Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2000-09-26
2001-12-25
Carr, Deborah D (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C514S544000, C514S885000, C426S648000
Reexamination Certificate
active
06333421
ABSTRACT:
FIELD OF INVENTION
This invention relates to novel capsaicinoid-like substances with an ester linkage, and to a food and pharmaceutical compositions comprising said substances.
PRIOR ART
Capsicum annuum L
. species, peppers, have been used worldwide as foods, spices and medicines. The major pungent components contained in them are capsaicin, (E)-N-[(4-hydroxy-3-methoxyphenyl)-methyl]-8-methyl-6-nonenamide, and dihydrocapsaicin, i.e., 6.7-dihydro derivative of capsaicin. Further, more than 12 other capsaicinoids have been found as minor pungent components such as nordihydrocapsaicin (that contains one less methylene group than dihydrocapsaicin), homocapsaicin (that contains one more methylene group than capsaicin) and homodihydrocapsaicin (that contains one more methylene group than dihydrocapsaicin).
Up to now, it has been found that capsaicin has many physiological activities such as promotion of adrenal catecholamine secretion so as to enhance the oxidation of fatty acids and to inhibit obesity (Buck, S. H.; Burks, T. F. ,
Phamacol. Rev.,
1986, 38, 179-226, Suzuki, T.; Iwai, K.,
Chemistry and Pharmacology,
1984, Vol.23, 1984, Szolcsanyi, J.,
Handbook of Experimental Pharmacology
, Vol.60, 1982).
However, since capsaicin has a strong pungency and nociceptive activity, it can not be used in a large amount and its usage as a food additive or a drug is considerably limited.
Several studies have reported that several non-pungent capsaicinoids as well as capsaicin have physiological activities such as promotion or enhancement of adrenal catecholamine secretion (Watanabe, T.; Kawada, T.; Kato, T.; Harada,T.; Iwai, K.,
Life Sci.,
1994, 54, 369-374). Since these capsaicinoids have no pungent components, it may be expected that they may be used as food additives and pharmaceutical ingredients.
It has been reported that the fruits of a non-pungent fixed variety of pepper, named “CH-19 sweet” (an introduction number at Kyoto Univ., Agr. Dept., vegetables and horiculture laboratory) which had been selected and fixed from a pungent fixed variety of pepper, “CH-19”, obtained in Thailand, contain only a small amount of capsaicinoids, but a considerable amount of capsaicinoid-like substances (CLSs) (Yazawa,S.; Suetome,N.; Okamoto,K.; Namiki,T., J. Japan Soc. Hort. Sci., 1989, 58, 601-607).
The present inventors have now tried a structural analysis of the capsaicinoid-like substances contained in the CH-19 sweet, and succeeded in their identification to complete the present invention.
SUMMARY OF THE INVENTION
The present invention relates to novel capsaicinoid-like substances represented by the following general formula:
The present capsaicinoid-like substances (Formula I) are characterized in that they consist of a branched non-saturated fatty acid that is combined via an ester linkage with vanillyl alcohol, whereas the prior capsaicinoids consist of a branched non-saturated fatty acid that is combined via an amide linkage with vanillyl alcohol.
The present capsaicinoid-like substances (Formula II) are those whose fatty acid moiety has been saturated.
In these formulae, the value “n” is preferably 3, 4 or 5, the structural formulae wherein said value is 4 are shown as follows:
DETAILED EXPLANATION OF THE INVENTION
Since the present capsaicinoid-like substances have no pungency and substantially no cytotoxicity, they may be used as food additives or pharmaceutical ingredients that show a variety of physiological activities such as enhancing energy metabolism and potentiating an immune system.
Further, the present capsaicinoid-like substances have a possibility to be used as food additives or pharmaceutical ingredients for enhancing endurance capacity in continuous excises, or as a non-narcotic analgesic.
Accordingly, the present invention relates to a food composition comprising said capsaicinoid-like substances. The present food composition may take any form such as solid, liquid, sol, gel, powder and granule, and it may be prepared by any method known in the art.
An amount of the present capsaicinoid-like k contained in the food composition may be optionally determined by those skilled in the art, depending on the purpose of their formulation, and the kind, form and purpose of the food composition, and the like. For example, the capsaicinoid-like substances may be comprised in an amount of at least 10
−5
% by weight in chocolate.
It is not necessary to purify the present capsaicinoid-like substances to be comprised in the food composition. Thus, the food composition may comprise the non-pungent fixed variety of pepper, “CH-19” per se, its dried and pulverized material or its extract with various solvents that are conventionally used in the art, for example, ethyl acetate, alcohols such as ethanol, and emulsifiers used for food stuff.
The present invention relates to a pharmaceutical composition comprising said capsaicinoid-like substances as well. The present pharmaceutical composition may take any form known in the art, such as solution buffered with various salts and buffers, suspension, emulsion and the like.
Buffering salts include alkali and alkaline earth metal salts, phosphate and sulfate. For example, citrate, phosphate, HEPES, Tris-hydroxy aminomethane may be used in a physiologically acceptable concentration.
The present pharmaceutical composition may be formulated in any form in addition to the above liquid ones, such as tablet, powder, sol, gel, granule and an embedded one with liposome.
In formulation, any excipients and additives known in the art may be used in a pharmaceutically acceptable amount. The amount of the capsaicinoid-like substances comprised in the pharmaceutical composition may be optionally determined by those skilled in the art, depending on the properties of other ingredients, the purpose of use, the age and weight of a patient, and effects required, and the like.
The present pharmaceutical composition may be administered by various routes depending on its formulation, form and the like, such as orally, intraveneously, subcutaneously, intramuscularly, intraperitonealy, pharyngonasally, etc.
Fushiki Tohru
Hashizume Shuichi
Imai Masatake
Kobata Kenji
Setoguchi Yuko
Carr Deborah D
Morinaga & Co., Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
LandOfFree
Capsaicinoide-like substances having ester bond does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Capsaicinoide-like substances having ester bond, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Capsaicinoide-like substances having ester bond will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2556800