Odoratin, an undecanortriterpenoid from Cedrela odorata L.

Chan, Wai-Shing; Taylor, David R.; Aplin, Robin T.

doi:10.1039/c19660000576

Cited by 6 publications

(6 citation statements)

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“…The absolute configuration of these compounds is assumed to be the same as their biogenetic precursor trijugic C (Wang et al 2008). Odoratin ( 22) was reported long ago from Cedrela odorata L. (Chan et al 1966;Farnswoth et al 1980;Nogueira et al 2020) and is an extensive decomposition of the intact limonoids. Its fused-tricyclic skeleton was established by NMR experiments and supported by a mass-spectral fragmentation pattern and is the only degraded limonoid isolated with these features.…”

Section: Degraded Limonoids Bearing a D-valerolactone As B Ringmentioning

confidence: 99%

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

et al. 2023

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Phytochemical studies on the roots, twigs and leaves of Meliaceae and Rutaceae family plants have revealed the presence of non-complex terpenes derived from limonoid fragmentation. The occurrence and chemical structure of these degraded limonoids isolated from 1930 to March 2022 are reported in this review. Particular attention is given to the degradation levels in these compounds and their absolute configuration to discover presumable deconstruction pathways from more complex limonoids. Plausible intermediates have been postulated for most of them that would explain their origin from limonoids. The total or semi-synthesis of the most isolated degraded limonoids or analogues remains undescribed. This review focuses on the bioactivity of these fragmented limonoids and their synthesized analogues. Based on pharmacological and agrochemical studies, degraded limonoids appear to be excellent structural leads to consider for the total or semi-synthesis of more potent derivatives with the aim of discovering new hits and clarifying their modes of action.

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Section: Degraded Limonoids Bearing a D-valerolactone As B Ringmentioning

confidence: 99%

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

et al. 2023

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“…An exhaustive revision of the chemical reports for Cedrela plants shows only 11 studied species: C. angustifolia, [9] C. ciliolate, [54] C. degussi, [55] C. fissilis, [8,[56][57][58][59] C. glazziovi, [39,43] C. mexicana, [60,61] C. montana, [22] C. odorata, [10,17,19,24,26,[44][45][46][47]53,[62][63][64][65][66][67][68][69][70][71][72] C. salvadorensis, [55,[73][74][75][76][77] C. sinensis, [33,52,[78][79][80] and C. toona. [81] C. odorata is the most studied with 21 chemical analysis, including two studies where it is grafted with Toona ciliata.…”

Section: Distribution (Table 1)mentioning

confidence: 99%

“…C. odorata [47] heartwood, [47] -, [26] - [71] C 6 H 6 ,-, -60 CDCl 3 [47] no reported data A-ring seco-limonoids (class IVa, type evoludone; Tables 19 and 20)…”

Section: [62]mentioning

confidence: 99%

Triterpenes and limonoids of Cedrela: Distribution, biosynthesis, and ¹H and ¹³C NMR data

Vasquez-Ruiz

Ramírez-Cisneros

Rios

2021

Magnetic Reson in Chemistry

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Cedrela genus, a member of the Meliaceae family, presents both chemical characteristics associated with and those that distinguish it from the rest of its members. The presence of triterpenes and limonoids is the characteristic of the Meliaceae family, but the class and type of these chemical constituents are distinctive for each genus. Cedrela includes cycloartane, ursane, oleanane, tirucallane, butyrospermane, and apotirucallane triterpenes, and its limonoids belongs to six class and nine types, known as class Ia-type havanensines, class Ib-type delevoyin, class II-type gedunin, class IIIb-type andirobin, class IIIgtype mexicanolide, class IVa-type evoludone, class Va-type obacunol, class Vtype limonin, and class VIII. Each of these structural arrangements includes specific traits, defined by their biosynthetic origin, which can be established by means of structural elucidation techniques, particularly 1 H and 13 C NMR, which assisted by 2D NMR techniques, allowing to deduce their structures unequivocally. The constant presence of these skeletal arrangements in Cedrela ensures that they are its chemophenetic markers and their recurrence is an important criterion for their identity. This review is a compilation of the occurrence of triterpenes and limonoids in Cedrela genus, detailing their biosynthetic association and collecting and organizing their NMR data, with the purpose of facilitating its location, analysis, and use in the phytochemical study of species from this genus.

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“…17 For the synthesis of 8 α -hydroxycarapin ( 6 ), the bicyclo[3.3.1]nonane could be forged through an acylation− Michael addition strategy using a suitable electrophile. Retro-synthetic design via 8 α -hydroxycarapin ( 6 ) would provide a means to test our hypothesis that this material can lead to andirolide N ( 5 ).…”

mentioning

confidence: 99%

“…We developed a general synthetic approach to access limonoids with differing A-ring structures, such as those in Figure , by envisioning that these materials might arise from the degraded limonoid iso -odoratin ( 7 ), the Δ 8(14) isomer of the natural product odoratin . For the synthesis of 8α-hydroxycarapin ( 6 ), the bicyclo[3.3.1]nonane could be forged through an acylation–Michael addition strategy using a suitable electrophile.…”

mentioning

confidence: 99%

Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin

Schuppe

Newhouse

2017

J. Am. Chem. Soc.

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We report the first total synthesis of the limonoid andirolide N using a 12-step sequence from commercially available materials. The final step of this route demonstrates the chemical feasibility of our biosynthetic proposal that andirolide N arises from 8α-hydroxycarapin. The strategic use of a degraded limonoid as a platform for the synthesis of more structurally complex congeners may be a general approach to obtain limonoids with diverse functional properties.

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Odoratin, an undecanortriterpenoid from Cedrela odorata L.

Abstract: EXTRACTION of the West Indian cedar (Cedrela odorata L., Meliaceae) has given variable results.lp2The extract from one specimen has given in small amount, odoratin, ClBH22O4, m.p. 216-223", [a],+ 155' (CHCl,), for which we suggest structure (I).

Cited by 6 publications

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Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

Triterpenes and limonoids of Cedrela: Distribution, biosynthesis, and ¹H and ¹³C NMR data

Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin

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Odoratin, an undecanortriterpenoid from Cedrela odorata L.

Abstract: EXTRACTION of the West Indian cedar (Cedrela odorata L., Meliaceae) has given variable results.lp2The extract from one specimen has given in small amount, odoratin, ClBH22O4, m.p. 216-223", [a],+ 155' (CHCl,), for which we suggest structure (I).

Cited by 6 publications

References 0 publications

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

Triterpenes and limonoids of Cedrela: Distribution, biosynthesis, and 1H and 13C NMR data

Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin

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Triterpenes and limonoids of Cedrela: Distribution, biosynthesis, and ¹H and ¹³C NMR data