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Phytochemistry
Volume 61, Issue 4, October 2002, Pages 367-372
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DOI: 10.1016/S0031-9422(02)00263-7
PII: S0031-9422(02)00263-7

Copyright © 2002 Elsevier Science Ltd. All rights reserved.

ent-Kaurane diterpenoid glycosides from a Malagasy endemic plant, Cussonia vantsilana

Liva Harinantenaina, Ryoji Kasai and Kazuo YamasakiCorresponding Author Contact Information, E-mail The Corresponding Author

Division of Medicinal Chemistry, Graduate School of Biomedical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8551, Japan

Received 16 April 2002;  revised 24 June 2002.  Available online 5 October 2002.

Abstract

Four ent-kaurane diterpenoid glycosides, cussovantosides A¯D, were isolated from the dried leaves of Cussonia vantsilana Baker, together with six known compounds. The structures of the compounds were deduced on the basis of their physical and spectral data.

Graphical Abstract

From the dried leaves of Cussonia vantsilana, cussovantosides A, B, C, and D were isolated. Their structures were deduced on the basis of their physical and spectral analysis.
View Image

Author Keywords: Cussonia vantsilana; Araliaceae; Cussovantosides A¯D; Cussovantonins A and B; ent-kaurane diterpene glycosides; Malagasy endemic plant

Article Outline

1. Introduction
2. Results and discussion
3. Experimental
3.1. General
3.2. Plant material
3.3. Extraction and isolation
3.4. Cussovantoside A (7)
3.5. Cussovantoside B (8)
3.6. Cussovantoside C (9)
3.7. Cussovantoside D (10)
3.8. Enzymatic hydrolysis of compounds 7 and 8
3.8.1. Cussovantonin A (7a)
3.8.2. Cussovantonin B (8a)
3.9. Sensory evaluation (Darise et al., 1984) of cussoracoside C ( 6)
Acknowledgements
References



Table 1. 1H NMR spectral data for compounds 7 and 8 (400 MHz in pyridine-d5) View Table (<1K)
Glc: small beta, Greek-View Table-glucopyranosyl.

Table 3. 13C NMR spectral data for compounds 7¯10 (100 MHz in pyridine-d5) View Table (<1K)
Assignment based on HSQC.Glc: small beta, Greek-View Table-glucopyranosyl, Api: small beta, Greek-View Table-apiofuranosyl, Rha: small alpha, Greek-View Table-rhamnopyranosyl.

Table 2. 1H NMR spectral data for compounds 9 and 10 (400 MHz in pyridine-d5) View Table (<1K)
Glc: small beta, Greek-View Table-glucopyranosyl; Api: small beta, Greek-View Table-apiofuranosyl; Rha: small alpha, Greek-View Table-rhamnopyranosyl.

References

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Darise et al., 1984. M. Darise, K. Mizutani, R. Kasai, O. Tanaka, S. Kitahata, S. Okada, S. Ogawa, F. Murakami and F.H. Chen Agric. Biol. Chem. 48 (1984), pp. 2483¯2488. Abstract-Beilstein Abstracts  

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Hara et al., 1987. S. Hara, H. Okabe and K. Mihashi , Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates. Chem. Pharm. Bull. 35 (1987), pp. 501¯506. Abstract-Beilstein Abstracts  

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Wu et al., 1996. Y.C. Wu, Y.C. Hung, F.R. Chang, M. Cosentino, H.K. Wang and K.H. Lee , Identification of ent- 16small beta, Greek,17-dihydroxykauran-19-oic acid as anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa. J. Nat. Prod. 59 (1996), pp. 635¯637. Abstract-MEDLINE   | Full Text via CrossRef

Yamasaki et al., 1976. K. Yamasaki, H. Kohda, T. Kobayashi, R. Kasai and O. Tanaka , Structures of Stevia diterpenes-glucosides: application of 13C NMR. Tetrahedron Lett. 13 (1976), pp. 1005¯1008. Abstract

Corresponding Author Contact Information Corresponding author. Tel.: +81-82-257-5285; fax: +81-82-257-5289; email: kazuoy@hiroshima-u.ac.jp
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Phytochemistry
Volume 61, Issue 4, October 2002, Pages 367-372


 
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