1-O-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] 16-O-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate | 42553-65-1

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-O-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] 16-O-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• CAS: 42553-65-1
• 化学式: C₄₄H₆₄O₂₄
• 分子量: 977.0
• InChiKey: SEBIKDIMAPSUBY-AWBRESQISA-N

物化性质

• 熔点：
  186° (effervescence)
• 沸点：
  1169.0±65.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微加热）、甲醇（非常轻微、超声处理）
• LogP：
  -4.742 (est)
• 颜色/状态：
  Solid /Di-gentiobiose ester/
• 稳定性/保质期：
  The kinetics of crocin and picrocrocin in whole and ground samples of saffron stored at different temperatures and relative humidities were studied. First-order kinetics were observed for crocin and second-order for picrocrocin. There was no deterioration of the samples stored at -17 °C or at 0 °C, the ideal storage conditions. A reduction in the relative humidity had a greater effect on stability than a decrease in temperature. Conditions that favor stability for picrocrocin also favor the stability of its aroma.

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  391
• 氢给体数：
  14
• 氢受体数：
  24

ADMET

代谢

这项研究调查了在大鼠口服给药后藏红素的药代动力学特性。单次口服给药后，血浆中未检测到藏红素，而其代谢物藏花酸在血浆中浓度较低。同时，在24小时内，藏红素主要存在于粪便和肠内容物中。

This study investigated the pharmacokinetic properties of crocin following oral administration in rats. After a single oral dose, crocin was undetected while crocetin, a metabolite of crocin, was found in plasma at low concentrations. Simultaneously, crocin was largely present in feces and intestinal contents within 24 hr.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

鉴定和使用：西红花素是藏红花的一种类胡萝卜素成分。它被用作实验室试剂、抗氧化剂以及在蛇咬伤和食品染料中的实验性解毒剂。人类接触和毒性：志愿者接受20毫克西红花素片剂或安慰剂，为期一个月。在研究期间记录了健康的一般指标，如治疗前后血液学、生化、激素和尿液参数。试验期间没有报告重大不良事件。西红花素片剂没有改变上述参数，除了在健康志愿者服用一个月后降低了淀粉酶、混合白细胞和PTT。藏红花提取物及其主要成分西红花素显著抑制了人结直肠癌细胞的生长，而对正常细胞没有影响。动物研究：评估了西红花素在小鼠中的急性毒性和亚急性毒性：在药理剂量下，西红花素没有对任何器官造成明显损害。在高剂量（3克/千克，IP或口服）24小时和48小时后，小鼠中没有观察到西红花素引起的死亡。发育研究表明，在怀孕小鼠中给予西红花素或藏花醛可诱导胚胎畸形。最常见的观察到的异常是轻微的骨骼畸形。在雄性大鼠的行为研究中，发现藏红花水提取物及其成分西红花素有催欲作用。西红花素在细菌致突变性测试（包括 Ames 测试）和DNA损伤中给出了阴性结果；它没有在培养的哺乳动物细胞中产生染色体损伤。

IDENTIFICATION AND USE: Crocin is a carotenoid constituent of saffron. It is used as a laboratory reagent, antioxidant and experimental antidote in snake bites and food dye. HUMAN EXPOSURE AND TOXICITY: Volunteers received 20 mg crocin tablets or placebo for one month. General measures of health were recorded during the study such as hematological, biochemical, hormonal and urinary parameters in pre and post-treatment periods. No major adverse events were reported during the trial. Crocin tablets did not change the above parameters except that it decreased amylase, mixed white blood cells and PTT in healthy volunteers after one month. Crocus sativus extract and its major constituent, crocin, significantly inhibited the growth of human colorectal cancer cells while not affecting normal cells. ANIMAL STUDIES: The acute and sub-acute toxicity of crocin was evaluated in mice: at pharmacological doses, crocin did not exhibit marked damages to any organs. With high doses (3 g/kg, IP or orally) after 24 and 48 hr no mortality was seen by crocin in mice. Developmental study suggests that crocin or safranal can induce embryonic malformations when administered in pregnant mice. Minor skeletal malformations were the most commonly observed abnormality. Behavioral studies in male rats revealed an aphrodisiac activity of saffron aqueous extract and its constituent crocin. Crocin gave negative results in bacterial test for mutagenicity (including the Ames test) and DNA damage; it did not produce chromosome damage in mammalian cells in culture.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

