Betulinic Acid methyl ester
(Synonyms: 桦木酸甲酯,Methyl Betulinate) 目录号 : GC46099
A triterpenoid with diverse biological activities
Cas No.:2259-06-5
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
Betulinic acid methyl ester is a lupane-type triterpenoid and an esterified version of betulinic acid that has been found in Helicteres hirsuta and has diverse biological activities.[1],[2],[3],[4],[5] It inhibits HIV-1 reverse transcriptase (IC50 = 11 μM).[1] Betulinic acid methyl ester is active against L. braziliensis and T. cruzi (IC50s = 69.9 and 93.3 μM, respectively).[2] It induces melanogenesis in (EC50 = 2.5 μM) and inhibits the growth of B16 2F2 melanoma cells in vitro (IC50 = 4.9 μM).[3] Betulinic acid methyl ester is cytotoxic to SK-LU-1, HepG2, HeLa, SK-MEL-2, and AGS cells (IC50s = 60.84, 77.43, 80.17, 66.17, and 69.94 μg/ml, respectively).[4]
Reference:
[1]. Akihisa, T., Ogihara, J., Kato, J., et al. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids 36(5), 507-512 (2001).
[2]. Domínguez-Carmona, D.B., Escalante-Erosa, F., García-Sosa, K., et al. Antiprotozoal activity of betulinic acid derivatives. Phytomedicine 17(5), 379-382 (2010).
[3]. Hata, K., Hori, K., and Takahashi, S. Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line. J. Nat. Prod. 65(5), 645-648 (2002).
[4]. Quang, D.N., Pham, C.T., Le, L.T.K., et al. Cytotoxic constituents from Helicteres hirsuta collected in Vietnam. Nat. Prod. Res. 34(4), 585-589 (2020).
[5]. Eyong, K.O., Bairy, G., Eno, A.A., et al. Triterpenoids from the stem bark of Vitellaria paradoxa (Sapotaceae) and derived esters exhibit cytotoxicity against a breast cancer cell line. Med. Chem. Res. 27(1), 268-277 (2017).
| Cas No. | 2259-06-5 | SDF | |
| 别名 | 桦木酸甲酯,Methyl Betulinate | ||
| 化学名 | (3β)-3-hydroxy-Lup-20(29)-en-28-oic acid, methyl ester | ||
| Canonical SMILES | CC([C@@H]1CC[C@]2(C(OC)=O)CC[C@@]3(C)[C@]4(C)CC[C@@]5([H])C(C)(C)[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3([H])[C@]21[H])=C | ||
| 分子式 | C31H50O3 | 分子量 | 470.7 |
| 溶解度 | Soluble in methanol, ethanol, DMSO, DMF | 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。 |
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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 | 2.1245 mL | 10.6225 mL | 21.245 mL |
| 5 mM | 0.4249 mL | 2.1245 mL | 4.249 mL |
| 10 mM | 0.2124 mL | 1.0622 mL | 2.1245 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。
Isolation of betulinic acid, its methyl ester and guaiane sesquiterpenoids with protein tyrosine phosphatase 1B inhibitory activity from the roots of Saussurea lappa C.B.Clarke
Molecules 2009 Jan 8;14(1):266-72.PMID:19136914DOI:10.3390/molecules14010266.
Activity-guided fractionation of a MeOH extract of the roots of Saussurea lappa C.B.Clarke (Compositae), using an in vitro protein tyrosine phosphatase 1B (PTP1B) inhibition assay, led to the isolation of four active constituents: betulinic acid (1), Betulinic Acid methyl ester (2), mokko lactone (3) and dehydrocostuslactone (4), along with nine inactive compounds. Our findings indicate that betulinic acid (1) and its methyl ester 2, as well as the two guaiane sesquiterpenoids 3 and 4 are potential lead moieties for the development of new PTP1B inhibitors.
Antiprotozoal activity of betulinic acid derivatives
Phytomedicine 2010 Apr;17(5):379-82.PMID:19748254DOI:10.1016/j.phymed.2009.08.002.
