Chemical Composition of the Bark Oil of Balsam Fir<i>Abies balsamea</i>(L.) Mill.

Ross, Josette; Gagnon, Hélène; Girard, Delphine; Hachey, Jean-Marie

doi:10.1080/10412905.1996.9700636

Cited by 11 publications

(7 citation statements)

References 5 publications

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“…Since the intensity of the ROESY cross-peak is correlated to r −6 , it suggested that abibalsamin F ( 6) could be related to model II, while abibalsamin I ( 9) could be linked to model I. Therefore, both compounds were proposed to be 24R,25R-[2-(4-methylpent-3enyl)but-2-ene-1,4-diyl]-23-oxo-3,4-seco-9βH-lanosta-4(28),6,8-( 14)-triene-3,26-dioic acid ( 6) and 24S,25S-[2-(4-methylpent-3-enyl)but-2-ene-1,4-diyl]-23-oxo-3,4-seco-9βH-lanosta-4-( 28),6,8( 14)-triene-3,26-dioic acid (9). Following this protocol, four calculated models (V−VIII) were also developed for tetraterpenoid 3 or 5 and with configurations defined as S,S or R,R at C-24/C-25 (Table 4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea

et al. 2015

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Eight non-carotenoid tetraterpenoids, abibalsamins C-J (3-10), were isolated from the oleoresin of Abies balsamea. Their chemical structures were determined based on analysis of 1D/2D NMR and MS data. The assignment of their relative configurations was accomplished using homonuclear coupling constants in tandem with ROESY data. However, the presence of two stereogenic centers on a flexible side chain complicated the characterization. In silico models and ROESY data were analyzed in order to assign relative configurations of the isolated tetraterpenoids. Abibalsamins B and H-J showed moderate cytotoxicity against human A549 lung carcinoma cells, with IC50 values ranging between 6.7 and 10 μM.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…The traditional medicinal uses of A. balsamea have prompted the search for bioactive compounds from this tree. Phytochemical studies of balsam fir extracts led to the identification of secondary metabolites such as monoterpenoids, − sesquiterpenoids, − ,,,− diterpenoids, − and triterpenoids, , as well as phenolic compounds and ionones …”

mentioning

confidence: 99%

DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea

et al. 2015

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“…The mean concentration of this compound greatly decreased in the summer collection. There are only a few reports on the presence of bornyl acetate in genus A bies (Guenther, 1952;Bagci et al, 1999;Ross et al, 1996). Strong positive correlation existed be tween camphene and bornyl acetate, which was significant at 0.1 level.…”

Section: Needle Oleoresinmentioning

confidence: 97%

Foliar and Cortex Oleoresin Variability of Silver Fir (Abies alba Mill.) in Albania

Zeneli

Tsitsimpikou

Petrakis³

et al. 2001

Zeitschrift Für Naturforschung C

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A bies alba, O leoresin, TerpenesTerpene com position o f needle and cortical oleoresin from lateral shoots were analyzed by GC/MS for four Silver fir (A bies alba Mill.) populations scattered in natural species range in Albania. More than sixty compounds were detected in the needle oleoresin, which was characterized by a high content of a-pinene, camphene, ß-pinene, limonene and bornyl ace tate. Three m onoterpenes, a-pinene, ß-pinene and limonene, and two sesquiterpenes, ß-caryophyllene and germacrene D, comprised the majority of cortical oleoresin. The terpene composition differences among the populations that led to the recognition o f two chemotypes. The needle oleoresin from the provinces of Puka, Bulqiza and Llogara were character ised by high amounts of ß-pinene, camphene and a-pinene and low amounts of limonene, while that from D renova had high amounts of ß-pinene and limonene. A similar pattern was found in the cortical oleoresin with the exception of camphene that was a minor contributor. Geographical and seasonal variation between the populations was, also, investigated. Multi variate analysis o f both needle and cortical oleoresin separated D renova (southeastern pop ulation) from the other sites. W hen both major m onoterpenes and sesquiterpenes were con sidered four chemical profiles could be attributed. Based on their chemical profiles, the populations can be divided into two groups:• Populations with high content of ß-pinene and a-pinene but a low content of limonene (Puka, Bulqiza and Llogara), typical of most of A. alba populations in all its distribution range.• Population with a high content of limonene and a moderate content of ß-pinene and apinene (D renova).

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“…Norris et al [ 6 ] demonstrated that guaiacwood oil was predominantly composed of guaiol along with the minor constituent sesquiterpenoids, bulnesol, and bulnesene. Canadian balsam fir is predominantly composed of α-pinene, β-pinene, and phellandrene, any of which may be responsible for its toxicity [ 20 ]. Further work is needed to characterize the biological activity of these oils and assess the contribution of each individual constituent towards overall toxicity.…”

Section: Discussionmentioning

confidence: 99%

Co-Toxicity Factor Analysis Reveals Numerous Plant Essential Oils Are Synergists of Natural Pyrethrins against Aedes aegypti Mosquitoes

Norris

Bloomquist

2021

Insects

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With insecticide-resistant mosquito populations becoming an ever-growing concern, new vector control technologies are needed. With the lack of new chemical classes of insecticides to control mosquito populations, the development of novel synergists may improve the performance of available insecticides. We screened a set of 20 plant essential oils alone and in combination with natural pyrethrins against Aedes aegypti (Orlando) female adult mosquitoes to assess their ability to synergize this natural insecticide. A co-toxicity factor analysis was used to identify whether plant oils modulated the toxicity of natural pyrethrins antagonistically, additively, or synergistically. Both knockdown at 1 h and mortality at 24 h were monitored. A majority of oils increased the toxicity of natural pyrethrins, either via an additive or synergistic profile. Many oils produced synergism at 2 µg/insect, whereas others were synergistic only at the higher dose of 10 µg/insect. Amyris, cardamom, cedarwood, and nutmeg East Indies (E.I.) oils were the most active oils for increasing the mortality of natural pyrethrins at 24 h with co-toxicity factors greater than 50 at either or both doses. A number of oils also synergized the 1 h knockdown of natural pyrethrins. Of these, fir needle oil and cypress oils were the most successful at improving the speed-of-action of natural pyrethrins at both doses, with co-toxicity factors of 130 and 62, respectively. To further assess the co-toxicity factor method, we applied selected plant essential oils with variable doses of natural pyrethrins to calculate synergism ratios. Only the oils that produced synergistic co-toxicity factors produced statistically significant synergism ratios. This analysis demonstrated that the degree of co-toxicity factor correlated well with the degree of synergism ratio observed (Pearson correlation coefficient r = 0.94 at 2 µg/insect; r = 0.64 at 10 µg/insect) and that the co-toxicity factor is a useful tool in screening for synergistic activity.

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Chemical Composition of the Bark Oil of Balsam FirAbies balsamea(L.) Mill.

Cited by 11 publications

References 5 publications

DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea

DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea

Foliar and Cortex Oleoresin Variability of Silver Fir (Abies alba Mill.) in Albania

Co-Toxicity Factor Analysis Reveals Numerous Plant Essential Oils Are Synergists of Natural Pyrethrins against Aedes aegypti Mosquitoes

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