New triterpenoids from the stem bark of Hypodaphnis zenkeri
New triterpenoids from the stem bark of Hypodaphnis zenkeri
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DOI：
10.1080/14786419.2012.662647
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发表时间：
2013-01
影响因子：
2.2
通讯作者：
Itbert Joseph Momo;Thi-hanh Dufat;J. Wandji;S. Michel;David Dako Chiozem
中科院分区：
文献类型：
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作者：
Itbert Joseph Momo;Thi-hanh Dufat;J. Wandji;S. Michel;David Dako Chiozem
本文报道了从红瑞香（Hypodaphnis zenkeri）茎皮中分离得到的一个新的五环三萜类化合物和三个以蒲公英-14-烯为骨架，碳28位上带有羧酸基团的新衍生物，以及六个已知化合物。新产物经鉴定为2α，3 α-二羟基蒲公英酸-14-烯-28-酸（1）。通过半合成得到2α，3 α-二乙酰基蒲公英-14-烯-28-酸（2），2α，3 α-二氧羰基蒲公英-14-烯-28-酸（3）和2α，3 α-二丙酰基蒲公英-14-烯-28-酸（4）。已知化合物被鉴定为3β-羟基蒲公英-14-烯-28-酸或紫胶桐酸（5）（McPhail，A.T.，D.R.麦克菲尔瓦尼，M.C.，沃尔法医& A.W.，尼古拉斯，A.W.（1989年）。梅普酸与紫胶桐酸的鉴别。马普酸结构的修正：乙酰马普酸对溴苄酯的X-射线晶体结构。Journal Natural Products，52，212）、3α-羟基蒲公英-14-烯-28-酸或异糊粉醇酸（6）、3α-乙酰基蒲公英-14-烯-28-酸乙酸酯或糊粉醇酸乙酸酯（7）（Chaudhuri，S.K.，Fullas，F.，布朗，D. M.，瓦尼，M.C.，沃尔法医蔡，L.，. Kinghorn，A.D.（1995）.非洲黑伞中五环三萜类化合物的分离与结构鉴定。Journal of Natural Products，58，1-9），3-氧代-蒲公英-14-烯或蒲公英酮（8）β-谷甾醇（9）和豆甾醇（10）（Kamboj & Saluja，2011），以及脂肪酸。它们的结构是建立在光谱研究和化学转化的基础上的。
A new pentacyclic triterpenoid and three new derivatives based on the taraxer-14-ene skeleton with a C-28 attached a carboxylic acid group have been isolated from the stem bark of Hypodaphnis zenkeri, together with six known compounds. The new product was identified as 2α,3α-dihydroxytaraxer-14-en-28-oic acid (1). Its derivatives, 2α,3α-diacetyltaraxer-14-en-28-oic acid (2), 2α,3α-di-O-carbonyl-2α,3α-dihydroxytaraxer-14-en-28-oic acid (3) and 2α,3α-dipropionyltaraxer-14-en-28-oic acid (4) were obtained by semisynthesis. The known compounds were identified as 3β-hydroxytaraxer-14-en-28-oic acid or aleuritolic acid (5) (McPhail, A.T., McPhail, D.R., Wani, M.C., Wall, M.E. & A.W., Nicholas, A.W. (1989). Identity of maprounic acid with aleuritolic acid. Revision of the structure of maprounic acid: X-ray crystal structure of p-bromobenzyl acetylmaprounate. Journal Natural Products, 52, 212), 3α-hydroxytaraxer-14-en-28-oic acid or isoaleuritolic acid (6), 3α-acetyltaraxer-14-en-28-oic acid acetate or aleuritolic acid acetate (7) (Chaudhuri, S.K., Fullas, F., Brown, D.M., Wani, M.C., Wall, M.E., Cai, L., … Kinghorn, A.D. (1995). Isolation and structural elucidation of pentacyclic triterpenoids from Maprounea africana. Journal of Natural Products, 58, 1–9), 3-oxo-taraxer-14-ene or taraxerone (8) β-sitosterol (9) and stigmasterol (10) (Kamboj & Saluja, 2011), together with fatty acids. Their structures were established on the basis of spectroscopic studies and chemical transformations.