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DOI: 10.1055/s-2005-864157
© Georg Thieme Verlag KG Stuttgart · New York
Androstane and Withanolides from Physalis cinerascens
Contribution No. 2477 of the Instituto de Química, UNAMPublikationsverlauf
Received: August 9, 2004
Accepted: January 3, 2005
Publikationsdatum:
21. Juni 2005 (online)

Abstract
Two new withanolides, cinerolide and 24,25-dihydrowithanolide S, together with the new androstane, cinedione, and the known withanolides, visconolide, physalactone, withanolide S and 4β-hydroxywithanolide E were isolated from the EtOAc extract of leaves, flowers and stems of Physalis cinerascens. The structures of these compounds were established by spectroscopic methods and that of cinerolide was confirmed by X-ray diffraction analysis.
Key words
Physalis cinerascens - Solanaceae - withasteroids - withanolides - androstane
References
- 1 Martínez M. Revision of Physalis section Epeteiorhiza (Solanaceae). Anales del Instituto de Biología, Universidad Nacional Autónoma de México. Serie Botánica. 1998; 69 71-117
- 2 Ray A B, Gupta M. Withasteroids, a growing group of naturally occurring steroidal lactones. In: Herz W, Kirby GW, Moore RE, Steglich W, Tamm Ch, editors Progress Chem Org Nat Prod Vol. 63 Wien; Springer-Verlag 1994: pp 1-106
- 3 Glotter E. Withanolides and related ergostane-type steroids. Nat Prod Reports. 1991; 8 415-40
- 4 Budhiraja R D, Krishan P, Sudhir S. Biological activity of withanolides. J Sci Ind Res. 2000; 59 904-11
- 5 Maldonado E, Torres F R, Martínez M, Pérez-Castorena A L. 18-Acetoxywithanolides from Physalis chenopodifolia . Planta Med. 2004; 70 59-64
- 6 Pérez-Castorena A L, García M, Martínez M, Maldonado E. Physalins from Physalis solanaceus . Biochem Syst Ecol. 2004; 32 1231-4
-
7 MEXU Herbarium data. Guanajuato, México, Ocampo R 134 (MEXU 935 914); San Luis Potosí, México, Alcorn, JB 1561 (MEXU 406 375).
- 8 Hernández L C, González F, González M. Plantas útiles de Tamaulipas, México. Anales del Instituto de Biología, Universidad Nacional Autónoma de México, Serie Botánica. 1991; 62 1-38
- 9 Sheldrick G M. SHELXS 97, Program for refining crystal structures. University of Göttingen Germany; 1999
- 10 Abdullaev N D, Maslennikova E A, Tursunova R N, Abubakirov N K, Yagudaev M R. IV. 28-Hydroxywithaphysanolide. 13C NMR spectrum of 14α- hydroxywithasteroids. Chem Nat Compounds. 1984; 20 182-91
- 11 Neogi P, Sahai M, Ray A B. Withaperuvins F and G, two withanolides of Physalis peruviana roots. Phytochemistry. 1987; 26 243-7
- 12 Sakurai K, Ishii H, Kobayashi S, Iwao T. Isolation of 4β-hydroxywithanolide E, a new withanolide from Physalis peruviana L. Chem Pharm Bull. 1976; 24 1403-5
- 13 Kirson I, Abraham A, Sethi P D, Subramanian S S, Glotter E. 4β-Hydroxywithanolide E, a new natural steroid with a 17α-oriented side chain. Phytochemistry. 1976; 15 340-2
- 14 Abdullaev N D, Vasina O E, Maslennikova V A, Abubakirov N K. V. A study of the 1H and 13C NMR spectra of the withasteroids visconolide and 28-hydroxywithaperuvin C. Chem Nat Compounds. 1985; 21 616-22
- 15 Glotter E, Abraham A, Günsberg G, Kirson I. Naturally occurring steroidal lactones with a 17α-oriented side chain. Structure of withanolide E and related compounds. J Chem Soc Perkin Trans I: 1977: 341-5
- 16 Gottlieb H E, Kirson I. 13C NMR spectroscopy of withanolides and other highly oxygenated C28 steroids. Org Magn Reson. 1981; 16 20-5
- 17 Khan P M, Ahmad S, Rubnawaz H, Malik A. The first report of a withanolide from the family Labiatae. Phytochemistry. 1999; 51 669-71
- 18 Kirson I, Gottlieb H E. 14α-Hydroxy-steroids from Withania somnifera (L.) Dun. (Solanaceae). J Chem Res 1980: (S) 338-9, (M) 4275 - 93
- 19 Nawaz H R, Malik A, Kahn P M, Ahmed S. Ajugin E and F: Two withanolides from Ajuga parviflora . Phytochemistry. 1999; 52 1357-60
- 20 Kennelly E J, Gerhäuser C, Song L L, Graham J G, Beecher C WW, Pezutto J M. et al . Induction of quinone reductase by withanolides isolated from Physalis philadelphica (Tomatillos). J Agric Food Chem. 1997; 45 3771-7
- 21 Su B N, Misico R, Park E J, Santarsiero B D, Mesecar A D, Fong H HS. et al . Isolation and characterization of bioactive principles of the leaves and stems of Physalis philadelphica . Tetrahedron. 2002; 58 3453-66
- 22 Glotter E, Kumar S, Sahai M, Goldman A, Kirson I, Mendelovici M. Synthetic modifications of withanolides with an α-oriented side-chain. J Chem Soc Perkin Trans I: 1991: 739-45
- 23 Ray A B, Sahai M, Das B C. Physalolactone: A new withanolide from Physalis peruviana . J Indian Chem Soc. 1978; LV 1175-8
Emma Maldonado, M.Sc.
Instituto de Química
Universidad Nacional Autónoma de México
Circuito Exterior
Ciudad Universitaria
Coyoacán, 04510 D. F.
México
Fax: +52-55-5616-2217
eMail: emmaldonado@correo.unam.mx