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1.
Three new kaurane diterpenoids, annoglabasin C (16alpha-acetoxy-ent-kauran-19-oic acid-17-methyl ester) (1), annoglabasin D (16alpha-acetoxy-ent-kauran-19-al-17-methyl ester) (2), and annoglabasin E (16alpha-hydro-19-ol-ent-kauran-17-oic acid) (3), and a new norkaurane diterpenoid, annoglabasin F (16alpha-acetoxy-19-nor-ent-kauran-4alpha-ol-17-methyl ester) (4), along with 13 known kaurane derivatives were isolated from the stems of Annona glabra. 16alpha-Methoxy-ent-kauran-19-oic acid (5) and 16alpha-hydro-ent-kauran-17,19-dimethyl ester (6) were obtained for the first time as natural products. The structures of compounds 1-6 were characterized by spectral analysis. 相似文献
2.
Hong SS Lee SA Lee C Han XH Choe S Kim N Lee D Lee CK Kim Y Hong JT Lee MK Hwang BY 《Journal of natural products》2011,74(11):2382-2387
Five new dimeric ent-kauranoids, biexcisusins A-E (1-5), were isolated from the aerial parts of Isodon excisus. The structures and relative configurations of these compounds were determined on the basis of spectroscopic data interpretation. Of these, biexcisusins C-E (3-5) are dimeric ent-kaurane diterpenoids exhibiting an unprecedented linkage through a nine-membered lactone ring between two ent-kaurane subunits. Compounds 1-5 showed no inhibitory effects on the LPS-induced production of nitric oxide in murine macrophage RAW264.7 cells, up to a dose of 50 μM. 相似文献
3.
ent-kaurane diterpenoids from Isodon lungshengensis. 总被引:1,自引:0,他引:1
Six new ent-kaurane diterpenoids, lungshengenins B-G (1-6), together with three known diterpenoids, lungshengenin A (7), inflexin (8), and lushanrubescinsin C (9), were isolated from the leaves and tender branches of Isodon lungshengensis. Their structures were elucidated by means of spectroscopy, mainly 1D and 2D NMR techniques. Lungshengenins A (7), C (2), and G (6) were cytotoxic toward K562 cells, having IC(50) values equal to or less than 10 microg/mL. 相似文献
4.
Qu JB Zhu RL Zhang YL Guo HF Wang XN Xie CF Yu WT Ji M Lou HX 《Journal of natural products》2008,71(8):1418-1422
Three new rearranged ent-kaurane-type diterpenoids (1-3) and seven new ent-kaurane-type diterpenoids (4-10) have been isolated from the liverwort Jungermannia atrobrunnea. Their structures were determined by extensive spectroscopic techniques and X-ray crystallographic analysis. The absolute configurations of these compounds were clarified by CD spectroscopic studies. Compound 1 is the first example of a rearranged ent-kaurane diterpenoid possessing a peroxide bridge. 相似文献
5.
目的:研究产自湖北省建始县的冬凌草(1sodon rubescens)地上部分的化学成分;方法:利用正反相硅胶柱色谱、高效液相色谱等现代分离技术进行分离;通过IR,UVMS,NMR等波谱方法鉴定了化合物结构式;对化合物1进行了单晶X-射线衍射分析,确定了其绝对构型;化合物1_9进行了对HL-60,SMMC-7721,A-549,MCF-7和SW-480细胞株的体外细胞毒活性测定:结果:分离鉴定了8个对映-贝壳杉烷二萜和1个对映-赤霉烷二萜;结论:建始冬凌草庚素-壬素(1-3)为新化合物,其中2是一个少见的、3位为半缩酮结构的3,20-环氧-对映-贝壳杉烷二萜;所有受试化合物中,4和5对某些细胞株表现出一定的体外抗增殖活性。 相似文献
6.
