Indole alkaloids and coumarins from the root bark of Murraya paniculata var. Omphalocarpa

Wu, Tian Shung; Liou, Meei Jen; Jong, Ting‐Ting; Chen, Yao Jung; Lai, Jeng Shiow

doi:10.1016/s0031-9422(00)98115-9

Cited by 21 publications

(19 citation statements)

References 8 publications

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“…Furthermore, three coumarins known as meranzin hydrate ( Figure 2c), murpanidin ( Figure 2d) and murragatin (Figure 2e) were isolated from M. paniculata leaves extract [18]. Other coumarins including 3-formylindole,omphalocar-pin,5,7-dimethoxy-8-(3'-methyl-2'oxobuty coumarin, coumurrayin, murragleinin, omphamurin, murraol, (-)-murracarpin, (±)-murracarpin, mupanidin, mexoticin, murrangatin, and ferulyl esters were also isolated from M. paniculata root bark [15]. While from the fresh flowers of this plant, yuehgesin-A, yuehgesin-B, yuehgesin-C, and 22 compounds were characterized [21].…”

Section: Introductionmentioning

confidence: 99%

Pharmacological Properties and Chemical Constituents of Murraya paniculata (L.) Jack

Sayar¹

2014

Medicinal Aromatic Plants

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Chemical Constituents of Murraya paniculata (L.) Jack M. paniculata has been investigated for its bioactive compounds by many research groups. To date, various compounds were identified, ranging from indole alkaloids, coumarins, phenols, terpenoids to flavonoids. Besides, 60 compounds have been identified from volatile and essential oil extracted from M. paniculata leaves. The chemical components from different parts of M. paniculata were identified using chromatographic techniques and the structures were elucidated using spectroscopic techniques. A number of these compounds exhibited significant biological activities, which serve as the scientific evidence for the traditional usage of M. paniculata. In 1986, an anti-implantation alkaloid, called Yuehcukene, 1β-(3,indolyl-7,9α,9β-trimethyl-5β,8,9,10β-tetrahydroindano-[2,3-b] indole was also isolated from M. paniculata leaves [14]. Moreover, the two indole alkaloids, murrayacarine [15] and murrayaculatine [16] were isolated from root bark and flowers of M. paniculata respectively. In early 1980s, different research groups isolated 3' ,4' ,5,5' ,7,8-hexamethoxyflavone (Figure 2a) and 3,3' , 4' ,5,5' ,7,8-heptamethoxyflavone (Figure 2b) from the methanolic extract of M. paniculata leaves [17,18]. Later, a flavone named 3,5,7,3' ,4' ,5'-hexamethoxyflavone, was isolated from M. paniculata flower [16]. Other research groups isolated eight flavonoids from M. paniculata leaves [12,19] and ten flavonoids from the peel and pulp of the fruits of the plant [20].

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Section: Introductionmentioning

confidence: 99%

Pharmacological Properties and Chemical Constituents of Murraya paniculata (L.) Jack

Sayar¹

2014

Medicinal Aromatic Plants

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“…20 A number of 3,5-and 3,6-diprenylated indoles have been reported for the Annonaceae genera Isolona, [21][22][23] Uvaria, 22 Annonidium, 24 Monodora, 25 Hexalobus, 26 Asteranthe, 27 Greenwayodendron, 28 and Polyalthia. 29 However, there are only a few examples of 3-, 5-, 6-and 7-and 3,7-prenylated indoles reported in the Rutaceae genera Raputia, 14 Esenbeckia, 30,31 Murraya, [32][33][34] Merrillia 35 and Glycosmis. 36,37 Four bisindoles (6-9; Figure 3) similar to compound 1 have been isolated from Raputia simulans.…”

Section: Resultsmentioning

confidence: 99%

“…Their use in this context shows that R. praetermissa differs substantially from Neoraputia species, and reinforce its inclusion in Raputia genus. Furthermore, the prenylindole alkaloids have been reported only from Esenbeckia and Raputia in Cusparieae, thus suggesting an affinity of this tribe with subfamily Aurantioideae, where similar prenylindoles occur in Murraya, [33][34][35] Merrillia 36 and Glycosmis. 37,38 It is noteworthy that Neoraputia shares with Murraya and Citrus a propensity for producing polymethoxylated flavonoids, 9,12,40,41 showing also chemical affinity with Aurantioideae.…”