蝰蛇咬伤会导致咬伤部位和靶器官发生炎症。中性粒细胞和其他多形核白细胞执行炎症解决机制，完成任务后会经历凋亡。然而，特定的靶毒素在咬伤部位和循环中诱导中性粒细胞在发挥作用前发生凋亡，从而减少它们的数量。循环中的活化中性粒细胞是炎症细胞因子的主要来源，以及活性氧种（ROS）/其他有毒中间体的泄漏，导致咬伤/靶部位的炎症反应加剧。因此，中和由毒素诱导的中性粒细胞凋亡不仅可以减少炎症，还可以增加功能中性粒细胞的数量。因此，本研究探讨了蝰蛇毒液对分离的人中性粒细胞的干扰以及藏红花素（藏红花）这种强大的抗氧化类胡萝卜素对其的中和作用。用毒液处理的人中性粒细胞导致ROS生成、细胞内Ca2+动员、线粒体膜去极化、细胞色素c转位、胱天蛋白酶激活、磷脂酰丝氨酸外化和DNA损伤的改变。另一方面，在藏红花预处理组中显著证明了对抗氧化应激和凋亡的保护作用。总之，蝰蛇毒液诱导中性粒细胞凋亡，导致炎症加剧和组织损伤。本研究要求除了抗毒液治疗外，还需要辅助治疗来治疗咬伤的次要/被忽视的并发症。

Viper envenomation results in inflammation at the bitten site as well as target organs. Neutrophils and other polymorphonuclear leukocytes execute inflammation resolving mechanism and will undergo apoptosis after completing the task. However, the target specific toxins induce neutrophil apoptosis at the bitten site and in circulation prior to their function, thus reducing their number. Circulating activated neutrophils are major source of inflammatory cytokines and leakage of reactive oxygen species (ROS)/other toxic intermediates resulting in aggravation of inflammatory response at the bitten/target site. Therefore, neutralization of venom induced neutrophil apoptosis reduces inflammation besides increasing the functional neutrophil population. Therefore, the present study investigates the venom induced perturbances in isolated human neutrophils and its neutralization by crocin (Crocus sativus) a potent antioxidant carotenoid. Human neutrophils on treatment with venom resulted in altered ROS generation, intracellular Ca2+ mobilization, mitochondrial membrane depolarization, cyt-c translocation, caspase activation, phosphatidylserine externalization and DNA damage. On the other hand significant protection against oxidative stress and apoptosis were evidenced in crocin pre-treated groups. In conclusion the viper venom induces neutrophil apoptosis and results in aggravation of inflammation and tissue damage. The present study demands the necessity of an auxiliary therapy in addition to antivenin therapy to treat secondary/overlooked complications of envenomation.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

这项研究调查了西红花素对环磷酰胺（CP）诱导的大鼠肝毒性的保护效果。实验大鼠在单次腹腔注射CP（150 mg/kg）后，连续6天口服给予西红花素（10 mg/kg）。通过评估氧化应激酶、炎症细胞因子和组织学切片，研究了西红花素对器官毒性的改善作用。单次腹腔注射CP显著提高了内源性活性氧物种以及肝脏和血清中脂质和蛋白质的氧化，这是肝脏和血清氧化损伤的标志。因此，主要的防御性还原型谷胱甘肽、总巯基和抗氧化酶（如超氧化物歧化酶、过氧化氢酶、谷胱甘肽-S-转移酶和谷胱甘肽过氧化物酶）显著降低。此外，肝脏和血清中的天门冬氨酸转移酶和丙氨酸转移酶以及酸性磷酸酶和碱性磷酸酶也显著增加。口服西红花素显著地将所有上述改变的标志物恢复到几乎正常状态。西红花素的保护效果得到了组织学评估以及与对照药物相比恢复CP诱导的炎症细胞因子和酶水平的进一步支持。所得结果提示西红花素对CP诱导的氧化损伤/炎症和器官毒性具有保护作用。

This study investigated the protective efficacy of crocin against hepatotoxicity induced by cyclophosphamide (CP) in Wistar rats. The experimental rats were treated with crocin orally at a dose of 10 mg/kg for 6 consecutive days after the administration of a single intraperitoneal dose of CP (150 mg/kg). The ameliorative effect of crocin on organ toxicity was studied by evaluating oxidative stress enzymes, inflammatory cytokines and histological sections. A single intraperitoneal CP injection significantly elevated endogenous reactive oxygen species and oxidation of lipids and proteins, which are the hallmarks of oxidative damage in liver and serum. In consequence, the primary defensive reduced glutathione, total thiol and antioxidant enzymes such as superoxide dismutase, catalase, glutathione-S-transferase and glutathione peroxidase, were significantly reduced. In addition, liver and serum aspartate aminotransferase and alanine aminotransferase along with acid and alkaline phosphatase were considerably increased. Oral administration of crocin significantly rejuvenated all the above altered markers to almost normal state. The protective efficacy of crocin was further supported by the histological assessment and restoration of CP-induced inflammatory cytokines and enzyme levels compared with the control drug. The results obtained suggest the protective nature of crocin against CP-induced oxidative damage/inflammation and organ toxicity.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

