Two novel ent-kauranoid diterpenoids from Isodon japonica leaves

Two novel ent-kaurane diterpenoids, taihangjaponicain A (1), and taihangjaponicain B ( 2), and nine known diterpenoids, epinodosin (3), oridonin (4), epinodosinol (5), lasiokaurin ( 6), 1alpha- O-beta- D-glucopyranosylenmenol (7), lasiodonin (8), rabdosichuanin D ( 9), shikokianin (10) and rabdoternin A (11) were isolated from I. japonica leaves. The structures of the two new compounds were elucidated using 1-D and 2-D NMR spectroscopy. Compounds 1 and 3 - 11 were tested against HL-60, HO-8910 and A-549 human tumor cells. Compounds 4, 6 and 10 showed significant cytotoxicity against HL-60 cells with IC (50) values of 4.6, 2.0 and 3.4 microM, respectively, and against A-549 cells with IC (50) values of 17.5, 11.4 and 18.8 microM, respectively. Compound 6 exhibited moderate cytotoxicity against HO-8910 cells with an IC (50) value of 17.9 microM.     

Two new rearranged abietane diterpenoids from tropical Isodon coetsa

Two new rearranged abietane diterpenoids, sincoetsin A (1) and sincoetsin B (2), were isolated from the aerial part of Isodon coetsa (Buth-Ham ex D.Don) Hara collected in Singapore, and their structures were determined by spectroscopic methods, especially 2D NMR techniques.     

Two new rearranged abietane diterpenoids from tropical Isodon coetsa

Two new rearranged abietane diterpenoids, sincoetsin A (1) and sincoetsin B (2), were isolated from the aerial part of Isodon coetsa (Buth-Ham ex D.Don) Hara collected in Singapore, and their structures were determined by spectroscopic methods, especially 2D NMR techniques.     

Cytotoxic diterpenoids from Isodon enanderianus

Five new ent-kaurane diterpenoids, enanderianins K-O (1-5), and one new ent-abietane diterpenoid, enanderianin P (6), together with five known ent-kaurane diterpenoids, rabdocoetsin A (7), rabdocoetsin B (8), rabdocoetsin D (9), megathyrin A (10), megathyrin B (11) were isolated from the aerial parts of Isodon enanderianus. Their structures were determined by spectral means. Some diterpenoids were tested for their cytotoxicity against the human tumor K562 cells. Compounds 1, 2, 6, 8, 9 showed significant inhibitory activities against K562 cells with IC50 values ranging from 0.13 to 0.87 microg/mL.     

Isolation, structural elucidation, and cytotoxicity of three new ent-kaurane diterpenoids from Isodon japonica var. glaucocalyx

Three new ENT-kaurane diterpenoids, glaucocalyxin H ( 1), glaucocalyxin I ( 2), and glaucocalyxin J ( 3), together with four known diterpenoids ( 4- 7), were isolated from the leaves of Isodon japonica Hara var. glaucocalyx. Their structures were elucidated by spectroscopic analysis, and the structures of compounds 2 and 3 were further confirmed by X-ray crystallographic analysis. Compounds 1, 4, and 5 were evaluated for their cytotoxicity IN VITRO against CE-1, U87, A-549, MCF-7, Hela, K-562, and HepG-2 human tumor cell lines. Compound 1 showed potent inhibitory activities against six tumor cell lines with IC (50) values ranging from 1.86-10.95 μM, and compounds 4 and 5 exhibited significant selective cytotoxicity on seven tumor cell lines.     

Cytotoxic ent-kaurane diterpenoids from Isodon weisiensis C. Y. Wu

A new ent-kaurane diterpenoid, weisiensin B (1), was isolated from the leaves of Isodon weisiensis C. Y. Wu, along with four known ones, kamebanin (2), kamebacetal A (3), macrocalyxin D (4) and excisanin D (5). Their structures were determined by spectroscopic means. Compound 1-4 showed significant cytotoxic activity against Bel-7402 and HO-8910 cells.     

Cytotoxic ent-kaurane diterpenoids from Isodon macrophyllus

Two new ent-kaurane diterpenoids, dayecrystals D–E (1–2), together with nine known compounds, isojaponin A (3), rabdosin A (4), lushanrubescensin J (5), wikstroemioidin B (6), maoyecrystal C (7), rabdosin B (8), isodonal (9), shikokianin (10), and effusanin A (11), were isolated from the leaves of Isodon macrophyllus. The structures of the new compounds were elucidated using 1D and 2D NMR spectroscopy. The ¹³C-NMR spectral data of compound 4 are reported for the first time. All of the compounds were tested for their cytotoxicities against DU145 and LoVo human tumor cells. Compounds 4, 10, and 11 showed inhibitory effects on DU145 cells with IC₅₀ values 5.90, 4.24, and 3.16 μM, and LoVo cells with IC₅₀ values 14.20, 17.55, and 3.02 μM, respectively.     

Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata

Four new ent-kaurane diterpenoids, sculponeatins F-I (1-4), together with six known compounds, sculponeatin E (5), epi-nodosin (6), epi-nodosinol (7), enmein (8), and macrocalyxoformins A and B (9 and 10), were isolated from the leaves of Isodon sculponeata. Also obtained were ursolic acid, 2alpha,3beta-dihydroxy-urs-12-en-28-oic acid, 2alpha,3beta,19alpha-trihydroxy-urs-12-en-28-oic acid, beta-sitosterol, daucosterol, quercetin, pedalitin, rosmarinic acid, caffeic acid and ethyl caffeic acid. Their structures were determined by spectral methods (1D-, 2D-NMR and MS). Some diterpenoids were tested for their cytotoxicity to inhibit three kinds of human tumor cells K562, A549 and T24. Compounds 3, 4, 6, 8, and 10 showed significant inhibitory effect toward K562 with IC(50) values ranging from 3.2 microg/ml to 8.2 microg/ml, while 3 and 6 exhibited potent antitumor activity against T24, but none exhibited cytotoxicity toward the cells of A549.     

19-oxygenated ent-kaurane diterpenoids from Isodon pharicus

Eight new 19-oxygenated ENT-kaurane diterpenoids were isolated from the aerial parts of Isodon pharicus. Their structures were determined by means of extensive spectroscopic techniques including interpretation of 1D and 2D?NMR spectra. Selected compounds were evaluated for their cytotoxicity against NB4, A549, PC-3, MCF-7, and SH-SY5Y cell lines.     

小叶香茶菜中二萜类化学成分的研究

目的 研究云南中甸产的小叶香茶菜地上部分的二萜化学成分.方法 采用硅胶色谱,半制备、制备HPLC分离纯化二萜化学成分,运用1HNMR、13CNMR、ESI-MS等技术鉴定结构.结果 从云南中甸的小叶香茶菜地上部分共分离得到了14个二萜化合物,分别鉴定为hebeirubescensin L(Ⅰ),adenolin E(Ⅱ),trichokaurin(Ⅲ),effusanin B(Ⅳ),rabdoternin C(Ⅴ),baiyecrystal A(Ⅵ),rabdoternin A(Ⅶ),rabescensin C(Ⅷ),sodoponin(Ⅸ),longikaurin E(Ⅹ),rabdolasional(Ⅺ),isodonal(Ⅻ),trichorabdal A(ⅩⅢ),trichorabdal H(ⅩⅣ).结论 化合物Ⅶ、Ⅷ、Ⅻ和ⅩⅣ为首次从小叶香茶菜中分离得到.     

ent-Kaurane diterpenoids from the leaves of Isodon xerophilus

From the ethanolic extract of the leaves of Isodon xerophilus, three new ent-kaurane diterpenoids named xerophilusins L-N (1 - 3), together with three known ones designated as rabdoternin A (4), longikaurin F (5) and ponicidin (6), were isolated and structurally elucidated. Compound 6 demonstrated most potent cytotoxic activity against K562 and T24 human tumor cell lines with IC(50) = 0.09 and 0.32 microg/ml, respectively.     

Glabcensin Q-U, five new ent-kaurane diterpenoids from Isodon angustifolius var. glabrescens

Examination of the diterpenoid constituents of the dried leaves of Isodon angustifolius var. glabrescens led to the isolation of five new ent-kaurane diterpenoids, named as glabcensin Q-U (2-6). The structures were elucidated on the basis of spectroscopic evidences.     

Cytotoxic ent-kaurane diterpenoids from Isodon rubescens var. rubescens

Five new ent-kauranoids, xindongnins C - G ( 1 - 5), together with five known ones, xindongnins A and B ( 6 and 7), melissoidesin G ( 8), dawoensin A ( 9), and glabcensin V ( 10), were isolated from the leaves of Isodon rubescens var. rubescens, and structurally elucidated. Compounds 1, 4, and 6 - 10 showed inhibitory effects against human tumor K562 cells with IC (50) values ranging from 0.3 to 7.3 microg/mL. The structure of 6 was revised on the basis of its 2D-NMR spectral data.     

