Deacetylasperulosidic acid

Deacetylasperulosidic acid
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
CAS Number	14259-55-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	10232875 ;
PubChem CID	44153559;
UNII	00399V6E44 ;
CompTox Dashboard (EPA)	DTXSID10931538 ;
	InChI 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 Key: ZVXWFPTVHBWJOU-YYFGDFGFSA-N ; 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;
	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;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[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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