Bisabolenes and Furanosesquiterpenoids of Kenyan<i>Commiphora kua</i>Resin

Manguro, Lawrence Onyango Arot; Mukonyi, Kavaka M.; Githiomi, Joseph K.

doi:10.1055/s-2006-957815

Cited by 15 publications

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“…Moreover, a previous study on the chemical composition of another Soqotri Commiphora species, namely C. kua [ 21 ], showed the absence of the major components in C. ornifolia and C. parvifolia such as camphor, α-fenchol, caryophyllene oxide and hexadecanoic acid. Generally, the comparison of our data with those of literature showed that the main constituents of chemical composition of the two investigated endemic Commiphora oils were markedly different from that of other known Commiphora species e.g., C. myrrha, C. kataf, C. holtziana, C. shaerocarpa, C. kua , C. opobalsamum and C. africana [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. The data obtained can be used as a chemotaxonomical marker for Commiphora sp.…”

Section: Resultssupporting

confidence: 43%

“…Such compounds e.g. α-pinene, β-pinene, p -cymene and α-thujene represented the most major compounds in many reported Commiphora oils [ 17 , 18 , 19 , 20 ]. Moreover, a previous study on the chemical composition of another Soqotri Commiphora species, namely C. kua [ 21 ], showed the absence of the major components in C. ornifolia and C. parvifolia such as camphor, α-fenchol, caryophyllene oxide and hexadecanoic acid.…”

Section: Resultsmentioning

confidence: 99%

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Chemical Analysis and Biological Activity of the Essential Oils of Two Endemic Soqotri Commiphora Species

2010

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The barks of two endemic Commiphora species namely, Commiphora ornifolia (Balf.f.) Gillett and Commiphora parvifolia Engl., were collected from Soqotra Island in Yemen and their essential oils were obtained by hydrodistillation. The chemical composition of both oils was investigated by GC and GC-MS. Moreover, the essential oils were evaluated for their antimicrobial activity against two Gram-positive bacteria, two Gram-negative bacteria and one yeast species by using a broth micro-dilution assay for minimum inhibitory concentrations (MIC) and for their antioxidant activity by measuring the DPPH radical scavenging activity. A total of 45 constituents of C. ornifolia (85.6%) and 44 constituents of C. parvifolia (87.1%) were identified. The oil of C. ornifolia was characterized by a high content of oxygenated monoterpenes (56.3%), of which camphor (27.3%), α-fenchol (15.5%), fenchone (4.4%) and borneol (2.9%) were identified as the main components. High contents of oxygenated sesquiterpenes (36.1%) and aliphatic acids (22.8%) were found in C. parvifolia oil, in which caryophyllene oxide (14.2%), β-eudesmol (7.7%), bulnesol (5.7%), T-cadinol (3.7%) and hexadecanoic acid (18.4%) predominated. The results of the antimicrobial assay showed that both oils exhibited moderate to high antibacterial activity especially against Gram-positive bacteria. C. ornifolia oil was the most active. In addition, the DPPH-radical scavenging assay exhibited only weak antioxidant activities for both oils at the high concentration tested.

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Section: Resultssupporting

confidence: 43%

Section: Resultsmentioning

confidence: 99%

Chemical Analysis and Biological Activity of the Essential Oils of Two Endemic Soqotri Commiphora Species

2010

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“…Compounds 1 and 2 were identified on the basis of their spectral data. Compound 1 (0.09% yield from the resin) was previously reported from C. molmol and C myrrha (8) and compound 2 (0.01 % yield from the resin) from C erythraea (10), C. myrrha (10), C.mo!mol (11), and C.kua (12). NMR spectral data of Genetically altered obese diabetic mice (designated C57BL/ l<s-db/db) served as experimental animals according to our protocol (13).…”

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confidence: 76%

Antihyperglycemic Furanosesquiterpenes fromCommiphora myrrha

et al. 1999

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“…The other component (3) considered novel afforded a molecular ion peak in the MS at m/z 476, calculated to be C 30 H 52 O 4 . From a preliminary observation, its mass spectrum exhibited the main features of a dammarane triterpene 9) as evidenced by fragment peaks at m/z 376, 315, 208, and 207.…”

