Bioprocess for the high-yield production of food...

Details Bioprocess for the high-yield production of food... Bioprocess for the high-yield production of food...

1999-12-21

2001-12-25

Lankford, Jr., Leon B. (Department: 1651)

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing oxygen-containing organic compound

C435S132000, C435S136000, C435S148000, C560S122000, C426S534000

Reexamination Certificate

active

06333180

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention concerns a microbial process for production of compositions of matter containing isomers of jasmonic acid having the structure:
which are flavor acceptable as well as isomers having the structure:
which are also flavor acceptable. This invention is also concerned with the production of methyl jasmonate isomers from the aforementioned jasmonic acid isomers.
Considerable time and effort have been expended by microbiologists in the search for better processes for the production of jasmonic acid and methyl jasmonate which are flavor acceptable isomers, including those isomers defined according to the structure:
wherein R is methyl or hydrogen. Thus, Broadbent in United Kingdom Patent Specification No. 1,286,266 published on Aug. 23, 1972 discloses and claims a process for the manufacture of jasmonic acid which comprises cultivation of the organism
Lasiodiplodia theobromae
in a nutrient medium containing an assimilable source of carbon and an assimilable source of nitrogen followed by isolation of the product from the culture medium. Günther, et al, German Democratic Republic Patent DD 279 688 published on Jun. 13, 1990 discloses a process for the production of 7-iso-jasmonic acid by strains of the organism
Botryodiplodia theobromae
in aerobic culture. This work is also discussed in the paper Miersch, et al,
Phytochemistry
, Volume 26, No. 4, pages 1037-1039, 1987, entitled “(+)-7-ISO-JASMONIC ACID AND RELATED COMPOUNDS FROM BOTRYODIPLODIA THEOBROAME.” The organisms,
Botryodiplodia theobromae
and
Lasiodermea theobromae
are synonyms of
Diplodia gossypina
as discussed in the paper Jones, MYCOTAXON, Volume VI, No. 1 at pages 24-26, July-September 1997 (title: “THE CURRENT TAXONOMIC STATUS OF DIPLODIA GOSSYPINA.” As confirmed by Häusler and Münch in the article entitled “Microbial Production of Natural Flavors,” Volume 63, No. 10, ASM News at pages 551-559:
“Another plant fatty acid metabolite, jasmonic acid, an endogenous plant growth regulator with a variety of physiological functions, is produced by means of a similar metabolic pathway. After a lipoxygenase produces a hydroperoxide derivative of linolenic acid, this compound is converted to its allene oxide, which cyclizes. &bgr;-Oxidation and double-bond reduction yields jasmonic acid. The methylester of jasmonic acid is not only a volatile plant hormone, possibly involved in interplant communication, but is also an important flavor and fragrance molecule that imparts a sweet-floral, jasmine-like note . . .
Otto Miersch and his collaborators at the Institute of Plant Biochemistry, Halle-Saale, Germany, who were studying fungal plant pathogens, including
Botryodiplodia theobromae
, discovered that such microorganisms produce jasmonic acid. The biosynthetic steps leading to jasmonic acid in this filamentous fungus are probably similar to those found in plants. Recently our laboratory, which is evaluating this strain's capacity for producing jasmonic acid, found that
B. theobromae
yields only very low concentrations of jasmonic acid in liquid culture. Such findings suggest that the biosynthesis and excretion of jasmonic acid is strictly controlled during the growth cycle of this fungus on plants in its natural habitat.”no bioprocesses for the high yield production of fruit flavor-acceptable jasmonic acid or methyl jasmonate exist. The Häusler and Münch paper was published in October 1997
. ASM News
is published by the American Society for Microbiology.
Thus, in the flavor and fragrance art, a need has arisen for the development and efficient high yield production of naturally occurring jasmonic acid and methyl jasmonate, which have heretofore been found to be useful and necessary for the creation of flavor formulations used in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpaste, medicinal products, chewing tobaccos and smoking tobaccos and also useful in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and the like).
Methyl jasmonate (without indicating which isomer) is disclosed by Arctander,
Perfume and Flavor Chemicals
at monograph 2093 to have a “Powerful floral-herbaceous, sweet-tenacious odor representing typical background notes of Jasmin absolute.” Arctander further discloses that this material “is an almost obvious candidate for work on improved artificial Jasmin absolute.” Acree, et al,
J. Agric. Food Chem
., 1985, Volume 33, pages 425-427, discloses that the isomer of methyl jasmonate having the structure:
and having an optical rotation (&agr;
D
20
) of +58 has a strong odor, whereas the other stereoisomers of (Z)-methyl jasmonate are substantially odorless.
No specific disclosures exist in the prior art showing the use of the jasmonic acid isomers of our invention defined according to the structure:
or defined according to the structure:
for use as flavor adjuvants (wherein R is methyl or hydrogen). Furthermore, nothing in the prior art discloses the stereoisomer of the compound having the structure:
particularly the stereoisomer having the optical rotation (&agr;
D
20
) of +58°.
THE INVENTION
Our invention relates to a bioprocess for the high yield production of food flavor acceptable jasmonic acid and methyl jasmonate, a novel jasmonic acid isomer produced thereby and uses thereof. The process of our invention yields at least 5% of the “cis” isomer defined according to the structure:
(wherein R is hydrogen or methyl) or the “cis” isomer defined according to the structure:
(wherein R is hydrogen or methyl). Compositions containing at least 98% of the isomer having the structure:
having an &agr;
D
20
of +58° are novel. Furthermore, compounds having the structure:
wherein R is methyl or hydrogen having an &agr;
D
20
of +58° are also novel.
The process of our invention comprises the cultivation under aerobic conditions of one or more specific strains of
Diplodia gossypina
in a nutrient medium followed by either (1) isolation of the jasmonic acid or (2) esterification of the jasmonic acid to form methyl jasmonate followed by isolation of the methyl jasmonate. More specifically, our process comprises cultivation under aerobic conditions of a strain of
Diplodia gossypina
organism selected from the group consisting of:
(i)
Diplodia gossypina
ATCC 10936;
(ii)
Diplodia gossypina
ATCC 20575;
(iii)
Diplodia gossypina
NRRL 25011; and
(iv)
Diplodia gossypina
ATCC 36037
in a nutrient medium containing an assimilable source of carbon and an assimilable source of nitrogen followed by isolation of the jasmonic acid product from the culture medium or followed by esterification of the jasmonic acid to form methyl jasmonate and then followed by isolation of the methyl jasmonate product from the reaction mass.
In one embodiment of the process of our invention, the compound, 10-oxo-trans-8-decenoic acid having the structure:
is intimately admixed in the nutrient medium in an amount of from about 0.7 up to about 10 ppm (parts per million) by weight of the nutrient medium prior to the cultivation step.
The 10-oxo-trans-8-decenoic acid having the structure:
is disclosed in U.S. Pat. No. 5,681,738 issued on Oct. 28, 1997 to be a fungal growth hormone to stimulate mycelial growth of cultivated mushrooms. The specification of U.S. Pat. No. 5,681,738 issued on Oct. 28, 1997 is incorporated by reference herein. The bioprocess of our invention is shown according to the reactions:
wherein D.G. strain is intended to mean “strain of
Diplodia gossypina.”
The esterification reaction following the bioprocess reaction of our invention is shown as follows:
Thus, the assimilable carbon source for our invention has been found to be glucose. The preferred assimilable nitrogen source is sodium nitrate.
Preferably, the aeration rate range for carrying out the cultivation step of our inven

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