ent-Kaurane Diterpenoids from Isodon albopilosus

Nine new diterpenoids, albopilosins B-J (1-9), together with six known analogues, albopilosin A (10), macrocalyxin C (11), rabdokunmin C (12), excisanin (13), amethystonoic acid (14), and coetsanoic acid (15), were isolated from the aerial parts of Isodon albopilosus. The structures of 1-9 were established using spectroscopic methods including extensive 1D and 2D NMR analysis. The diterpenoids isolated were evaluated for their inhibitory activities against HepG2 (hepatoma) cells. Compounds 7 and 13 were the most active, with both having IC(50) values of <15 microM.     

ent-Kaurane Diterpenoids from Isodon nervosus

A pentacyclic ent-kauranoid, nervonin A ( 1), with an unprecedented cyclobutane moiety in the structure, and nine other new ent-kaurane diterpenoids, nervonins B-J ( 2- 10), along with 10 known ones ( 11- 20), were isolated from Isodon nervosus. Their structures were elucidated by detailed spectroscopic analysis. All diterpenoids were assayed for their cytotoxicity against K562, A549, and HepG2 human cell lines. Compounds 2, 11, 16, 17, and 20 showed significant cytotoxicity.     

川藏香茶菜中五个新的对映-贝壳杉烷二萜

目的：研究川藏香茶菜（Isodon pharicus）地上部分化学成分。方法：利用正反相硅胶、高效液相色谱等现代分离技术进行分离,利用IR,UV,MS和NMR等现代波谱技术手段鉴定了它们的结构。结果：分离得到5个对映坝壳杉烷二萜：pharicunins N—R（1～5）;结论：这5个化合物均为新二萜。     

ent-Kaurane and beyerane diterpenoids from Excoecaria agallocha

The roots of Excoecaria agallocha yielded four new diterpenoids, ent-3 beta,20-epoxy-3 alpha,6 alpha-dihydroxykaur-16-ene (agallochin F) (1), 3beta,20-epoxy-3 alpha-hydroxybeyer-15-ene (agallochin G) (2), 3 beta,20:15R,16S-diepoxy-3 alpha-beyeranol (agallochin H) (3), and 3 beta,20-epoxy-3 alpha,6 alpha-dihydroxy-18-nor-beyer-15-ene (agallochin I) (4), along with three known derivatives, 2-acetoxy-1,15-beyeradiene-3,12-dione (5), 2-hydroxy-1,15-beyeradiene-3,12-dione (6), and ent-kauran-16 beta-ol-3-one. The structures of 1-4 were determined by spectroscopic (NMR and MS) data interpretation.     

Dimeric ent-kaurane diterpenoids from Isodon excisus

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.     

毛叶香茶菜中的二萜化合物

目的：对河南产毛叶香茶菜化学成分进行研究。方法：运用各种色谱技术和波谱分析对其化学成分进行分离鉴定。结果：分离鉴定了20个二萜化合物。结论：化合物1—3为三个新的对映-贝壳杉烷二萜类化合物，结构分别为7β，15β，16β—三羟基—6β，17β—二乙酰氧基—7α，20-环氧—对映—贝壳衫烷(1)、16（S)—6β，11α，17β—三羟基-6，20-环氧—1α，7β—内酯—6，7—断裂—对映—贝壳杉-15酮(2)和6α，11α—二海基—1α—乙酰氧基—7，20内酯—6，7—断裂—对映—贝壳杉—16—烯—15—酮(3)，依次命名为毛叶香茶菜丙素、丁素和戊素；化合物4和5为—对新化合物，其结构为3α，15α，1β6，17β，18β—五羟基。对映—松香—7(8)—烯的丙酮化物，其丙酮化缩合部分互为对映体，分别命名为毛叶香茶菜庚素(4)和辛素(5)。     

ent-Kaurane diterpenoids from Croton tonkinensis stimulate osteoblast differentiation

Four new ent-kaurane diterpenoids (1-4) were isolated from the leaves of Croton tonkinensis by bioactivity-guided fractionation using an in vitro osteoblast differentiation assay. Their structures were identified as ent-11β-acetoxykaur-16-en-18-ol (1), ent-11α-hydroxy-18-acetoxykaur-16-ene (2), ent-14β-hydroxy-18-acetoxykaur-16-ene (3), and ent-7α-hydroxy-18-acetoxykaur-16-ene (4). Compounds 1-4 significantly increased alkaline phosphatase activity and osteoblastic gene promoter activity. Compounds 1-3 also increased the levels of ALP and collagen type I alpha mRNA in C2C12 cells in a dose-dependent manner. These results suggest that ent-kaurane diterpenoids from C. tonkinensis have a direct stimulatory effect on osteoblast differentiation and may be potential therapeutic molecules against bone diseases such as osteoporosis.     

ent-kaurane diterpenoids from Isodon lungshengensis.

