Yangambin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598981

CAS#: 13060-14-5

Description: Yangambin is a lignan isolated from Ocotea duckei Vattimo (Lauraceae).


Chemical Structure

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Yangambin
CAS# 13060-14-5

Theoretical Analysis

MedKoo Cat#: 598981
Name: Yangambin
CAS#: 13060-14-5
Chemical Formula: C24H30O8
Exact Mass: 446.1941
Molecular Weight: 446.49
Elemental Analysis: C, 64.56; H, 6.77; O, 28.67

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2021-03-05. Prices are subject to change without notice.

Yangambin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: Yangambin; Lirioresinol B, dimethyl-; (+)-Yangabin; O,O-Dimethyllirioresinol B;

IUPAC/Chemical Name: (1R,4R)-1,4-bis(3,4,5-trimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan

InChi Key: HRLFUIXSXUASEX-WZRIXLNXSA-N

InChi Code: InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3/t15?,16?,21-,22-/m0/s1

SMILES Code: COC1=C(OC)C(OC)=CC([C@@H]2OCC3[C@H](C4=CC(OC)=C(OC)C(OC)=C4)OCC32)=C1

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 446.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Araújo IG, Silva DF, do Carmo de Alustau M, Dias KL, Cavalcante KV, Veras RC, Barbosa-Filho JM, Neto Mdos A, Bendhack LM, de Azevedo Correia N, Almeida de Medeiros I. Calcium influx inhibition is involved in the hypotensive and vasorelaxant effects induced by yangambin. Molecules. 2014 May 23;19(5):6863-76. doi: 10.3390/molecules19056863. PubMed PMID: 24858272.

2: Monte Neto RL, Sousa LM, Dias CS, Barbosa Filho JM, Oliveira MR, Figueiredo RC. Morphological and physiological changes in Leishmania promastigotes induced by yangambin, a lignan obtained from Ocotea duckei. Exp Parasitol. 2011 Jan;127(1):215-21. doi: 10.1016/j.exppara.2010.07.020. Epub 2010 Aug 5. PubMed PMID: 20691682.

3: Castro-Faria-Neto HC, Bozza PT, Cruz HN, Silva CL, Violante FA, Barbosa-Filho JM, Thomas G, Martins MA, Tibiriçá EV, Noel F, et al. Yangambin: a new naturally-occurring platelet-activating factor receptor antagonist: binding and in vitro functional studies. Planta Med. 1995 Apr;61(2):101-5. PubMed PMID: 7753913.

4: Monte Neto RL, Sousa LM, Dias CS, Filho JM, Oliveira MR. Yangambin cytotoxicity: a pharmacologically active lignan obtained from Ocotea duckei vattimo (Lauraceae). Z Naturforsch C. 2008 Sep-Oct;63(9-10):681-6. PubMed PMID: 19040107.

5: Castro-Faria-Neto HC, Araújo CV, Moreira S, Bozza PT, Thomas G, Barbosa-Filho JM, Cordeiro RS, Tibiriçá EV. Yangambin: a new naturally-occurring platelet-activating factor receptor antagonist: in vivo pharmacological studies. Planta Med. 1995 Apr;61(2):106-12. PubMed PMID: 7753914.

6: Araújo CV, Barbosa-Filho JM, Cordeiro RS, Tibiriçá E. Protective effects of yangambin on cardiovascular hyporeactivity to catecholamines in rats with endotoxin-induced shock. Naunyn Schmiedebergs Arch Pharmacol. 2001 Mar;363(3):267-75. PubMed PMID: 11284440.

7: Monte RL, Barbosa JM, Sousa LM, Athayde PF, Dias CS, Oliveira MR. Crude ethanolic extract, lignoid fraction and yangambin from Ocotea duckei (Lauraceae) show antileishmanial activity. Z Naturforsch C. 2007 May-Jun;62(5-6):348-52. PubMed PMID: 17708438.

8: Serra MF, Diaz BL, Barreto EO, Pereira AP, Lima MC, Barbosa-Filho JM, Cordeiro RS, Martins MA, de Silva PM. Anti-allergic properties of the natural PAF antagonist yangambin. Planta Med. 1997 Jun;63(3):207-12. PubMed PMID: 9225600.

