β-Agarofurans from seeds of Maytenus boaria

Alarcón, Julio; Becerra, José; Silva, Mario; Morgenstern, T.; Jakupovic, Jasmin

doi:10.1016/0031-9422(95)00422-4

Cited by 18 publications

(7 citation statements)

References 3 publications

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“…It has leaves of a lanceolate form of about 3 to 9 cm in length and between 1 and 3 cm in width. Previous reports of natural compounds from the seeds of Maytenus boaria showed highly oxygenated sesquiterpenes with a dihydro--agarofuran skeleton, as determined by 1D (one-dimensional) and 2D (two-dimensional) NMR (Alarcó n et al, 1995). As part of our search for new compounds from Chilean flora, we report herein a new related compound with a hydroxy group at position C-4, viz.…”

Section: Introductionmentioning

confidence: 84%

A dihydro-β-agarofuran sesquiterpene from Maytenus boaria

Paz

Dossow

Tiznado

et al. 2017

Acta Crystallogr C Struct Chem

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The natural compound (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9,10-trihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin-5-yl furan-3-carboxylate, CHO, (I), is a β-agarofuran sesquiterpene isolated from the seeds of Maytenus boaria as part of a study of the secondary metabolites from Chilean flora. The compound presents a central structure formed by a decalin system esterified with acetate at site 1 and furan-3-carboxylate at site 9. The chirality of the skeleton can be described as 1S,4S,5S,6R,7R,8R,9R,10S, which is consistent with that suggested by NMR studies. Unlike previously reported structures of sesquiterpenes containing a pure dihydro-β-agarofuran skeleton, (I) exhibits a three-dimensional hydrogen-bonded network.

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Section: Introductionmentioning

confidence: 84%

A dihydro-β-agarofuran sesquiterpene from Maytenus boaria

Paz

Dossow

Tiznado

et al. 2017

Acta Crystallogr C Struct Chem

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“…Compounds 1 α ,6 β -diacetoxy-8 α -hydroxy-9 β -furoyloxy- β -agarofuran ( 1 89 ), 1 α -acetoxy-6 β ,8 α -dihydroxy-9 β -furoyloxy- β -agarofuran ( 1 90 ), 1 α -benzoyloxy-2 α ,3 β ,6 β ,9 β ,14-pentaacetoxy-8-oxo- β -agarofuan ( 1 91 ) and 1 α -furoyloxy-2 α ,3 β ,6 β ,9 β ,14-pentaacetoxy-8-oxo- β -agarofuan ( 19 2 ) were obtained from an extract of the seeds of M. boaria [ 67 ]. Bilocularins A−I ( 193 – 201 ) were isolated from M. bilocularis .…”

Section: Chemical Constituents Of Maytenusmentioning

confidence: 99%

“…Two novel trimer triscutins, A and B (65)(66), have been isolated from extracts of the root bark of M. scutioides [40]. Four new triterpene dimers, xuxuarine Eα (67), scutionin αB (68), 6 ,7 -dihydro-scutionin αB (69) and 6 β-methoxy-6 ,7 dihydro-scutionin αB (70), have been isolated from the extracts of the roots of M. blepharodes and M. magellanica [41,42] (Table 1 and Figure 1). 76) and (3β)lup-20(30)-ene-3,29-diol (77) have been obtained from the hexane extracts of the stems and branches of M. imbricate [45].…”

Section: Friedelane Friterpenoidsmentioning

confidence: 99%

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

Huang

Chen

et al. 2021

Molecules

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The genus Maytenus is a member of the Celastraceae family, of which several species have long been used in traditional medicine. Between 1976 and 2021, nearly 270 new compounds have been isolated and elucidated from the genus Maytenus. Among these, maytansine and its homologues are extremely rare in nature. Owing to its unique skeleton and remarkable bioactivities, maytansine has attracted many synthetic endeavors in order to construct its core structure. In this paper, the current status of the past 45 years of research on Maytenus, with respect to its chemical and biological activities are discussed. The chemical research includes its structural classification into triterpenoids, sesquiterpenes and alkaloids, along with several chemical synthesis methods of maytansine or maytansine fragments. The biological activity research includes activities, such as anti-tumor, anti-bacterial and anti-inflammatory activities, as well as HIV inhibition, which can provide a theoretical basis for the better development and utilization of the Maytenus.

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“…The seeds of Maytenus boaria are known to be rich in natural products, and many reports on the subject disclosed a number of highly oxygenated sesquiterpenes with a dihydroagarofuran skeleton, as determined by one-and two-dimensional NMR (e.g. Alarcó n et al, 1995). It is to be noted that the curative properties of the plant were already well known and thoroughly used by the ancient inhabitants of the Araucania.…”

Section: Introductionmentioning

confidence: 99%

Three new dihydro-β-agarofuran sesquiterpenes from the seeds ofMaytenus boaria

et al. 2018

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As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new β-agarofuran sesquiterpenes, namely (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9-dihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepine-5,10-diyl bis(furan-3-carboxylate), CHO, (II), (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepine-5,10-diyl bis(furan-3-carboxylate), CHO, (III), and (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-10-(benzoyloxy)-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin-5-yl furan-3-carboxylate, CHO, (IV), obtained from the seeds of Maytenus boaria and closely associated with a recently published relative [Paz et al. (2017). Acta Cryst. C73, 451-457]. In the (isomorphic) structures of (II) and (III), the central decalin system is esterified with an acetate group at site 1 and furoate groups at sites 6 and 9, and differ at site 8, with an OH group in (II) and no substituent in (III). This position is also unsubstituted in (IV), with site 6 being occupied by a benzoate group. The chirality of the skeletons is described as 1S,4S,5S,6R,7R,8R,9R,10S in (II) and 1S,4S,5S,6R,7R,9S,10S in (III) and (IV), matching the chirality suggested by NMR studies. This difference in the chirality sequence among the title structures (in spite of the fact that the three skeletons are absolutely isostructural) is due to the differences in the environment of site 8, i.e. OH in (II) and H in (III) and (IV). This diversity in substitution, in turn, is responsible for the differences in the hydrogen-bonding schemes, which is discussed.

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β-Agarofurans from seeds of Maytenus boaria

Cited by 18 publications

References 3 publications

A dihydro-β-agarofuran sesquiterpene from Maytenus boaria

A dihydro-β-agarofuran sesquiterpene from Maytenus boaria

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

Three new dihydro-β-agarofuran sesquiterpenes from the seeds ofMaytenus boaria

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