Cancer Chemopreventive Activity of Oleanane‐Type Triterpenoids from the Stem Bark of Betula ermanii

In search for cancer chemopreventive agents from natural sources, three oleanane‐ and four known lupane‐type triterpenoids, and sitosterol from the stem bark of Betula ermanii were tested for their inhibitory effects on Epstein–Barr virus early antigen (EBV‐EA) activation induced by 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA). Among them, 3β‐acetoxy‐12α‐hydroxyoleanan‐13β,28‐olide ( 1 ) and 3β‐acetoxy‐11α,12α‐epoxyoleanan‐13β,28‐olide ( 2 ) were investigated for the inhibitory effect in a two‐stage carcinogenesis test on mouse skin using 7,12‐dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. 3β‐Acetoxy‐11α,12α‐epoxyoleanan‐13β,28‐olide ( 2 ) was found to exhibit the potent antitumor promoting activity in the in vivo carcinogenesis test.     

Lupane,friedelane, oleanane,and ursane triterpenes from the stem of Siphonodon celastrineus Griff

Twenty-one triterpenes consisting of a lupane derivative, two friedelanes, an oleanane derivative, and 17 ursane-type triterpenoids, together with three known triterpenes, three sterols, a fatty acid, a sesquiterpene alkaloid, and a glycerol derivative, were isolated from the stem of Siphonodon celastrineus. Their structures were characterized by various spectroscopic techniques, as well as comparison with literature data. Twenty-seven metabolites of these were evaluated for cytotoxic activity against six human cancer cell lines. The biosynthetic formation of a 1,4-dioxane bridge is also discussed.     

Natural Friedelanes

This review covers the occurrence and biological activities of all natural friedelane triterpenoids found between 1977 and March 2011. The biogeneses of dimeric friedelanes and several rearranged friedelanes are discussed. The pharmacological properties of representative compounds, including celastrol and correolide, have also been compiled, on the basis of 344 references.     

Six New Pentacyclic Triterpenoids from the Fruit of Camptotheca acuminata

Six new pentacyclic triterpenoids were isolated from the fruit of Camptotheca acuminata. The chemical structures of the new compounds were elucidated by extensive spectroscopic analysis including HR‐ESI‐MS, IR, UV, 1D‐ and 2D‐NMR. Moreover, the antibacterial activities of compounds 1 , 2 , 4 , 5 , and 6 were evaluated against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Dickeya zeae. All these tested compounds showed moderate antibacterial activity against Bacillus subtilis and Dickeya zeae.     

Betulinic Acid,The First Lupane‐Type Triterpenoid Isolated from Both a Phomopsis sp. and Its Host Plant Diospyros carbonaria Benoist

Following a biological screening using a dengue replicon virus‐cell‐based assay, Diospyros carbonaria AcOEt extract was investigated, affording six known lupane‐type triterpenoids endowed with anti‐DENV‐2 NS5 polymerase activity. The study of the associated microbial community of this species permitted us to identify 38 endophytes belonging to five different orders. Nine out of these 38 strains showed significant activity on the dengue replicon assay. The chemical investigation of the most active one, Phomopsis sp. SNB‐LAP1‐7‐32, led to the isolation of betulinic acid, an anti‐viral secondary metabolite isolated previously from the host plant. This result is the first example of a lupane‐type triterpenoid isolated from both an endophyte and its host plant. Its presence in the Phomopsis strain may result from gene transfer and/or specific niche selection.     

Cytotoxic Triterpenoids from the Barks of Betula platyphylla var. japonica

Phytochemical investigation on the barks of Betula platyphylla var. japonica (Betulaceae) was carried out, resulting in the isolation and identification of three new triterpenoids, 27‐O‐cis‐caffeoylcylicodiscic acid ( 1 ), 27‐O‐cis‐feruloylcylicodiscic acid ( 2 ), and 27‐O‐cis‐caffeoylmyricerol ( 3 ), along with six known triterpenoids, obtusilinin ( 4 ), winchic acid ( 5 ), 27‐O‐trans‐caffeoylcylicodiscic acid ( 6 ), uncarinic acid E ( 7 ), myriceric acid B ( 8 ), and 3‐O‐trans‐caffeoyloleanolic acid ( 9 ). The structures of the new compounds were elucidated by extensive spectroscopic methods, including 1D‐ and 2D‐NMR, and HR‐ESI‐MS. All of the isolated compounds were evaluated for cytotoxicity against four human tumor cell lines (A549, SK‐OV‐3, SK‐MEL‐2, and Bt549). Compounds 2 , 6 , 8 , and 9 exhibited potent cytotoxicity against all of the tumor cells tested (IC₅₀ < 10.0 μm ), while compounds 3 , 4 , 5 , and 7 showed moderate cytotoxicity against all of the tumor cells tested (IC₅₀ < 20.0 μm ).     