Ethnopharmacological relevance
Seeds of Annona squamosa L. have been used in the south of China as a folk remedy to treat “malignant sores” (cancer).Aim of the study
To investigate the chemical constituents and the anti-tumor activity of the standardized A. squamosa seeds extract in vitro and in vivo.Materials and methods
Annonaceous acetogenin profiles of the standardized extract were determined by using Fourier transform infrared (FT-IR) and high performance liquid chromatography (HPLC) techniques. The anti-tumor activity of the extract was tested by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) cytotoxicity in vitro and H22 hepatoma cells transplantation tumor model in vivo.Results
The FT-IR spectroscopy showed the presence of annonaceous acetogenin compounds in the extract. Two major annonaceous acetogenins: 12, 15-cis-squamostatin-A and bullatacin were identified and quantified by HPLC. The seed extract showed significant anti-tumor activity against four human tumor cell lines, especially for MCF-7 (IC50. 0.25 μg/ml) and Hep G2 (IC50. 0.36 μg/ml) cells in vitro. The extract inhibited the growth of H22 tumor cells in mice with a maximum inhibitory rate of 69.55% by oral administration.Conclusion
A. squamosa seed extract showed significant anti-tumor activities against human hepatoma cells in vitro and in vivo, indicating a potential for developing the extract as a novel anti-liver cancer drug. 相似文献7.
Three new bistetrahydrofuran annonaceous acetogenins (1-3) were isolated from a 95% EtOH extract of Annona squamosa seeds. Four known annonaceous acetogenins, uvarigrandin A (4), bullatacin (5), squamostatin-A (6), and squamostatin-D (7), were also isolated. Their structures were elucidated by spectroscopic analyses, and the absolute configurations of the carbinol centers of 1-3 were defined by application of the Mosher method. These compounds all exhibited significant cytotoxic activity in vitro against five human tumor cell lines. 相似文献
8.
Two new hemiterpene glucosides named pubescenosides A and B were isolated from the root of Ilex pubescens. Their structures were elucidated on the basis of spectroscopic and chemical evidence as 2-(trans-caffeoyloxy)methyl-3-hydroxy-1-butene-4-O-beta-D-glucopyranoside and 2-hydroxymethyl-3-caffeoyloxy-1-butene-4-O-beta-D-glucopyranoside, respectively. Pharmacological investigation on pubescenosides A and B indicated that both possess potent anti-platelet aggregation activities. 相似文献
9.
Morita H Sato Y Chan KL Choo CY Itokawa H Takeya K Kobayashi J 《Journal of natural products》2000,63(12):1707-1708
A benzooxyquinazoline alkaloid, samoquasine A (1), has been isolated from the seeds of Annona squamosa, and its structure was elucidated by spectroscopic and chemical methods. 相似文献
10.
Antidiabetic activity of aqueous leaf extract of Annona squamosa in streptozotocin-nicotinamide type 2 diabetic rats 总被引:1,自引:0,他引:1
The claim by some tribal populations in parts of Northern India that the young leaves of the custard apple tree, Annona squamosa L. (Annonaceae) has antidiabetic properties was investigated. Diabetes mellitus was induced with streptozotocin-nicotinamide and graded doses of the aqueous leaf extracts were then administered in drinking water to normal and experimental diabetic rats for 12 days. Fasting plasma glucose levels, serum insulin levels, serum lipid profiles and changes in body weight were evaluated in normal rats while liver glycogen levels and pancreatic TBARS levels were evaluated additionally in diabetic rats. The diabetic groups treated with the aqueous leaf extract were compared with standard glibenclamide. The findings of the study support the antidiabetic claims of Annona squamosa. 相似文献
11.
Eight new mono-tetrahydrofuran (THF)-type annonaceous acetogenins, squafosacins B, C, F, and G (1-4), squadiolins A-C (5-7), and cis-annotemoyin-1 (8), as well as eight known annonaceous acetogenins, glabranin, annotemoyins-1 and -2, bullatencin, cis-bullatencin, and uvariamicins-I, -II, and -III, were isolated from the seeds of Annona squamosa by HPLC. The structures of all new isolates were elucidated by using spectroscopic and chemical methods. Squadiolins A (5) and B (6) showed ng/mL potency against human Hep G2 hepatoma cells and significant cytotoxic activity against human MDA-MB-231 breast cancer cells. Squafosacin B (1) also exhibited significant cytotoxic activity against human Hep G2 and 3B hepatoma and MCF-7 breast cancer cells. In addition, the chelation of mono-THF acetogenins with calcium ions was investigated using isothermal titration calorimetry. 相似文献
12.
13.
New alkaloids from Annona purpurea 总被引:2,自引:0,他引:2
Three new alkaloids, promucosine (1), romucosine F (2), and romucosine G (3), along with 28 known compounds, were isolated from the MeOH extract of stems of Annona purpurea. The structures of 1-3 were determined on the basis of spectral data and chemical evidence. 相似文献
14.
