Sesquiterpenoids from the Fruits of Alpinia oxyphylla and Their Anti‐Acetylcholinesterase Activity

Fourteen sesquiterpenoids were isolated from the fruits of Alpinia oxyphylla Miq . Their structures were elucidated based on NMR analyses (¹H, ¹³C, DEPT, ¹H,¹H‐COSY, HMQC, HMBC, and NOESY) and identified as 12‐nornootkaton‐6‐en‐11‐one ( 3 ), (+)‐(3S,4aS,5R)‐2,3,4,4a,5,6‐hexahydro‐3‐isopropenyl‐4a,5‐dimethyl‐1,7‐naphthoquinone ( 5 ), nootkatene ( 6 ), 9β‐hydroxynootkatone ( 7 ), 2β‐hydroxy‐δ‐cadinol ( 8 ), 4‐isopropyl‐6‐methyl‐1‐tetralone ( 11 ), oxyphyllone E ( 12 ), oxyphyllone D ( 13 ), oxyphyllanene B ( 15 ), oxyphyllone A ( 16 ), oxyphyllol E ( 17 ), (9E)‐humulene‐2,3;6,7‐diepoxide ( 18 ), mustakone ( 20 ), and pubescone ( 21 ). Among them, 3 was a new norsesquiterpenoid, 8 was a new natural product, and 5, 6, 11, 20, 21 were isolated from A. oxyphylla for the first time. Twenty sesquiterpenoids, 1 – 5 and 7 – 21 , were investigated for their in vitro acetylcholinesterase (AChE) inhibitory activities, including previously isolated seven sesquiterpenoids from A. oxyphylla, (11S)‐12‐chloronootkaton‐11‐ol ( 1 ), (11R)‐12‐chloronootkaton‐11‐ol ( 2 ), nootkatone ( 4 ), oxyphyllenodiol A ( 9 ), oxyphyllenodiol B ( 10 ), 7‐epiteucrenone B ( 14 ), and alpinenone ( 19 ). TLC‐Bioautographic assay indicated that 1 – 4, 7, 14, 16, 18, 19 , and 21 displayed anti‐AChE activities at 10 nmol. Microplate assay confirmed that 19, 18, 16 , and 21 displayed moderate‐to‐weak anti‐AChE activities at the concentration of 100 μM , and 19 was the most potent inhibitor with an IC₅₀ value of 81.6±3.5 μM . The presence of anti‐AChE sesquiterpenoids in A. oxyphylla may partially support the traditional use of this fruit for the treatment of dementia.     

Cytotoxic activity and molecular docking of a novel biflavonoid isolated from Jacaranda acutifolia (Bignoniaceae)

A novel biflavonoid [kaempferol (6→8″) apigenin] was isolated from the leaves of Jacaranda acutifolia. The structure was elucidated based on chemical evidence, 1D and 2D spectroscopic analyses as well as spectrometric techniques. The compound showed promising cytotoxic activity against breast cancer cell line MCF-7. The anticancer activity was explained via virtual docking of the isolated compound to the main sites in the human cyclin-dependent kinase2 (CDK2) crystal structure.     

益智及其种植区土壤中汞含量研究

采用氢化物原子荧光法测定了益智种植区土壤与益智各部位中的痕量汞,比较了HNO3＋HF＋H2O2、HNO3＋HF、HNO3＋HClO43种混酸消解体系的消解效果。结果表明,HNO3＋HF＋H2O2为最佳消解体系;样品加标回收率为93．70％～102．25％;土壤及益智果实、根、茎、叶中汞含量分别为0．3583、0．1632、0．0950、0．0700、0．0747mg·kg^-1,土壤中汞在益智果实、根、茎、叶间的迁移率分别为45．55％、26．51％、19．52％、20．83％,土壤及益智各部位的汞含量均在国家规定标准以内。说明海南益智种植区地理环境良好,未受到汞污染。     

气相色谱-质谱法检测益智药材中16种多环芳烃

建立了气相色谱-质谱联用技术同时测定益智药材中16种多环芳烃(PAHs)的分析方法.最佳萃取条件为:取样品2.0 g,加入同位素内标后用无水乙醇、水混合溶解,以10 mL正己烷提取;提取液先过Flo-risil柱固相萃取,经氢氧化钾-乙醇溶液皂化,多环芳烃分子印迹柱固相萃取后,以5 mL二氯甲烷-正己烷(1 ∶ 1,体...     

Antioedematogenic activity,acetylcholinesterase inhibition and antimicrobial properties of Jacaranda oxyphylla

Jacaranda oxyphylla Cham. (Bignoniaceae) is a shrub found in the Brazilian cerrado and used in folk medicine to treat microbial infections. The aim of this study was to carry out a phytochemical screening and evaluate antioedematogenic, antimicrobial and antiacetylcholinesterase properties of J. oxyphylla crude extracts. All extracts analysed showed presence of terpenoids, which are potentially active chemical substances. A high AChE inhibitory activity for hexane extract from leaves and for the extracts from twigs was found. Ethanol extract from leaves of J. oxyphylla showed activity against Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative (Escherichia coli) bacteria. This extract was also effective in inhibiting the stages of inflammation evaluated. Biological investigation and phytochemical screening of J. oxyphylla extracts provided additional evidence of its traditional medicinal value.     