Section: Resultsmentioning

confidence: 99%

Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance

Rosas¹,

Veiga²,

Fernandes³

et al. 2011

J. Braz. Chem. Soc.

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O extrato diclorometano do caule de Raputia praetermissa levou ao isolamento de quatro compostos novos, 4-desóxi-raputindol C (1), raputimonoindol A-B (2, 3) e hexadecanil 2-hidróxi-4-metóxi-cinnamato (5), juntamente com os alcalóides 5-(4-metóxi-metilfuran-2-il)-1H-indol (raputimonoindol C), furoquinolinos maculosidine, robustine, evolitrine e dictamnine. O estudo do extrato hexano levou ao isolamento de N-metil-4-metóxi-quinolin-2(1H)-ona, skimmianina, cicloartenona, sitosterol, stigmasterol e sitostenona. Os alcalóides antranílicos isolados indicam que o gênero possui afinidade química relevante com aqueles da tribo Cusparieae, mas difere de Neoraputia devido à ausência de alcalóides prenilindois neste último, cujas espécies foram anteriormente incluídas em Raputia.The dichloromethane extract from the stems of Raputia praetermissa afforded four new compounds, 4-deoxyraputindole C (1), raputimonoindole A-B (2, 3), and hexadecanyl 2-hydroxy-4-methoxy-cinnamate (5), besides the alkaloids 5-(4-methoxymethylfuran-2-yl)-1H-indole (raputimonoindole C), furoquinolines maculosidine, robustine, evolitrine and dictamnine. The hexane extract yielded N-methyl-4-methoxyquinolin-2(1H)-one, skimmianine, cycloartenone, sitosterol, stigmasterol and sitostenone. The anthranilate alkaloid content indicates that the genus is strongly related to those included in Cusparieae tribe, but differs from Neoraputia by the absence of prenylindole alkaloids in the late, whose species have previously been placed in Raputia. Previous investigations of Neoraputia reported the presence of eleven polymethoxylated flavonoids, six flavones, three 5,6-(2",2"-dimethylpyrano)flavones, one 6,7-(2",2"-dimethylpyrano)flavone and one flavanone from N. alba (Engler) Emmerich; 6,7 five polymethoxylated flavones and two flavanones, 2'-hydroxy-3,4,4',5,6'-pentamethoxychalcone, three 5',6'-(2",2"-dimethylpyrano)-polymethoxylated chalcones from N. magnifica var. magnifica (Engler) Emmerich; 8,9 ten polymethoxylated flavonoids, six flavones, three 6,7-(2",2"-dimethylpyrano) flavones and one 6-(3"-hydroxy,3"-methyl-trans-but-1"-enyl)flavone from N. paraensis. Keywords10,11 A reinvestigation of N. paraensis searching for alkaloids afforded flindersine, skimmianine, 8-methoxyflindersine and dictamnine.12 Rosas et al. 1347 Vol. 22, No. 7, 2011 C-glycosylflavones were also reported from N. paraensis, 13 which was cited as Raputia paraensis, but this species was transferred to Neoraputia by Emmerich. 1The first investigation about the chemistry of Raputia reported the presence of cyclopentyl bisindole alkaloids raputiindoles A-D from R. simulans Kllunki. 14 In this paper we report a phytochemical study on R. praetermissa Pirani & Kallunki, and the chemosystematic significance of isolated compounds is discussed in order to clarify the relationships between Raputia and Neoraputia. Results and DiscussionThe dichloromethane extract from the stems of Raputia praetermissa afforded four prenylindole alkaloids (1-4), a cinnamic acid derivative (5) (Figure 1 -5b), a...

