Sesquiterpene compounds

Details Sesquiterpene compounds Sesquiterpene compounds

1997-09-26

1998-11-24

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549460, 549461, C07D30792, C07D30791

Patent

active

058409270

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to a new family of sesquiterpene compounds which are isolated from fruit bodies of Basidiomycota, and expected to be applied to the medication because of their anti-fungal activities.


BACKGROUND OF THE INVENTION

Development of anti-microbial drugs with antibiotics playing the central role has been achieved remarkably, while that of anti-fungal drugs is not necessarily satisfactory from the perspective of their varieties and effectivities. Especially, the opportunistic mycoses of internal organs caused by infections with Candida, Aspergillus and Cryptococcus mycetes due to the decrease in bodily defense capability induced by extensive administration of carcinostatic agents, immunosuppressants, steroid hormones, etc. as well as AIDS (acquired immunodeficiency syndrome) in recent years are posing an important medical problem. Therefore, there is a strong demand for the development of remedies for mycoses.
On the other hand, physiologically active ingredients contained in mushrooms have been examined extensively since olden times. Elfvingia applanata (kofuki-saru-no-koshikake, Ganodermataceae) and Coriolus versicolor (Kawara-take, Polyporaceae have been used as legendary herb medicines or folk medicines for gastric cancer, esophagus cancer, breast cancer, prostate cancer, etc. Especially, .beta.-D-glucan-protein complex (PS-K) extracted from mycelia of Coriolaceae (Kawara-take) in culture has been used extensively as a carcinostatic agent. Furthermore, the isolation of a carcinostatic protein-polysaccharide from aqueous extracts and ergosterol from CHCl.sub.3 -MeOH extracts of Hitokuchitake, has been reported by Lee et al. (1981) and Kim et al. (1982) in Korea, respectively Trans. Mycol. Soc. Japan, 29, 281-296 (1988); Asakawa et al., Hirotani et al., Phytochemistry, 30 (5), 1555-1559 ( 1991)! from this Hitokuchitake has been reported.


SUMMARY OF THE INVENTION

Searching for novel physiologically active ingredients contained mushrooms, the present inventors made tremendous efforts to find compounds having strong anti-fungal activity against the above mentioned eumycetes which induce the opportunistic mycosis of internal organs, that is, compounds effectively usable as anti-fungal agents. The present invention aims at providing effective compounds as anti-fungal agents.
Based on thorough study, the present inventors succeeded in isolating novel sesquiterpene compounds from the lower alcohol or acetone extracts of fruit bodies of Roseofomes subflexibilis (Hounen-take) (Berk. et Curt. Aoshi.) in Polyporaceae family, and accomplished the present invention by further finding the anti-fungal activity of these compounds in the assay of antibiotic action. In the chemical formulas described in the present invention, when residues denoted by R.sup.1 are present plurally in a given compound, they may represent the same residue or different ones. The same rule will be applied to R.sup.3 and R.sup.4.
Namely, the present invention relates to sesquiterpene compounds represented by the following general structural formula I: ##STR2## wherein one of the two R.sup.1 groups is --COOR.sup.3, and the other one is any one of the groups represented by the following formulas, wherein R.sup.2 and R.sup.3 are hydrogen atom or alkyl group, and R.sup.4 is hydroxyl group or alkoxy group. ##STR3##
In the most preferred embodiments of the present invention, R.sup.2 and R.sup.3 are hydrogen atom or lower alkyl group, and R.sup.4 is hydroxyl group.
The present invention also includes anti-microbial agents comprising sesquiterpene compounds represented by the following general formula II: ##STR4## wherein R.sup.1 is --COOR.sup.2 group (wherein R.sup.2 is hydrogen atom, alkyl group or acyloxyalkyl group), or any one of the groups represented by the following formulas (wherein R.sup.3 is hydroxyl group or alkoxy group). ##STR5##
Of these anti-microbial agents described above, those comprising sesquiterpene compounds represented by the following Formula I are most preferable: ##STR6## whe

REFERENCES:
Asakawa et al., Trans. mycol. Soc. Japan, 29:281-296 (1988).
Hashimoto et al., "The bitter sesquiterpenoids from the fungus Cryptoporus volvatus", Trans. Mycol. Soc. Japan, 29:281-296 (1988).
Hirotani et al., Phytochemistry, 30(5):1555-1559 (1991).
Lee et al., "Studies on the Constituents of Higher Fungi of Korea", Kor. J. Mycol., 9(3):153-155 (1981).
Kim et al., "Antitumor Components of Cryptoporus volvatus", Kor. j. Mycol., 10(3):111-117 (1982).

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