24 June 2015, Volume 5 Issue 3

    

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Review
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  Sugar Derivatives of Morphine: A New Window for the Development of Potent Anesthetic Drugs

  Shyamal K. Jash, Dilip Gorai

  Natural Products and Bioprospecting. 2015, 5(3): 111-127. https://doi.org/10.1007/s13659-015-0060-8

  Abstract ( 6887) Download PDF ( 11308 )   Knowledge map   Save

  This review provides a short account of carbohydrate derivatives of an important natural drug, morphine, along with their comparative efficacies as anesthetic agent. Sugar derivatives are found to have more prospect as anesthetic drug than morphine itself owing to their enhanced bioavailability. Synthetic schemes of these sugar derivatives and information on related patents are also included in this manuscript.
Original article
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  Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents

  Kun Wei, Gang-Qiang Wang, Xue Bai, Yan-Fen Niu, He-Ping Chen, Chun-Nan Wen, Zheng-Hui Li, Ze-Jun Dong, Zhi-Li Zuo, Wen-Yong Xiong, Ji-Kai Liu

  Natural Products and Bioprospecting. 2015, 5(3): 129-157. https://doi.org/10.1007/s13659-015-0062-6

  Abstract ( 8040) Download PDF ( 17373 )   Knowledge map   Save

  The unusual fused β-lactone vibralactone was isolated from cultures of the basidiomycete Boreostereum vibrans and has been shown to significantly inhibit pancreatic lipase. In this study, a structure-based lead optimization of vibralactone resulted in three series of 104 analogs, among which compound C1 exhibited the most potent inhibition of pancreatic lipase, with an IC₅₀ value of 14 nM. This activity is more than 3000-fold higher than that of vibralactone. The effect of compound C1 on obesity was investigated using high-fat diet(HFD)-induced C57BL/6 J obese mice. Treatment with compound C1 at a dose of 100 mg/kg significantly decreased HFD-induced obesity, primarily through the improvement of metabolic parameters, such as triglyceride levels.
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  A Triterpenoid Inhibited Hormone-Induced Adipocyte Differentiation and Alleviated Dexamethasone-Induced Insulin Resistance in 3T3-L1 adipocytes

  Ji-Huan Qin, Jun-Zeng Ma, Xing-Wei Yang, Ying-Jie Hu, Juan Zhou, Lin-Chun Fu, Ru-Hua Tian, Shan Liu, Gang Xu, Xiao-Ling Shen

  Natural Products and Bioprospecting. 2015, 5(3): 159-166. https://doi.org/10.1007/s13659-015-0063-5

  Abstract ( 7297) Download PDF ( 10984 )   Knowledge map   Save

  6α-Hydroxylup-20(29)-en-3-on-28-oic acid(1), a natural triterpenoid, was found to possess the ability in a dose-dependent manner inhibiting hormone-induced adipocyte differentiation in 3T3-L1 preadipocytes, and restoring glucose consuming ability in dexamethasone(DXM)-induced insulin resistant 3T3-L1 adipocytes. Compound 1 was also found to ameliorate DXM-induced adipocyte dysfunction in lipolysis and adipokine secretion. Mechanistic studies revealed that 1 inhibited adipocyte differentiation in 3T3-L1 preadipocytes via down-regulating hormone-stimulated gene transcription of peroxisome proliferator-activated receptor γ and CCAAT-enhancer-binding protein alpha which are key factors in lipogenesis, and restored DXM-impaired glucose consuming ability in differentiated 3T3-L1 adipocytes via repairing insulin signaling pathway and activating down-stream signaling transduction by phosphorylation of signaling molecules PI3K/p85, Akt2 and AS160, thus leading to increased translocation of glucose transporter type 4 and transportation of glucose.
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  Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)

  Frank Surup, Eric Kuhnert, Elena Liscinskij, Marc Stadler

  Natural Products and Bioprospecting. 2015, 5(3): 167-173. https://doi.org/10.1007/s13659-015-0065-3

  Abstract ( 7791) Download PDF ( 11517 )   Knowledge map   Save

  A culture isolated from ascospores of Hypoxylon rickii, a xylariaceous ascomycete collected in Martinique, had yielded botryane, noreremophilane and abietane-type terpenoids in a preceding study, but additional metabolites were detected by extensive HPLC-MS analysis in other fractions. Herein we report the further isolation of four new sesquiterpenoids with a silphiperfol-6-ene skeleton from extracts of H. rickii. The planar structures were elucidated by NMR and HRMS data as 13-hydroxysilphiperfol-6-ene(1), 9-hydroxysilphiperfol-6-en-13-oic acid(2), 2-hydroxysilphiperfol-6-en-13-oic acid(3) and 15-hydroxysilphiperfol-6-en-13-oic acid(4). For compounds 2-4 we propose the trivial names rickinic acids A-C. Their stereochemistry was assigned by ROESY correlations as well as by the specific optical rotation. Additionally, the known compounds, botryenanol, dehydrobotrydienol, cyclo(Phe-Pro), cyclo(Pro-Leu),(+)-ramulosin and aeleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported.
Erratum
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  Erratum to: New Dimeric and seco-Abietane Diterpenoids from Salvia wardii

  Qiu-Li Xiao, Fan Xia, Xing-Wei Yang, Yang Liao, Li-Xin Yang, Yu-Kun Wei, Xian Li, Gang Xu

  Natural Products and Bioprospecting. 2015, 5(3): 175-175. https://doi.org/10.1007/s13659-015-0061-7

  Abstract ( 6996) Download PDF ( 10523 )   Knowledge map   Save

  In the HTML version of the original publication, the graphical abstract was inadvertently omitted. The graphical abstract is given in this erratum.