Cycloartane-Type Triterpenes from Amberboa ramosa

Akhtar, Nasima; Malik, Abdul; Afza, Nighat; Badar, Yasmeen

doi:10.1021/np50092a019

Cited by 19 publications

(18 citation statements)

References 15 publications

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“…The CSs of the neighboring C atoms are sensitive to epimerization of C-22. CSs were compared using the 13 C NMR spectrum for cycloartane 86, which was isolated from Amberboa ramose [71] and has a 22R-OH in the acyclic sidechain. Table 7 shows that the CSs of C-22 depend on its configuration.…”

Section: Structural Studies Of Cycloartane Triterpenoids Using 13 C Nmentioning

confidence: 99%

Structural Studies and Biological Activity of Plant Triterpenoids from the Thalictrum Genus

et al. 2005

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Structures and chemical and spectral properties of triterpenoids isolated from plants of the Thalictrum genus were systematized for the first time. Features of 13 C NMR spectra of cycloartane triterpenoids were discussed. Data for the biological activities of certain cycloartane and oleanane triterpenoids were given.Triterpenoids are natural isoprenoids, the skeleton of which is constructed of 30 C atoms. They are widely distributed in both terrestrial plants and marine flora and fauna. They occur in the free state and as esters and glycosides called saponins. Triterpenoids are usually classified by the number of rings in the C skeleton. Tetra-and pentacyclic compounds are most widely distributed in nature. This review covers representatives of them.Plants of the Thalictrum (Ranunculaceae) genus produce a large quantity of triterpenoids and other secondary metabolites. The former are interesting because of their chemical structures and practical uses. It should be noted that investigations of secondary metabolites from these plants focused rather successfully and until recently on the alkaloids [1-5]. The first publications devoted to the study of triterpene saponins from plants of the Thalictrum genus appeared at the start of the 1981s [6].There is a reason for the interest in representatives of the broad Thalictrum genus. Plants of this genus have been used since long ago by peoples of many nations for medicinal purposes to treat gastrointestinal and gynecological illnesses, various neoplasms, and tuberculosis [7-10]. This, in turn, stimulated studies of the chemical composition of the plants, the isolation of biologically active compounds, and investigations of their pharmacologic activity.We have for the first time systematized and generalized information on triterpenoids from plants of the Thalictrum genus (from 1981 to 2003), features of their spectral and chemical properties, and their biological activity. Individual representatives of these compounds were included in reviews on triterpenoids [11,12] and cycloartanes [13,14]. However, the complete picture will be given for the first time. TRITERPENOID GENINS AND THEIR GLYCOSIDESTriterpenoid saponins from plants of the Thalictrum genus were first isolated and characterized in 1981-1983 from T. minus and T. foetidum collected in eastern Siberia [6,15,16]. Compounds of this type were not observed in the same species from Middle Asia and Europe. Based on this, which indicates that the chemical composition of a species is dependent on the ecological and geographical habitat, it was proposed [17,18] to separate the species growing in eastern Siberia into a Siberian chemorace. Then, the triterpenoid compounds were isolated only from species growing in the east (Japan, China, Korea). Now it is probably possible to generalize and view the Siberian chemorace as the "eastern Asian" one.

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Section: Structural Studies Of Cycloartane Triterpenoids Using 13 C Nmentioning

confidence: 99%

Structural Studies and Biological Activity of Plant Triterpenoids from the Thalictrum Genus

et al. 2005

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“…Unlike compound 1 described above, its 1 H-and 13 C-NMR spectral data suggested a trisubstituted benzene ring with a monounsaturated side chain at C-5. 15) In its mass spectrum, a characteristic McLafferty process involving the elimination of the side chain produced an ion at m/z 148 [MϪC 5 H 10 O] ϩ and another one at m/z 135 [MϪC 6 H 10 O] ϩ , both fragments were consistent with the presence of a secondary hydroxyl function. 16) The complete 1 H-and 13 C-NMR chemical shift assignments for 2 were deduced from concerted application of 1 H-1 H COSY and 1 H detected 'one bond' and long range (C, H) correlation experiments as well as comparison with already reported data on the compound.…”

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confidence: 97%

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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“…The butyrylcholinesterase inhibitory activity of the chloroform soluble fraction has also been reported previously [2]. Literature survey revealed that triterpenoids, flavonoids, steroids, and sesquiterpene lactones have previously been reported from this species [1,3]. The chemotaxonomic and ethnopharmacological significance of the genus Amberboa prompted us to reinvestigate the constituents of A. ramosa.…”

Section: Introductionmentioning

confidence: 57%

“…Amberboa ramosa is an annual herbaceous plant that is mainly found in Pakistan and India. A. ramosa has tonic, aperient, febrifuge, deobstruent, cytotoxic, and antibacterial properties [1]. The butyrylcholinesterase inhibitory activity of the chloroform soluble fraction has also been reported previously [2].…”

Section: Introductionmentioning

confidence: 75%

“…The chemotaxonomic and ethnopharmacological significance of the genus Amberboa prompted us to reinvestigate the constituents of A. ramosa. As a result, we herein report the isolation and structural elucidation of one new sesquiterpene lactone named as amberin (1). In addition, the previously reported compounds apigenin (2) [4], jaseocidine (3) [5], crysoeriol (4) [6], and 3b, 8a-dihydroxy-11a-methyl-1aH, 5aH, 6bH, 7aH, 11bH-guai-10(14), 4 (15)-dien-6, 12-olide (5) [2] have also been isolated and characterized.…”

Section: Introductionmentioning

confidence: 97%

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