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1.
Eight new limonoids named thaixylogranins A–H (1–8), including seven mexicanolides (1–3 and 5–8), were isolated from the seeds of a Thai mangrove, Xylocarpus granatum. The structures of these limonoids were established on the basis of HRESIMS and NMR spectroscopic data. Compounds 1–4 possess an 8α, 30α-epoxy ring, whereas compounds 5−8 have a C8C30 bond. Compounds 1–8 exhibited weak cytotoxicities against the MDA-MB-231 cell with IC50 values of 49.4, 58.3, 53.6, 61.1, 57.9, 44.6, 40.6, and 38.5 μM, respectively. 相似文献
2.
Ono E Inoue J Hashidume T Shimizu M Sato R 《Biochemical and biophysical research communications》2011,(3):677-681
TGR5 is a member of the G protein-coupled receptor family and is activated by bile acids (BAs). TGR5 is thought to be a promising drug target for metabolic diseases because the activation of TGR5 prevents obesity and hyperglycemia in mice fed a high-fat diet (HFD). In the present study, we identified a naturally occurring limonoid, nomilin, as an activator of TGR5. Unlike BAs, nomilin did not exhibit the farnesoid X receptor ligand activity. Although the nomilin derivative obacunone was capable of activating TGR5, limonin (the most abundant limonoid in citrus seeds) was not a TGR5 activator. When male C57BL/6J mice fed a HFD for 9 weeks were further fed a HFD either alone or supplemented with 0.2% w/w nomilin for 77 days, nomilin-treated mice had lower body weight, serum glucose, serum insulin, and enhanced glucose tolerance. Our results suggest a novel biological function of nomilin as an agent having anti-obesity and anti-hyperglycemic effects that are likely to be mediated through the activation of TGR5. 相似文献
3.
柑桔果实中柠檬苦素类化合物的研究现状与展望 总被引:17,自引:0,他引:17
柠檬苦素类似物(limonoid)是三萜类的植物次生代谢产物,主要存在于芸香科和楝科植物中。柠檬苦素(limonin)及其类似物存在于柑桔属(Citrus)的多种植物中。至今已从柑桔属植物中分离出36种柠檬苦素类似物及17种柠檬苦素类似物配糖体。柑桔中苦味原因之一为柠檬苦素类似物。作为其代表具有强烈苦味的柠檬苦素和诺米林如果在柑桔果汁中含量超过6mg/L,那么这种柑桔用于饮食业已不适合[1]。近年来,笔者对柑桔果实中的柠檬苦素类似物的生理变化及生物合成作过系统研究[1~9],并提出将柠檬苦素类似… 相似文献
4.
The stem bark of Cedrelopsis gracilis (Ptaeroxylaceae) has yielded three known prenylated coumarins, O-methylalloptaeroxylin, ptaerochromenol and umtatin and the novel pentanortriterpenoids, cedkathryn A and cedkathryn B. 相似文献
5.
Limonoids are a group of chemically related bitter tetranortriterpene derivatives found predominantly in Rutaceae and Meliaceae plants (Ourison et al., 1964). Interest in the Rutaceae limonoids has centered around limonoid removal from consumable citrus products. For example, bitterness in citrus juices (as well as in other citrus products) due to limonoids has become an increasingly serious economic problem (Wilson & Crutchfield, 1968; Sinclair, 1972). Interest in the Meliaceae limonoids, on the other hand, has centered on their efficacy as pest control and/or antitumor agents (Kubo & Klocke, 1981, 1982; Nakanishi, 1977, 1980). For example, azadirachtin, isolated from several Meliaceae trees, has proven to be a potent natural product against a myriad of insect and nematode pests (Warthen, 1979). In fact, we have isolated azadirachtin from the fresh fruit of Azadirachta indica as a potent insect ecdysis inhibitor against four agricultural pest insects with artificial diet feeding assay (Kubo & Klocke, in litt). 相似文献
6.
Sheng Su Liqin Shen Yan Zhang Jiangyun Liu Jinna Cai Lili Hao Yuling Feng Shilin Yang 《Phytochemistry letters》2013,6(3):418-424
Four nimbolinin-type limonoids, 12α/β-1-O-tigloyl-1-O-deacetyl-nimbolinin B (1), 1-deacetylnimbolinin B (2), nimbolinin B (3) and nimbolinin A (4), were isolated from the fruits of Melia toosendan. 1 was a new compound and existed as a mixture of a pair of tautomers, 12α- (1a) and 12β- (1b). The structures of both tautomers were fully determined by extensive spectroscopic methods including UV, IR, NMR and ESI-MS. Tautomeric behaviors and their relative molar ratios in compounds 1–4 were further investigated using optical rotation, TLC, 1H NMR and HPLC. Equilibrium equation of nimbolinin was proposed accordingly, with 12α- and 12β-isomers interchanging via a 12-hemiacetal intermediate. 相似文献
7.
Subash C. Gupta Sajin K. Francis Mangalam S. Nair Yin-Yuan Mo Bharat B. Aggarwal 《The Journal of biological chemistry》2013,288(45):32343-32356
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The limonoid derivative, methyl uguenenoate, the azole, uguenenazole, and the amide, uguenenonamide, together with the known furoquinoline alkaloids flindersiamine and maculosidine, and syringaldehyde have been isolated from the root of the East African Rutaceae Vepris uguenensis. While methyl uguenenoate and the furoquinoline alkaloids displayed mild antimalarial activity, the azole and amide were completely inactive. 相似文献
10.
Five khayanolides (1-O-acetylkhayanolide B 1, khayanolide B 2, khayanolide E 3, 1-O-deacetylkhayanolide E 4, 6-dehydroxylkhayanolide E 5) were isolated from the stem bark of African mahogany Khaya senegalensis (Meliaceae). Their structures and absolute configurations were determined through extensive spectroscopic analyses including MS, NMR, and single-crystal X-ray diffraction experiments. The results established that two previously reported khayanolides, 1α-acetoxy-2β,3α,6,8α,14β-pentahydroxy-[4.2.110,30.11,4]-tricyclomeliac-7-oate 6 and 1α,2β,3α,6,8α,14β-hexahydroxy-[4.2.110,30.11,4]-tricyclomeliac-7-oate 7, were, in fact, 1-O-acetylkhayanolide B 1 and khayanolide B 2, and that the two reported phragmalin derivatives, methyl 1α-acetoxy-6,8α,14β,30β-tetrahydroxy-3-oxo-[3.3.110,2.11,4]-tricyclomeliac-7-oate 8 and methyl 1α,6,8α,14β,30β-pentahydroxy-3-oxo-[3.3.110,2.11,4]-tricyclomeliac-7-oate 9, were, in fact, khayanolide E 3 and 1-O-deacetylkhayanolide E 4, respectively. Based on the results from this study and consideration of the biogenetic pathway, the methyl 6-hydroxyangolensate in African mahogany K. senegalensis should have a C-6 S configuration while methyl 6-hydroxyangolensate in genuine mahogany Swietenia species should have a C-6 R configuration. 相似文献