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Abstract

Synthesis and Bioactivity of Teasterone and Typhasterol Analogs

Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Pabellón II, 3er Piso, Ciudad Universitaria, (1428) Buenos Aires, Argentina
Molecules 2000, 5(3), 367-369; https://doi.org/10.3390/50300367
Published: 22 March 2000

Abstract

:
Four brassinosteroids analogs of homoteasterone and homotyphasterol bearing 5α-OH and 5α-F groups have been synthesized and their bioactivities evaluated.

Introduction

Brassinosteroides are a new class of phytohormones with properties of enhancing plant growth and plant cell division. Since the discovery of brassinolide, in 1979 –first compound of this series— a wide variety of research programs arose concerning biosynthesis, mechanisms of action [1] and possible applications in agriculture [2].
It has been already stablished that the presence of a substituent at C-5 with the ability to form an hydrogen bonding with the substituent of C-3 may change the bioactivity response of these compounds [3]. In our laboratory we have already synthesized two natural brassinosteroids homoteasterone (I) and homotyphasterol [4] (II) and in this work we introduce the synthesis of four new analogs in which the 5α-H group of compounds I and II has been replaced by a 5α-OH group (compounds III and IV) or a 5α-F group (compounds V and VI), respectively.
Molecules 05 00367 i001
Bioactivities of new compounds have been evaluated with the rice lamina inclination bioassay [5] using the mentioned natural brassinosteroids as standards.

Results and Discussion

New compounds have been synthesized as shown in the following scheme.
All the compounds have been characterized by 1H, 13C and 19F NMR spectroscopy. First data concerning bioactivities of the analogs show the same decreasing effect when an OH or a F group were introduced at C-5. This result may induce some interesting information concerning biochemical action of these compounds at a molecular level.

Acknowledgements:

This work has been done with grants from UBACyT and CONICET. We wish to thank UMYMFOR for spectroscopic determinations.

References and Notes

  1. Clouse, S.; Sasse, J. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1998, 49, 427. [PubMed]
  2. Kamuro, Y.; Takatsuto, S. Brassinosteroids: Steroidal Plant Hormones; Sakurai, A., Yokota, T., Clouse, S., Eds.; Springer-Verlag: Tokyo, 1999; pp. 223–241. [Google Scholar]
  3. Brosa, C.; Zamora, I.; Terricabras, E.; Soca, L.; Peracaula, R.; Rodríguez, C. Lipids 1997, 32, 12, 1341.
  4. Takatsuto, S.; Ikekewa, N. J. Chem. Soc.Perkin Trans I: 1984, 439.
  5. Wada, K.; Marumo, S.; Abe, H.; Morishita, T.; Nakamura, K.; Uchishama, M.; Mori, K. Agric. Biol. Chem. 1984, 48(3), 719.
a) BF3·Et2O / Et2O / t.a. b) PCC / CH2Cl2 / t.a. c) K2CO3 / MeOH / THF / t.a. d) K2OsO4. 2H2O / (DHQD)2Phal / methansulfonamide / K3Fe(CN)6 / K2CO3 / t-BuOH / H2O / t.a. / e) Jones / t.a. f) DEAD / PPh3 / HCOOH / benzene / t.a. g) Li2CO3 / DMF / water / reflux.
a) BF3·Et2O / Et2O / t.a. b) PCC / CH2Cl2 / t.a. c) K2CO3 / MeOH / THF / t.a. d) K2OsO4. 2H2O / (DHQD)2Phal / methansulfonamide / K3Fe(CN)6 / K2CO3 / t-BuOH / H2O / t.a. / e) Jones / t.a. f) DEAD / PPh3 / HCOOH / benzene / t.a. g) Li2CO3 / DMF / water / reflux.
Molecules 05 00367 sch001

Share and Cite

MDPI and ACS Style

Ramírez, J.A.; Mancusso, R.; Sarno, S.; Galagovsky, L.R. Synthesis and Bioactivity of Teasterone and Typhasterol Analogs. Molecules 2000, 5, 367-369. https://doi.org/10.3390/50300367

AMA Style

Ramírez JA, Mancusso R, Sarno S, Galagovsky LR. Synthesis and Bioactivity of Teasterone and Typhasterol Analogs. Molecules. 2000; 5(3):367-369. https://doi.org/10.3390/50300367

Chicago/Turabian Style

Ramírez, Javier A., Romina Mancusso, Silvina Sarno, and Lydia R. Galagovsky. 2000. "Synthesis and Bioactivity of Teasterone and Typhasterol Analogs" Molecules 5, no. 3: 367-369. https://doi.org/10.3390/50300367

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