First synthesis of (±)-monotesone B and new syntheses of (±)-lonchocarpol A and (±)-bavachin

Natural Product Communications

Volumn 1, Issue 1, 2006, Pages 51-55

  Kenéz, Ágnes ^a   Antus, Sándor ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Antifungal activity; Bavachin; C prenylated flavanones; Lonchocarpol A; Monotesone B; Synthesis

Indexed keywords

EID: 34247363255     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0600100110     Document Type: Article

References (15)

1. Seo EK, Silva GL, Chai HB, Chagwedera TE, Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn AD. (1997) Cytotoxic prenylated flavanones from Monotes engleri. Phytochemistry, 45, 509-515.
2. Bu X, Zhao L, Li Y. (1997) A facile synthesis of 6-C-prenylflavanones. Synthesis, 11, 1246-1248.
3. Xiao L, Tan W, Li Y. (1998) First total synthesis of (±)- kenusanone B. Synthetic Communications, 28, 2861-2869.
4. Miranda CL, Aponso GLM, Stevens JF, Deinzer ML, Buhler DR. (2000) Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Cancer Letters, 149, 21-29.
5. Gester S, Metz P, Zierau O, Wollmer G. (2001) An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1- dimethylallyl) naringenin by europium(III)-catalyzed Claisen rearrangement. Tetrahedron, 57, 1015-1018.
6. Jang DS, Cuendet M, Hawthorne ME, Kardono LBS, Kawanishi K, Fong HHS, Mehta RG, Pezzuto JM, Kinghorn AD. (2002) Prenylated flavonoids of the leaves of Macaranga conifera with inhibitory activity against cyclooxygenase-2. Phytochemistry, 61, 867-872.
7. Garo E, Wolfender JL, Hostettmann K, Hiller W, Antus S, Mavi S. (1998) Prenylated flavanones from Monotes engleri: On-line structure elucidation by LC/UV/NMR. Helvetica Chimica Acta, 81, 754-763.
8. Roussis V, Ampofo SA, Wiemer DF. (1987) Flavanones from Lonchocarpus minimiflorus. Phytochemistry, 26, 2371-2375.
9. Jain AC, Gupta RC, Sarpal PD. (1978) Synthesis of (±)-lupinifolin, di-O-methylxanthohumol and isoxanthohumol and related compounds. Tetrahedron, 34, 3563-3567.
10. Bhalla VK, Nayak UR, Dev S. (1968) Some new flavonoids from Psoralea corylifolia. Tetrahedron Letters, 20, 2401-2406.
11. Jain AC, Lal P, Seshadri TR. (1970) A study of nuclear prenylation of b-resacetophenone-II: synthesis of bavachalcone, 4'-Omethylbavachalcone and bavachin. Tetrahedron, 26, 2631-2635.
12. Kenéz Á, Juhász L, Antus S. (2002) A simple synthesis of selinone, an antifungal component of Monotes engleri. Heterocyclic Communications, 8, 543-548.
13. Alonso R, Brossi A. (1988) Synthesis of hormothamnione. Tetrahedron Letters, 29, 735-738.
14. Antus S, Gulácsi K, Juhász L, Kiss L, Kurtán T. (2004) Synthesis of naturally occurring O-heterocyclic compounds of biological activity. Pure and Applied Chemistry, 76, 1025-1032.
15. Matsumoto J, Fujimoto T, Takino C, Saittoh M, Hano Y, Fukai T, Nomura T. (1985) Component of Broussonetia papyrifera (L.) Vent. I. Structures of two new isoprenylated flavonols and two chalcone derivatives. Chemical and Pharmaceutical Bulletin, 33, 3250-3256.