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.     

Alboatisins A-C, ent-atisene diterpenoids from Isodon albopilosus

Three biogenetically interesting ent-kaurane-derived metabolites, alboatisins A-C (1-3), featuring a C-13-oxygenated ent-atisane skeleton, have been isolated from the aerial parts of Isodon albopilosus. Their structures were determined on the basis of spectroscopic evidence. Compound 2 exhibited cytotoxicity against A549 and HT-29 human cancer cells, with IC50 values of 8.3 and 7.9 microM, respectively.     

Structure and cytotoxicity of diterpenoids from Isodon adenolomus

Twelve new diterpenoids, isoadenolins A-L (1-12), and 24 known ones were isolated from the aerial parts of Isodon adenolomus. Their structures were identified using spectroscopic data, and the absolute configurations of 1 and 14 were determined by single-crystal X-ray diffraction. Selected compounds were evaluated for their in vitro cytotoxicity against human tumor HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. Compounds 9, 13-16, and 21 showed significant inhibitory effects on all five cells, with IC50 values in the range 0.7-9.7 μM.     

Structure and cytotoxicity of diterpenoids from Isodon eriocalyx

A new ent-atisanoid, eriocatisin A (1), six new ent-abietanoids, eriocasins B-E (2-4, 7), 3-acetyleriocasin C (5), and 3β-acetoxyeriocasin D (6), and seven new ent-kauranoids, maoesins A-F (8, 10-14) and 3α-acetoxy-maoesin A (9), together with 21 known compounds, were isolated from the aerial parts of Isodon eriocalyx. The structures of 1-14 were determined by spectroscopic data interpretation. All compounds isolated were evaluated for their in vitro growth inhibitory activity against the HT-29, BEL-7402, and SK-OV-3 human cancer cell lines. Compounds 17, 18, and 20 showed inhibitory effects for all three tumor cell lines used, with IC(50) values in the range 2.1-7.3 μM.     

黄花香茶菜的二萜成分研究

目的：研究黄花香茶菜Isodon sculponeata(Vanior)Hara的化学成分。方法：利用反复硅胶柱层析进行分离和纯化,通过理化方法及光谱分析鉴定其结构。结果：从黄花香茶菜占的丙酮提取物中分得6个对映－贝壳杉烷型二萜化合物,其中一个为新化合物,命为为黄花香茶菜戊素（sculponeatin,E,Ⅰ）,其余二萜化合物分别鉴定为延命草素（enmein,Ⅱ),epinodosin(Ⅲ),epinodosinol(Ⅳ),大萼变形甲素（macrocalyxoforminA,Ⅴ)和大萼变型乙素（macrocalyxoforminB,Ⅵ).结论：化合物Ⅰ为新化合物,化合物Ⅳ和Ⅵ系首次从该植物中分得。     

ent-Kaurane diterpenoids from croton tonkinensis inhibit LPS-induced NF-kappaB activation and NO production

Four ent-kaurane diterpenoids including two known, ent-7alpha,14beta-dihydroxykaur-16-en-15-one (1) and ent-18-acetoxy-7alpha-hydroxykaur-16-en-5-one (2), and two new, ent-1beta-acetoxy-7alpha,14beta-dihydroxykaur-16-en-15-one (3) and ent-18-acetoxy-7alpha,14beta-dihydroxykaur-16-en-15-one (4), were isolated from the leaves of Croton tonkinensis in a search for inhibitors of NF-kappaB activation and nitric oxide production. These ent-kauranoids inhibited LPS-induced NF-kappaB activation in murine macrophage RAW264.7 cells at IC50 values between 0.07 and 0.42 microM. Consistently, the ent-kauranoids markedly reduced LPS-induced NO production in a comparable concentration-dependent manner.     

冬凌草中三个新的对映-贝壳杉烷二萜及其细胞毒活性

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。     

Cytotoxic 3,20-epoxy-ent-kaurane diterpenoids from Isodon eriocalyx var. laxiflora

Four new ent-kaurane diterpenoids, laxiflorins J-M (1-4), along with maoecrystal A (5) and maoecrystal P (6), were isolated from the leaves of Isodon eriocalyx var. laxiflora. Their structures were determined by spectroscopic analyses. All the compounds were assayed for their cytotoxic effects on human tumor K562, A549, and T24 cell lines. Compounds 1 and 6 showed significant inhibitory effects on human tumor K562 and T24 cells, with IC(50) values less than 0.5 microg/mL. Compound 3 also demonstrated cytotoxic activities against all three types of human tumor cells, with IC(50) values in the range of 1-25 microg/mL.     