丙烯酰胺（ACR）在人类和动物模型中是一种强效的神经毒素。在本研究中，评估了藏红花（Crocus sativus L.）的主要成分藏红花素对ACR诱导的细胞毒性的影响，使用PC12细胞作为适宜的体外模型。将PC12细胞暴露于ACR后，细胞存活率降低，DNA断裂细胞和磷脂酰丝氨酸暴露增加，以及Bax/Bcl-2比例升高。结果显示，ACR增加了细胞内活性氧种（ROS）的产生，并且ROS在ACR的细胞毒性中发挥了重要作用。在ACR处理前，用10-50微摩尔浓度的藏红花素预处理细胞，可以剂量依赖性地显著减轻ACR的细胞毒性。藏红花素抑制了Bcl-2的下调和Bax的上调，并减少了处理细胞的凋亡。此外，藏红花素还抑制了暴露于ACR的细胞中ROS的产生。总之，我们的结果表明，用藏红花素预处理可以保护细胞免受ACR诱导的凋亡，部分是通过抑制细胞内ROS的产生。

Acrylamide (ACR) is a potent neurotoxic in human and animal models. In this study, the effect of crocin, main constituent of Crocus sativus L. (Saffron) on ACR-induced cytotoxicity was evaluated using PC12 cells as a suitable in vitro model. The exposure of PC12 cells to ACR reduced cell viability, increased DNA fragmented cells and phosphatidylserine exposure, and elevated Bax/Bcl-2 ratio. Results showed that ACR increased intracellular reactive oxygen species (ROS) in cells and ROS played an important role in ACR cytotoxicity. The pretreatment of cells with 10-50 uM crocin before ACR treatment significantly attenuated ACR cytotoxicity in a dose-dependent manner. Crocin inhibited the downregulation of Bcl-2 and the upregulation of Bax and decreased apoptosis in treated cells. Also, crocin inhibited ROS generation in cells exposed to ACR. In conclusion, our results indicated that pretreatment with crocin protected cells from ACR-induced apoptosis partly by inhibition of intracellular ROS production.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

藏红花（Crocus sativus L.）已被证明与阿片系统相互作用。因此，评估了藏红花雄蕊的水提物和醇提物及其成分对小鼠吗啡戒断综合症的影响。通过连续3天皮下注射吗啡来诱导依赖性。在第4天，吗啡在腹腔注射提取物、藏红花素、藏红醛、可乐定（0.3 mg/kg）或生理盐水前0.5小时注射。在最后一次吗啡注射后2小时注射纳洛酮（5 mg/kg 腹腔注射），并在30分钟内记录跳跃的次数作为戒断综合症的强度。可乐定、藏红花的水提物和醇提物减少了跳跃活动。藏红醛在吗啡注射前30分钟和注射后1小时和2小时皮下注射，它增强了一些戒断综合症的迹象。水提物在所有剂量（80, 160, 320 mg/kg）下都减少了活动，而醇提物在800 mg/kg剂量下减少了开阔场测试中的活动。但是藏红花素和400 mg/kg醇提物在这个测试中对活动没有影响。可以得出结论，提取物和藏红花素可能与阿片系统相互作用，以减少戒断综合症。

Crocus sativus L. has been shown to interact with the opioid system. Thus, the effects of aqueous and ethanolic extracts of stigma and its constituents were evaluated on morphine-withdrawal syndrome in mice. Dependence was induced using subcutaneous (s.c.) injections of morphine for 3 days. On day 4, morphine was injected 0.5 hr prior the intraperitoneal (i.p.) injections of the extracts, crocin, safranal, clonidine (0.3 mg/kg) or normal saline. Naloxone was injected (5 mg/kg i.p.) 2 hr after the final dose of morphine and the number of episodes of jumping during 30 min was considered as the intensity of the withdrawal syndrome. Clonidine, the aqueous and ethanolic extracts of saffron reduced the jumping activity. Safranal was injected (s.c.) 30 min prior and 1 and 2 hr after the injection of morphine. It potentiated some signs of withdrawal syndrome. The aqueous extract decreased the movement in all of the doses (80, 160, 320 mg/kg) and the ethanolic extract decreased it in the dose of 800 mg/kg in open field test. But crocin and the dose of 400 mg/kg ethanolic extract showed no effect on activity in this test. It is concluded that the extracts and crocin may have interaction with the opioid system to reduce withdrawal syndrome.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

