General

Scientific Names: Taxus yunnanensis

Common Names: Yun Nan Hong Dou Shan

BOTANICAL:

来 源: 云南红豆衫树皮中含有紫杉醇,为近年来发现的高效治癌药用树种。

植物特征: 云南红豆杉学名Taxus yunnanensis Cheng et LKFu属红豆杉科(Taxace)植物,常绿针叶树种。一年生小枝绿色,秋季变黄绿色或淡红褐色。叶螺旋状着生,基部扭转排成2列,条形微弯,长 2~3cm,宽3mm,边缘微反曲,先端渐尖,表面绿色,背面黄绿色,有二条淡黄绿色气孔带,雌雄异株,球花单生叶腋,雄球花淡色,雌球花胚珠单生于花柱 上,基部托呈园盘状的假种皮,种子椭园形着生于红色杯状肉质假种皮中,种脐卵园形,种子9~10月成熟。

 

 

 

Pharmacology

紫杉醇是现有的抗癌天然药物中疗效最好、最具潜力的药物之一,由于其独特的化学结构和作 用机制而倍受世人关注[1],由此引发了人们对红豆杉属(Taxus)植物的研究热潮。到目前为止化学家们已从红豆杉属植物中分离出紫杉烷类二萜化合物 300多个。云南红豆杉是我国特有树种,自1990年来我国学者对云南红豆杉化学成分作了较多研究,但是这些研究大多集中在其枝叶部分,而对其根部很少有 人研究,因此有必要对其根部作进一步研究,以寻找新的活性成分和新一代紫杉醇的药物前体。我们从云南红豆杉中分离并鉴定了5个紫杉烷类化合物,其中1为新 的紫杉烷类化合物。 (source)

化学成分: 云南红豆杉Taxus yunnanensis的树皮中分得5个紫杉烷类化合物,通过1H-NMR、13C-NMR、MS、IR、DORdecoupling、13C- 1Hcosy等方法鉴定其结构为:2α,7β,9α,10β,13α,20-hexaacetoxy-4α,5α-dihydroxy-taxa-11 (12)-ene(1)、Taxa-4(20),11-diene-2α,5α,10β-triacetoxy-14β(α-Methyl) butyrate(2)、Taxol(3)、Baccatin Ⅳ(4)、7-Xyloxy-10-Deacetoxy-taxol(5)。其中1为新的紫杉烷类化合物。

  1. Chen WM, et al., [Studies on the chemical constituents of Taxus yunnanensis]. Yao Xue Xue Bao. 1991; 26(10):747-54. Chinese.

 

 

 

Efficacy

Three new C-14 oxygenated taxane-type diterpenes, hongdoushans A-C (1-3), were isolated from the wood of Taxus yunnanensis together with four known diterpenes and two lignans. The absolute stereochemistry of the 2-methylbutyryloxy group attached at C-14 of the taxane skeleton was determined to be S by GC analysis of the methyl ester of 2-methylbutyric acid obtained after alkaline hydrolysis of 1 and 4 followed by treatment with CH(2)N(2). The complete stereostructure of the known compound 2alpha,5alpha,10beta-triacetoxy-14beta-[(S)-2-methylbutyryloxy]-4(20),11-taxadiene (4) was established for the first time. The isolates obtained were evaluated for their antiproliferative activity toward murine colon 26-L5 carcinoma and human HT-1080 fibrosarcoma cell lines. (source)

Twelve taxane diterpenes (1-12), which were isolated previously from the EtOH extract of the aerial parts of Taxus yunnanensis or Taxus chinensis, were evaluated for cytotoxicity against the multidrug resistant cancer cells KB-VIN and KB-7d. Compounds and showed significant cytotoxicity in these cell lines. Compounds and also demonstrated significant activity against KB-7d. The biflavonoid isolated from T. yunnanensis was only marginally cytotoxic against the A549 (lung) cell line, but a simple methoxylated analogue (14) was inactive. (source)

The ethanolic extract of the bark of Taxus yunnanensis Cheng et L. K. Fu. showed significant antineoplastic effect on the transplantable tumors in mice. The life survival of P388 leukemic bearing mice was increased (84%) and the growth of B16 melanoma in mice was inhibited (53%). From this extract eight taxane diterpenoids and taxane alkaloids have been isolated. Seven of them have been identified as taxinine E(1), taxinine J(2), 1-acetoxy-5-deacetyl baccatin I(4), baccatin III(5), taxol (6), cephalomannine (7), 7-xylosyl-10-deacetyl taxol (8) from their physical and spectroscopic properties. A new taxane diterpenoid, named yunnanxane (3) was elucidated as taxa-4 (20), 11-diene-2 alpha, 5 alpha, 10 beta, 14 beta-tetraoln2 alpha,5 alpha,10 beta-triacetaten-14 beta-alpha-methyl-beta- hydroxylbutyratebyhighfield 1H NMR, 13C NMR, 1H-1HCOSY, 13C-1HCOSY, 13C-1HCOLOC and X-ray analysis. It showed the inhibitory effect on A2780 DDP, KB and HCT-8 cell line in vitro. (source)

紫杉醇(paclitaxel)是一种从红豆杉植物中获得的具有独特疗效的抗癌天然植物产物,现已被多个国家批准应用于临床治疗卵巢癌和乳腺癌等。

IN VITRO:

  1. Banskota AH, et al., Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis. J Nat Prod. 2002 Nov; 65(11):1700-2.
  2. Shinozaki Y, et al., Multidrug resistant cancer cells susceptibility to cytotoxic taxane diterpenes from Taxus yunnanensis and Taxus chinensis. Bioorg Med Chem Lett. 2002 Oct 7; 12(19):2785-8.




IN VIVO:

  1. Chen WM, et al., [Studies on the chemical constituents of Taxus yunnanensis]. Yao Xue Xue Bao. 1991; 26(10):747-54. Chinese.

 

 

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