Betulonaldehyde
(Synonyms: 白桦脂醛,半合成) 目录号 : GC48520
A pentacyclic triterpenoid
Cas No.:4439-98-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Betulonaldehyde is a pentacyclic triterpenoid and derivative of the cholesterol biosynthesis inhibitor betulin that has been found in Betula.1 It is active against P. falciparum (IC50 = 3.36 µg/ml) and cytotoxic to NCI H187 lung cancer cells and non-cancerous Vero cells (IC50s = 19.23 and 17.09 µg/ml, respectively).2 Topical application of betulonaldehyde (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate in mice.3 It has also been used a precursor in the semisynthesis of C-2 and C-28 betulonic aldehyde derivatives.1
1.Ayers, S., Benkovics, T., Marshall, J., et al.Autoxidation products of betulonaldehydeJ. Nat. Prod.79(10)2758-2761(2016) 2.Wisetsai, A., Schevenels, F.T., and Lekphrom, R.Chemical constituents and their biological activities from the roots of diospyros filipendulaNat. Prod. Res.1-5(2019) 3.Yasukawa, K., Yu, S., Yamanouchi, S., et al.Some lupane-type triterpenes inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skinPhytomedicine1(4)309-313(1995)
| Cas No. | 4439-98-9 | SDF | |
| 别名 | 白桦脂醛,半合成 | ||
| Canonical SMILES | C[C@]1([C@]2([C@]([C@@]3([C@@](C(C)(C(CC3)=O)C)([H])CC2)C)([H])CC4)C)[C@@]4([H])[C@]([C@@H](CC5)C(C)=C)([H])[C@@]5(C=O)CC1 | ||
| 分子式 | C30H46O2 | 分子量 | 438.7 |
| 溶解度 | DMF: 10 mg/ml | 储存条件 | -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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.2795 mL | 11.3973 mL | 22.7946 mL |
| 5 mM | 0.4559 mL | 2.2795 mL | 4.5589 mL |
| 10 mM | 0.2279 mL | 1.1397 mL | 2.2795 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。
Autoxidation Products of Betulonaldehyde
J Nat Prod 2016 Oct 28;79(10):2758-2761.PMID:27684353DOI:10.1021/acs.jnatprod.6b00735.
Three major degradation products resulted from the exposure of Betulonaldehyde (1) to air in solution at room temperature. From HRMS and NMR data, the products, which were isolated by preparative supercritical fluid chromatography (SFC), were identified as betulonic acid (2) and C-17 hydroperoxide epimers 3 (β-OOH) and 4 (α-OOH). For 3 and 4, the H-18 multiplet pattern of the isolated products established the configuration at C-17.
Bioassay Directed Fractionation of Petroleum Ether Extract of Aerial Parts of Ceriops tagal: Isolation of Lupeol as the Nematicidal Agent against Cyst Nematode Heterodera zeae
Chem Biodivers 2022 Mar;19(3):e202100759.PMID:35001512DOI:10.1002/cbdv.202100759.
Plant parasitic cyst nematode Heterodera zeae is a pest, causing substantial economic losses in agriculture. Organic pesticides, based on plant products have emerged as eco-benign nematicidal agents. Ceriops tagal is a well-known marine medicinal plant which has not been evaluated against any nematode. Petroleum ether extract of the aerial parts of the plant (CTP), exhibited promising activity against infective stage larvae of H. zeae. On subjecting to classical solvent-solvent separation, it afforded petroleum ether soluble (CTP-S), methanol soluble (CTPMS-1, CTPMS-2) and insoluble (CTPM-IN-2) fractions, which exhibited activity against the cyst nematode within 24 h exposure. GC, GC/MS and HR-ESI-MS analyses of CTPMS-1 and CTPMS-2 fractions resulted in the identification of a number of compounds, including pentacyclic triterpenoids, lupeol (1), betunal (2), betulin (3), lupenone (4), Betulonaldehyde (5), betulonic acid (7), methyl 3-acetoxy-27-O-(3,4-dihydroxy-E-cinnamoyl)-20(29)-lupen-28-oate (8) and β-amyrin, along with phenylpropanoid esters, fatty acids and their derivatives, benzamide, and indole derivatives. CTPM-IN-2 which mainly contained lupeol (1) exhibited maximum nematicidal activity, with 91 % and 93 % mortality of the larvae of H. zeae, after exposure for 72 h at the concentration of 0.5 % and 1 %, respectively. Its fractionation and purification through column chromatography resulted in the isolation and identification of four lupane-type triterpenoids 1, 3, 4 and betulinic acid (6). One of its most abundant column fractions CC-9-18 (145 mg) which exhibited substantial activity, with 81 % mortality at the lowest concentration of 0.125 % after 48 h of incubation mainly contained lupeol. It seems lupeol, a wide spread bio-privileged triterpenoid is the nematicidal principle of the plant as its authentic sample showed LC50 value of 0.061 after 72 h exposure. It is for the first time that nematicidal activity is reported for any part of C. tagal and that of lupeol against H. zeae. Pentacyclic triterpenoids 1-8 are biosynthetically related. Of the twenty-four compounds isolated or identified in the present investigation only five constituents 1, 3, 6, 7 and palmitic acid have been isolated previously from C. tagal.
Cytotoxic activity of moronic acid and identification of the new triterpene 3,4-seco-olean-18-ene-3,28-dioic acid from Phoradendron reichenbachianum
Planta Med 2001 Jul;67(5):443-6.PMID:11488459DOI:10.1055/s-2001-15823.
The cytotoxic compound moronic acid (1) and the new tetracyclic triterpene 3,4-seco-olean-18-ene-3,28-dioic acid (2), were isolated from the aerial parts of the medicinal plant Phoradendron reichenbachianum (mistletoe, Loranthaceae) through a bioassay-guided fractionation. In addition, squalene, glycerol trilinoleate, morolic acid, Betulonaldehyde, betulinaldehyde, alpha-germanicol, lupeol, beta-sitosterol and beta-sitosteril glucopyranoside, were identified in this plant species. The structures were elucidated on the basis of chemical and spectroscopic evidence.