Monoterpenoid Coumarins from the Peels of Clausena lansium

Deng, Hui-Dong; Mei, Wen‐Li; Guo, Zhi‐Kai; Лю, Шуай; Zuo, Wei; Dong, Wei; Li, Shaopeng; Dai, Hao‐Fu

doi:10.1055/s-0034-1382839

Cited by 17 publications

(12 citation statements)

References 15 publications

(24 reference statements)

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“…2) all have the same physical state as a colorless oil with a blue fluorescence under the ultraviolet lamp (254 nm), so, they are the same series of compounds with a similar furanocoumarin skeleton. Comparing the experimental data of compounds 3-9 with those described in the literature, their phytochemical structures were identified as: wampetin (3), 17 anisolactone (4), 14,15 11 lansiumarin A (6), 20 8-[(2E)-6-oxo-3,7-dimethyloct-2-enyloxy] psoralen (7), 21 (S,E,E)-8-[(6-hydroxy-3,7-dimethylocta-2,7-dien-1-yl)oxy]-psoralen (8) 11 and 8-geranyloxypsolaren (9). 22 Compounds 10-15 (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Further analysis of the carbon‐13 ( 13 C)‐NMR spectrum (Table 1) of compound 1 suggested a furanocoumarin system and an additional C 10 side‐chain moiety with one methoxy ( δ C 61.4), which consisted of one ester carbonyl ( δ C 173.7), two vinyl methyl groups ( δ C 16.9, 10.7), one oxymethine ( δ C 77.9), oxy methylene ( δ C 71.7), one methylene ( δ C 43.0), and two trisubstituted double bonds ( δ C , 147.9, 148.2, 130.4, 119.8), respectively. Detailed comparison of the 1 H‐ and 13 C‐NMR data and the MS (ESI‐MS m/z : 419 [M + Na] + ) of compound 1 and anisolactone 14–17 indicated them to be similar O ‐monoterpenoid furanocoumarins, differing only in the presence of a more methoxy ( δ H 3.38, δ C 61.4) in compound 1 than in anisolactone. In the heteronuclear multiple‐bond correlation (HMBC) experiment of compound 1 (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The experiments were conducted in three replicates and statistical calculation was carried out by Origin software. [14][15][16][17] indicated them to be similar O-monoterpenoid furanocoumarins, differing only in the presence of a more methoxy (⊐ H 3.38, ⊐ C 61.4) in compound 1 than in anisolactone. In the heteronuclear multiple-bond correlation (HMBC) experiment of compound 1 (Fig.…”

Section: Bioassay Of Herbicidal Activitiesmentioning

confidence: 99%

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Chemical components from the stems and leaves of Clausena lansium (Lour.) Skeels and their potential herbicidal effects

Peng

Xiong

et al. 2020

Pest Management Science

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BACKGROUND Clausena lansium (Lour.) Skeels, belonging to the genus Clausena of the family Rutaceae, has a wide range of medical and agricultural activities. Previous studies on agricultural activities have shown that C. lansium extracts and some components have obvious herbicidal activities. In order to study systematically herbicidal activity of this plant, we studied the herbicidal effect of ethyl acetate (EtOAc) extract from the stems and leaves of this plant and further isolated the active compounds. RESULTS The EtOAc extract inhibited the growth of roots and shoots of Echinochloa crus‐galli (L.) Beauv., and the inhibitory effect of the EtOAc extract on roots were stronger than those on shoots with half maximal inhibitory concentration (IC50) values of 420.45 and 585.05 mg L−1, respectively. Fifteen compounds were subsequently isolated and identified from the stems and leaves of C. lansium, including nine O‐monoterpenoid furanocoumarins and six cinnamamides. Our results showed that most compounds exhibited varying degrees of herbicidal activities to E. crus‐galli. Among them, compounds 3, 8, and 13–15 showed the best inhibitory activities on the growth of E. crus‐galli roots, with inhibition rate values ranging from 70% to 83% at a concentration of 300 mg L−1. Compounds 1 and 2 are two new compounds, and their structures were established as 5‐O‐monoterpenoid furanocoumarin and 8‐O‐monoterpenoid furanocoumarin, and named as claulansicoumarin‐A and ‐B, respectively. CONCLUSION The EtOAc extract and pure compounds showed noticeable herbicidal activities against E. crus‐galli and indicated a great potential for these natural compounds to be developed as a herbicide. © 2020 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Bioassay Of Herbicidal Activitiesmentioning

confidence: 99%

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Chemical components from the stems and leaves of Clausena lansium (Lour.) Skeels and their potential herbicidal effects

Peng

Xiong

et al. 2020

Pest Management Science

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“…Some monoterpenoid coumarins and seven carbazole alkaloids were also isolated from the peels of Clausena lansium (Lour.) Skeels, and claulansine J exhibited moderate antibacterial activity against Staphylococcus aureus [ 39 , 40 ]. Three new jasmonoid glucosides, two new sesquiterpenes, two new coumarins, and others were isolated from the fruit of C. lansium .…”

Section: Resultsmentioning

confidence: 99%

Bioactive Compounds from the Stems of Clausena lansium

Liu

et al. 2017

Molecules

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In view of the significant neuroprotective effect of Clausena lansium, we continued to separate the n-butanol and the water extracts from the stems of C. lansium in order to find the leading compounds with significant activity. Two new phenolic glycosides, Clausenolside A–B (1–2), one new pair of phenolic enantiomers (3a, 3b), and two new monoterpenoids, clausenapene A–B (4–5), together with twelve known analogues (6–17) were isolated from the stems of C. lansium. Compounds 1–17 were obtained from C. lansium for the first time. Compounds 3a, 3b, 4, 16, and 17 showed strong or moderate potential neuroprotective effects on inhibited PC12 cell injury induced by okadaic acid, and compound 9 exhibited strong potential hepatoprotective activities. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, NMR experiments, and electronic circular dichroism (ECD) spectra.

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“…C. lansium is famous for their fruits, which are usually very popular tropical, health-promoting fruits, while their roots, stems, leaves, and seeds have also been extensively applied in folk medicine or traditional Chinese medicine for the treatments of abdominal pain, malaria, cold, dermatopathy, and snake bites [2,3]. Various biological studies, on the alkaloids, coumarins, and sesquiterpenes from this plant have reported the neuroprotective [4,5], antitumor [6,7], hepatoprotective [8], anti-inflammatory [9], antifungal [10], antioxidant [11], antiobesity [12], nematicidal [13], antimicrobial [14], and hypoglycemic [15] effects of the C. lansium . In our previous studies, some carbazole alkaloids [16] and coumarins [17] were separated from the stem and leaf of C. lansium .…”

Section: Introductionmentioning

confidence: 99%

Phytochemical Study of Stem and Leaf of Clausena lansium

Peng

et al. 2019

Molecules

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Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.

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Monoterpenoid Coumarins from the Peels of Clausena lansium

Cited by 17 publications

References 15 publications

Chemical components from the stems and leaves of Clausena lansium (Lour.) Skeels and their potential herbicidal effects

Chemical components from the stems and leaves of Clausena lansium (Lour.) Skeels and their potential herbicidal effects

Bioactive Compounds from the Stems of Clausena lansium

Phytochemical Study of Stem and Leaf of Clausena lansium

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