Tanaka R, Matsunaga S
Osaka University of Pharmaceutical Sciences, Japan.
Yakugaku Zasshi. 1999 May;119(5):319-39. doi: 10.1248/yakushi1947.119.5_319.
During the course of a search for biologically active constituents from unexamined plant sources, several biogenetically interesting new di- and tri-terpenes and steroids were isolated from several weeds and shrubs of Euphorbiaceae and the bark, leaves and cones of several Pinaceae trees which had been treated as wastes in the forestry industry. Euphorbia supina contained 3,4-seco-5 alpha- and 5 beta-adian-4(23)-ene-3,5-diols and related oxides, oxygenated fern-8-en-3 beta-ols named supinenolones A-E and unusually migrated oxyfernanes having (9S)- and (9R)-7(8-->9)abeo-9-D:C-friedo-B':A'-neogammacerane skeletons named spirosupinane and neospirosupinane, while E. chamaesyce contained 3,4-seco-oleana-4(23), 18-dien-3-oic acid, 3,4-seco-8 beta H-ferna-4(23),9(11)-dien-3-oic acid and two oxygenated obtusifoliols. The bark of Phyllanthus flexuosus (Euphorbiaceae) contained 11 beta-hydroxy-D:A-friedo-olean-1-en-3-one, lup-20(29)-ene-3 beta, 15 alpha-diol, olean-12-ene-3 beta,15 alpha-diol and olean-12-ene-3 beta,15 alpha,24-triol together with trichadenic acid B for which we revised the structure to 3 beta-hydroxy-D:A-friedo-oleanan-27-oic acid. Two 26-nor-D:A-friedo-olean-14-enes were isolated from P. watsonii. Regarding Pinaceae trees, an unusually migrated abieslactone [(3R, 7S, 9R, 23R)-7-hydroxy-3-methoxy-8-oxo-7(8-->9)abeo-lanost-24-eno-26,23-lactone], named spiroveitchionolide, was isolated from the bark of Abies species, besides nine abieslactone analogues. Two pairs of unusually migrated serratanes, piceanonols A and B and jezananals A and B having novel skeletal systems of 14(13-->12) abeo- and 16(15-->14) abeo-serratanes named piceanane and jezanane, respectively, were also isolated from the stem bark of Picea species, besides three 14 beta,15 beta-epoxyserratanes and two 13 alpha,14 alpha-epoxyserratanes. The leaves of Larix kaempferi contained two deformed abietanes named karamatsuic acid (9,10-seco-9,10 alpha-epoxyabieta-8,11,13-trien-18-oic acid) and larikaempferic acid [9 alpha,13 alpha-epoxy-8-oxo-9(8-->7)abeo-7 beta-abietan-18-oic acid], as well as the cones to contain 8 alpha,12 alpha-epidioxy-15-hydroxyabiet-13-en-18-oic acid, three diepoxy-abietan-18-oic acids and two new dehydroabietic acid analogues. Several of the above compounds exhibited inhibitory effects against tumor-promoting and DNA topoisomerase II activities.
在从未经研究的植物来源中寻找生物活性成分的过程中，从大戟科的几种杂草和灌木以及林业行业中被视为废弃物的几种松科树木的树皮、树叶和球果中分离出了几种具有生物合成意义的新型二萜和三萜以及甾体化合物。泽漆含有3,4-断-5α-和5β-乌苏-4(23)-烯-3,5-二醇及相关氧化物、名为泽漆醇酮A - E的氧化蕨-8-烯-3β-醇以及具有(9S)-和(9R)-7(8→9)失碳-9-D:C-原- B':A'-新伽马蜡烷骨架的异常迁移氧化蕨烷，即螺旋泽漆烷和新螺旋泽漆烷，而地锦含有3,4-断-齐墩果-4(23),18-二烯-3-酸、3,4-断-8βH-蕨-4(23),9(11)-二烯-3-酸以及两种氧化钝叶醇。皱叶叶下珠（大戟科）的树皮含有11β-羟基-D:A-原-齐墩果-1-烯-3-酮、羽扇-20(29)-烯-3β,15α-二醇、齐墩果-12-烯-3β,15α-二醇和齐墩果-12-烯-3β,15α,24-三醇以及毛盘孢酸B，我们将其结构修订为3β-羟基-D:A-原-齐墩果烷-27-酸。从沃森叶下珠中分离出了两种26-降-D:A-原-齐墩果-14-烯。关于松科树木，从冷杉属植物的树皮中分离出了一种异常迁移的冷杉内酯[(3R,