Kaurane diterpenoids from Isodon excisus inhibit LPS-induced NF-kappaB activation and NO production in macrophage RAW264.7 cells

As part of an ongoing search for plant-derived compounds that inhibit the activation of NF-kappaB, the methanol extract of the aerial parts of Isodon excisus was found to have significant inhibitory effects on the activation of NF-kappaB in murine macrophage RAW264.7 cells. Bioactivity-guided isolation of the extract yielded five new diterpenoids, excisusin A-E (1-5), along with seven known compounds, inflexarabdonin I (6), inflexarabdonin G (7), inflexin (8), inflexanin A (9), inflexanin B (10), inflexinol (11), and inflexarabdonin A (12). The structures were determined by analysis of the spectroscopic data including 2D NMR. All of the isolates were evaluated for their inhibitory effects on LPS-induced NF-kappaB activation and nitric oxide production in RAW264.7 cells.     

Diterpenoids from Isodon melissoides

Nine new diterpenoids, melissoidesins M-U (1-9), along with five known analogues, melissoidesin F (10), xindongnin B (11), melissoidesin G (12), melissoidesin E (13), and dawoensin A (14), were isolated from the aerial parts of Isodon melissoides. The structures of new compounds were elucidated by analysis of spectral evidence including extensive 2D NMR data. Compounds 2, 3, 7, 11, 12, and 14 showed cytotoxicity against the human tumor BGC-823 cell line with IC(50) values less than 10 microg/mL, respectively.     

矮慈姑中新的对映贝壳杉烷二萜

目的：研究矮慈姑（Sagittaria pygmaea Miq）全草中的二萜类成分。方法：采用硅胶柱层析、Sephadex LH-20柱层析等方法进行分离和纯化化学成分，结合化学方法和渡谱学方法进行结构鉴定。结果：从矮慈姑乙醇提取物的石油醚萃取部分中分离得到5个二萜类化合物，包括一个对映贝壳杉烷，为19-β-L-3′-acetoxyarabinofuranosyl-eru-kaur-16-ene（1），3个半日花烷，分别为13-epi-manoyloxide-18-ol（2），13-epi-manoyloxide-18-oic acid（3）和13-epi-manoyl oxide-18-O-α-L-2′，5′-diacetoxyarabinofuranoside（4），一个玫瑰烷为5α-hydroxy-ent-rosa-15-en-19-oic acid（5）。结论：上述化合物均从该属植物中首次得到，其中化合物1为新化合物。     

黄花香茶菜二萜化学成分研究

目的研究产自云南中甸的黄花香茶菜Isodon sculponeatus(Vaniot)Kudo茎叶的二萜化学成分。方法采用硅胶色谱、HPLC制备色谱分离、纯化化学成分,通过波谱数据鉴定化合物结构。结果从产自云南中甸的黄花香茶菜茎叶中分离得到了14个二萜化合物,分别鉴定为延命草素(enmein,1),表诺多星(epinodosin,2),黄花香茶菜甲素(sculponeatin A,3),黄花香茶菜乙素(sculponeatin B,4),诺多星(nodosin,5),sculponin F(6),大鄂变形甲素(macrocalyxoformin A,7),isodocarpin(8),sculponin B(9),皱叶香茶菜素(rugosanin,10),黄花香茶菜素D(sculponeatin D,11),黄花香茶菜素K(sculponeatin K,12),黄花香茶菜丙素(sculponeatin C,13),显脉香茶菜新素(rabdonervosin A,14)。结论化合物7、8、10、12和14为首次从黄花香茶菜中分离得到。     

旱生香茶菜中的三萜成分(英文)

目的:研究旱生香茶菜的化学成分。方法:采用多种色谱技术和方法进行分离,通过波谱分析鉴定化合物结构。采用MTT法进行人体肿瘤细胞毒体外活性实验。结果:从旱生香茶菜叶中分离并鉴定了10个三萜类化合物:齐墩果酸(1),乌苏酸(2),maslinicacid(3),2α-羟基乌苏酸(4),hederagenin(5),3β,23-dihydroxy-urs-12-en-28-oicacid(6),arjunolicacid(7),asiaticacid(8),2α,3α,24-trihydroxyolean-12-en-28-oicacid(9),2α,3α,24-trihydroxyurs-12-en-28-oicacid(10)。测试了10个化合物对3种(K562,MKN45,HepG2)人体肿瘤细胞株的细胞毒活性。结论:化合物1-10均首次从该植物中分离得到,并讨论了它们的生源关系。所有三萜化合物对上述三种人体肿瘤细胞株都没有细胞毒活性。