9: Tibiriçá E. Cardiovascular properties of yangambin, a lignan isolated from Brazilian plants. Cardiovasc Drug Rev. 2001 Winter;19(4):313-28. Review. PubMed PMID: 11830750.

10: Marques RC, de Medeiros SR, Dias Cda S, Barbosa-Filho JM, Agnez-Lima LF. Evaluation of the mutagenic potential of yangambin and of the hydroalcoholic extract of Ocotea duckei by the Ames test. Mutat Res. 2003 Apr 20;536(1-2):117-20. PubMed PMID: 12694751.

11: Cabral MM, Mendonça PM, Gomes CM, Barbosa-Filho JM, Dias Cda S, Soares MJ, Queiroz MM. Biological activity of yangambin on the postembryonic development of Chrysomya megacephala (Diptera: Calliphoridae). J Med Entomol. 2007 Mar;44(2):249-55. PubMed PMID: 17427693.

12: Herbert JM, Castro-Faria-Neto HC, Barbosa-Filho JM, Cordeiro RS, Tibiriça E. Pharmacological evidence for the putative existence of two different subtypes of PAF receptors on platelets and leukocytes; studies with yangambin. J Lipid Mediat Cell Signal. 1997 Sep;17(1):1-14. PubMed PMID: 9302650.

13: Bala M, Pratap K, Verma PK, Singh B, Padwad Y. Validation of ethnomedicinal potential of Tinospora cordifolia for anticancer and immunomodulatory activities and quantification of bioactive molecules by HPTLC. J Ethnopharmacol. 2015 Dec 4;175:131-7. doi: 10.1016/j.jep.2015.08.001. Epub 2015 Aug 5. PubMed PMID: 26253577.

14: de Sousa FC, Pereira BA, Lima VT, Lacerda CD, Melo CT, Barbosa-Filho JM, Vasconcelos SM, Viana GS. Central nervous system activity of yangambin from Ocotea duckei Vattimo (Lauraceae) in mice. Phytother Res. 2005 Apr;19(4):282-6. PubMed PMID: 16041767.

15: Jesus-Morais CM, Assis EF, Cordeiro RS, Barbosa-Filho JM, Lima WT, Silva ZL, Bozza PT, Castro-Faria-Neto HC. Yangambin, a lignan obtained from Ocotea duckei, differentiates putative PAF receptor subtypes in the gastrointestinal tract of rats. Planta Med. 2000 Apr;66(3):211-6. PubMed PMID: 10821044.

16: Tibiriçá EV, Mosquera K, Abreu M, Ribeiro R, Carvalho FA, Barbosa-Filho JM, Cordeiro RS. Antagonistic effect of yangambin on platelet-activating factor (PAF)-induced cardiovascular collapse. Phytomedicine. 1996 Jan;2(3):235-42. doi: 10.1016/S0944-7113(96)80048-1. PubMed PMID: 23194622.

17: Ribeiro R, Carvalho FA, Barbosa-Filho JM, Cordeiro RS, Tibiriçá EV. Protective effects of Yangambin - a naturally occurring platelet-activating factor (PAF) receptor antagonist - on anaphylactic shock in rats. Phytomedicine. 1996 Nov;3(3):249-56. doi: 10.1016/S0944-7113(96)80062-6. PubMed PMID: 23195079.

18: Hänsel R, Pelter A. [Relative and absolute configuration of yangambin and aschantin]. Arch Pharm Ber Dtsch Pharm Ges. 1969 Dec;302(12):940-2. German. PubMed PMID: 5266521.

19: Santhanam RK, Ahmad S, Abas F, Safinar Ismail I, Rukayadi Y, Tayyab Akhtar M, Shaari K. Bioactive Constituents of Zanthoxylum rhetsa Bark and Its Cytotoxic Potential against B16-F10 Melanoma Cancer and Normal Human Dermal Fibroblast (HDF) Cell Lines. Molecules. 2016 May 24;21(6). pii: E652. doi: 10.3390/molecules21060652. PubMed PMID: 27231889.

20: Wang HM, Lo WL, Huang LY, Wang YD, Chen CY. Chemical constituents from the leaves of Michelia alba. Nat Prod Res. 2010 Mar;24(5):398-406. doi: 10.1080/14786410802394132. PubMed PMID: 20306361.