1H-NMR assignment of HIV protease inhibitor, procyanidin B3 isolated from Rosa rugosa

Natural Product Sciences

Volumn 9, Issue 2, 2003, Pages 49-51

  Park, Jong Cheol ^a   Ito, Hideyuki ^b   Yoshida, Takashi ^b  

^a Sunchon National University   (South Korea)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

HIV 1 protease; Procyanidin B3; Rosa rugosa

Indexed keywords

PLANT EXTRACT; PROCYANIDIN B3; PROCYANIDIN DERIVATIVE; PROTEINASE INHIBITOR; ROSA RUGOSA EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG INHIBITION; DRUG ISOLATION; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; MEDICINAL PLANT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; ROSE;

EID: 0038164602     PISSN: 12263907     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Hashidoko, Y., Tahara, S. and Mizutani, J., Antimicrobial sesquiterpene from damaged Rosa rugosa leaves. Phytochemistry, 28, 425-430 (1989).
2. Hashidoko, Y., Tahara, S. and Mizutani, J., 2-Phenoxychromones and a structurally related flavone from leaves of Rosa rugosa. Phytochemistry, 30, 3837-3838 (1991).
3. Hashidoko, Y., Tahara, S. and Mizutani, J., Long chain alkyl esters of 4′-hydroxycinnamic acids from leaves of Rosa rugosa. Phytochemistry. 31, 3282-3283 (1992).
4. Hashidoko, Y., Tahara, S. and Mizutani, J., Sesquiterpenoids from Rosa rugosa leaves. Phytochemistry, 32, 387-390 (1993).
5. Hashidoko, Y., Tahara, S. and Mizutani, J., Six sesquiterpenoids from glandular trichome exudates of Rosa rugosa. Phytochemistry, 35, 325-329 (1994).
6. Hatano, T., Ogawa, N., Yasuhara, T. and Okuda, T., Tannins of Rosaceous plants. VIII. Hydrolyzable tannin monomers having a valoneoyl group form flower petal of Rosa rugosa Thunb. Chem. Pharm. Bull., 38, 3308-3313 (1990a).
7. Hatano, T., Ogawa, N., Shingu, T. and Okuda, T., Tannins of Rosaceous plants. IX. Rugosin D, E, F and G, dimeric and trimeric hydrolyzable tannins with valoneoyl group (s), from flower petal of Rosa rugosa Thunb. Chem. Pharm. Bull., 38, 3341-3346 (1990b).
8. Kusumoto, I. T., Nakabayashi, T., Kida, H., Miyashiro, H., Hattori, M., Namba, T. and Shimotohno, K., Screening of various plant extracts used in Ayurvedic medicine for inhibitory effects on HIV-1 protease. Phytother. Res., 9, 180-184 (1995).
9. Mcquade, T. J., Tomasselli, A. G. and Liu, L., A synthetic HIV-1 protease inhibitor with antiviral activity arrests HIV-like particle maturation. Science, 247, 454-456 (1990).
10. Meek, T. D., Dayton, B. D. and Metcalf, B. W., Human immunodeficiency virus 1 protease expressed in Escherichia coli behaves as a dimeric aspartic protease. Proc. Natl Acad. Sci. USA, 86, 1841-1845 (1989).
11. Okuda, T., Hatano, T., Yazaki, K. and Ogawa, N., Rugosin A, B, C and praecoxin A, Tannins having a valoneoyl group. Chem. Pharm. Bull., 30, 4230-4233 (1982a).
12. Okuda, T., Hatano, T. and Ogawa, N., Rugosin D, E, F and G, Dimeric and trimeric hydrolyzable tannins. Chem. Pharm. Bull., 30, 4234-4237 (1982b).
13. Park, J. C. and Ok, K.D., Phenolic compounds isolated from Rosa rugosa in Korea. Yakhak Hoeji, 37, 365-369 (1993a).
14. Park, J. C., Young, H. S. and Lee, S. H., A tannin compound isolated from the underground parts of Rosa rugosa Thunb. Kor. J. Pharmacogn., 24, 319-321 (1993b).
15. Petereit, F., Kolodziej, H. and Nahrstedt, A., Flavan-3-ols and proanthocyanidins from Cistus incanus, Phytochemisty, 30, 981-985 (1991).
16. Razungles, A., Oszmianski, J. and Sapis, J. C., Determination of carotenoids in fruits of Rosa sp. (Rosa canina and Rosa rugosa) and of chokeberry (Aronia melanocarpa). J. of Food Science, 54, 774-775 (1989).
17. Tanaka, T., Nonaka, G. and Nishioka, I., 7-O-Galloyl-(+)-catechin and 3-O-galloylprocyanidin B-3 from Sanguisorba officinalis, Phytochemistry, 11, 2575-2578 (1983).
18. Thomson, R. S., Jacques, D., Haslam, E. and Tanner, R. J. N., Plant proanthocyandins. part I. Introduction: the isolation, structure, and distribution in nature of plant procyanidins. J.C.S. Perkin I, 1387-1396 (1972).
19. Yazaki, K., Shida, S. and Okuda, T., Galloylhomoarbutin and related polyphenols from Pyrola incarnata, Phytochemistry, 28, 607-609 (1989).
20. Yazaki, K., Yoshida, T. and Okuda, T., Tannin production in cell suspension cultures of Geranium thunbegii, Phytochemistry, 30, 501-503 (1991)
21. Yoshida, T., Tanaka, K., Chen, X. and Okuda, T., Tannins of Rosaceae medicinal plants. V., Hydrolyzable tannins with dehydrodigalloyl group from Rosa laevigata, Chem. Pharm. Bull., 37, 920-924 (1989).
22. Young, H. S., Park, J. C. and Choi, J. S., Triterpenoid glycosides from Rosa rugosa. Arch. Pharm. Res., 10, 219-222 (1987).