Three Unusual New Sesquiterpenes from Alpinia oxyphylla

Two new norcadinene sesquiterpenes oxyphyllones C and D ( 1 and 2 , resp.), and one new 1,10‐secoguaiane sesquiterpene, (+)‐mandassidion ( 3 ), together with two known compounds, oxyphyllenodiol B ( 4 ) and (1R,2R)‐p‐menth‐3‐ene‐1,2‐diol ( 5 ), were isolated from the fruits of Alpinia oxyphylla. Their structures were determined on the basis of spectroscopic analysis, including 2D‐NMR spectroscopic techniques. Compounds 1, 2 , and 3 exhibited no cytotoxicity against three cancer cell lines.     

益智红外指纹图谱的研究

益智产区的鉴别对于药材市场的质量控制以及提高药材的质量显得极为重要。益智为我国四大南药之一, 主要药效成分是诺卡酮和益智酮。红外指纹图谱用于中药质量控制研究有着良好的发展前景,借助红外光谱的指纹特性,以八种益智精油红外指纹图谱的共有峰率和变异峰率为指标,计算了样品相对于该标准品的共有峰率和变异峰率, 并按照共有峰率、变异峰率的大小建立了不同的序列。结果表明：广东、广西和海南的益智油红外图谱比较吻合,但也存在一定的差异。益智油的红外图谱特征峰为1 710和1 666 cm-1 ,广东和海南的益智油的红外指纹图谱(400～4 000 cm-1)共有峰率为62%,广西和海南的共有峰率为52%,海南的益智油共有峰率为66%～84%。从多维共有峰率和变异峰率双指标序列分析法可以对不同产地具有准确、精细且非常直观的鉴别能力, 该方法可以准确地区别不同产地的益智。     

Composition and antimicrobial activity of the essential oil from the branches of Jacaranda cuspidifolia Mart. growing in Sichuan,China

This study represents the first report on the chemical composition and antimicrobial activity of the essential oil from the branches of Jacaranda cuspidifolia Mart. Thirty-three compounds were identified by Gas Chromatography-Mass Spectrometry (GC-MS) and the major constituents of the essential oil were Palmitic acid (31.36%), (Z) ? 9,17-Octadecadienal (12.06%), Ethyl palmitate (3.81%), Perhydrofarnesyl acetone (2.07%), γ-Maaliene (1.88%), and Cedro (1.42%) and 9,12-Octadecadienoic acid ethyl ester (1.42%). The in vitro antimicrobial activities of the essential oil were evaluated by the disc diffusion method, and the inhibition zones against Escherichia coli, Staphylococcus aureus and Candida albicans were 7.10, 8.20 and 7.25 mm, respectively. The oil showed moderate activities against E. coli, S. aureus and C. albicans with minimum inhibition concentration (MIC) values of 17.3 mg/mL, 12.9 mg/mL and 16.0 mg/mL, respectively.     

Eudesmane and Eremophilane Sesquiterpenes from the Fruits of Alpinia oxyphylla with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells

Alpinia oxyphylla Miquel (Zingiberaceae) has been reported to show antioxidant, anti-inflammatory, and neuroprotective effects. In this study, two new eudesmane sesquiterpenes, 7α-hydroperoxy eudesma-3,11-diene-2-one (1) and 7β-hydroperoxy eudesma-3,11-diene-2-one (2), and a new eremophilane sesquiterpene, 3α-hydroxynootkatone (3), were isolated from the MeOH extract of dried fruits of A. oxyphylla along with eleven known sesquiterpenes (4–14). The structures were elucidated by the analysis of 1D/2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and optical rotation data. Compounds (1–3, 5–14) were evaluated for their protective effects against tert-butyl hydroperoxide (tBHP)-induced oxidative stress in adipose-derived mesenchymal stem cells (ADMSCs). As a result, treatment with isolated compounds, especially compounds 11 and 12, effectively reverted the damage of tBHP on ADMSCs in a dose-dependent manner. In particular, 11 and 12 at 50 µM improved the viability of tBHP-toxified ADMSCs by 1.69 ± 0.05-fold and 1.61 ± 0.03-fold, respectively.     

Phytochemical studies on the Australian native plant species Acacia pycnantha and Jacaranda mimosifolia D.Don*

In ongoing investigations into colours in Nature, the chemical constituents from the flowers of Acacia pycnantha and Jacaranda mimosifolia D.Don grown in Australia are reported. Eight known secondary metabolites were isolated from the A. pycnantha flower including isosalipurposide (7) which may be responsible for their distinctive colouration. Nine secondary metabolites were isolated from the J. mimosifolia D.Don flower including the new phenylethanoid β-D-glucopyranose (10). All isolated compounds were inactive against bacteria tested at concentration of 32 μg/mL.