Daphcalycinosidines A and B, new iridoid-alkaloids from Daphniphyllum calycinum

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 515-518

  El Bitar, Hoda ^a   Nguyen, Van Hung ^b   Gramain, Anthony ^b,c   Sévenet, Thierry ^c   Bodo, Bernard ^a  

^a MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^b GRADUATE UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Viet Nam)

^c CNRS   (France)

Author keywords

Daphniphyllum calycinum; Daphniphyllum alkaloid; Iridoid alkaloid; NMR; Structure determination

Indexed keywords

ALKALOID DERIVATIVE; DAPHCALYCIC ACID; DAPHCALYCINOSIDINE A; DAPHCALYCINOSIDINE B; DAPHNIPHYLLUM CALYCINUM EXTRACT; IRIDOID; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DAPHNIPHYLUM CALYCINUM; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY;

DAPHNIPHYLLUM; DAPHNIPHYLLUM CALYCINUM;

EID: 0345732576     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.005     Document Type: Article

References (14)

1. (a) Arthur H.R., Chan R.P.K., Loo S.N. Phytochemistry. 4:1965;627-629
2. (b) Gamez E.J.C., Luyengi L., Lee S.K., Zhou B.-N., Fong H.H.S., Pezzuto J.M., Kinghorn A.D. J. Nat. Prod. 61:1998;706-708
3. (c) Gray D.E., Leung W.N. Asian J. Med. 7:1971;409-412
4. (d) Fang S.D., Chou W., Chen Y., Chu J.-H. Acta Chim. Sinica. 30:1964;271-274.
5. Jossang A., El Bitar H., Pham V.C., Sévenet T. J. Org. Chem. 63:2003;300-304.
6. Morita H., Yoshida N., Kobayashi J. Org. Lett. 5:2003;2895-2898.
7. (a) Yamamura S., Hirata Y. Manske R.H.F. The Alkaloids. Vol. 15:1975;41-81 Academic, NewYork,
8. (b) Yamamura S. Brossi A. The Alkaloids. Vol. 29:1986;265-286 Academic, NewYork,
9. (c) Heathcock C.H. Angew. Chem., Int. Ed. Engl. 31:1992;665-681
10. (d) Heathcock C.H. Proc. Natl. Acad. Sci. U.S.A. 93:1996;14323-14327.
11. Morita H., Takatsu H., Kobayashi J. Tetrahedron. 59:2003;3575-3579.
12. Guarnaccia R., Madyastha K.M., Tegmeyer E., Coscia C.J. Tetrahedron Lett. 13:1972;5125-5127.
13. 1H(400.13MHz):3.80(d,J7.2Hz,H-1),2.28(brddd,J7.5, 7.5,7.2Hz,H-2),1.73(dddd,J15.0,15.0,15.0,7.5Hz,H-3a),1.60(dddd,J15.0,3.5,3.5,2. 0Hz,H-3b),1.57(m,H-4a),1.51(m,H-4b),2.07(m,H-6),4.56(s,H-7),2.37(m,H-10),1.73(m, H-11a),1.63(m,H-11b),2.05(m,H-12a),1.68(m,H-12b),2.15(dd,J13.2,12.8Hz,H-13a),1. 74(dd,J13.2,9.0Hz,H-13b),3.15(ddd,J12.8,11.3,7.0Hz,H-14),2.81(ddd,J12.8,12.0,7. 5Hz,H-15),1.90(m,H-16a),1.28(m,H-16b),1.77(m,H-17a),1.28(m,H-17b),2.48(dddq,J11. 9,7.7,7.5,7.0Hz,H-18),3.02(dd,J8.9,7.7Hz,H-19a),2.78(dd,J11.9,8.9Hz,H-19b),1. 10(d,J7.0Hz,H-20),1.20(s,H-21)
14. 13C (75.43 MHz) ( δ ): 95.7 (1), 146.4 (3), 117.0 (4), 36.4 (5), 38.7 (6), 125.5 (7), 144.7 (8), 46.1 (9), 59.7 (10), 169.5 (11), 98.4 (1′), 73.4 (2′), 77.2 (3′), 70.0 (4′), 76.7 (5′), 60.9 (6′).