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confidence: 99%

Further Bisabolenes and Dammarane Triterpenes of Commiphora kua Resin

Manguro

Ugi²,

Lemmen³

2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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The plant species Commiphora kua (Burseraceae) is known for an oleoresin exudate which is an important article of commerce. 1) The plant is also used in herbal medicine as a remedy for snakebite, gonorrhoea, stomach disorders, and livestock related diseases. 2) Previous phytochemical studies on the plant resin afforded cycloartane triterpenes, 3) bisabolenes, and furanosesquiterpenoids based on a germacrane skeleton, 4) dammarane triterpenes, and octanordammaranes. 5) In continuing with our study, we now report the isolation and structural elucidation of bisabolene; 6-hydroxy-2-methyl-5-(5Ј-hydroxy-1Ј(R),5Ј-dimethylhex-3Ј-enyl)-phenol (1) along with two novel dammarane triterpenes; 3b,16b,20(S),25-tetrahydroxydammar-23-ene (3) and its acetate derivative, 3b-acetoxy-16b,20(S),25-trihydroxydammar-23-ene (4). Also being reported from the plant are known compounds characterised as 2-methyl-5-(4Ј(S)-hydroxy-1Ј(R),5Ј-dimethylhex-5Ј-enyl)-phenol (2), 6) 2-methoxyfuranodienone and 2-acetoxyfuranodienone, 7) b-amyrin and its acetate derivative, 8) 3b,16b,20(R)-trihydroxydammar-24-ene (5) and its acetate, 3b-acetoxy-16b,20(R)-dihydroxydammar-24-ene (6). 9) Their structures have been established based on extensive spectroscopic (UV, IR, 1 H-and 13 C-NMR and MS) and chemical studies.Compound 2 inhibited the growth of the plant pathogenic fungus Cladosporium cucumerinum on thin layer chromatography plates. Results and DiscussionCompound 1 displayed a molecular ion peak at m/z 250 in the mass spectrum, corresponding to C 15 H 22 O 3 . In its 1 H-NMR spectrum the main features of a tetra-substituted benzene ring were evident: two low field protons appearing as doublets at d H 6.90 and 6.70, a benzenoid methyl singlet (d H 2.23), a benzylic proton (d H 2.60), and two benzenoid hydroxyls (d H 7.20, D 2 O exchangeable) were present. The two dimensional total correlation spectroscopy (2D TOCSY) experiments 10,11) together with 1 H-1 H correlation spectroscopy (COSY) correlations were used to identify the spin system for the two protons, thus locating them at positions C-3 and C-4, respectively, a fact further corroborated by nuclear Overhauser effect spectroscopy (NOESY) cross peaks (Fig. 1). The structure of the 5Ј-hydroxy-1Ј(R),5Ј-dimethylhex-3Ј-enyl side chain at C-5 was confirmed by 1 H-and 13 C-NMR, 1 H-detected heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) experiments. 12) Also characteristic of the 1 H-NMR spectrum were the presence of a hydroxy isopropyl moiety at d H 1.30 and a twoproton multiplet at d H 5.56. The latter resolved in benzene-d 6 indicating the presence of a trans double bond. 6) The 13 C-NMR data (Table 1) ascertained these molecular features and peaks at d C 72.6 (C-5Ј), 124.7 (C-3Ј), and 138.2 (C-4Ј) were in accordance with the foregoing evidence. Furthermore, the two carbons at d C 124.7 and 138.2 represented an internal double bond and were linked to protons at d H 5.50 and 5.46, respectively. The HMBC correlations (Fig. 1) confirmed the double bon...

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Bisabolenes and Furanosesquiterpenoids of KenyanCommiphora kuaResin

Cited by 15 publications

References 0 publications

Chemical Analysis and Biological Activity of the Essential Oils of Two Endemic Soqotri Commiphora Species

Chemical Analysis and Biological Activity of the Essential Oils of Two Endemic Soqotri Commiphora Species

Antihyperglycemic Furanosesquiterpenes fromCommiphora myrrha

Further Bisabolenes and Dammarane Triterpenes of Commiphora kua Resin

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