Cytotoxic ent-kaurane diterpenoids from Isodon eriocalyx var. laxiflora

Three new ent-kaurane diterpenoids laxiflorin E (1), laxiflorin H (6) and laxiflorin I (8) were isolated from the leaves of Isodon eriocalyx var. laxiflora, along with nine known diterpenoids, eriocalyxin A (2), laxiflorin C (3), laxiflorin D (4), laxiflorin A (5), maoecrystal S (7), maoecrystal Q (9), eriocalyxin B (10), maoecrystal C (11) and enmelol (12). The structures of the new compounds were determined by spectroscopic methods. Compounds 1-5 are 6,7-seco-ent-kaurane-7,20-olide diterpenoids, and 6-12 belong to 7,20-epoxy-ent-kauranoids. The spectral data of enmelol (12) are reported here for the first time. Ten of these compounds were tested for their cytotoxicity toward K562 and T24 human tumor cells. Compounds 1, 3 and 10 showed significant inhibitory effects on K562 cells with IC50 values 0.077, 0.569 and 0.373 microg/mL, and compounds 1 and 10 also demonstrated significant inhibitory activities toward T24 cells with IC50 values 0.709 and 0.087 microg/mL. Compounds 8 and 11 also displayed inhibitory effect on both two kinds of cells with IC 50 value less than 6.5 microg/mL.     

锈毛野桐中的两个新二萜anomalusin A和anomalusin B(英文)

从锈毛野桐中分离得到两个新的ent-rosane型二萜anomalusin A(1)和anomalusin B(2),以及10个已知化合物。化合物1和2的结构和相对构型通过波谱学方法确定,它们的绝对构型通过CD谱确定。     

Clemochinenosides C and D,two new macrocyclic glucosides from Clematis chinensis

Abstract

The EtOH extract of the roots and rhizomes of Clematis chinensis afforded two new macrocyclic glucosides clemochinenosides C (1) and D (2). Their structures were elucidated on the basis of spectroscopic means and hydrolysis products. These compounds were evaluated for inhibitory activity against lipopolysaccharides-induced TNF-α production in RAW 246.7 macrophages. Compounds 1 and 2 showed moderate inhibitory activity with IC₅₀ values of 12.9 ± 2.3 and 18.4 ± 2.7 μM, respectively. In addition, a proliferation study was used to evaluate the anti-angiogenic effects of these compounds in vitro (VEGF-induced human umbilical vein endothelial cell proliferation). Compounds 1 and 2 displayed weak inhibitory effects with inhibition rates of 26.3 ± 1.8 and 19.2 ± 2.6% at 50 μM, respectively.     

Three new compounds from Isodon melissoides

Reinvestigation of the aerial parts of Isodon melissoides has afforded two new ent-diterpenoids, melissoidesins V (1) and W (2), together with five known ones, glabcensin W (3), melissoidesin C (4), melissoidesin A (5), melissoidesin B (6) and melissoidesin D (7), one new ionone derivative 3alpha,4alpha-isopropyliden-beta-ionol (8), as well as three analogues, 3-hydroxy-4-oxo-beta-ionol (9), megastigma-7-en-3,5,6,9-tetraol (10) and blumenol A (11), and three phenolic compounds salicylic acid (12), syringic acid (13) and cirsiliol (14). The new structures were elucidated on the basis of spectroscopic techniques, especially the 2D-NMR spectral analysis.     

Three new 11,20-epoxy-ent-kauranoids from Isodon rubescens

Three rare and new 11,20-epoxy-ent-kaurane diterpenoids, named jianshirubesins D-F (1-3), along with one known analogue (4), were isolated from the aerial parts of Isodon rubescens. Their structures were established by analysis of spectroscopic data. Found in the MTT assay to evaluate the cytotoxicity of compounds 1, 2, and 4, only 1 could selectively inhibit certain cell lines from proliferating. In addition, a simple structure-activity relationship discussion might suggest a new bioactive moiety, different from the α,β-unsaturated ketone group.     

Two new bislabdane-type diterpenoids and three new diterpenoids from the roots of Cunninghamia lanceolata

Two new bislabdane-type diterpenoids lanceolatin (1), lancelatol (2) and three new diterpenoids 15-nor-14-oxo-8(17),12-labdanien-14,18-dionic acid (3), 8(17),12,14-labdantrien-18-oic acid (4) and 8(17),12,14-labdantrien-18-ol (5), together with 7 known diterpenoids were isolated from the roots of Cunninghamia lanceolata. Their structures were determined by spectroscopic and chemical methods. All of these compounds were isolated from the species for the first time. One of the isolated compounds showed a significant inhibition effect on mouse hind-paw edema induced by carrageenan.     

A new abietane diterpenoid from Isodon inflexus

A new ent-abietane diterpenoid, 3α,6β-dihydroxy-7,17-dioxo-ent-abieta-15(16)-ene (1), and three known ent-kaurane diterpenids, kamebacetal A (2), kamebakaurin (3), and excisanin A (4), and a known triterpenoid, ursolic acid (5), were isolated from the aerial parts of Isodon inflexus. Their chemical structures were determined by extensive analysis of spectroscopic data including 1D-and 2D-NMR experiments. All isolates (1–5) were evaluated for their potential to inhibit LPS-induced nitric oxide production in RAW264.7 cells. Of these, compounds 1–4 inhibited the production of NO with IC₅₀ values ranging from 1.0 to 26.5 μM.