Sesquiterpenoids of Cinnamosma fragrans baillon: Structure of cinnamolide, cinnamosmolide and cinnamodial

doi:10.1016/S0040-4020(01)82921-5

Tetrahedron

Volume 25, Issue 17, 1969, Pages 3895-3902

https://doi.org/10.1016/S0040-4020(01)82921-5 Get rights and content

Abstract

The constitution and absolute stereochemistry of three new sesquiterpenoid lactons with drimane skeleton have been elucidated by correlating them to confertifolin.

References (5)

CanonicaL. et al.
Tetrahedron Letters
(1967)
de La BâthieH. Perrier et al.

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Cited by (56)

2016, Comptes Rendus Chimie
Citation Excerpt :
In C. fragrans, phytochemical explorations until today have been able to detect 7 drimane-type sesquiterpene lactones. Cinnamolide (C15H22O2) (compound 6 in Fig. 3) and cinnamosmolide (C17H24O5) (compound 7 in Fig. 3) were identified at the same time as cinnamodial from an acetone extract of the bark [16,17]. In parallel, the same research team has identified the same year three other minority compounds: bemarivolide (C17H24O4) (compound 8 in Fig. 3), bemadienolide (C15H20O2) (compound 9 in Fig. 3) and fragrolide (C15H20O3) (compound 10 in Fig. 3) [18].
Cinnamosma fragrans is an endemic plant used in traditional medicine. The geographical distribution of this Canellaceae is limited to Madagascar. Few phytochemical investigations performed on this plant have described atypical sesquiterpenes including drimane-type sesquiterpenes, drimane-type sesquiterpene lactones, sesquiterpene lactams and coloratane sesquiterpenes. These original sesquiterpenes are associated with pharmaceutical activities.
Cinnamosma fragrans est une plante endémique utilisée en médecine traditionnelle. La répartition géographique de cette Canellacée est limitée à Madagascar. Les rares investigations phytochimiques réalisées sur cette plante ont permis de décrire des sesquiterpènes atypiques, dont des sesquiterpènes de type drimane, des lactones sesquiterpéniques de type drimane, des lactames sesquiterpéniques et des sesquiterpéniques de type coloratane. Ces sesquiterpènes originaux sont associés à des activités pharmacologiques.
Terpenoids with alpha-glucosidase inhibitory activity from the submerged culture of Inonotus obliquus
2014, Phytochemistry
Citation Excerpt :
The IR and NMR spectra of 6 strongly resembled those of 5 (Table 2), suggesting that they were isomers with similar structures. Detailed NMR spectroscopic analyses established that compound 6 was 6β-hydroxy-trans-dihydroconfertifolin, a synthetic intermediate reported during the structure determination of several drimane sesquiterpenoids from Cinnamosma fragrans (Canonic et al., 1969). However, only the melting point and IR data of the intermediate were reported.
Lanostane-type triterpenoids, inotolactones A and B, a drimane-type sesquiterpenoid, inotolactone C, and five known terpenoids 6β-hydroxy-trans-dihydroconfertifolin, inotodiol, 3β,22-dihydroxyanosta-7,9(11),24-triene, 3β-hydroxycinnamolide, and 17-hydroxy-ent-atisan-19-oic acid, were isolated from the submerged culture of chaga mushroom, Inonotus obliquus. Their structures were characterized by spectroscopic methods, including MS and NMR (1D and 2D) spectroscopic techniques. Inotolactones A and B, examples of lanostane-type triterpenoids bearing α,β-dimethyl, α,β-unsaturated δ-lactone side chains, exhibited more potent alpha-glucosidase inhibitory activities than the positive control acarbose. This finding might be related to the anti-hyperglycemic properties of the fungus and to its popular role as a diabetes treatment. In addition, a drimane-type sesquiterpenoid and an atisane-type diterpenoid were isolated from I. obliquus.
Composition and antimicrobial activity of essential oils of Cinnamosma fragrans
2009, Food Chemistry
Essential oil samples of Cinnamosma fragrans from two regions in Madagascar, Tsaramandroso (38 samples) and Mariarano (30 samples), were analysed by GC/MS. Fifty-seven components were identified, accounting from 88.3% to 99.4% of the oils’ composition. The major components were linalool (72.5 ± 23.3%) in Tsaramandroso and 1,8-cineole (47.3 ± 10.2%) in Mariarano.