Protostane‐Type Triterpenoids from Alisma orientale

Twenty‐eight protostane triterpenoids, including a new degraded one ( 1 ), nine new ones ( 2 – 10 ), and two new natural ones ( 11 and 12 ), have been isolated from the dried rhizomes of Alisma orientale. Alisol R ( 1 ) was the first 20,21,22,23,24,25,26,27‐octanorprotostane triterpenoid. The absolute configurations of 25‐methoxyalisol F ( 2 ) and 16β‐hydroperoxyalisol B 23‐acetate ( 3 ) were determined by X‐ray diffraction analysis. In addition, alismaketone‐B 23‐acetate ( 28 ) showed potent vasorelaxant activity on endothelium‐intact thoracic aorta rings precontracted with KCl.     

腺花香茶菜中的三萜化合物

对云南大理产腺花香茶菜（Isodon adenanthus)进行了系统的研究。从中分离得到了包括1个新三萜（1）在内的一系列乌索烷型三萜类化合物,其结构通过现代波谱分析方法确定。活性筛选结果表明,化合物1对肿瘤细胞株K562,A549以及T24具有一定的细胞毒活性。     

锥序蜜心果中的三萜成分

从水东哥科植物锥序蜜心果( Saurauia napaulensis )中分离得到8个三萜类化合物,其中一个为新的三萜,鉴定其结构为2α, 3α, 24-三羟基-12-熊果烯-23-醛-28-酸.     

布渣叶中三萜和黄酮类成分的研究

从布渣叶(Microcos paniculata L.)的叶中分离得到10个化合物.通过光谱和波谱分析,分别鉴定为无羁萜(1)、阿江榄仁树葡糖苷Ⅱ(2)、山柰酚-3-O-β-D-[3,6-二(对羟基桂皮酰)]-葡萄糖苷(3)、山柰酚-3-O-β-D-葡萄糖苷(4)、异鼠李素3-O-β-D-葡萄糖苷(5)、异鼠李素3-O-β-D-芸香糖苷(6)、牡荆苷(7)、佛来心苷(8)、异佛来心苷(9)、异牡荆苷(10).10个化合物均为首次从布渣叶中分离得到.     

Chemical and Pharmacological Studies of the Plants from Genus Celastrus

The plants of genus Celastrus, distributed in Asia, have been used as natural insecticides and folk medicines to treat fever, chill, joint pain, edema, rheumatoid arthritis, and bacterial infection in China for a long time. This contribution reviews the chemical constituents, 1 – 144 , isolated from the plants in genus Celastrus in the past few decades, and their biological activities. The compounds listed are sesquiterpenes (β‐agarofurans), diterpenes, triterpenes, alkaloids, and flavonoids.     

Triterpenoids from Sanguisorba officinalis

Seven triterpenoids, i.e., 3beta-[(alpha-L-arabinopyranosyl)oxy]-19beta-hydroxyurs-12,20(30)-dien-28-oic acid (1), 3beta-[(alpha-L-arabinopyranosyl)oxy]-urs-11,13(18)-dien-28-oic acid beta-D-glucopyranosyl ester (2), 2alpha,3alpha,23-trihydroxyurs-12-en-24,28-dioic acid 28-beta-D-glucopyranosyl ester (3), 3beta-[(alpha-L-arabinopyranosyl)oxy]-urs-12,19(20)-dien-28-oic acid (4), 3beta-[(alpha-L-arabinopyranosyl)oxy]-urs-12,19(29)-dien-28-oic acid (5), 3beta-[(alpha-L-arabinopyranosyl)oxy]-19alpha-hydroxyolean-12-en-28-oic acid (6), 2alpha,3beta-dihydroxy-28-norurs-12,17,19(20),21-tetraen-23-oic cid (7), together with three known ones (8-10), were isolated from the roots of Sanguisorba officinalis. Their structures were determined by spectroscopic and chemical methods. Compounds 7 and 10 showed marginal inhibition activity against the growth of tumor cell lines.     

Triterpenoids from Cassine xylocarpa and Celastrus vulcanicola (Celastraceae)

Two new pentacyclic triterpenoids, xyloketal (1), a 3,25-epoxy-olean-12-ene, and 3β,21α-dihydroxyglut-5-ene (2) along with seven known triterpene compounds (3–9) were isolated from the root barks of Cassine xylocarpa and Celastrus vulcanicola. Their structures were characterized by spectroscopic methods, mainly NMR (¹H, ¹³C, HSQC, HMBC and ROESY) and EIMS, and comparison with data reported in the literature. Also molecular mechanic calculations were used to calculate the minimum energy conformer of compound 1 and its epimer.     

Nematicidal Triterpenoids from Lantana camara

A new triterpene, lancamarolide ( 1 ), and seven known triterpenes, oleanonic acid ( 2 ), lantadene A ( 3 ), 11α‐hydroxy‐3‐oxours‐12‐en‐28‐oic acid ( 4 ), betulinic acid ( 5 ), lantadene B ( 6 ), and lantaninilic acid ( 7 ) were isolated from the aerial parts of Lantana camara in the course of bioassay‐guided isolation, and their nematicidal activities against Meloidogyne incognita, the root knot nematode, were carried out. Oleanonic acid was found to be the most active compound and exhibited 80% mortality after 72 h at 0.0625% concentration, which is comparable with that of the standard furadan.     

中国南蛇藤属 (卫矛科) 一新记录种及其意义

在开展南蛇藤属分类修订的过程中,于 2011 年在中国云南省西双版纳傣族自治州勐腊县发现南蛇藤属中国分布新记录——拟独子藤 ( Celastrus monospermoides) 。该种形态与独子藤 ( C. monospermus) 较为相似,主要区别为前者叶片窄椭圆形,先端渐尖,果实成熟后不具雌蕊柄,种子长12 mm 以内; 后者叶片椭圆形、阔椭圆形至倒卵椭圆形,果实具有明显的雌蕊柄,种子长15 mm 以上。分子系统学研究表明,拟独子藤与独子藤处于不同分支中,与青江藤 ( C. hindsii) 系统关系最近。由于原记录仅分布于印度尼西亚、马来西亚和菲律宾等热带地区,因此在原产地和我国云南省之间的地区应有更多居群分布,这为探讨南蛇藤属的起源和扩散提供了线索。     

Biological Activities of Triterpenoids and Phenolic Compounds from Myrica cerifera Bark

Seven triterpenoids, 1  –  7 , two diarylheptanoids, 8 and 9 , four phenolic compounds, 10  –  13 , and three other compounds, 14  –  16 , were isolated from the hexane and MeOH extracts of the bark of Myrica cerifera L. (Myricaceae). Among these compounds, betulin ( 1 ), ursolic acid ( 3 ), and myricanol ( 8 ) exhibited cytotoxic activities against HL60 (leukemia), A549 (lung), and SK‐BR‐3 (breast) human cancer cell lines (IC₅₀ 3.1 – 24.2 μm ). Compound 8 induced apoptotic cell death in HL60 cells (IC₅₀ 5.3 μm ) upon evaluation of the apoptosis‐inducing activity by flow cytometric analysis and by Hoechst 33342 staining method. Western blot analysis on HL60 cells revealed that 8 activated caspases‐3, ‐8, and ‐9 suggesting that 8 induced apoptosis via both mitochondrial and death receptor pathways in HL60. Upon evaluation of the melanogenesis‐inhibitory activity in B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), erythrodiol ( 7 ), 4‐hydroxy‐2‐methoxyphenyl β‐d ‐glucopyranoside ( 13 ), and butyl quinate ( 15 ) exhibited inhibitory effects (65.4 – 86.0% melanin content) with no, or almost no, toxicity to the cells (85.9 – 107.4% cell viability) at 100 μm concentration. In addition, 8 , myricanone ( 9 ), myricitrin ( 10 ), protocatechuic acid ( 11 ), and gallic acid ( 12 ) revealed potent DPPH radical‐scavenging activities (IC₅₀ 6.9 – 20.5 μm ).     

锐尖山香圆叶中三萜类成分的研究

从锐尖山香圆(Turpinia arguta (Lindl.) Seem.)叶中分离得到了11个三萜类化合物。通过光谱分析,分别鉴定其结构为熊果酸(1), 3β,6β,23-trihydroxy-12-oleanen-28-oic acid (2), 3β,6β,23-trihydroxyurs-12-en-28-oic acid (3), 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic acid (4), 1 α, 3β,23-trihydroxy-12-oleanen-28-oic acid (5), arjunglucoside II (6), rosamultin (7), 3β-O-β-D-glucopyranoylcincholic acid (8), cinchonaglycoside C (9), mussaendoside S (10) 和3β-O-β-D-glucopyranosyl quinovic acid 28-O-β-D-glucopyranosyl ester (11)。除化合物1和6,其它化合物均为首次从山香圆叶中分离得到。     

New Triterpenoids from the Fruiting Bodies of Ganoderma lucidum and Their Bioactivities

Phytochemical investigation of the AcOEt extract of G. Lucidum has led to the isolation of two new triterpenoids, 1 and 2 , together with five known ones, 3 – 7 . The structures of the new compounds were identified as 12β‐acetoxy‐3β,7β‐dihydroxy‐11,15,23‐trioxolanost‐8‐en‐26‐oic acid butyl ester ( 1 ) and 12β‐acetoxy‐3,7,11,15,23‐pentaoxolanost‐8‐en‐26‐oic acid butyl ester ( 2 ) on the basis of detailed spectroscopic analysis (mass spectrometry, and 1D‐ and 2D‐NMR experiments). The antimicrobial activities of 1 and 2 were also evaluated.