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US 2011 0033525A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0033525 A1 Liu (43) Pub. Date: Feb. 10, 2011 (54) DITERPENE GLYCOSIDES AS NATURAL A63L/05 (2006.01) SOLUBLIZERS A6II 3L/22 (2006.01) A6II 3/343 (2006.01) (76) Inventor: Zhijun Liu, Baton Rouge, LA (US) A63L/436 (2006.01) A638/3 (2006.01) Correspondence Address: A63L/366 (2006.01) PATENT DEPARTMENT A63L/352 (2006.01) TAYLOR, PORTER, BROOKS & PHILLIPS, A6II 35/60 (2006.01) LLP A63/496 (2006.01) P.O. BOX 2471 A63L/45 (2006.01) BATON ROUGE, LA 70821-2471 (US) B82Y5/00 (2011.01) (52) U.S. Cl. ......... 424/450; 514/777: 514/449; 514/283; (21) Appl. No.: 12/937,055 514/627: 514/568: 514/27: 514/679; 514/458: 514f731: 514f678; 424/94.1 : 514/468: 514/29: (22)22) PCT Fled:1. Apr.pr. 13,15, 2009 514/31; 514/291;s 514/20.5:s 514/450,s 514/463:s s 977/773;977/915 S371 (c)(1), 57 ABSTRACT (2), (4) Date: Oct. 8, 2010 (57) Several diterpene glycosides (e.g., rubusoside, rebaudioside, Related U.S. Application Data Steviol monoside and Stevioside) were discovered to enhance (60) Provisional application No. 61/044,176, filed on Apr. thenally solubility important of acompounds, number of pharmaceuticallyincluding but not and limited medici to, 11, 2008, provisional application No. 61/099,823, paclitaxel, camptothecin, curcumin, tanshinone HA, capsai filed on Sep. 24, 2008. cin, cyclosporine, erythromycin, nystatin, itraconazole, and O O celecoxib. The use of the diterpene glycoside rubusoside Publication Classification increased solubility in all tested compounds. The diterpene (51) Int. Cl. glycosides are a naturally occurring class of water solubility A 6LX 9/27 (2006.01) enhancing compounds that are non-toxic and that will be A6 IK 47/26 (2006.01) useful as new complexing agents or excipients in the phar A6 IK3I/337 (2006.01) maceutical, agricultural (e.g., Solubilizing pesticides), cos A6 IK 3/4375 (2006.01) metic and food industries. Aqueous solutions by using rubu A6 IK3I/I65 (2006.01) soside to increase the solubility of otherwise insoluble drugs A6 IK3I/92 (2006.01) will have several new routes of administration. In addition, A6 IK3I/7048 (2006.01) aqueous solutions of therapeutic compounds with rubusoside A6 IK 3L/2 (2006.01) were shown to retain the known pharmacological activity of A 6LX 3L/355 (2006.01) the compounds. OH Gallic acid 170 Gallotannin Patent Application Publication Feb. 10, 2011 Sheet 1 of 23 US 2011/0033525 A1 999u?UunºunO Patent Application Publication Feb. 10, 2011 Sheet 2 of 23 US 2011/0033525 A1 HI‘61-I L IL’61-I | Patent Application Publication Feb. 10, 2011 Sheet 3 of 23 US 2011/0033525 A1 O H?O Hõ? WIL’61-I HOºp|OJOWN?uÐÁIod XII,’61-I SOº, ºHOOOOºH Patent Application Publication Feb. 10, 2011 Sheet 4 of 23 US 2011/0033525 A1 HO OL‘61-I >|-61-I HOO || Patent Application Publication Feb. 10, 2011 Sheet 5 of 23 US 2011/0033525 A1 LI‘61-I AL‘61-I O SI‘61-I Patent Application Publication Feb. 10, 2011 Sheet 6 of 23 US 2011/0033525 A1 OH OH OH HO OH OH Fig. 2 Patent Application Publication Feb. 10, 2011 Sheet 7 of 23 US 2011/0033525 A1 OH OH HO OH Fig. 3 Patent Application Publication Feb. 10, 2011 Sheet 8 of 23 US 2011/0033525 A1 HO OH Fig. 4 Patent Application Publication Feb. 10, 2011 Sheet 9 of 23 US 2011/0033525 A1 OH OH HO OH bH Steviomonoside OH OII Paniculoside IV OH OH HO CH-O OH "OH Suavioside A Suavioside B OH Suavioside C, OH OH OH O H O N I HC C OH Suavioside E OH HO IO Suavioside D, HO Suavioside D, OH OH OH OH OH OH OH O OH OI HO I HO OH OH I C=O OH Suavioside G OH Suavioside H Suavioside F HO HO OH OH OH OH OII H) OI HO Suavioside OH SuavioSide J OH HO OII Patent Application Publication Feb. 10, 2011 Sheet 10 of 23 US 2011/0033525 A1 O O O N O-7 O cy N 3 o C O O ca C 3 C O SP L N OC g T 5 Y-O 2 O III S. O O T III 8 O-O O Y-O O O C C O 9. O O O bS I O O r P N 2 CD O O O O w C N 5 c)I- III co 9 O 3 CD C 9 III. 3 O-O C CD O Y-O 1 O O C : O Patent Application Publication Feb. 10, 2011 Sheet 11 of 23 US 2011/0033525 A1 0'07 W Patent Application Publication Feb. 10, 2011 Sheet 12 of 23 US 2011/0033525 A1 O O v S s v O o v v O LO O is S 9 X - v s O N c\ O O O O v C O O O O O O O O O O O CO N. CO O s CY) CN r SIleo |OJ)uOOJO UAOJ6 JOlueOued Patent Application Publication Feb. 10, 2011 Sheet 13 of 23 US 2011/0033525 A1 O O O r O X - 5 S O H.X S.O) O)S. SR SR O O O CC < n n- O S on 3. O S C in E CD CD C O O O O O O O O O O CO CO r CN v uMOJ6 ||eo |OJuOOJOlueoel Patent Application Publication Feb. 10, 2011 Sheet 14 of 23 US 2011/0033525 A1 Patent Application Publication US 2011/0033525 A1 |||-61-I CO f W Patent Application Publication Feb. 10, 2011 Sheet 16 of 23 US 2011/0033525 A1 ZL‘61-I W Patent Application Publication Feb. 10, 2011 Sheet 17 of 23 US 2011/0033525 A1 Sg5 s W Patent Application Publication Feb. 10, 2011 Sheet 18 of 23 US 2011/0033525 A1 |\ 1(|) ? |\, y],'61-I ? x|,?