Citation: Xu Kuo, Feng Zi-Ming, Jiang Jian-Shuang, Yang Ya-Nan, Zhang Pei-Cheng. Sesquiterpenoid and C₁₄-polyacetylene glycosides from the rhizomes of Atractylodes lancea[J]. Chinese Chemical Letters, ;2017, 28(3): 597-601. doi: 10.1016/j.cclet.2016.10.036 shu

Sesquiterpenoid and C₁₄-polyacetylene glycosides from the rhizomes of Atractylodes lancea

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China

Corresponding author: Zhang Pei-Cheng, pczhang@imm.ac.cn
Received Date: 8 August 2016
Revised Date: 24 September 2016
Accepted Date: 13 October 2016
Available Online: 2 March 2016

Figures(6)

Four new glycosides including a eudesmane-type sesquiterpenoid (1), a guaiane-type sesquiterpenoid (2), and two C₁₄-polyacetylenes (3, 4) were isolated from the rhizomes of Atractylodes lancea. Their structures were elucidated by means of spectroscopic and spectrometric analyses (UV, IR, 1D and 2D NMR, and HR-ESIMS). The absolute configurations of their aglycones were established based on the experimental and calculated electronic circular dichroism (ECD), whereas those of monosaccharide moieties were determined by the GC method after chiral derivatization. Compound 4 showed weak anti-inflammatory effects on the LPS-induced NO production in microglia BV2 cells at a concentration of 10 μmol L^-1.
- Atractylodes lancea,
- Eudesmane-type sesquiterpenoid,
- Guaiane-type sesquiterpenoid,
- C₁₄-Polyacetylene,
- Anti-inflammatory effect
1. [1]
  Chinese Pharmacopoeia Commission, Chinese Pharmacopoeia, vol.Ⅰ, China Medical Science Press, Beijing, 2015, pp. 161-162.
2. [2]
  Koonrungsesomboon N., Na-Bangchang K., Karbwang J.. Therapeutic potential and pharmacological activities of Atractylodes lancea (Thunb.) DC[J]. Asia Pac. J. Trop. Med., 2014,7:421-428. doi: 10.1016/S1995-7645(14)60069-9
3. [3]
  Meng H., Li G.Y., Dai R.H.. Chemical constituents of Atractylodes chinensis (DC.) Koidz[J]. Biochem. Syst. Ecol., 2010,38:1220-1223. doi: 10.1016/j.bse.2010.12.023
4. [4]
  Resch M., Steigel A., Chen Z.L., Bauer R.. 5-Lipoxygenase and cyclooxygenase-1 inhibitory active compounds from Atractylodes lancea[J]. J. Nat. Prod., 1998,61:347-350. doi: 10.1021/np970430b
5. [5]
  Resch M., Heilmann J., Steigel A., Bauer R.. Further phenols and polyacetylenes from the rhizomes of Atractylodes lancea and their anti-inflammatory activity[J]. Planta Med., 2001,67:437-442. doi: 10.1055/s-2001-15817
6. [6]
  Wang H.X., Liu C.M., Liu Q., Gao K.. Three types of sesquiterpenes from rhizomes of Atractylodes lancea[J]. Phytochemistry, 2008,69:2088-2094. doi: 10.1016/j.phytochem.2008.04.008
7. [7]
  Lehner M.S., Steigel A., Bauer R.. Diacetoxy-substituted polyacetylenes from Atractylodes lancea[J]. Phytochemistry, 1997,46:1023-1028. doi: 10.1016/S0031-9422(97)00342-7
8. [8]
  Meng H., Li G.Y., Dai R.H.. Two new polyacetylenic compounds from Atractylodes chinensis (DC.) Koidz[J]. J. Asian Nat. Prod. Res., 2011,13:346-349. doi: 10.1080/10286020.2011.557662
9. [9]
  Xu K., Jiang J.S., Feng Z.M.. Bioactive sesquiterpenoid and polyacetylene glycosides from Atractylodes lancea[J]. J. Nat. Prod., 2016,79:1567-1575. doi: 10.1021/acs.jnatprod.6b00066
10. [10]
  Kamauchi H., Kinoshita K., Takatori K.. New sesquiterpenoids isolated from Atractylodes lancea fermented by marine fungus[J]. Tetrahedron, 2015,71:1909-1914. doi: 10.1016/j.tet.2015.02.041
11. [11]
  Snatzke G.. Circulardichroismus-Ⅸ:modifizierung der octantenregel für α, β-ungesättigte ketone:transoide enone[J]. Tetrahedron, 1965,21:421-438. doi: 10.1016/S0040-4020(01)98283-3
12. [12]
  Gawronski J.K.. Circular dichroism and stereochemistry of chiral conjugated cyclohexenones[J]. Tetrahedron, 1982,38:3-26. doi: 10.1016/0040-4020(82)85040-0
13. [13]
  Yu Y., Gao H., Dai Y.. Guaiane-type sesquiterpenoid glucosides from Gardenia jasminoides Ellis[J]. Magn. Reson. Chem., 2011,49:258-261. doi: 10.1002/mrc.v49.5
14. [14]
  He J., Shen Y., Jiang J.S.. New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities[J]. Carbohydr. Res., 2011,346:1903-1908. doi: 10.1016/j.carres.2011.06.015
15. [15]
  He J.Y., Zhu S., Komatsu K.. HPLC/UV analysis of polyacetylenes, phenylpropanoid and pyrrolidine alkaloids in medicinally used Codonopsis species[J]. Phytochem. Anal., 2014,25:213-219. doi: 10.1002/pca.v25.3
16. [16]
  Gan M.L., Liu M.T., Gan L.S.. Dammarane glycosides from the root of Machilus yaoshansis[J]. J. Nat. Prod., 2012,75:1373-1382. doi: 10.1021/np300310a
17. [17]
  Hara S., Okabe H., Mihashi K.. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4-(R)-carboxylates[J]. Chem. Pharm. Bull., 1987,35:501-506. doi: 10.1248/cpb.35.501
18. [18]
  Feng Z.M., Song S., He J.. Acyl glycosides with rare β-D-apiofuranosyl-β-D-glucopyranosyl-β-D-apiofuranosyl from Erycibe hainanesis[J]. Carbohydr. Res., 2013,380:59-63. doi: 10.1016/j.carres.2013.07.011
19. [19]
  Shen Y., Feng Z.M., Jiang J.S., Yang Y.N., Zhang P.C.. Dibenzoyl and isoflavonoid glycosides from Sophora flavescens:inhibition of the cytotoxic effect of Dgalactosamine on human hepatocyte HL-7702[J]. J. Nat. Prod., 2013,76:2337-2345. doi: 10.1021/np400784v
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Sesquiterpenoid and C14-polyacetylene glycosides from the rhizomes of Atractylodes lancea

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Sesquiterpenoid and C₁₄-polyacetylene glycosides from the rhizomes of Atractylodes lancea