Dioxadispiroketal compounds and a potential acyclic precursor from Amomum aculeatum

Tetrahedron Letters

Volumn 48, Issue 10, 2007, Pages 1849-1853

  Salim, Angela A ^a   Su, Bao Ning ^a   Chai, Hee Byung ^a   Riswan, Soedarsono ^b   Kardono, Leonardus B S ^b   Ruskandi, Agus ^b   Farnsworth, Norman R ^c   Swanson, Steven M ^c   Douglas Kinghorn, A ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b INDONESIAN INSTITUTE OF SCIENCES   (Indonesia)

^c Chicago College of Pharmacy   (United States)

Author keywords

5R Hydroxy 1 (4 hydroxyphenyl) eicosan 3 one; Aculeatols A D; Amomum aculeatum; Dioxadispiroketals; NMR data; Zingiberaceae

Indexed keywords

ACULEATIN A; ACULEATIN B; ACULEATOL A; ACULEATOL B; ACULEATOL C; ACULEATOL D; HERBACEOUS AGENT; PLANT EXTRACT; UNCLASSIFIED DRUG;

AMOMUM; AMOMUM ACULEATUM; ARTICLE; CANCER CELL CULTURE; CHEMICAL ANALYSIS; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR OVERHAUSER EFFECT;

AMOMUM; ZINGIBERACEAE;

EID: 33846804203     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.017     Document Type: Article

References (20)

1. Holdsworth K.D., and Mahana P. Int. J. Crude Drug Res. 21 (1983) 121-133
2. Heilmann J., Mayr S., Brun R., Rali T., and Sticher O. Helv. Chim. Acta 83 (2000) 2939-2945
3. Heilmann J., Brun R., Mayr S., Rali T., and Sticher O. Phytochemistry 57 (2001) 1281-1285
4. Aculeatin is also a trivial name for a prenylated coumarin isolated from Toddalia aculeata (T. asiatica):. Ishii H., Kobayashi J., Sakurada E., and Ishikawa T. J. Chem. Soc., Perkin Trans. 1 (1992) 1681-1684
5. Wong Y.-S. Chem. Commun. (2002) 686-687
6. Baldwin J.E., Adlington R.M., Sham V.W.-W., Marquez R., and Bulger P.G. Tetrahedron 61 (2005) 2353-2363
7. Falomir E., Álvarez-Bercedo P., Carda M., and Marco J.A. Tetrahedron Lett. 46 (2005) 8407-8410
8. Álvarez-Bercedo P., Falomir E., Carda M., and Marco J.A. Tetrahedron 62 (2006) 9641-9649
9. Kinghorn A.D., Farnsworth N.R., Soejarto D.D., Cordell G.A., Swanson S.M., Pezzuto J.M., Wani M.C., Wall M.E., Oberlies N.H., Kroll D.J., Kramer R.A., Rose W.C., Vite G.D., Fairchild C.R., Peterson R.W., and Wild R. Pharm. Biol. 41 (2003) 53-67
10. The leaves and rachis of A. aculeatum were collected by S.R. and A.R. at Cinta Asih village, Warung Kondang district, Cianjur, West Java, Indonesia, in August 2003. A voucher specimen (SR-CJR 8) has been deposited at Herbarium Bogoriense, Bogor, Indonesia.
11. 5Na, 431.27679).
12. This was confirmed by the absence of any NOE correlations between the methine proton H-2 and one methylene proton at C-15. This enhancement was observed for aculeatin B (7), which has the opposite configuration at C-6.
13. 5Na, 431.27679).
14. 5Na, 459.30809).
15. 5Na, 431.27679).
16. 3Na, 427.318263).
17. Su B.-N., Park E.J., Mbwambo Z.H., Santarsiero B.D., Mesecar A.D., Fong H.H.S., Pezzuto J.M., and Kinghorn A.D. J. Nat. Prod. 65 (2002) 1278-1282
18. Su B.-N., Park E.J., Santarsiero B.D., Mesecar A.D., Soejarto D.D., Fong H.H.S., Pezzuto J.M., and Kinghorn A.D. Phytochemistry 64 (2003) 293-302
19. Shoji N., Iwasa A., Takemoto T., Ishida Y., and Ohizumi Y. J. Pharm. Sci. 71 (1982) 1172-1175 and references cited therein
20. Performed according to standard protocols:. Seo E.-K., Kim N.-C., Mi Q., Chai H., Wall M.E., Wani M.C., Navarro H.A., Burgess J.P., Graham J.G., Cabieses F., Tan G.T., Farnsworth N.R., Pezzuto J.M., and Kinghorn A.D. J. Nat. Prod. 64 (2001) 1483-1485