Agarotetrol
(Synonyms: 沉香四醇) 目录号 : GC30663
A chromone derivative
Cas No.:69809-22-9
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Agarotetrol is a chromone derivative originally isolated from agarwood, a component of incense and traditional medicines.1,2
1.Yoshii, E., Koizumi, T., Oribe, T., et al.The structure of agarotetrol, a novel highly oxygenated chromone from agarwood (jinko)Tetrahedron Lett.19(41)3921-3924(1978) 2.Sugiyama, T., Narukawa, Y., Shibata, S., et al.Three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone derivatives enantiomeric to agarotetrol from agarwoodJ. Nat. Med.72(3)667-674(2018)
| Cas No. | 69809-22-9 | SDF | |
| 别名 | 沉香四醇 | ||
| Canonical SMILES | O=C1C=C(CCC2=CC=CC=C2)OC3=C1[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3O | ||
| 分子式 | C17H18O6 | 分子量 | 318.32 |
| 溶解度 | DMSO : ≥ 250 mg/mL (785.37 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.1415 mL | 15.7075 mL | 31.4149 mL |
| 5 mM | 0.6283 mL | 3.1415 mL | 6.283 mL |
| 10 mM | 0.3141 mL | 1.5707 mL | 3.1415 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Agarotetrol as an index for evaluating agarwood in crude drug products
Agarotetrol in agarwood has been detected in water extracts or decoctions from medical use agarwood but the detection of agarotetrol has not been reported from other crude drugs. Agarwood generates the sedative benzylacetone upon heating. In this study, crude drug products containing many kinds of crude drugs in addition to agarwood were analyzed. Agarotetrol was detected and quantified, demonstrating that agarotetrol is useful for the quality evaluation of agarwood in complex prescriptions. High-performance liquid chromatography conditions to clearly separate agarotetrol from crude drug products were established and agarotetrol from Kampo decoctions was detected and quantified. Agarotetrol was also detected even from small crude drug product samples. These results suggest that agarotetrol is a useful component for the quality evaluation of agarwood in crude drug products.
Agarotetrol in agarwood: its use in evaluation of agarwood quality
Agarwood, which is used as medicine and incense, contains sesquiterpenes and chromones. Agarotetrol is a chromone derivative found in high concentrations in the water-extract fraction of agarwood and thus may be present in pharmaceutical products made from decoctions of agarwood. Agarotetrol has been reported to be present at the early stages of cell death in calli. We therefore examined the presence of agarotetrol in medical- and incense-grade agarwood, in agarwood-source plants lacking resin deposits, and in artificially made agarwood. Agarotetrol appeared as a large peak in the HPLC chromatograms of all samples of medical-grade and artificially made agarwood, and in most incense-grade agarwood samples. In contrast, agarwood samples lacking resin deposits did not contain agarotetrol. These results show that agarotetrol is characteristic of resin formation. Agarotetrol was also detected in decoctions of agarwood. A newly developed TLC method for the detection of agarotetrol in agarwood is described.
Agarotetrol: a source compound for low molecular weight aromatic compounds from agarwood heating
Agarwood is known to generate a distinct fragrance upon heating and is used as both a medicine and a fragrant wood. Low molecular weight aromatic compounds (LACs) such as benzylacetone are emitted from agarwood on heating and have a sedative effect on mice. These are detected exclusively in the headspace vapor of heated agarwood and are absent in the wood itself; hence, some compounds in agarwood are thought to be converted to LACs by the process of heating. In this study, different fractions obtained from agarwood were analyzed to reveal the source compounds of LACs. Some LACs detected in the resinous agarwood were absent from the non-resinous parts and confirmed as characteristic of the resinous parts. The essential oil and hydrosol of agarwood obtained by distillation were analyzed by gas chromatography-mass spectrometry (GC-MS). Sesquiterpenes were detected in the essential oil, and sesquiterpenes and a variety of LACs were detected in the hydrosol. A hot water extract of agarwood remaining in the distillation flask after distillation was analyzed by high-performance liquid chromatography (HPLC), and agarotetrol was found to be the main compound. Purified agarotetrol was heated in a glass vial and its headspace vapor was analyzed by solid-phase microextraction GC-MS. Benzylacetone and other LACs were detected. These results indicate that agarotetrol, a chromone derivative, contributes to the fragrance of agarwood through the generation of LACs upon heating.
Three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone derivatives enantiomeric to agarotetrol from agarwood
Agarwood (jinkoh in Japanese) is a resinous wood from Aquilaria species of the family Thymelaeaceae and has been used as incense and in traditional medicines. Characteristic chromone derivatives such as agarotetrol have been isolated from agarwood. In previous study, we isolated two new 2-(2-phenylethyl)chromones together with six known compounds from MeOH extract of agarwood. Further chemical investigation of the MeOH extract led to isolation of eighteen 2-(2-phenylethyl)chromones, including three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromones with stereochemistry enantiomeric to agarotetrol-type, viz. (5R,6S,7S,8R)-2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (2), (5R,6S,7S,8R)-2-[2-(4'-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (6), and (5R,6S,7S,8R)-2-[2-(4'-hydroxy-3'- methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (13). The absolute configurations of the new compounds were determined by exciton chirality method. All isolated compounds were tested for their phosphodiesterase (PDE) 3A inhibitory activity by fluorescence polarization method. Compounds 8, 12-15, 21-24 showed moderate PDE 3A inhibitory activity.
Correction to: Agarotetrol: a source compound for low molecular weight aromatic compounds from agarwood heating
In the original publication of the article, under the paragraphs "Collection of volatile compound" and "Analysis of essential oil and hydrosol" holding time for the end of GC and GC-MS programs at 180 ～C was incorrectly published as "10 min". The correct time limit is "30 min".