Mulavanins A–E: Limonoids from Munronia delavayi

Lin, Bing‐Dong; Chen, Huadong; Liu, Jia; Zhang, Sheng; Wu, Yan; Dong, Lei; Yue, Jian‐Min

doi:10.1016/j.phytochem.2010.06.010

Cited by 32 publications

(31 citation statements)

References 21 publications

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“…A comprehensive analysis of the HSQC and HMBC spectra allowed the establishment of 3 and 4 as shown, and they were named trichanolide B and C, respectively. Detailed analysis of the 1 H and 13 C NMR spectroscopic data of 5 and 6 indicated that they were mexicanolide-type limonoids as in 2, but were lacking the characteristic signals for the furan ring which was replaced by the rare γ-hydroxybutenolide moiety [18,19]. The NMR data of 5 were similar to those of granatumin E [20], except for the presence of one additional hydroxyl.…”

Section: Resultsmentioning

confidence: 87%

“…As a result, 23 components (l " Fig. 1) were isolated including one new 1,2-seco phragmalin-type limonoid with a rare 9-oxa-tricyclo [3.3.2.1 7,10 ]undecane-2-ene moiety (secotrichagmalin A, 1), five new mexicanolides (trichanolides A-E, 2-6), two new highly rearranged 30-nortrijugins (trijugins I-J, [7][8], and five known limonoids (9)(10)(11)(12)(13), five pregnanes (14)(15)(16)(17)(18), and five lignans (19)(20)(21)(22)(23). Their structures were elucidated on the basis of spectroscopic methods, or by comparison with the reported data in the literature.…”

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confidence: 99%

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Chemical Constituents from Trichilia connaroides and Their Nitric Oxide Production and α-Glucosidase Inhibitory Activities

Wang

Shan

et al. 2013

Planta Med

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Phytochemical investigation of the stem and bark of Trichilia connaroides led to the isolation of eight new nortriterpenoids (1-8), along with fifteen known compounds (9-23). Their structures were established based on extensive spectroscopic analysis. The absolute configuration of 2 was confirmed by X-ray crystallographic study. The nitric oxide production and α-glucosidase inhibitory effects for these isolates were evaluated: moderate to strong nitric oxide production inhibitory activities were found for 5, 6, and 11-15, with IC50 values ranging from 7.5 to 26.3 µM; marked α-glucosidase inhibitory effects were observed for 22 and 23, with IC50 values of 2.3 and 0.4 µM, respectively.

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Section: Resultsmentioning

confidence: 87%

mentioning

confidence: 99%

Chemical Constituents from Trichilia connaroides and Their Nitric Oxide Production and α-Glucosidase Inhibitory Activities

Wang

Shan

et al. 2013

Planta Med

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“…[ 11 ] At present, there are only a few reports on the research of M. unifoliolata , but a large number of limonoids with significant anti‐inflammatory, antimicrobial, and anti‐TMV biological activities have been isolated from its genus. [ 12‐19 ] In order to understand the main and active ingredients of M. unifoliolata , the systematic extraction and separation of dichloromethane extract, the main anti‐inflammatory active portion of the whole plants (IC 50 = 17.9 ± 4.6 μmol/L), were carried out in our current research. This resulted in isolation of twenty‐two new limonoids ( 1 — 22 ), including rings A, B‐ seco , ring A‐ seco , and ring‐intact types.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Diverse Ring‐seco Limonoids from Munronia unifoliolata and Their Biological Activities

Sun

Cui

et al. 2021

Chin. J. Chem.

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Comprehensive Summary Twenty‐two new limonoids, mufolinoids A—V (1—22), including six rings A, B‐seco limonoids (1—6), twelve ring A‐seco limonoids (7—18), four ring‐intact limonoids (19—22), together with thirteen known compounds (23—35) were isolated from Munronia unifoliolata. Their structures including absolute configurations were elucidated by combination of NMR, HR‐MS, single‐crystal X‐ray diffraction and calculations of ECD and NMR technologies. Compounds 24, 25, 33, 34 could be significantly reversed the multidrug resistance of MCF‐7/doxorubicin (DOX) cells, and the reversal fold (RF) was much higher than that of positive drug Verapamil. Compounds 24, 28, and 29 exhibited significant anti‐inflammatory activity with the IC50 values in the range of 17.7—39.4 μmol/L. Furthermore, compound 29 could markedly inhibit the release of IL‐1β by inhibiting the initiation and assembly of NLRP3 inflammasome, which demonstrates the great potential of limonoids as an anti‐inflammatory agent.

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“…1 Up to now, some phytochemical studies have been reported on M. delavayi [2][3][4][5] and M. henryi [6][7][8][9] , and tetranortriterpenoids and triterpenoids are their main components. Especially, tetranortriterpenoids exhibit chemical defensive function in nature, such as antibacterium, antifungal, 2 and antifeeding 8 activities. M. sinica Diels grows in Jinfoshan of Sichuan, which is low subshrubs and an endemic species of China.…”

Section: Introductionmentioning

confidence: 99%

Chemical constituents from Munronia sinica and their bioactivities

Zhang

et al. 2012

Nat. Prod. Bioprospect.

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Abstract:Two new minor constituents, musinisins A (1) and B (2), together with five known compounds (3-7), were isolated from the aerial parts of Munronia sinica. Their structures were established by means of spectroscopic methods and the absolute stereochemistry of 1 was determined by single crystal X-ray experiment. Compound 4 showed antiangiogenic activity evaluated by a zebrafish model and apoptosis-inducing effect on A549 lung cancer cells.

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Mulavanins A–E: Limonoids from Munronia delavayi

Cited by 32 publications

References 21 publications

Chemical Constituents from Trichilia connaroides and Their Nitric Oxide Production and α-Glucosidase Inhibitory Activities

Chemical Constituents from Trichilia connaroides and Their Nitric Oxide Production and α-Glucosidase Inhibitory Activities

Diverse Ring‐seco Limonoids from Munronia unifoliolata and Their Biological Activities

Chemical constituents from Munronia sinica and their bioactivities

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