Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en...Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en-15-one (1) and 3 beta,11 beta-diacetoxy-2 beta,6 alpha-dihydroxy-ent-kaur-16-en-15-one (2) on the basis of spectroscopic analysis.展开更多
Terpenoids comprise the largest family of natural products and include various structurally different genus which play important roles in living organisms. Biosynthetically, diterpenoids are derived from （E,E,E）-ger...Terpenoids comprise the largest family of natural products and include various structurally different genus which play important roles in living organisms. Biosynthetically, diterpenoids are derived from （E,E,E）-geranylgeranyl diphosphate （GGPP）. From GGPP, diterpene cyclase catalyzes a sequence of carbocation- mediated cyclizations, rearrangements, and further oxidations, leading to a class of structurally unique ent-kaurenes, such as cafestol, gibberellin A3 and oridonin. According to the biosynthesis pathway of ent-kaurene, we designed a chiral acetal-enabled and SnCln-promoted biomimetic polyene cationic cyclization. With a following Birch reduc- tiort/alkylation cascade, a core skeleton of representative ent-kaurenes diterpenoids was completed.展开更多
从河南新县产道孚香茶菜[Rabdosia dowoensis(Hand—Mazz)Hara]叶、茎的醇和醚提取物中分离得到3个二萜化合物,根据各种光谱数据解析,推断其中一个为新化合物,化学结构为对映—11β-羟基-3β,6α,7β-三乙酰氧基—16—贝壳杉烯—15—酮...从河南新县产道孚香茶菜[Rabdosia dowoensis(Hand—Mazz)Hara]叶、茎的醇和醚提取物中分离得到3个二萜化合物,根据各种光谱数据解析,推断其中一个为新化合物,化学结构为对映—11β-羟基-3β,6α,7β-三乙酰氧基—16—贝壳杉烯—15—酮,定名为道孚香茶菜素(dowoensin)1,另两个2,3为已知化合物.分别与信阳冬凌草甲素和乙素(Xindongnin A and B)为同一化合物。展开更多
On the basis of the investigation on natural product antitumor agents,a new diterpenoid named macrocalyxin J was isolated from the leaves of Rabdosia macrocalyx（Dunn） Hara by silica gel column chromatography.Based o...On the basis of the investigation on natural product antitumor agents,a new diterpenoid named macrocalyxin J was isolated from the leaves of Rabdosia macrocalyx（Dunn） Hara by silica gel column chromatography.Based on IR,MS,1H NMR,13C NMR and 2D NMR spectroscopies,the structure of macrocalyxin J was determined as（1α,6β,11β,14α）-1,7∶6,20-diepoxy-6,11-dihydroxy-6,7-seco-ent-kaur-16-ene-7,15-dione-14-acetate.The antitumor activity of the compound was assayed by MTT method.Macrocalyxin J was shown to have a potency in vitro against the cultures of Hela cells.展开更多
文摘Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en-15-one (1) and 3 beta,11 beta-diacetoxy-2 beta,6 alpha-dihydroxy-ent-kaur-16-en-15-one (2) on the basis of spectroscopic analysis.
文摘Terpenoids comprise the largest family of natural products and include various structurally different genus which play important roles in living organisms. Biosynthetically, diterpenoids are derived from （E,E,E）-geranylgeranyl diphosphate （GGPP）. From GGPP, diterpene cyclase catalyzes a sequence of carbocation- mediated cyclizations, rearrangements, and further oxidations, leading to a class of structurally unique ent-kaurenes, such as cafestol, gibberellin A3 and oridonin. According to the biosynthesis pathway of ent-kaurene, we designed a chiral acetal-enabled and SnCln-promoted biomimetic polyene cationic cyclization. With a following Birch reduc- tiort/alkylation cascade, a core skeleton of representative ent-kaurenes diterpenoids was completed.
文摘为了快速、简便地评价冬凌草(Isodon rubescens(Hemsley)H.Hara)活性成分的抗肿瘤活性,以冬凌草活性成分冬凌草甲素和冬凌草乙素及其乙酰化产物与对硝基苯甲酰乙酸乙酯(ENBA)进行迈克尔加成反应,以反应动力学得出迈克尔加成反应的反应活性,首次以反应活性预测了对冬凌草甲素(1)、冬凌草乙素(2)、1,14-二乙酰基冬凌草甲素(1a)和1,6-二乙酰基冬凌草乙素(2a)4个对映-贝壳杉烯的抗肿瘤活性。结果表明:4种活性成分的迈克尔加成反应均符合二级动力学方程,反应活性1>1a>2>2a,根据阿伦尼乌斯公式,测得冬凌草甲素活化能(Ea)为(38.7±5.8)kJ/mol,冬凌草乙素Ea为(46.8±7.1)kJ/mol。采用~1H NMR和^(13) C NMR等波谱技术鉴定冬凌草甲素与ENBA经迈克尔加成反应得到的新化合物为1α,6β,7β,14β-四羟基-7α,20-环氧-17-(2-(3-(4-硝基苯基))-3-氧-丙酸乙酯)-对映贝壳杉烷-15-酮,命名为nitrobenoridonin(1b)。4个对映-贝壳杉烯具有较强的体外抗肿瘤活性,经测定它们的抗肿瘤活性大小依次为1>1a>2>2a,与其迈克尔加成反应活性排序一致,表明迈克尔加成反应活性与抗肿瘤活性之间存在较好的相关性,可以通过测定迈克尔加成反应活性预测对映-贝壳杉烯的抗肿瘤活性。
文摘从河南新县产道孚香茶菜[Rabdosia dowoensis(Hand—Mazz)Hara]叶、茎的醇和醚提取物中分离得到3个二萜化合物,根据各种光谱数据解析,推断其中一个为新化合物,化学结构为对映—11β-羟基-3β,6α,7β-三乙酰氧基—16—贝壳杉烯—15—酮,定名为道孚香茶菜素(dowoensin)1,另两个2,3为已知化合物.分别与信阳冬凌草甲素和乙素(Xindongnin A and B)为同一化合物。
文摘On the basis of the investigation on natural product antitumor agents,a new diterpenoid named macrocalyxin J was isolated from the leaves of Rabdosia macrocalyx（Dunn） Hara by silica gel column chromatography.Based on IR,MS,1H NMR,13C NMR and 2D NMR spectroscopies,the structure of macrocalyxin J was determined as（1α,6β,11β,14α）-1,7∶6,20-diepoxy-6,11-dihydroxy-6,7-seco-ent-kaur-16-ene-7,15-dione-14-acetate.The antitumor activity of the compound was assayed by MTT method.Macrocalyxin J was shown to have a potency in vitro against the cultures of Hela cells.
