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(12) United States Patent (10) Patent No.: US 7,582,677 B2 Korte Et Al

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(12) United States Patent (10) Patent No.: US 7,582,677 B2 Korte Et Al US007582677B2 (12) United States Patent (10) Patent No.: US 7,582,677 B2 Korte et al. (45) Date of Patent: Sep. 1, 2009 (54) LIGNAN FORMULATIONS JP 6-016525 1, 1994 JP 9-013031 1, 1997 (75) Inventors: Helena Korte, Turku (FI); Veli-Matti JP 9-0954.17 4f1997 JP 10-279432 10, 1998 Lehtola, Turku (FI); Mikko Unkila, JP 10-279461 10, 1998 Littoinen (FI); Mervi Hilovaara-Teijo, JP 10-279462 10, 1998 Riihikoski (FI); Markku Ahotupa, JP 10-279485 10, 1998 Turku (FI) JP 11-255639 9, 1999 WO WO 88,03800 6, 1988 (73) Assignee: Hormos Medical Corp., Turku (FI) WO WO 98.21946 5, 1998 WO WOOO. 59.946 10, 2000 (*) Notice: Subject to any disclaimer, the term of this WO WOO1,03687 1, 2001 patent is extended or adjusted under 35 WO WOO1,08651 2, 2001 U.S.C. 154(b) by 727 days. WO WOO1,08652 2, 2001 (21) Appl. No.: 10/513,218 OTHER PUBLICATIONS Cabral et al., “Effects of Some Lignans and Neolignans on the Devel (22) PCT Filed: May 15, 2003 opment and Excretion of Rhodnius Prolixus.” 71 Fitoterapia 1-9 (Feb. 2000) (Abstract). (86). PCT No.: PCT/FO3/00375 Ekman, "Analysis of Lignans in Norway Spruce by Combined Gas Chromatography Mass Spectrometry.” 30 Holzforschung 79-85 S371 (c)(1), (1976). (2), (4) Date: Nov. 3, 2004 Ito Ryuhei. “Antioxidant.” JP 2000 129256 Patent Abstracts of Japan Publication (May 9, 2000). (87) PCT Pub. No.: WO04/000304 Oikarinen et al., Chemopreventive Activity of Crude Hydroxymatairesinol (HMR) Extract in Apec'" Mice, 161 Cancer PCT Pub. Date: Dec. 31, 2003 Letters 253–258 (2000). Saarinen et al., “Hydroxymatairesinol, a Novel Enterolactone Pre (65) Prior Publication Data cursor With Antitumor Properties From Coniferous Tree (Picea abies).” 36 Nutrition and Cance 207-216 (2000). US 2005/O169947 A1 Aug. 4, 2005 Midori et al., “Anti-Tumor-Promoting Activity of Lignans from the Aerial Part of Saussurea Medusa,” 158 Cancer Letters 53-59 (Sep. (30) Foreign Application Priority Data 2000) (Abstract). Prieto et al., “Diphyllin Acetylapioside, a 5-lipoxygenase Inhibitor Jun. 19, 2002 (FI) .................................. 20021184 from Haplophyllum Hispanicum.” 137 Chemical Abstracts 304484 (2002). (51) Int. Cl. Mori et al., "Lignan Glycosides in Germinating Sesame Seeds as A6 IK3I/34 (2006.01) Anti-Aging Cosmetic Raw Materials.” 136 Chemical Abstracts (52) U.S. Cl. ........................ 514/.461; 514/844; 514/947 299429 (2002). (58) Field of Classification Search ................. 514/718, * cited by examiner 514/731, 754, 461, 844, 947; 424/401 See application file for complete search history. Primary Examiner Taylor Victor Oh (74) Attorney, Agent, or Firm—James C. Lydon (56) References Cited U.S. PATENT DOCUMENTS (57) ABSTRACT 4,708,964 A 1 1/1987 Allen ......................... 514,533 A topical formulation which includes alignan or lignan ester 5,276,060 A 1/1994 Neiss et al. ................. 514,731 in a dermatologically acceptable vehicle. The formulation 6,271,257 B1 8/2001 Mutanen ..................... 514,461 can be either a cosmetic formulation or a pharmaceutical 6,689,809 B2 * 2/2004 Ahotupa et al. ............. 514,473 formulation. FOREIGN PATENT DOCUMENTS EP O 297 733 1, 1989 3 Claims, No Drawings US 7,582,677 B2 1. 2 LGNAN FORMULATIONS No topical preparations, either for cosmetic or pharmaceu tical use, comprising lignans, especially lignans which can be This application is a U.S. National Stage of International derived from wood in great quantities, or lignans or lignan application PCT/FI2003/000375, filed May 15, 2003. derivatives, such as phenolic esters, manufactured from Such wood-derivable lignans, have been described in the art. FIELD OF THE INVENTION SUMMARY OF THE INVENTION This invention relates to topical formulations comprising lignans or lignan esters, either as active ingredients to One object of the present invention is to provide topical improve the health and/or physical appearance of the skin, or 10 formulations comprising lignans or esters thereof as active as preservatives or stabilizers for other active ingredients or ingredients, either for cosmetic or pharmaceutical use. vehicles in topical formulations. Another object is to provide topical formulations compris ing lignans or esters thereof, active as preservatives or stabi BACKGROUND OF THE INVENTION lizers for other active ingredients and/or vehicle components, 15 wherein said formulations are useful either as cosmetics or pharmaceuticals. The publications and other materials used herein to illumi Thus, the present invention concerns a topical formulation nate the background of the invention, and in particular, cases comprising an active agent, which is alignan oralignan ester, to provide additional details respecting the practice, are incor in a dermatologically acceptable vehicle, wherein the active porated by reference. agent is Lignans are phenolic-compounds widely distributed in i) alignan selected from the group consisting of hydroxy plants. They can be found in different parts (roots, leafs, stem, matairesinol, lariciresinol, secoisolariciresinol, isolar