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Five new ent-kaurane diterpenoids xindongnins H-L (1-5), together with five known ones, xindongnins A and B (6, 7), melissoidesins G (8), dawoensin A (9), and glabcensin V (10) were isolated from Isodon rubescens var. rubescens. Their structures were elucidated by spectroscopic methods including extensive 2D NMR techniques.
A phytochemical investigation on the leaves of Isodon parvifolius yielded three new ent-abietanoids parvifolines L-N (1-3), together with five known ent-abietanoids (4-8) and one known ent-labdane diterpenoid (9). Their structures were determined on the basis of extensive spectroscopic analysis.
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.
OBJECTIVE: To study the chemical constituents of the volatile oil from the aerial parts of Isodon eriocalyx var. laxiflora. METHOD: The oil was obtained by hydrodistillation. The chemical compositions were separated and identified by GC-MS. The relative contents in the oil were determined by area normalization. RESULT: 163 peaks were separated and 105 compounds were identified, constituting 85.68% of the total peak area. CONCLUSION: 105 compounds characterized by GC-MS analysis were found from I. eriocalyx var. laxiflora for the first time.
OBJECTIVE: To study the protective effects of Isodon lophanthoides var. gerardianus (ILVG) aqueous extract on the acute hepatic injury induced by carbon tetrachloride (CCl4) in rats. METHOD: Sixty rats were allocated into control group, model group, low, middle and high dosage group and Bifendate group randomly. At the test group, rats received either ILVG aqueous extract (15, 7.5, 3.75 g x kg(-1)) or Bifendate (45 mg x kg(-1)) by gastric perfusion daily for 10 consecutive days. In 1st, 4th, 7th and 10th days, 10% CCl4 (2 mL x kg(-1)) was given to rats by intraperitoneal (ip) injection. The rats were killed 24 h after the last adminiction with drug, the levels of ALT, AST, ALP and total bilirubin in serum were analyzed, the body weight, liver weight, spleen weight and thymus weight of each rat were measured, and the hepatic tissue pathology was observed. RESULT: ILVG could decrease the ALT, AST, ALP and T-Bil in serum, restrain the enlargement of liver and the shrinkage of thymus, and reduce the necrosis in pathological observation. CONCLUSION: ILVG aqueous extract possesses the effects of protecting on the acute hepatic injury induced by CCl4 in rats.
A significant antitumor activity of oridonin (1) and lasiokaurin (2), the kaurene-type diterpenoids of Isodon species, was shown by their i.p. injection to the test mice inoculated by Ehrlich ascites carcinoma. Enmein (8), compounds 9 and 3 were also active under larger dose. Subsequently, the relationship between their chemical structure and antitumor activity was investigated, and the activity of oridonin (1) and lasiokaurin (2) was rationalized in terms of their structural feature.
The diethyl ether extract of Isodon excisus var. coreanus exhibited significant inhibitory activity in aromatase assay. Bioactivity-guided fractionation of the extract led to the isolation of three active compounds: inflexin (ent-1alpha-hydroxy-3beta,6a-diacetoxykaur-16-en-11,15-dione ) (1), ursolic acid (2), and ursolic acid 3-O-acetate (3).
From Isodon loxothyrsa, one new diterpenoid, loxothyrin A, together with one known diterpenoid, adenolin B, from I.pleiophyllus, three known diterpenoids, coetsoidins A, B and G, and from I. adenoloma, one known diterpenoid, longikaurin F, were isolated. The structure determination of loxothyrin A, and the unambiguous NMR spectral assignments of the known compounds were made by a combination of 1D and 2D NMR techniques and computer modelling calculations. The isolates showed potent cytotoxic activities.
Three new, seco-ent-kaurane diterpenoids, laxiflorins A, B and C, together with four known diterpenoids eriocalyxin B, oriodonin, and maeocrystals A and B, were isolated from the leaves of Isodon eriocalyx var. laxiflora. Their structures were assigned by a combination of one- and two-dimensional NMR techniques and computer modeling calculations. Laxiflorin C displayed weak cytotoxic activity.
From Isodon gesneroides, three new cytotoxic diterpenoids, gesneroidins A, B and C, together with one known diterpenoid, dawoensin A, were isolated, and the structure determination and unambiguous assignment of their stereochemistry and NMR spectral data were made by a combination of one-and two-dimensional NMR techniques, computer modelling calculations and X-ray analysis.