Four new clerodane-type diterpenoids, ptychonolide (1), 20-O-methylptychonal acetal (2), and an equilibrium mixture of ptychonal hemiacetal (3) and ptychonal (4), were isolated from the MeOH extract of the bark of a Brazilian plant, Ptychopetalum olacoides. The structure of 1 was elucidated as a clerodane-type diterpenoid on the basis of spectroscopic data, whereas 2 was assigned to an acetal derivative of 1. Compounds 3 and 4 existed as an equilibrium mixture. A mixture of compounds 3 and 4 was found to exhibit neurite outgrowth-promoting activities on NGF-mediated PC12 cells at concentrations ranging from 0.1 to 10.0 microM. 相似文献
15.
Chuang PH Hsieh PW Yang YL Hua KF Chang FR Shiea J Wu SH Wu YC 《Journal of natural products》2008,71(8):1365-1370
Four new cyclopeptides, cyclomontanins A-D (1- 4), annomuricatin C (5), and (+)-corytuberine were isolated from a methanol extract of Annona montana seeds. Their structures were elucidated by 2D NMR analysis, ESIMS/MS fragment evidence, and chemical means. The structure of 1 was confirmed by synthesis. Compounds 1, 3, and 4 exhibited anti-inflammatory activity in vitro using the J774.1 macrophage model. 相似文献
16.
Eight new vibsane-type diterpenoids, vibsanins P-W (1-8), were isolated from the methanol extracts of the leaves and twigs of Viburnum awabuki. The structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro. 相似文献
17.
Nongluck Sookvanichsilp Wandee Gritsanapan Aim-On Somanabandhu Khanong Lekcharoen Pongkrit Tiankrop 《Phytotherapy research : PTR》1994,8(6):365-368
Some organic solvent extracts of seeds and leaves from Annona squamosa exhibit insecticidal activity. They were studied for the management of human lice. However, toxicological data of these extracts have not yet been widely reported. In this experiment, the extracts of active compounds of leaves and seeds from A. squamosa in four organic solvents, i.e. petroleum ether, ether, chloroform and ethanol were tested for toxicity to the eyes and ear skin of rabbits, using 1:10 (w/v) dilutions of dried extracts in propylene glycol as test substances. The results revealed that some extracts caused conjunctival redness, chemosis, rugged cornea, skin erythema and oedema. The organic solvent extracts that produced adverse effects on rabbit eyes were in the following order of severity: ether > petroleum ether > chloroform > ethanol, and those on rabbit ear skin were petroleum ether > ether > chloroform > ethanol. Ethanol extracts of leaves and seeds seemed to produce mildest toxicity to rabbit eyes and no toxicity to rabbit ear skin. 相似文献
18.
Konishi T Yamazoe K Konoshima T Maoka T Fujiwara Y Miyahara K 《Journal of natural products》2003,66(1):108-111
Two new bis-secolabdane diterpenoids, excoecarins R1 (1) and R2 (2), were isolated from the resinous wood of Excoecaria agallocha. The structures of 1 and 2 were established on the basis of spectroscopic data interpretation and chemical evidence. 相似文献
19.
A pyrimidine-beta-carboline and other alkaloids from Annona foetida with antileishmanial activity 总被引:1,自引:0,他引:1
Costa EV Pinheiro ML Xavier CM Silva JR Amaral AC Souza AD Barison A Campos FR Ferreira AG Machado GM Leon LL 《Journal of natural products》2006,69(2):292-294
Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-beta-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-beta-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis. 相似文献
20.
X H Li Y H Hui J K Rupprecht Y M Liu K V Wood D L Smith C J Chang J L McLaughlin 《Journal of natural products》1990,53(1):81-86
Activity-directed fractionation of the stem bark of Annona squamosa, monitoring with brine shrimp lethality, led to the isolation of the highly bioactive acetogenins bullatacin [1] and bullatacinone [2], thus demonstrating a new abundant plant source for these potent compounds. A new keto-monotetrahydrofuran acetogenin with a ketolactone terminus, as first seen in bullatacinone [2], was also isolated, characterized by spectral analyses, and named squamone [3]. The cytotoxicities of 3 were increased significantly by reduction of the two keto groups to hydroxyls, and the tetrahydrosquamone [7] and bullatacinone [2] both showed selective cytotoxicities to MCF-7 human breast carcinoma. Liriodenine and (-)-kaur-16-en-19-oic acid were also isolated. 相似文献