Anticancer sesquiterpene lactones of Michelia compressa (magnoliaceae)

Ogura, Masaru; Cordell, Geoffrey A.; Farnsworth, Norman R.

doi:10.1016/s0031-9422(00)88656-2

Cited by 126 publications

(83 citation statements)

References 10 publications

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“…One singlet at δ 3.32 (3H, H-16) and one triplet at δ 3.99 (1H, J 10.3 Hz, H-6) confirmed that 7 was the single product of this reaction. In the 13 C NMR spectrum was only observed one signal of sp 2 carbon (δ 175.9; C=O) confirming thus the hydrogenation of double bond C 1 -C 10 . The stereochemistry of the stereogenic carbons C 1 and C 10 was determined by NOE experiment.…”

Section: Resultsmentioning

confidence: 82%

“…R f 0.50 (50% EtOAc/hexane). IR (film) ν max / cm H NMR, 13 C NMR and IR spectra and NPPN -UFRJ for mass spectra. The author also thanks the referees for helpful suggestions about English grammar and the JBCS editorial staff for patience and understanding.…”

Section: (R)10(r) -Dihydromicheliolide (8)mentioning

confidence: 99%

“…Continuing the research programme of chemical transformations of eremanthine (1), this compound was converted to the diol 5, 12 a potential precursor for the synthesis of micheliolide (9), an anticancer sesquiterpene lactone isolated from Michelia compressa 13 and Michelia champaca. 14 In this paper we report the obtention of diol 5 and its transformation into micheliolide (9) and 1(R),10(R)-dihydromicheliolide (8).…”

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confidence: 99%

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Chemical transformations of eremanthine: synthesis of micheliolide and 1(R),10(R)-dihydromicheliolide

Alves¹,

Fantini²

2005

J. Braz. Chem. Soc.

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Eremantina (1), uma substância natural abundante, foi transformada em quatro etapas no diol 5. Após hidrogenólise de 5 (55 psi de H 2 , Pd/C, 30 min) obteve-se 7. Hidrogenação de 5 usando-se uma baixa pressão de hidrogênio (5 psi) e um menor tempo de reação (15 min) forneceu uma mistura de 6 e 7 (3:1). Os compostos 6 e 7 foram, a seguir, transformados nas respectivas α-metileno-γ-lactonas miqueliolido (9) e 1(R),10(R)-diidromiqueliolido (8), após eliminação de metanol.Eremanthine (1), an abundant natural substance, was transformed in four steps into diol 5. Hydrogenolysis of 5 (55 psi of H 2 , Pd/C, 30 min) furnished 7. Hydrogenation of 5 using a low hydrogen pressure (5 psi) and a short reaction time (15 min) led to a mixture of 6 and 7 (3:1). Compounds 6 and 7 were then transformed respectively to the α-methylene-γ-lactones micheliolide (9) and 1(R),10(R)-dihydromicheliolide (8), after elimination of methanol.

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Section: Resultsmentioning

confidence: 82%

Section: (R)10(r) -Dihydromicheliolide (8)mentioning

confidence: 99%

mentioning

confidence: 99%

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Chemical transformations of eremanthine: synthesis of micheliolide and 1(R),10(R)-dihydromicheliolide

Alves¹,

Fantini²

2005

J. Braz. Chem. Soc.

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“…The structures were elucidated by spectroscopy data.From the large genus Achillea (compositae-anthemideae) several sesquiterpene lactones were reported 31 . We now have studied Achillea micrantha M. B.…”

Section: Sesquiterpene Lactones From Achillea Micrantha Mbmentioning

confidence: 99%

Sesquiterpene Lactones of Iranian Compositae Family (Astraceae); Their Chemical Constituents and Anti-plasmodial Properties of Tehranolide (A.Review)

Rustaiyan¹,

Faridchehr²,

Bakhtiyar³

2017

Orient. J. Chem

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Sesquiterpene lactones constitute a large and diverse group of biologically active plant chemical that have been identified in the several plant families.The pharmacological properties of interest involving the sesquiterpene lactones are their antibacterial, antifungal and anti-plusmodial activities.Indeed, assessing the biological activities of the sesquiterpene lactones found in plants and their essential oil is of great medicinal importance because they could potentially be utilized as therapeutic agents for the treatment of such infections.

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“…With substituted hydroazulene (Ϯ)-44 in hand, the group of Vandewalle embarked on the total synthesis of (Ϯ)-compressanolide (5), [19a] a guaianolide first isolated from Michelia compressa. [21] Furthermore, variation of this route allowed the synthesis of (Ϯ)-estafiatin (4), [19a,19c] a natural product first isolated by Romo and coworkers from Artemisia mexicana. [22] The opening step entails the epoxidation of the double bond in the five-membered ring of (Ϯ)-44.…”

Section: Total Synthesis Of (؎)-Compressanolide and (؎)-Estafiatinmentioning

confidence: 99%

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

Schall

Reiser

2008

Eur J Org Chem

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The biosynthetic pathways of sesquiterpene lactones are described in conjunction with recent developments in the total syntheses of various biologically active guaianolides. Different strategies towards the 5,7,5‐membered ring system are highlighted. Oxidative diol cleavages, aldol reactions, and intramolecular cyclopropanations were used as key reactions to construct the racemic guaianolide core system. Radical cyclizations, as well as ring closing metathesis, were successfully applied in asymmetric approaches. Biomimetic reactions were also applied as versatile tools for the construction of these highly complex natural products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Anticancer sesquiterpene lactones of Michelia compressa (magnoliaceae)

Cited by 126 publications

References 10 publications

Chemical transformations of eremanthine: synthesis of micheliolide and 1(R),10(R)-dihydromicheliolide

Chemical transformations of eremanthine: synthesis of micheliolide and 1(R),10(R)-dihydromicheliolide

Sesquiterpene Lactones of Iranian Compositae Family (Astraceae); Their Chemical Constituents and Anti-plasmodial Properties of Tehranolide (A.Review)

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

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