这项研究调查了在大鼠口服给药后藏红素的药代动力学特性。单次口服给药后，血浆中未检测到藏红素，但其代谢物藏花酸在血浆中低浓度被发现。同时，在24小时内，藏红素主要存在于粪便和肠内容物中。连续口服给药6天后，血浆中仍未检测到藏红素，而血浆中藏花酸的浓度与单次口服给药后的相应数据相当。此外，使用肠内循环灌注法对藏红素的吸收特性进行了原位评估。在循环过程中，血浆中未检测到藏红素，但检测到低浓度的藏花酸。藏红素在灌注液中的浓度通过不同的肠段降低，且在整个结肠中药物的丢失量更大。这些结果表明：（1）口服给药的藏红素在单次或多次给药后均不被吸收，（2）藏红素在口服给药后主要通过肠道排出，（3）多次口服藏红素后，血浆中藏花酸的浓度没有累积的趋势，（4）肠道是藏红素水解的重要场所。

This study investigated the pharmacokinetic properties of crocin following oral administration in rats. After a single oral dose, crocin was undetected while crocetin, a metabolite of crocin, was found in plasma at low concentrations. Simultaneously, crocin was largely present in feces and intestinal contents within 24 hr. After repeated oral doses for 6 days, crocin remained undetected in plasma and plasma crocetin concentrations were comparable to the corresponding data obtained after the single oral dose. Furthermore, the absorption characteristics of crocin were evaluated in situ using an intestinal recirculation perfusion method. During recirculation, crocin was undetected and low concentrations of crocetin were detected in plasma. The concentrations of crocin in the perfusate were reduced through different intestinal segments, and the quantities of drug lost were greater throughout the colon. These results indicate that (1) orally administered crocin is not absorbed either after a single dose or repeated doses, (2) crocin is excreted largely through the intestinal tract following oral administration, (3) plasma crocetin concentrations do not tend to accumulate with repeated oral doses of crocin, and (4) the intestinal tract serves as an important site for crocin hydrolysis.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  32129000
• RTECS号：
  HL7380000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

这段文字详细介绍了栀子黄色素和藏红花色素的生产方法及其用途。以下是对主要信息的总结：

栀子黄色素 生产方法：

1. 水提取法：将黄栀子果烘干、去皮、粉碎，加入10倍的软水浸泡3小时；过滤后滤渣用等量清水搅拌洗涤2次，并滤干。合并滤液静置4小时，先过滤上层清液再过滤沉淀得清液，控制含干物在3.0%~5.0%，常压浓缩至含干物约40%，然后减压(87-96kPa)进一步浓缩，加入酒精使果胶等杂质沉淀。静置2-3小时后过滤得提纯液，蒸馏回收乙醇后喷雾干燥得到粉末产品。

2. 乙醇提取法：将干燥的栀子果实去皮、粉碎(过0.21mm)，用一定比例的乙醇浸泡48小时；过滤成透明液体。经浓缩和灭菌处理制成水溶液制品，加入丙撑二醇或直接喷雾干燥成为粉末制品。

用途：

• 作食品着色剂（最大使用量为0.3g/kg）。
• 主要用于果汁饮料类、配制酒、糖果等食品中。
• 具有良好的耐光性、耐热性和抗金属离子能力，适用于各种食品。

藏红花色素 生产方法：

1. 传统摘取干燥法：从藏红花(Crocus sativus L)未盛开的雌蕊（柱头和花柱）中摘取。然后使用约30℃温度进行烘干制成粉末，需大量花朵才能得到1kg干粉。

2. 组织培养法制备：近年来日本已采用组织培养法来制备藏红花色素。

用途：

• 主要用于食品的着色，如糕点、果冻、糖果等。
• 具有良好的耐光性和耐热性，特别适用于各种需要长时间保存的食物。

总结

两种色素在生产方法和应用范围上有所不同。栀子黄色素因其稳定性较好，在面类、糕点等食品中有广泛的应用；而藏红花色素则主要应用于高端食品或需特别着色的产品中。两者都因其优良的性能而在现代食品工业中占有重要地位。

希望这些信息对你有帮助！如果你有任何具体问题或者需要进一步解释，请随时告知我。