Diarylheptanoids from the Rhizomes of Curcuma kwangsiensis
Diarylheptanoids from the Rhizomes of Curcuma kwangsiensis
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DOI：
10.1021/np100392m
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发表时间：
2010-10-01
影响因子：
5.1
通讯作者：
Qiu, Feng
中科院分区：
文献类型：
--
作者：
Li, Jun;Zhao, Feng;Qiu, Feng
从广西姜黄根茎中分离得到12个新的二芳基庚烷类化合物和6个已知化合物。新化合物的结构经光谱和化学方法鉴定为（3S）-和（3R）-1，7-二（4-羟基苯基）-（6 E）-6-庚烯-3-醇（1a和1b）、（3S）-和（3R）-1-（3，4-二羟基苯基）-7-（4-羟基苯基）-（6 E）-6-庚烯-3-醇（2a和2b）、（3S）-和（3R）-1-（3，4-二羟基苯基）-7-（4-羟基苯基）庚-3-醇（3a和3b）、（3R）-1-（3，4-二羟基苯基）-7-苯基-（6 E）-6-庚烯-3-醇（4 b），（3S）-和（3R）-3-乙酰氧基-1-（3，4-二羟基苯基）-7-（4-羟基苯基）-（6 E）-6-庚烯（5a和5 b），（3S）-和（3R）-3-乙酰氧基-1-（3，4-二羟基苯基）-7-（4-羟基苯基）庚烷（6a和6 b），和（E）-1，7-双（4-羟基苯基）-6-庚烯-3-酮（7）。用改进的Mosher方法测定了它们的绝对构型。对映体混合物（1a和1b、2a和2b、3a和3b、4a和4 b、5a和5 b、6a和6 b）在手性柱上使用乙腈-水混合物作为洗脱剂实现分离。S对映体在甲醇中的比旋光度为负，R对映体为正。评价了化合物对脂多糖激活的巨噬细胞中一氧化氮产生的抑制作用。
Twelve new diarylheptanoids and six known compounds were isolated from rhizomes of Curcuma kwangsiensis. Structures of the new compounds were elucidated by spectroscopic and chemical methods as (3S)- and (3R)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (1a and 1b), (3S)- and (3R)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (2a and 2b), (3S)- and (3R)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-ol (3a and 3b), (3R)-1-(3,4-dihydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (4b), (3S)- and (3R)-3-acetoxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-(6E)-6-heptene (5a and 5b), (3S)- and (3R)-3-acetoxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptanes (6a and 6b), and (E)-1,7-bis(4-hydroxyphenyl)-6-hepten-3-one (7). The absolute configurations were determined using the modified Mosher's method. Separation of the enantiomeric mixtures (1a and 1b, 2a and 2b, 3a and 3b, 4a and 4b, 5a and 5b, 6a and 6b) was achieved on a chiral column using acetonitrile-water mixtures as eluents. The S enantiomers exhibited negative specific optical rotations in MeOH, and the R enantiomers were positive. Inhibitory effects of the compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated.