On the origins of triterpenoid skeletal diversity

The triterpenoids are a large group of natural products derived from C(30) precursors. Nearly 200 different triterpene skeletons are known from natural sources or enzymatic reactions that are structurally consistent with being cyclization products of squalene, oxidosqualene, or bis-oxidosqualene. This review categorizes each of these structures and provides mechanisms for their formation.     

Triterpenoid saponins and acylated prosapogenins from Harpullia austro-caledonica

Three new triterpenoid saponins have been isolated from the stem bark of Harpullia austro-caledonica and identified as 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-protoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-16-desoxyprotoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-24-oxo-camelliagenin D. The 21,22-di-O-angeloate esters of protoaescigenin and barringtogenol C were isolated in the acid hydrolysate of the saponin extract together with a new prosapogenin identified as 21beta,22alpha-di-O-angeloyl camelliagenin D. The structures were established using one- and two- dimensional NMR and mass spectrometry.     

矩叶蓝果树的订正

据笔者对采自云南勐腊的“矩叶蓝果树”模式标本及曾被定为该变种的标本研究,该变种具聚伞花序,花梗长3－5mm,雌花子房上位,核果果皮极薄,内具1种子,并非蓝果树属植物,与茶茱萸科粗丝术属之粗丝本完全同种。粗丝木产中国西南至东南部,印度、斯里兰卡、缅甸、泰国、印度支那也有分布。     

蓣知子的化学成份研究（Ⅲ）

从木通科木通属植物白木通[Akebia trifolinta (Thunb.) Koidz. var. australis(Dies)Rehd]的种子(蓣知子)抗肿瘤活性的乙醇提取物中以硅胶层析等方法分得一种三萜皂甙。经波谱分析及酸碱水解确定了其化学结构,命名为:3-O-α-L-吡喃阿拉伯糖常春藤皂甙元-28-O-β-D吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖甙(即Saponin D),为首次自该植物中获得。     

东北雷公藤三萜成分的研究

从东北雷公藤(Tripterygium regeli)根的乙醇提取物分得10种三萜化合物,经波谱分析和化学转化,鉴定为雷公藤内酯甲(wilforlide A 1)、雷公藤内酯乙(wilfo rlide B 2)、黑蔓内酯(regelide 3)、3β-羟基-11,13(18)-齐墩果二烯(3β-hydroxy-olean-11,13(18)-diene4)、orthosphenic acid(5)、salaspermic acid(6)、3-epikatonic acid(7)、maytenfolic acid(8)、3β-acecyl-oleanolic acid(9)和南蛇藤素(celastrol 10)。化合物3—10首次从该植物分得,3是新化合物.     

Bacterial triterpenoids of the hopane series from the methanotrophic bacteria Methylocaldum spp.: phylogenetic implications and first evidence for an unsaturated aminobacteriohopanepolyol

The hopanoid content of the two methanotrophic bacteria Methylocaldum szegediense and Methylocaldum tepidum was investigated. 35-Aminobacteriohopane-30R,31R,32R,33S, 34S-pentol and its 3beta-methyl homologue were present in both strains. In M. tepidum, they were accompanied by 35-aminobacteriohopane-31R,32R,33S, 34S-tetrol and its 3beta-methyl homologue. The side chain structure was identical to those previously reported from two other obligate methanotrophs, Methylococcus capsulatus and Methylomonas methanica. The two Methylocaldum species shared with the Methylococcus species the presence of 3beta-methylhopanoid as well as of a hopanoid releasing adiantol upon H(5)IO(6)/NaBH(4) treatment. A rare feature was in addition found in M. szegediense. The saturated hopanoids were accompanied by an unsaturated aminobacteriohopanepentol with a Delta(11) double bond. Comparison of the hopanoid fingerprints was in accordance with the close phylogenetic relationship of Methylococcus and Methylocaldum. The major difference was the absence of sterols in Methylocaldum which were always detected in the Methylococcus species.     

中药王不留行化学成分的研究Ⅲ

从经产麦蓝菜（Ｖａｃｃａｒｉａ ｓｅｇｅｔａｌｉｓ（Ｎｅｃｋ）Ｇａｒｃｈｅ．）的种子王不留行中分离得到５个化合物,经波谱分析和化学方法分别鉴定为化学方法分别鉴定为：ＶａｃｃａｒｏｓｉｄｅＢ（１）、Ｃ（２）、Ｄ、（３）,６－Ｎ－ｍｅｔｈｙｌａｄｅｎｏｓｉｎｅ（４）和Ｎ,Ｎ－ｄｉｍｅｔｈｙｌ－Ｌ－ｔｒｙｐｔｏｐｈａｎ（５）。其中化合物４和５为首次从该植物中分得。     

Lanostane triterpenoids from the inedible mushroom Fomitopsis spraguei

Investigation of the methanolic extract of the inedible mushroom Fomitopsis spraguei (Polyporaceae) led to the isolation of five lanostane-type triterpenoids (1-5): three new compounds named fomitopsins A-C (2-4), and two known compounds, quercinic acid C (1) and 3alpha-carboxyacetyl-12beta-hydroxyquercinic acid (5). Their structures were determined by 2D NMR, MS, IR, UV spectra, and X-ray crystallographic analyses. An X-ray crystal structure analysis of quercinic acid C (1) established its stereochemistry as 3R,12R-dihydroxy-24R-methyl-23-oxo-25S-lanost-8-en-26-oic acid.     

Triterpenoid glycosides from Bacopa monnieri

Two triterpenoid glycosides have been isolated along with 10 known saponins from Bacopa monnieri. Structures of the compounds have been elucidated as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] jujubogenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] pseudojujubogenin (2) by high resolution NMR spectral data and chemical correlations. Further, the chemical compositions of bacosides A and B have been delineated.     

Triterpenoid saponins from the aerial parts of Trifolium argutum Sol. and their phytotoxic evaluation

Four triterpenoid saponins (1–4) were isolated from the aerial parts of Trifolium argutum Sol. (sharp-tooth clover) and their structures were elucidated by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and chemical methods. Two of them are new compounds, characterized as 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (1) and 3-O-[β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (2). The occurrence of 3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (melilotigenin) in its natural form is reported for the first time as a triterpenoid aglycone within Trifolium species. The phytotoxicity of compounds was evaluated on four STS at concentration 1 μM to 333 μM. Compound 1 was the most active, showing more than 60% inhibition on the root growth of L. sativa at the higher dose, with IC₅₀ (254.1 μM) lower than that of Logran^® (492.6 μM), a commercial herbicide used as positive control. The structure–activity relationships indicated that both aglycones and glycosidic parts may influence the phytotoxicity of saponins.