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• Pereira, MD. P.
• da Silva, T
• Lopes, LM. X.
• Krettli, AU.
• Madureira, LS.
• Zukerman-Schpector, J
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• Pereira, MD. P.
• da Silva, T
• Lopes, LM. X.
• Krettli, AU.
• Madureira, LS.
• Zukerman-Schpector, J
• [+] on PubMed
• Pereira, MD. P.
• da Silva, T
• Lopes, LM. X.
• Krettli, AU.
• Madureira, LS.
• Zukerman-Schpector, J

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Molecules 2012, 17(12), 14046-14057; doi:10.3390/molecules171214046

Article

4,5-Seco-Guaiane and a Nine-Membered Sesquiterpene Lactone from Holostylis reniformis

Marcos D. P. Pereira ¹ , Tito da Silva ^1,† , Lucia M. X. Lopes ^1,* , Antoniana U. Krettli ² , Lucas S. Madureira ³  and Julio Zukerman-Schpector ³

¹ Institute of Chemistry, São Paulo State University, UNESP, C.P. 355, 14801-970, Araraquara, SP, Brazil ² Laboratory of Malaria, Institute René Rachou/FIOCRUZ, Av. Augusto de Lima 1715, 30190-002, Belo Horizonte, MG, Brazil ³ Department of Chemistry, Federal University of São Carlos, C.P. 676, 13565-905, São Carlos, SP, Brazil ^† Current address: Federal University of Maranhão, Rua Urbano Santos, s/n, 65900-410, Centro de Ciências Sociais, Saúde e Tecnologia, Campus de Imperatriz, MA, Brazil.

* Author to whom correspondence should be addressed.

Received: 24 September 2012; in revised form: 30 October 2012 / Accepted: 20 November 2012 / Published: 27 November 2012

(This article belongs to the Section Natural Products)

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Abstract: Root extracts of Holostylis reniformis (Aristolochiaceae) yielded three new natural sesquiterpenes, a sesquiterpene with an unusual carbon skeleton, 4,5-seco-guaiane (7-epi-11-hydroxychabrolidione A, 1), a nine-membered lactone with new carbon skeleton (holostylactone, 2), and a new megastigmane [(6S,7E)-6,9-dihydroxy-10-(2'-hydroxy-ethoxy)-4,7-megastigmadien-3-one, 3], together with bulnesol and sitosterol-3-O-β-D-glucopyranoside. The structures of these compounds were determined by spectroscopic analyses and B3LYP/STO-3G** theoretical studies.

Keywords: Holostylis reniformis; Aristolochiaceae; sesquiterpene; 4,5-seco-guaiane; megastigmane

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