes the cloning and expression of the Cupressus arizonica pollen protein Cup a 3. In addition, we present its modulation under polluted environmental conditions. Species of the Cupressaceae family are important because of their high sensitization prevalence. METHODS: Cup a 3 cloning is based on the sequence of the homologous protein Jun a 3. Cup a 3 was expressed with good yield in the methylotropic yeast Pichia pastoris. RESULTS: Recombinant Cup a 3 (rCup a 3) contains 199 amino acids, 10 potential phosphorylation sites and no glycosylation sites. By immunoblot 63% of cypress allergic patients had specific immunoglobulin E antibodies against rCup a 3 (n = 104). This major allergen is homologous to members of the pathogenesis-related proteins (PR-5 group) and contributes to the overall allergenicity of C. arizonica pollen. Our results show that the increased expression of Cup a 3 is dependent on the pollution in the area where the pollen has been collected, being higher under polluted conditions. CONCLUSIONS: Cup a 3 is a PR-5 protein derived from C. arizonica pollen. The expression of the protein under polluted conditions has a direct incidence on the pollen allergenicity, as has been demonstrated by skin tests and Radioallergosorbent test inhibition.     

干香柏的化学成分研究

目的:研究我国特有柏科植物干香柏(Cupressus duolouxianaHickel)的化学成分,为阐明其有效成分提供依据。方法:利用各种色谱技术进行分离,根据化合物的光谱数据和理化常数鉴定其结构。结果:从干香柏枝叶的乙醇提取物中分离得到6个化合物,分别是(7S,8S)-3-甲氧基-3′,7-环氧-8,4′-氧化新木脂素-4,9,9′-三醇((7S,8S)-3-methoxy-3′,7-epoxy-8,4′-oxyneoligna-4,9,9′-triol,Ⅰ),山柰素(kaempferol,Ⅱ),槲皮素(quercetin,Ⅲ),胡桃宁(juglanin,Ⅳ),槲皮素-3′-甲氧基-3-O-α-L-阿拉伯呋喃糖苷(quercetin-3′-methoxy-3-O-α-L-arabinofuranoside,Ⅴ)和槲皮素-3-O-α-L-阿拉伯呋喃糖苷(avicularin,Ⅵ)。结论:所有化合物均为首次从该植物中分离得到。     

Growth inhibitory activity of biflavonoids and diterpenoids from the leaves of the Libyan Juniperus phoenicea against human cancer cells

Three biflavonoids [cupressuflavone ( 1 ), amentoflavone ( 2 ), and sumaflavone ( 3 )], four diterpenoids [13‐epi‐cupressic acid ( 4 ), imbricatholic acid ( 5 ), 3‐hydroxy‐sandaracopimaric acid ( 6 ), and dehydroabietic acid ( 7 )], and one lignan [β‐peltatin methyl ether ( 8 )] were isolated from the cytotoxic fractions of the extracts of the leaves of the Libyan Juniperus phoenicea L. The structures of these compounds were elucidated by spectroscopic means. Cytotoxicity of compounds 1 – 6 were assessed against the human lung cancer cell line A549 using the MTT assay. Compounds 1 and 3 showed cytotoxicity against the A549 cells (IC₅₀ = 65 and 77 μM, respectively), whereas compound 2 did not show any activity. Diterpenes 4 – 6 exhibited weak cytotoxicity against the A549 cells with the IC₅₀ values of 159, 263, and 223 μM, respectively. The cytotoxicity of each compound was compared with the anticancer drug, etoposide (IC₅₀ = 61 μM). Cupressuflavone ( 1 ) was evaluated also for cytotoxicity against both the human PC3 cancer cell line and the normal prostate cell line (PNT2), and this compound revealed a high degree of cytotoxic selectivity towards the prostate cancer cells (PC3), with IC₅₀ value of 19.9 μM, without any evidence of cytotoxicity towards the normal prostate cell line (PNT2).     

Juniperus oxycedrus: A new allergenic pollen from the Cupressaceae family

Background: Cupressaceae allergy is a worldwide pollinosis caused by several species. Some species in limited geographic areas pollinate in fall and winter. Juniperus oxycedrus matches these features. Objective: We sought to define the immunochemical, allergologic, and environmental aspects of J. oxycedrus pollen. Methods: Pollen extract from J. oxycedrus was prepared and characterized by biochemical analysis and human specific IgE binding by means of ELISA and immunoblotting. A 3-year phenological study was conducted to define the pollinating period of J. oxycedrus. Forty consecutive patients allergic to cypress were recruited in two areas and divided into two groups according to their exposure to J. oxycedrus pollen. Clinical evaluation, skin prick tests, and specific IgE determination with J. oxycedrus, J. ashei, and Cupressus arizonica extracts were carried out on both groups. Results:J. oxycedrus pollen extract was obtained, and it showed specific IgE binding and wide cross-reactivity with other Cupressaceae species. The extract caused a positive skin test response in all the patients tested, with about 80% of them having detectable specific IgE. Symptoms related to J. oxycedrus pollen exposure were recorded in 72% of the directly exposed patients and occasionally in 9% of the nonexposed patients. In the Mediterranean coastal area considered, J. oxycedrus was the first Cupressaceae species that started to pollinate at the beginning of November and ended in the first part of December. Conclusions:J. oxycedrus represents a newly characterized pollen species of the Cupressaceae family that cross-reacts with other members of the same family. Subjects with cypress allergy have in vivo and in vitro positive test responses for J. oxycedrus and can show symptoms when exposed to its pollen. Finally, the most important feature of J. oxycedrus is its early pollinating period in southern Europe (Italy), causing a further extension of the cypress pollen season in areas where other Cupressaceae species are present. (J Allergy Clin Immunol 1998;101:755-61.)     

Further antibacterial diterpenes from the bark and leaves of Juniperus procera hochst. ex Endl

The bark of Juniperus procera yielded three antibacterial diterpenoids, (+)-E-communic acid (1), (+)-Z-communic acid (2) and (+)-totarol (3). Compound 2 exhibited significant activity against Gram-positive bacteria, while 1 was found to be less active. Compound 3, on the other hand, demonstrated potent activity against Mycobacterium organisms, while its corresponding 3β-hydroxy-derivative 4 was found to be inactive. The chromatographic separation of (+)-Z-communic acid (2) from (+)-E-communic acid (1) and those previously unreported spectral data of 1 and 2 are described. In addition, the leaves yielded (+)-8α-acetoxyelemol, β-peltatin A methyl ether and deoxypodophyllotoxin.