Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol

Taber, Douglass F.; Nelson, Christopher G.

doi:10.1021/jo200075v

Cited by 28 publications

(5 citation statements)

References 50 publications

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“…These results were consistent with those obtained by Menut et al (1997), although some discrepancies were found. They consisted in a lower amount of presilphiperfolan-8-ol (6.5 %) and the absence of cameroonan-7-α-ol that is the major contributor to the strong woody and patchouli-like smell of the root oil (Taber and Nelson, 2011). Conversely, we did not find presilphiperfol-7(8)-ene that was characterized as a new compound by these authors.…”

Section: Chemical Composition Of the Essential Oilscontrasting

confidence: 76%

Traditional herbal remedies and dietary spices from Cameroon as novel sources of larvicides against filariasis mosquitoes?

et al. 2016

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In Cameroon, many dietary spices are used by traditional healers to cure several diseases such as cancer and microbial infections. Aframomum daniellii, Dichrostachys cinerea and Echinops giganteus are Cameroonian spices widely used as flavourings and as food additives. Moreover, they are traditionally herbal remedies employed to treat several diseases, as well as to control populations of insect pests. In this research, we analysed the chemical composition of A. daniellii, D. cinerea and E. giganteus essential oils and we evaluated their larvicidal potential against larvae of the filariasis and West Nile virus vector Culex quinquefasciatus. The essential oils were obtained from different plant parts by hydrodistillation and their composition was analysed by GC-MS. The three spices exhibited different volatile chemical profiles, being characterized by 1,8-cineole, sabinene and β-pinene (A. daniellii), geraniol and terpinen-4-ol (D. cinerea), and silphiperfol-6-ene and presilphiperfolan-8-ol (E. giganteus). Results showed that the highest larvicidal toxicity on Cx. quinquefasciatus was exerted by D. cinerea essential oil (LC 50 = 39.1 μL L −1 ), followed by A. daniellii ) and E. giganteus (LC 50 = 227.4 μL L −1 ). Overall, the chance to use the D. cinerea essential oil against Cx. quinquefasciatus young instars seems promising, since it is effective at moderate doses and could be an advantageous alternative to build newer mosquito control tools.

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Section: Chemical Composition Of the Essential Oilscontrasting

confidence: 76%

Traditional herbal remedies and dietary spices from Cameroon as novel sources of larvicides against filariasis mosquitoes?

et al. 2016

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“…Another noteworthy constituent occurring in the oil was ( E )-caryophyllene (6.3%). The cameroonan-7-α-l, is responsible for the patchouli-like smell of the root oil [ 52 ]. The reported composition was quite consistent with that previously reported by Menut et al [ 49 ] for root samples collected in Cameroon.…”

Section: Resultsmentioning

confidence: 99%

Trypanosoma brucei Inhibition by Essential Oils from Medicinal and Aromatic Plants Traditionally Used in Cameroon (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea and Echinops giganteus)

Kamte

Ranjbarian

Campagnaro

et al. 2017

IJERPH

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Essential oils are complex mixtures of volatile components produced by the plant secondary metabolism and consist mainly of monoterpenes and sesquiterpenes and, to a minor extent, of aromatic and aliphatic compounds. They are exploited in several fields such as perfumery, food, pharmaceutics, and cosmetics. Essential oils have long-standing uses in the treatment of infectious diseases and parasitosis in humans and animals. In this regard, their therapeutic potential against human African trypanosomiasis (HAT) has not been fully explored. In the present work, we have selected six medicinal and aromatic plants (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea, and Echinops giganteus) traditionally used in Cameroon to treat several disorders, including infections and parasitic diseases, and evaluated the activity of their essential oils against Trypanosma brucei TC221. Their selectivity was also determined with Balb/3T3 (mouse embryonic fibroblast cell line) cells as a reference. The results showed that the essential oils from A. indica, A. daniellii, and E. giganteus were the most active ones, with half maximal inhibitory concentration (IC50) values of 15.21, 7.65, and 10.50 µg/mL, respectively. These essential oils were characterized by different chemical compounds such as sesquiterpene hydrocarbons, monoterpene hydrocarbons, and oxygenated sesquiterpenes. Some of their main components were assayed as well on T. brucei TC221, and their effects were linked to those of essential oils.

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“…201 The red alga Laurencia dendroidea contains a silphiperfolane sesquiterpene with leishmanicidal activity. 123 The synthesis of (À)-cameroonan-7a-ol from (+)-citronellal has been achieved, 202 whilst (R)-limonene has been used as starting material in the synthesis of the angular triquinane system present in the sesquiterpenes norsilphiperfolanes and norcameroonanes. 203 Boledulins A-C 209-211 are three botryane sesquiterpenoids, which have been obtained from the basidiomycete Boletus edulis.…”

Section: Chamigrane and Thujopsanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga¹

2012

Nat. Prod. Rep.

102

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Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol

Abstract: In the course of a synthesis of the tricyclic sesquiterpene (−)-cameroonan-7α-ol from the acyclic (+)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established.

Cited by 28 publications

References 50 publications

Traditional herbal remedies and dietary spices from Cameroon as novel sources of larvicides against filariasis mosquitoes?

Traditional herbal remedies and dietary spices from Cameroon as novel sources of larvicides against filariasis mosquitoes?

Trypanosoma brucei Inhibition by Essential Oils from Medicinal and Aromatic Plants Traditionally Used in Cameroon (Azadirachta indica, Aframomum melegueta, Aframomum daniellii, Clausena anisata, Dichrostachys cinerea and Echinops giganteus)

Natural sesquiterpenoids

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