|| W Patent Application Publication Feb. 10, 2011 Sheet 19 of 23 US 2011/0033525 A1 W Patent Application Publication Feb. 10, 2011 Sheet 20 of 23 US 2011/0033525 A1 00°02 |OJOdOld 9|-61-I W Patent Application Publication Feb. 10, 2011 Sheet 21 of 23 US 2011/0033525 A1 3 S.g 34: ce ------ W Patent Application Publication Feb. 10, 2011 Sheet 22 of 23 US 2011/0033525 A1 O969 8|-61-I (C&126 W Patent Application Publication Feb. 10, 2011 Sheet 23 of 23 US 2011/0033525 A1 80 W US 2011/0033525 A1 Feb. 10, 2011 DITERPENE GLYCOSDES AS NATURAL ing or reducing these limitations are needed for the formula SOLUBLIZERS tions of pharmaceutical, cosmetic, agricultural chemicals, and foods products. 0004 Diterpenes. Taxanes are diterpenes produced by the 0001 (In countries other than the United States:) The ben plants of the genus Taxus (yews) such as the Pacific Yew efit of the 11 Apr. 2008 filing date of U.S. provisional patent (Taxus brevifolia) in the family of Taxaceae. Taxanes include application 61/044,176 and the benefit of the 24 Sep. 2008 paclitaxel and docetaxel. Paclitaxel is the anti-cancer drug filing date of Unites States provisional patent application under the drug name of TAXOL(R) and docetaxel is used under 61/099,823 are claimed under applicable treaties and conven the name of TAXOTERE(R) (Medicinal Natural Products. A tions. (In the United States:) The benefit of the 11 Apr. 2008 Biosynthetic Approach, 1997, John Wiley & Sons, Chiches filing date of U.S. provisional patent application 61/044, 176 ter, England; pp 186-188). Paclitaxel is a known anti-cancer and the benefit of the 24 Sep. 2008 filing date of Unites States diterpenoid alkaloid and is not soluble in water. The structure provisional patent application 61/099,823 are claimed under of paclitaxel is shown in FIG. 1H. Therapeutic solutions of 35 U.S.C. S 119(e) in the United States. paclitaxel currently contain either an oil or dehydrated alco hol or both; or paclitaxel is bound to albumin. None of these TECHNICAL FIELD formulations are true water solutions. Other taxanes include baccatin III, 10-deacetylbaccatin III, cephalomannine, and 0002 This invention pertains to new uses for diterpene 10-deacetylcephalomannine. These taxanes are characterized glycosides as non-toxic, natural solubilizers for use in pre with a four-membered oxetane ring and a complex ester side paring aqueous Solutions of various drugs, agricultural chain in their structures. All taxane compounds have poor chemicals, cosmetics, and foods. water solubility. (U.S. Patent Application Publication no. 2007/0032438). Other medicinally important, but insoluble BACKGROUND ART or poorly soluble diterpenes include retinoids (vitamin A, retinol (vitamin A1), dehydroretinol (vitamin A2), retinoic Important Compounds Insoluble in Water acid, 13-cis-retinoic acid and other retinol derivatives, 0003 Poor aqueous solubility is a common obstacle to ginkgolides, and forsakolin (a promising drug for the treat delivering pharmaceuticals or other bioactive compounds and ment of glaucoma, congestive heart failure, and bronchial is a major challenge in formulating new drug products. In a asthma). study of kinetic aqueous solubility of commercial drugs, 87% 0005 Quinoline alkaloids. Quinoline alkaloids are alka were found to have solubility in water of 265 lug/mL and loids that possess quinoline in their structures and are terpe 7%s20 ug/mL (Lipinski, C., et al., Adv. Drug Deliv. Rev. noid indole alkaloid modifications. Camptothecins isolated (1997) 23:3-25). The minimum acceptable aqueous solubility from the Camptotheca acuminata trees (Family Nyssaceae) for a drug is about 52 ug/mL Solubility based on 1 mg/kg are quinoline alkaloids.