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“…In traditional medicine, Murraya paniculata was used as an analgesic, digestion stimulant, antiswelling, anti-ecchymotic, expectorant, tonic, and toothache remedy [1,2]. Phytochemical studies of Murraya lead to the isolation of indol akaloid [3], polymethoxylated flavonoid [4], essential oils [5], and a number of coumarins [6][7][8].…”

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Coumarins Isolated from Murraya paniculata in Vietnam and Their Inhibitory Effects against Enzyme Soluble Epoxide Hydrolase (sEH)

Khanh

Spiga

Trezza

et al. 2017

PMIO

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!In the search for bioactive constituents from Vietnam medicinal plants, the leaves and stems of Murraya paniculata collected in HoaBinh Province, Vietnam were selected for chemical investigation. From the n-hexane fraction, two sterols, including β-sitosterol (6) and stigmasterol (7), and from the chloroform fraction, five coumarins, including mexoticin (1), omphalocarpin (2), murrangatin (3), kimcuongin (4), and murracarpin (5), were obtained. The structures of the isolated compounds were determined from ESI-MS, HR-ESI-MS, and NMR (1D and 2D) spectroscopic data. Coumarins (1-5) were elucidated for inhibitory effects against soluble epoxide hydrolase. Among them, coumarins (2-4) showed soluble epoxide hydrolase inhibitory activity with IC 50 values 2.2 ± 4.7, 13.9 ± 6.5, and 3.2 ± 4.5 µM, respectively. A kinetic study of the five coumarins revealed the noncompetitive enzymatic mode for 3 and 4, and a mixture of competitive/noncompetitive enzymatic modes for coumarin 2. Using molecular modelling, the coumarin kimcuongin (4) showed the best binding outline into active sites of human soluble epoxide hydrolase. Key wordsMurraya paniculata · Rutaceae · coumarin · kimcuongin · murracarpin · AutoDock/Vina · soluble epoxide hydrolase (sEH)12-(3-adamantan-1-yl-ureido) dodecanoic acid DHETs: dihydroxyeicosatrienoicdiols EETs:epoxyeicosatrienoic acidsMichaelis-Menten constant PHOME: 3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid PLIP:protein-ligand interaction profiler sEH:soluble epoxide hydrolaseSupporting information available online at http://www.thieme-connect.de/productsThe sEH is the main enzyme that catalyzes the metabolism of EETs into the more polar and usually less potent metabolites DHETs [1]. Early studies have indicated that chemical compounds that can inhibit the sEHsʼ activity and stabilize the endogenous EET levels may represent potential therapeutic agents for cardiovascular disease [2,3] and the onset of several other diseases [4,5]. Murraya paniculata (L.) Jack (Rutaceae), local name "Nguyet que", is mostly grown as ornaments for its glossy green foliage and white fragrant flowers. It is used as a medicinal plant in Vietnamese traditional medicine. There were several publications of phytochemical studies of Murraya (see Supporting Information). In this study, we describe the inhibitory activity against the sEH of coumarins isolated from this plant and explain this effect by molecular modelling. The methanol extract of the dry leaves of M. paniculata was suspended with water and subsequently fractioned with n-hexane, chloroform, and ethyl acetate. From the n-hexane fraction, two sterols, β-sitosterol (6) and β-stigmasterol (7), were isolated. From the chloroform fraction of the leaves of M. paniculata, five coumarins (1-5) were subsequently isolated through column chromatography including mexoticin (1) [6], omphalocarpin (2) [7], murrangatin (3) [8], kimcuongin (4), and (−)-murracarpin (5; l " Fig. 1). The latter two coumarins are reported to possess vasorelaxing acti...

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Indole alkaloids and coumarins from the root bark of Murraya paniculata var. Omphalocarpa

Cited by 21 publications

References 8 publications

Pharmacological Properties and Chemical Constituents of Murraya paniculata (L.) Jack

Pharmacological Properties and Chemical Constituents of Murraya paniculata (L.) Jack

Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance

Coumarins Isolated from Murraya paniculata in Vietnam and Their Inhibitory Effects against Enzyme Soluble Epoxide Hydrolase (sEH)

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