718
Notes
Biol. Pharm. Bull. 24(6) 718—719 (2001)
Vol. 24, No. 6
Antifungal Activity of Modified Hederagenin Glycosides from the Leaves
of Kalopanax pictum var. chinense
a
Min-Won LEE,*,a Sung Uk KIM,b and Dug-Ryoung HAHN
College of Pharmacy, Chung Ang University,a 221 Huksuk-dong Dong Jak-Ku Seoul 156–756, Korea, Antibiotics Research
Lab., Korea Research Institute of Bioscience and Biotechnology,b P. O. Box 115, Yusung, Taejon 305–333, Korea.
Received December 11, 2000; accepted March 7, 2001
Monodesmosides which were obtained from the partial degradation of hederagenin bisdesmosides exhibited
significant antifungal effect against Microsporum canis, Coccidioides immitis, Trichophyton mentagrophytes, Cryp-
tococcus neoformans, and Candida albicans at the minimal inhibitory concentrations of 6.25—25 mg/ml. The hed-
eragenin glycosides were isolated from the leaves of Kalopanax pictum var. chinense.
Key words hederagenin glycoside; triterpenoid; antifungal activity; Kalopanax pictum var. chinense; Araliaceae
The barks of Kalopanax spp.(Araliaceae) have been used tivity but the monodesmosides (compounds 4, 5, 6) obtained
as a Korean traditional medicine for the remedies of paraly- by partial hydrolysis of C-28 ester likage of 1, 2 and 3, ex-
sis, rheumatic arthritis, tonics and cutaneous fungal infec- hibited antifungal activity against Microsporum canis, Coc-
tion.1) Several triterpene glycosides were isolated as main cidioides immitis, Trichophyton mentagrophytes, Cryptococ-
components of Kalopanax plants sources.2—4) Noticeable bio- cus neoformans and Candida albicans at the minimal in-
logical effects of triterpene glycosides are not known yet but hibitory concentrations of 6.25—25 mg/ml (Table 1). These
some saponin is known to have fungitoxic activity.5) It has results suggest that a-hederin, sapindosides B and C ob-
been also reported that the antifungal and molluscidal tained by partial degradation of bisdesmosides are shown to
saponins have monodesmoside form6) and hereragenin glyco- be antifungal agents. The inactive bisdesmosides, major in-
side with a free carboxyl group at C-28 show antifungal ac- gredients of Kalopanax pictum var. chinense, might be
tivity against yeast.7) Recently, it was reported that mon- sources of fungicidal agent.
odesmosides from Kalopanax pictum inhibited the human
pathogenic fungi significantly.8) But it was known that the
contents of hederagenin glycoside with monodesmoside form
in the kalopanax plant were low as compared with those of
bisdesmoside.9)
We have attempted proving the antifungal activities of the
monodesmosides obtained by alkali hydrolysis (ester degra-
dation) of the bisdesmosides, penta (kalopanax saponin B,
1), hexa (kalopanax saponin H, 2) and hepta [3-O-b-D-glu-
copyranosyl (1—4)-b-D-xylopyranosyl (1—3)-a-L-rhamnopy-
ranosyl (1—2)-a-L-arabinopyranosyl-23-hydroxyolean-12-
en-28-O-a-L-rhamnopyranosyl (1—4)-b-D-glucopyranosyl
(1—6)-b-D-glucopyranosyl ester, 3] glycosides of hedera-
genin (see Chart 1) which were isolated from the leaves of
Kalopanax pictum var. chinense, one of the kalopanax
species growing in Korea. The partial hydrolysis of 1, 2 and
3 by 0.5 N-KOH produced compounds 4, 5 and 6 which were
identified as a-hederin, sapindoside B and C respectively by
comparison with published spectral data and authentic sam-
ples.3,4) All these bisdesmosides did not show anti-fungal ac-
Chart 1
Table 1. Antifungal Activities of the Hederagenin Glycosides (Bisdesmosides and Monodesmosides) against Human Pathogenic Fungi
Compound
Fungi
1
2
3
4
5
6
Nystatina)
Candida albicans ATCC 10231
Ͼ100
Ͼ100
100
>100
100
Ͼ100
Ͼ100
100
100
100
Ͼ100
Ͼ100
100
100
50
100
12.5
50
50
25
25
12.5
6.25
50
50
100
50
6.25
50
50
3.125
NDb)
25
1.56
3.125
Microsporum canis ATCC 11622
Trichophyton mentagrophytes ATCC9533
Cryptococcus neoformans ATCC 36556
Coccidioides immitis ATCC 34020
MIC : mg/ml. a) Nystatin: Positive control. b) ND: Not determined.
To whom correspondence should be addressed. e-mail: mwlee@cau.ac.kr
© 2001 Pharmaceutical Society of Japan