Betulinic acid (1), isolated from the crude extract of the leaves of Pentalinon andrieuxii (Apocynaceae), together with betulinic acid acetate (2), betulonic acid (3), Betulinic Acid methyl ester (4), and betulin (5) were evaluated for their antiprotozoal activity. The results showed that modifying the C-3 position increases leishmanicidal activity while modification of the C-3 and C-28 positions decreases trypanocidal activity.
Antimalarial activity of betulinic acid and derivatives in vitro against Plasmodium falciparum and in vivo in P. berghei-infected mice
Parasitol Res 2009 Jul;105(1):275-9.PMID:19367418DOI:10.1007/s00436-009-1394-0.
Malaria is one of the most important tropical diseases and mainly affects populations living in developing countries. Reduced sensitivity of Plasmodium sp. to formerly recommended antimalarial drugs places an increasing burden on malaria control programs as well as on national health systems in endemic countries. The present study aims to evaluate the antimalarial activity of betulinic acid and its derivative compounds, betulonic acid, betulinic acid acetate, Betulinic Acid methyl ester, and Betulinic Acid methyl ester acetate. These substances showed antiplasmodial activity against chloroquine-resistant Plasmodium falciparum parasites in vitro, with IC(50) values of 9.89, 10.01, 5.99, 51.58, and 45.79 microM, respectively. Mice infected with Plasmodium berghei and treated with betulinic acid acetate had a dose-dependent reduction of parasitemia. Our results indicate that betulinic acid and its derivative compounds are candidates for the development of new antimalarial drugs.
Cytotoxic constituents from Helicteres hirsuta collected in Vietnam
Nat Prod Res 2020 Feb;34(4):585-589.PMID:30445838DOI:10.1080/14786419.2018.1490907.
Phytochemical study on the extract of Vietnamese medicinal plant Helicteres hirsuta Lour. has led to the isolation and structural elucidation of twelve secondary metabolites, 3-O-trans-caffeoylbetulinic acid (1), 3β-benzoylbetulinic acid (2), Betulinic Acid methyl ester (3), betulinic acid (4), lupeol (5), 4-hydroxybenzoic acid (6), 3,4-dihydroxybenzoic acid methyl ester (7), 4-hydroxy-3,5-dimethoxybenzoic acid (8), 5,8-dihydroxy-7,4'-dimethoxyflavone (9), isoscutellarein 4'-methyl ether 8-O-β-D-glucopyranoside (10), methyl caffeate (11) and stigmasterol (12). Especially, compound 2 was reported as a new natural product. Their structures were elucidated by a combination of 2D NMR and ESI-FT-ICR-MS spectroscopies. Furthermore, eight compounds were tested for their cytotoxicity against five cancer cell lines (Hela, HepG2, SK-LU-1, AGS and SK-MEL-2). The results showed that compounds (1, 3-5, 9) have moderate activities. This is the first study on the chemical constituents and their cytotoxicity of the Vietnamese Helicteres hirsuta L.
Melanogenesis inhibitory compounds from Saussureae Radix
Arch Pharm Res 2008 Mar;31(3):294-9.PMID:18409040DOI:10.1007/s12272-001-1154-0.
Ten compounds were isolated from the EtOAc soluble part of the MeOH extract of Saussureae Radix, with their effects on melanin production also evaluated in B-16 mouse melanoma cell lines stimulated with 3-isobutyl-1-methylxanthine (IBMX), an elevator of cellular cAMP. The compounds were identified as aplotaxene (1), 1 beta-hydroxy arbusculin A (2), costunolide (3), dehydrocostuslactone (4), 11 beta,13-dihydrocostunolide (5), reynosin (6), heptadec-(9Z)-enoic acid (7), beta-sitosterol (8), linoleic acid methyl ester (9) and Betulinic Acid methyl ester (10). Compounds 2, 9 and 10 were identified from Saussureae Radix for the first time. Furthermore, compounds 2, 3 and 6 showed potent inhibitory effects on the IBMX-induced melanogenesis, in dose-dependent manners, with IC50 values of 11, 3 and 2.5 microg/mL, respectively. As a positive control, arbutin exhibited an IC50 value of 29 microg/mL.