Muconin and mucoxin: Additional nonclassical bioactive acetogenins from Rollinia mucosa

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 7988-7989

  Shi, Guoen ^a   Kozlowski, John F ^a   Schwedler, Jon T ^a   Wood, Karl V ^b   MacDougal, John M ^c   McLaughlin, Jerry L ^a  

^a PURDUE UNIVERSITY   (United States)

^b PURDUE UNIVERSITY   (United States)

^c MISSOURI BOTANICAL GARDEN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; DOXORUBICIN; MUCENIN; OXETACAINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG IDENTIFICATION; DRUG ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PHYTOCHEMISTRY; TUMOR CELL;

EID: 0029801581     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9613949     Document Type: Article

References (15)

1. For our most recent review on Annonaceous acetogenins, see: Zeng, L.; Ye, Q.; Oberlies. H. N.; Shi, G; Gu, Z. M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 29, 249-310, and the references indicated therein.
2. Shi, G.; Alfonso, D.; Fatope, M. O.; Zeng, L.; Gu, Z. M.; Zhao, G. X.; He, K.; MacDougal, J. M.; McLaughlin, J. L. J. Am. Chem. Soc. 1995, 117, 10409-10410.
3. 1
4. 7.)
5. Shi, G.; Zeng, L.; Gu, Z. M.; MacDougal, J. M.; McLaughlin, J. L. Heterocycles 1995, 41, 1785-1796.
6. 1
7. 2 and 2 provide convenient examples for these situations.
8. Born, L.; Lieb, F. J.; Lorentzen, P.; Moeschler, H.; Nonfon, M.; Sollner, R.; Wendisch, D. Planta Med. 1990, 56, 312-316.
9. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, Y. J. Am. Chem. Soc. 1991, 113, 4092-4096.
10. 1,2,5
11. H(S-R)) are as follows: H-11, 1.56, 1.60 (-0.04); H-12, 5.11, 5.04 (+0.07); H-13, 3.43, 3.40 (+0.03); H-17, 3.33, 3.26 (+0.07); H-18, 3.76, 3.92 (-0.16); H-21, 4.03, 3.98 (+0.05); H-22, 5.03, 5.01 (+0.02); H-23, 1.62, 1.45 (+0.17).
12. H(S-R) values have been observed in several well-characterized adjacent bis-THF acetogenins, and certain theoretical explanations were suggested: Zhao, G. X.; Chao, J. F.; Zeng, L.; Rieser, M. J.; McLaughlin, J. L. Bioorg. Med. Chem. 1996, 4, 25-32.
13. 2O (or TMSiOH) may take place before the cleavage at C-12/13, providing the kinetic driving force for this ion pathway. All the product and intermediate ions in the above proposed process were observed (Figure 1).
14. While negative NOESY results were generally viewed as being indecisive, oxymethines on cis THF rings, however, always have shown strong NOESY correlation in our experience.
15. -2.