:Deacetylasperulosidic acid

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 419403279

| ImageFile = Deacetylasperulosidic acid structure.png

| ImageSize = 180px

| IUPACName = (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

| OtherNames = 10-Deacetylasperulosidic acid; 10-Desacetylasperulosidic acid

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 14259-55-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 00399V6E44

| PubChem = 44153559

| SMILES = 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

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 10232875

| 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

| InChIKey = ZVXWFPTVHBWJOU-YYFGDFGFBO

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZVXWFPTVHBWJOU-YYFGDFGFSA-N

}}

| Section2 = {{Chembox Properties

| C=16 | H=22 | O=11

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Deacetylasperulosidic acid is an iridoid compound found in a few medicinal plants, such as Morinda citrifolia.{{cite journal | doi = 10.1021/jf071359a |vauthors=Potterat O, Von Felten R, Dalsgaard PW, Hamburger M | title = Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived products | journal = J. Agric. Food Chem. | year = 2007 | volume = 55 | issue = 18 | pages = 7489–7494 | pmid = 17696360}} 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.{{cite journal | last1 = Akihisa | first1 = T | last2 = Matsumoto | first2 = K | last3 = Tokuda | first3 = H | last4 = Yasukawa | first4 = K | last5 = Seino | first5 = K | last6 = Nakamoto | first6 = K | last7 = Kuninaga | first7 = H | last8 = Suzuki | first8 = T | last9 = Kimura | first9 = Y | title = Anti-inflammatory and potential cancer chemopreventive constituents of the fruits of Morinda citrifolia (Noni) | journal = Journal of Natural Products | volume = 70 | issue = 5 | pages = 754–7 | year = 2007 | pmid = 17480098 | doi = 10.1021/np068065o }}{{cite journal | last1 = Liu | first1 = G | last2 = Bode | first2 = A | last3 = Ma | first3 = WY | last4 = Sang | first4 = S | last5 = Ho | first5 = CT | last6 = Dong | first6 = Z | title = Two novel glycosides from the fruits of Morinda citrifolia (noni) inhibit AP-1 transactivation and cell transformation in the mouse epidermal JB6 cell line. | journal = Cancer Research | volume = 61 | issue = 15 | pages = 5749–56 | year = 2001 | pmid = 11479211}}{{cite journal | doi = 10.1248/bpb.26.352 | last1 = Ling | first1 = SK | last2 = Tanaka | first2 = T | last3 = Kouno | first3 = I | title = Effects of iridoids on lipoxygenase and hyaluronidase activities and their activation by beta-glucosidase in the presence of amino acids. | journal = Biological & Pharmaceutical Bulletin | volume = 26 | issue = 3 | pages = 352–6 | year = 2003 | pmid = 12612446| url = http://naosite.lb.nagasaki-u.ac.jp/dspace/bitstream/10069/8383/1/BPBul26_352.pdf | doi-access = free }}{{cite journal | doi = 10.1007/BF02972979 |vauthors=Kim DH, Lee HJ, Oh YJ, Kim MJ, Kim SH, Jeong TS, Baek NI | title = Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidation | journal = Arch Pharm Res | year = 2005 | volume = 28 | pages = 1156–1160 | issue = 10|pmid=16276972 |s2cid=11924214 }}{{cite journal | last1 = Nakamura | first1 = T | last2 = Nakazawa | first2 = Y | last3 = Onizuka | first3 = S | last4 = Satoh | first4 = S | last5 = Chiba | first5 = A | last6 = Sekihashi | first6 = K | last7 = Miura | first7 = A | last8 = Yasugahira | first8 = N | last9 = Sasaki | first9 = YF | title = Antimutagenicity of Tochu tea (an aqueous extract of Eucommia ulmoides leaves): 1. The clastogen-suppressing effects of Tochu tea in CHO cells and mice | journal = Mutation Research | volume = 388 | issue = 1 | pages = 7–20 | year = 1997 | pmid = 9025787 | doi=10.1016/s1383-5718(96)00096-4}}