The structure and stereochemistry of lantanilic acid, the β,β-dimethylacryloyl ester of lantaninilic acid, isolated from Lantana camara

Barua, A.K.; Chakrabarti, Parul; Chowdhury, M.K.; Basak, Arijita; Basu, K.

doi:10.1016/s0031-9422(00)84386-1

Cited by 20 publications

(12 citation statements)

References 6 publications

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“…OH and COOH). In the HMBC spectrum, correlations of the signal of H a ÀC (22) with those of C(16), C(17), C (18), and C(28) further supported this assignment. Six tertiary Me groups were inferred from six 3-H singlets at d(H) 0.69, 0.82, 0.89, 0.95, 1.02, and 1.05 in the 1 H-NMR spectrum ( Table 1).…”

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confidence: 70%

“…On treatment with CH 2 N 2 , 1 yielded a methyl ester derivative, 1a (d(MeO) 3.61 (s)) suggesting the presence of a COOH group in the natural product. Cross-peaks between H a ÀC (22) and Me (29) in the NOESY spectrum Table 2))), and a COOH group at C(17) indicated by the IR and 13 C-NMR (d(C) 179.0) and corroborated through esterification with CH 2 N 2 to 2a (d(H) 3.61 (s, MeO)) and 13 C-NMR data of rings D and E ( Table 2). A double doublet at d(H) 2.92 (dd, J ¼ 14.0, 4.1, HÀC (18)) and a triplet at d(H) 5.26 (t, J ¼ 3.4, HÀC (12)) were also detected [5] ( Table 1).…”

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confidence: 89%

“…ursolic acid (4) [19], lantadene A (5) [20], betulinic acid (6) [21], lantanilic acid (7) [22], and camarinic acid (8) [23] (Fig. 1).…”

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confidence: 99%

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ChemInform Abstract: Leishmanicidal Triterpenes from Lantana camara.

et al. 2014

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Leishmanicidal Triterpenes from Lantana camara. -[isolation, structure elucidation and leishmanicidal activity of two new triterpenes, lantaninilic acid (I) and lantoic acid (II) along with six known triterpenes]. -(BEGUM*, S.; AYUB, A.; QAMAR ZEHRA, S.; SHAHEEN SIDDIQUI, B.; IQBAL CHOUDHARY, M.; SAMREEN; Chem. Biodiversity 11 (2014) 5, 709-718, http://dx.doi.org/10.1002/cbdv.201300151 ; H. E. J. Res. Inst. Chem., Univ. Karachi, Karachi 75270, Pak.; Eng.) -H. Toeppel 45-212

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confidence: 70%

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confidence: 89%

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ChemInform Abstract: Leishmanicidal Triterpenes from Lantana camara.

et al. 2014

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“…Moreover, L. camara plants that do not contain lantadenes A and B are non toxic and are characterized by triterpene acids which have a C-3/C-25 oxide bridge as in lantic acid (Hart et al, 1976). Lantic acid and lantanilic acid were earlier known triterpenoids from L. camara (Barua et al, 1969(Barua et al, , 1972(Barua et al, , 1985, but their complete spectral data were presented recently with those of camaric and camarinic acids (Siddiqui et al, 1995). …”

Section: Resultsmentioning

confidence: 99%

Antibacterial Triterpenoids Isolated from Lantana camara

Saleh

Kamel

et al. 1999

Pharmaceutical Biology

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The known triterpenoids lantic acid, camaric acid, camarinic acid and lantanilic acid were isolated from Lantana camara (L.) cultivated in Egypt. The antibacterial activity of lantic acid was carried out using bioautography assays for Gram-positive and Gramnegative bacteria. Lantic acid was found to possess strong antibacterial activity against Escherichia coli and Bacillus cereus, in which 0.08 and 0.1 g were the minimum inhibition doses, respectively, compared to 0.05 and 0.005 g for chloramphenicol, respectively. The results indicate that lantic acid has broad spectrum antibacterial activity and may hold potential as a non-selective antimicrobial agent.

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“…Retention time of β-caryophyllene was 16.7 min. Area of the peak corresponding to β-caryophyllene in USPE was used in 12 Icterogenin, 13 Camarinic acid, 14 Camaric acid, 14 Oleanolic acid, 14 Pomolic acid, 14 Camarilic acid, 15 Camaricinic acid, 15 Lantanoic acid, 16 Lantanolic acid, 17 Lantic acid, 18,19 Lantanilic acid, 20 β, β-Dimethylacryloyl ester of lantanilic acid, 20 calculations for determination β-caryophyllene content, which on triplicate analysis, was found to be ranging between 31.01 to 31.8%.…”

Section: Phytochemical Prospectionmentioning

confidence: 99%

Evaluation of Unsaponified Petroleum Ether Extract of Lantana camara L. leaves for Antioxidant Activity and Oxidative Stability

Patil¹,

Kumbhar²,

Ambhore³

2017

IJPER

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Background: Lantana camara L. leaves have been traditionally claimed to be used in treatment of different illnesses. Leaves are rich in lower terpenes in the form of essential oil, however they also contain lipids like waxes. Both classes, lipids and terpenes are soluble in petroleum ether, but only lipids can be saponified, not terpenes. Aim: The present study was aimed towards preparation of unsaponified terpene-rich extract of L. camara L. leaves; its assessment for anti-oxidant activity and capacity to impart oxidative stability. Methods: In order to remove lipids and retain terpenes, in present study, petroleum ether extract of Lantana camara L. leaves was saponified using aqueous potassium hydroxide and unsaponified matter was standardized using β-caryophyllene as marker; screened for anti-oxidant activity, using DPPH radical scavenging model and estimated for its capacity to impart oxidative stability using Rancimat test. Results: Tested extract showed considerable antioxidant activity (IC 50 value:13 μg/ml) and imparts 74.83% protection against oxidation as compared to standards used. Conclusion: Lipids can be removed by saponification and thereby, petroleum ether extract can be made rich in terpenes. This unsaponified petroleum ether extract of L. camara L. leaves shows better antioxidant results as compared to petroleum ether extract and comparable with standards used.

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The structure and stereochemistry of lantanilic acid, the β,β-dimethylacryloyl ester of lantaninilic acid, isolated from Lantana camara

Cited by 20 publications

References 6 publications

ChemInform Abstract: Leishmanicidal Triterpenes from Lantana camara.

ChemInform Abstract: Leishmanicidal Triterpenes from Lantana camara.

Antibacterial Triterpenoids Isolated from Lantana camara

Evaluation of Unsaponified Petroleum Ether Extract of Lantana camara L. leaves for Antioxidant Activity and Oxidative Stability

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