Deacetylasperulosidic acid

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Deacetylasperulosidic acid
Deacetylasperulosidic acid structure.png
Names
IUPAC name
(1S,4aS,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
Other names
10-Deacetylasperulosidic acid; 10-Desacetylasperulosidic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C16H22O11/c17-2-5-1-7(19)10-6(14(23)24)4-25-15(9(5)10)27-16-13(22)12(21)11(20)8(3-18)26-16/h1,4,7-13,15-22H,2-3H2,(H,23,24)/t7-,8+,9+,10-,11+,12-,13+,15-,16-/m0/s1 X mark.svgN
    Key: ZVXWFPTVHBWJOU-YYFGDFGFSA-N X mark.svgN
  • InChI=1/C16H22O11/c17-2-5-1-7(19)10-6(14(23)24)4-25-15(9(5)10)27-16-13(22)12(21)11(20)8(3-18)26-16/h1,4,7-13,15-22H,2-3H2,(H,23,24)/t7-,8+,9+,10-,11+,12-,13+,15-,16-/m0/s1
    Key: ZVXWFPTVHBWJOU-YYFGDFGFBO
  • O=C(O)C1=CO[C@@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@]3([H])[C@]1([H])[C@@H](O)C=C3CO
Properties
C16H22O11
Molar mass 390.341 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Deacetylasperulosidic acid is an iridoid compound found in a few medicinal plants, such as Morinda citrifolia . [1] Some in vitro and in vivo bioactivities of deacetylasperulosidic acid include anti-inflammatory, analgesic, anti-cancer, antioxidant, anti-arthritic, anti-mutagenic, anti-clastogenic, and hepatoprotection. [2] [3] [4] [5] [6]

References

  1. ↑ Potterat O, Von Felten R, Dalsgaard PW, Hamburger M (2007). "Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived products". J. Agric. Food Chem. 55 (18): 7489–7494. doi:10.1021/jf071359a. PMID   17696360.
  2. ↑ Akihisa, T; Matsumoto, K; Tokuda, H; Yasukawa, K; Seino, K; Nakamoto, K; Kuninaga, H; Suzuki, T; Kimura, Y (2007). "Anti-inflammatory and potential cancer chemopreventive constituents of the fruits of Morinda citrifolia (Noni)". Journal of Natural Products. 70 (5): 754–7. doi:10.1021/np068065o. PMID   17480098.
  3. ↑ Liu, G; Bode, A; Ma, WY; Sang, S; Ho, CT; Dong, Z (2001). "Two novel glycosides from the fruits of Morinda citrifolia (noni) inhibit AP-1 transactivation and cell transformation in the mouse epidermal JB6 cell line". Cancer Research. 61 (15): 5749–56. PMID   11479211.
  4. ↑ Ling, SK; Tanaka, T; Kouno, I (2003). "Effects of iridoids on lipoxygenase and hyaluronidase activities and their activation by beta-glucosidase in the presence of amino acids" (PDF). Biological & Pharmaceutical Bulletin. 26 (3): 352–6. doi: 10.1248/bpb.26.352 . PMID   12612446.
  5. ↑ Kim DH, Lee HJ, Oh YJ, Kim MJ, Kim SH, Jeong TS, Baek NI (2005). "Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidation". Arch Pharm Res. 28 (10): 1156–1160. doi:10.1007/BF02972979. PMID   16276972. S2CID   11924214.
  6. ↑ Nakamura, T; Nakazawa, Y; Onizuka, S; Satoh, S; Chiba, A; Sekihashi, K; Miura, A; Yasugahira, N; Sasaki, YF (1997). "Antimutagenicity of Tochu tea (an aqueous extract of Eucommia ulmoides leaves): 1. The clastogen-suppressing effects of Tochu tea in CHO cells and mice". Mutation Research. 388 (1): 7–20. doi:10.1016/s1383-5718(96)00096-4. PMID   9025787.
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