seeds, fruits) but mainly in Small amounts. In many sources iciresinol, oxomatairesinol, alpha-conidendrin, liovil, (seeds, fruits), lignans are found as glycosidic conjugates picearesinol, Syringaresinol or nortrachelogenin, or associated with fiber component of plants. The most common dietary sources of mammalian lignan precursors are unre 25 ii) alignan ester of formula (I) fined grain products. The highest concentrations in edible plants have been found in flaxseed, followed by unrefined (I) grain products, particularly rye. CHO OCH Considerable amounts of lignans are also found in conif erous trees. The type of lignans differs in different species and 30 the amounts of lignans vary in different parts of the trees. The typical lignans in heartwood of Norway spruce (Picea abies) - - - or formula (II) are hydroxymatairesinol (HMR), alpha-conidendrin, alpha R R conidendric acid, matairesinol, isolariciresinol, secoisolar (II) iciresinol, liovil, picearesinol, lariciresinol and pinoresinol 35 (Ekman R: Distribution of lignans in Norway spruce. Acta Academiae Aboensis, Ser B, 39:1–6, 1979). The far most abundant single component of lignans in Ry-CS spruce is HMR, about 60 percent of total lignans, which occurs mainly in unconjugated free form. Plant lignans Such 40 as hydroxymatairesinol, matairesinol, lariciresinol and sec wherein L is a lignan skeleton, which optionally includes a oisolariciresinol, are converted by gut microflora to mamma bridge forming a ring with one of the phenyl groups in the lian lignans, enterolactone or enterodiol. The mammalian formulae, and L in formula (I) is a lignan skeleton of any of lignans can also be manufactured synthetically (MB Groen the lignans hydroxymatairesinol, matairesinol, lariciresinol, 45 secoisolariciresinol, isolariciresinol, oxomatairesinol, alpha and J Leemhius, Tetrahedron Letters 21, 5043, 1980). conidendrin, pinoresinol, liovil, picearesinol, arctigenin, Lignans are known to possess beneficial effects on human Syringaresinol or nortrachelogenin and L in formula (II) is a health. The health benefits obtained with lignan rich dietare, lignan skeleton of enterodiol or enterolactone; for example, decreased risk for various cancers and cardio R is H or methoxy; vascular diseases (Adlercreutz (1998) Phytoestrogens and 50 R is methyl, R' CO or R' SO in both of the phenyl human health, In: Reproductive and Developmental Toxicol groups in (I) and (II) or ogy (edited by Korach, K.). pp. 299-371, Marcel & Dekker, R is H in one of the phenyl groups in (I) or (II) and methyl, NY). R" CO - or Lignans, such as hydroxymatairesinol, WO 00/59946, R' SO - in the other phenyl group; have also been reported to inhibit lipid peroxidation and LDL 55 oxidation and thus be useful as antioxidants. wherein Also lignans other than hydroxymatairesinol have power R" is a C to C alkyl, alkenyl, arylalkyl, aralkenyl, or an ful antioxidant and anti-inflammatory potential. The antioxi aromatic group, and R" is unsubstituted or substituted with one or more hydroxy dant action involves all the major free radicals such as Super groups and/or oxide anions and peroxyl radicals (K Prasad: Antioxidant 60 activity of secoisolariciresinol diglucoside-derived metabo one or more carboxyl groups, an oxo group or an amino lites, secoisolariciresinol, enterodiol and enterolactone. Int J grOup, Angiology 9:220-225 (2000)). or a geometric isomer or a stereoisomer thereof, According to studies, lignans may also prevent skin can provided that cers (Thompson L. U. (1993): Potential health benefits and 65 R is methyl only in a single R-O- Substituent in a com problems associated with antinutrients in foods. Food Res. pound of formula (I) where L is a skeleton of the lignan Int. 26, 131-149). arctigenin, and US 7,582,677 B2 3 4 R is other than acetyl or propionyl if the lignan ester is a The ester is preferable a phenolic ester, more preferable a compound of formula (II). phenolic diester. Especially preferable are phenolic esters where the ester groups are the same. DETAILED DESCRIPTION OF THE INVENTION Preferable diphenolic esters are, for example, esters of mono- or dicarboxylic fatty acids, hydroxy acids and Sulfonic acids. As examples of suitable dicarboxylic acid esters can be Definitions: mentioned succinates, glutarates, and malonic acid esters. A “topical formulation” refers to a composition intended to Lactic acid esters are examples of esters with hydroxySubsti be directly laid onto or spread on the surface of skin. tuted acids. Tartaric acid and citric acid esters are examples of A "dermatologically acceptable vehicle' refers to excipi 10 esters of acids with several carboxylic groups and one or more ents that are suitable for use in direct contact with human hydroxy groups. tissues without undue adverse effects or toxicity, and that Particularly preferable lignan esters to be added into topi further is compatible with other components in the formula cal formulations are aliphatic fatty acid diesters of lignans. tion. Good aesthetic properties are also needed when said Such lignan esters may be Superior with regard to miscibility formulation is intended for cosmetic purposes.
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