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  • Different Approaches to Evaluate Tannin Content and Structure of Selected Plant Extracts – Review and New Aspects M

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    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by JKI Open Journal Systems (Julius Kühn-Institut) Journal of Applied Botany and Food Quality 86, 154 - 166 (2013), DOI:10.5073/JABFQ.2013.086.021 1University of Kiel, Institute of Crop Science and Plant Breeding – Grass and Forage Science / Organic Agriculture, Kiel, Germany 2Institute of Ecological Chemistry, Plant Analysis and Stored Product Protection; Julius Kühn-Institute, Quedlinburg, Germany Different approaches to evaluate tannin content and structure of selected plant extracts – review and new aspects M. Kardel1*, F. Taube1, H. Schulz2, W. Schütze2, M. Gierus1 (Received July 2, 2013) Summary extracts, tannins, salts and derivates was imported to the EU in the year 2011, mainly from Argentina, with a trade value of nearly Tannins occur in many field herbs and legumes, providing an im- 63.5 mio. US Dollar (UN-COMTRADE, 2013). These extracts are pro- mense variability in structure and molecular weight. This leads to duced industrially on a large scale. They could therefore maintain complications when measuring tannin content; comparability of a relatively constant quality and thus provide an advantage in rumi- different methods is problematic. The present investigations aimed at nant feeding. characterizing four different tannin extracts: quebracho (Schinopsis Tannins from different sources can react very diverse regarding lorentzii), mimosa (Acacia mearnsii), tara (Caesalpinia spinosa), protein affinity (MCNABB et al., 1998; BUENO et al., 2008). Diffe- and gambier (Uncaria gambir) and impact of storage conditions. rences in tannin structure can occur even between similar plant Using photometrical methods as well as HPLC-ESI-MS, fundamen- species (OSBORNE and MCNEILL, 2001; HATTAS et al., 2011) and a tal differences could be determined.
  • Anticancer Mechanisms of Flaxseed and Its Derived Mammalian

    Anticancer Mechanisms of Flaxseed and Its Derived Mammalian

    ANTICANCER MECHANISMS OF FLAXSEED AND ITS DERIVED MAMMALIAN LIGNAN ENTEROLACTONE IN LUNG A Dissertation Submitted to the Graduate Faculty of the North Dakota State University of Agriculture and Applied Science By Shireen Chikara In Partial Fulfillment of the Requirements for the Degree of DOCTOR OF PHILOSOPHY Major Program: Cellular and Molecular Biology April 2017 Fargo, North Dakota North Dakota State University Graduate School Title ANTICANCER MECHANISMS OF FLAXSEED AND ITS DERIVED MAMMALIAN LIGNAN ENTEROLACTONE IN LUNG By Shireen Chikara The Supervisory Committee certifies that this disquisition complies with North Dakota State University’s regulations and meets the accepted standards for the degree of DOCTOR OF PHILOSOPHY SUPERVISORY COMMITTEE: Dr. Katie Reindl Chair Dr. Jane Schuh Dr. Yeong Rhee Dr. Steven Qian Approved: 04-13-2017 Dr. Jane Schuh Date Department Chair ABSTRACT Whole flaxseed and its derived lignans have shown anti-cancer properties in a variety of malignancies. However, their potential remains uninvestigated in lung cancer, the leading cause of cancer-related deaths worldwide. We investigated the anti-tumor effects of flaxseed-derived mammalian lignan enterolactone (EL) in human lung cancer cell cultures and the chemopreventive potential of 10% whole flaxseed in a mouse model of lung carcinogenesis. We found that EL inhibits in vitro proliferation and motility of a panel of non-small cell lung cancer cell (NSCLC) lines. EL-mediated inhibition in lung cancer cell proliferation was due to a decrease in mRNA and protein expression levels of G1-phase cell cycle promoters and a simultaneous increase in mRNA and protein expression levels of p21WAF1/CIP1, a negative regulator of the G1-phase.