Antifungal Enantiomeric Styrylpyrones from Sanrafaelia ruffonammari and Ophrypetalum odoratum

doi:10.1007/s13659-014-0014-6

应用天然产物 ›› 2014, Vol. 4 ›› Issue (2): 129-133.DOI: 10.1007/s13659-014-0014-6

• Short communication • 上一篇

Antifungal Enantiomeric Styrylpyrones from Sanrafaelia ruffonammari and Ophrypetalum odoratum

Hamisi M. Malebo¹, Charles Kihampa², Clarence A. Mgina³, Fortunatus Sung'hwa³, Reiner Waibel⁴, Stephan A. Jonker³, Mayunga H. H. Nkunya³

1. Department of Traditional Medicine Research, National Institute for Medical Research, P. O. Box 9653, Dar es Salaam, Tanzania;
2. Department of Traditional Medicine Research, National Institute for Medical Research, P. O. Box 9653, Dar es Salaam, Tanzania;
3. Department of Chemistry, University of Dar es Salaam, P. O. Box 35061, Dar es Salaam, Tanzania;
4. Department of Pharmaceutical Chemistry, Institute of Pharmacy, University of Erlangen, Schuhstrasse 19, 91052 Erlangen, Germany

收稿日期:2014-03-14 修回日期:2014-04-01 出版日期:2014-04-24 发布日期:2018-02-11
通讯作者: Hamisi M.Malebo,e-mail:Malebo@hotmail.com
基金资助:
This work was financially supported by the Norwegian Agency for International Development(NORAD) through the NORAD Chemistry Project. Mrs. Anna Lyatuu and Mr. Abdul Waziri Kidukuli are thanked for carrying out the brine shrimp tests.

Antifungal Enantiomeric Styrylpyrones from Sanrafaelia ruffonammari and Ophrypetalum odoratum

Hamisi M. Malebo¹, Charles Kihampa², Clarence A. Mgina³, Fortunatus Sung'hwa³, Reiner Waibel⁴, Stephan A. Jonker³, Mayunga H. H. Nkunya³

1. Department of Traditional Medicine Research, National Institute for Medical Research, P. O. Box 9653, Dar es Salaam, Tanzania;
2. Department of Traditional Medicine Research, National Institute for Medical Research, P. O. Box 9653, Dar es Salaam, Tanzania;
3. Department of Chemistry, University of Dar es Salaam, P. O. Box 35061, Dar es Salaam, Tanzania;
4. Department of Pharmaceutical Chemistry, Institute of Pharmacy, University of Erlangen, Schuhstrasse 19, 91052 Erlangen, Germany

Received:2014-03-14 Revised:2014-04-01 Online:2014-04-24 Published:2018-02-11
Supported by:
This work was financially supported by the Norwegian Agency for International Development(NORAD) through the NORAD Chemistry Project. Mrs. Anna Lyatuu and Mr. Abdul Waziri Kidukuli are thanked for carrying out the brine shrimp tests.

摘要/Abstract

摘要： Phytochemical investigation of Sanrafaelia ruffonammari Verd and Ophrypetalum odoratum Diels that belongs to the rare genera confined to East African coastal forests led to the isolation of enantiomeric styrylpyrone dimer,(±)-5-methoxy-7-phenyl-[4-methoxy-2-pyronyl]-1-(E)-styryl-2-oxabicyclo-[4.2.0]-octa-4-en-3-one(1) alongside(+)-6-styryl-7, 8-epoxy-4-methoxypyran-2-one(2) and the enantiomeric(+)-(3) and(-)-6-styryl-7, 8-dihydroxy-4-methoxypyran-2-ones(4). Their structures were established by means of spectroscopic methods. In this paper we reveal for the first time the occurrence of styrylpyrones in East African biodiversity.(+)-6-Styryl-7, 8-epoxy-4-methoxypyran-2-one(2) and the dihydroxystyrylpyrone enantiomer(3) showed in vitro antifungal activity against Candida albicans at a concentration of 24.4 and 26.2 lM with zones of inhibition of 17 and 9 mm, respectively. Compound 2 exhibited strong activity in the brine shrimp test with LC₅₀=1.7 μg/mL. Their high cytotoxic and antifungal activities render them candidates for further scientific attention for drug development programs against cancer and microbial infections.

关键词: Sanrafaelia ruffonammari Verd, Ophrypetalum odoratum Diels, Styrylpyrones, Antifungal

Abstract: Phytochemical investigation of Sanrafaelia ruffonammari Verd and Ophrypetalum odoratum Diels that belongs to the rare genera confined to East African coastal forests led to the isolation of enantiomeric styrylpyrone dimer,(±)-5-methoxy-7-phenyl-[4-methoxy-2-pyronyl]-1-(E)-styryl-2-oxabicyclo-[4.2.0]-octa-4-en-3-one(1) alongside(+)-6-styryl-7, 8-epoxy-4-methoxypyran-2-one(2) and the enantiomeric(+)-(3) and(-)-6-styryl-7, 8-dihydroxy-4-methoxypyran-2-ones(4). Their structures were established by means of spectroscopic methods. In this paper we reveal for the first time the occurrence of styrylpyrones in East African biodiversity.(+)-6-Styryl-7, 8-epoxy-4-methoxypyran-2-one(2) and the dihydroxystyrylpyrone enantiomer(3) showed in vitro antifungal activity against Candida albicans at a concentration of 24.4 and 26.2 lM with zones of inhibition of 17 and 9 mm, respectively. Compound 2 exhibited strong activity in the brine shrimp test with LC₅₀=1.7 μg/mL. Their high cytotoxic and antifungal activities render them candidates for further scientific attention for drug development programs against cancer and microbial infections.

Key words: Sanrafaelia ruffonammari Verd, Ophrypetalum odoratum Diels, Styrylpyrones, Antifungal

Hamisi M. Malebo, Charles Kihampa, Clarence A. Mgina, Fortunatus Sung'hwa, Reiner Waibel, Stephan A. Jonker, Mayunga H. H. Nkunya. Antifungal Enantiomeric Styrylpyrones from Sanrafaelia ruffonammari and Ophrypetalum odoratum[J]. 应用天然产物, 2014, 4(2): 129-133.

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Antifungal Enantiomeric Styrylpyrones from Sanrafaelia ruffonammari and Ophrypetalum odoratum

Antifungal Enantiomeric Styrylpyrones from Sanrafaelia ruffonammari and Ophrypetalum odoratum

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