Samples B8 (95.8% linalool) from Tsaramandroso and B143 (71.6% 1,8-cineole) from Mariarano containing the highest proportions of the two main components identified, were selected to determine antimicrobial activities against 10 microbial strains. Bacillus subtilis and Staphylococcus aureus were the most sensitive strains to both oils. Minimum inhibitory concentration (MIC) values were lower for B143 against all tested Gram-negative strains than pure 1,8-cineole. B8 showed higher MIC values than pure linalool against Salmonella typhimurium and Vibrio alginolyticus, and similar MIC values to linalool towards the other Gram-negative strains. Both essential oils exhibited higher MIC values towards Fusarium oxysporum than their respective pure major component. These results suggested the occurrence of synergism or antagonism effects between the different oil constituents.
Inhibition of mycobacterial arylamine N-acetyltransferase contributes to anti-mycobacterial activity of Warburgia salutaris
2007, Bioorganic and Medicinal Chemistry
In this study, we show that extracts and a purified compound of Warburgia salutaris exhibit anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv and Mycobacterium bovis BCG Pasteur. The extracts did not inhibit growth of Escherichia coli and were not toxic to cultured mammalian macrophage cells at the concentrations at which anti-mycobacterial activity was observed. The extract and pure compound inhibited pure recombinant arylamine N-acetyltransferase (NAT), an enzyme involved in mycobacterial cell wall lipid synthesis. Moreover, neither extract nor pure compound inhibited growth of a strain of M. bovis BCG in which nat has been deleted suggesting that NAT may indeed be a target within the mycobacterial cell. The purified compound is a novel drimane sesquiterpenoid lactone, 11α-hydroxycinnamosmolide. These studies show that W. salutaris is a useful source of anti-tubercular compounds for further analysis and supports the hypothesis of a link between NAT inhibition and anti-mycobacterial activity.
Synthetic investigations in the field of drimane sesquiterpenoids
2006, Studies in Natural Products Chemistry
In this article, the results of the author’s investigations in the field of the synthesis of drimane sesquiterpenoids, a group of terpenic compounds which possess a wide variety of biological activities (antifeedant, antibacterial, antifungal, anticomplemental, cytotoxic, antiallergic, piscicidal, molluscicidal, plant growth regulatory, insecticidal and others) have been reviewed. The original structural- and stereoselective methods for obtaining natural compounds in the optically-active form, and also of important intermediates on the pathway to them, including alcohols, poliols, ketones, lactones and acids, have been elaborated. Most of the compounds obtained are polyfunctional. Much attention has been focussed on the synthesis of drimenol, a drimanic sesquiterpene key compound, which is widely used as a starting substance in syntheses of many biologically active drimanes. Much effort has been devoted to elaborate the syntheses of drim-8-en-7-one and drim-5,8-diene-7-one, compounds possessing a great synthetic potential. Indeed, using those above a large number of natural compounds, such as isodrimenin, 7-oxoisodrimenin, 7-oxo-5,6-dehydroisodrimenin, trans-tetrahydroactinidiolide and intermediates for the syntheses of polygodial and warburganal, compounds with various and high biological activities, were prepared.
Microbiologically-assisted hemisynthesis of 1α-hydroxydrimenol
2001, Tetrahedron Asymmetry
The hemisynthesis of 1α-hydroxydrimenol has been selected to illustrate a synthetic route involving an initial microbial 3β-hydroxylation of a drimenol derivative followed by a functionalization transfer to position 1α, thus generating a new potentially bioactive hydroxylated terpenic compound. Several methods have been investigated for the protection and the regeneration of the 7,8-double bond of drimenyl derivatives.

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¹: Postdoctoral fellow of CNR, Italy.

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Sesquiterpenoids of Cinnamosma fragrans baillon: Structure of cinnamolide, cinnamosmolide and cinnamodial

Abstract

Tetrahedron Letters