Four 7,20-epoxy ent-kaurane diterpenoids, xerophilusins G (1) and I-K (2-4), were isolated from the leaves of Isodon xerophilus, along with four known ones, enanderianin C (5), rosthorin A (6), longikaurin B (7), and rabdoternin D (8). Their structures were determined primarily using NMR spectroscopic techniques. The structure and stereochemistry of 3 were confirmed by X-ray crystallography. Compounds 4 and 7 exhibited broad cytotoxicity against four kinds of human tumor cells (K562, HL-60, HCT, and MKN-28 cells) in the range of 2.23-15.35 and 0.30-8.61 microg/ml, respectively.
Two enmein type diterpenoids, taibaijaponicains A and B, were isolated from the ethanol extract of the leaves and branches of Isodon japonica. Their structures are designated as 6beta,11alpha-dihydroxy-16alpha-methoxymethyl-6,20-epoxy-6,7-seco-ent-kaur-15-one-1,7-olide and 3beta-acetoxy-6beta,11alpha-dihydroxy-16alpha-methoxymethyl-6,20-epoxy-6,7-seco-ent-kaur-15-one-1,7-olide, respectively, on the basis of detailed spectroscopic analyses.
Four ent-kauranoids, 6-epiangustifolin and enanderinanins F-H, as well as 11 known ent-kaurane diterpenoids, macrocalin B, xerophilusin A, trichorabdal A, trichorabdal B, effusin, angustifolin, longikaurin D, longikaurin F, enanderinanin B, xerophilusin G and shikokianin were isolated from the aerial parts of Isodon enanderianus. The new diterpenoids were identified as 6-epiangustifolin (11alpha-hydroxy-6alpha-methoxy-6,19-epoxy-6,7-seco-ent-kaur-16-en-15-one-7,20-olide), enanderinanin F (19-acetoxy-6,20:6,11beta-diepoxy-6,7-seco-ent-kaur-16-en-15-one-1beta,7-olide), enanderinanin G (1beta,6beta,7beta-trihydroxy-19-acetoxy-16beta-methoxymethyl-7alpha,20-epoxy-ent-kaur-15-one) and enanderinanin H (6beta,7beta,14beta-trihydroxy-1alpha,11beta-acetonide-7alpha,20-epoxy-ent-kaur-16-en-15-one), respectively, on the basis of spectral data, especially by 2D NMR techniques. 6-Epiangustifolin showed significant cytotoxic activity against K562 cell.
Two kaurenoids, taibairubescensins A and B, were isolated from the ethanol extract of the leaves and branches of Isodon rubescens. Their structures are designated as 2 beta, 3 beta-diacetoxy-11 beta, 13 alpha-dihydroxy-ent-kaur-16-en-15-one and 3 beta, 11 beta-diacetoxy-2 beta, 6 alpha-dihydroxy-ent-kaur-16-en-15-one, respectively, on the basis of detailed spectroscopic analyses.
A new diterpenoid was isolated from the leaves of Isodon lophanthoides, together with two known diterpenoids, lophanic acid and 8(17),12,14-labdatriene-19-oic acid. The structure of the new compound was determined to be 11 beta-hydroxyisopimara-8,15-diene-3-one (1) on the basis of spectroscopic evidence.
A new ent-kaurane diterpenoid, phyllostachysin C (1), together with five known compounds, sculponeatins B and C, nodosin, ursolic acid and 2 alpha-hydroxyursolic acid, were isolated from the leaves of Isodon phyllostachys. The structure of 1 was elucidated on the basis of its spectral properties.
Investigation of the whole plant of Isodon excisus resulted in the isolation of two new apoptosis inhibitors (1 and 2). Compounds 1 and 2 inhibited etoposide-induced apoptosis in U937 cells with IC50 values of 10.2 and 52.4 microg/mL, respectively. The structures of 1 and 2 were determined by spectral data interpretation.
A new ent-kaurene diterpene, pseudoirroratin A (1), and a known diterpene, pseurata A, were isolated from Isodon pseudo-irrorata. Compound 1 showed significant cytotoxicity against the Lu1, SW626, LNCaP, KB, and HOS cancer cell lines with IC(50) values of 0.26 (0.75), 0.20 (0.57), 0.90 (2.59), 0.90 (2.59), and 0.50 (1.44) microg/mL (microM), respectively. The structure of 1 was elucidated by spectroscopic means including 1D and 2D NMR techniques.