Bryonolic acid

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

MedKoo CAT#: 581105

CAS#: 24480-45-3

Description: Bryonolic acid (BA) is a triterpenoid found in the Cucurbitaceae family of plants, has anti-inflammatory and antioxidant activities. A pentacyclic triterpenoid of D:C-friedooleanane-type triterpenoids isolated from the stems of Lagenaria siceraria and roots of Coriaria intermedia and has been found to exhibit antineoplastic activity.

Chemical Structure

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Bryonolic acid
CAS# 24480-45-3
Instruction

Theoretical Analysis

MedKoo Cat#: 581105
Name: Bryonolic acid
CAS#: 24480-45-3
Chemical Formula: C30H48O3
Exact Mass: 456.36
Molecular Weight: 456.710
Elemental Analysis: C, 78.90; H, 10.59; O, 10.51

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Bryonolic acid; UNII-J7YR6A878I;

IUPAC/Chemical Name: (2S-(2alpha,4aalpha,6aalpha,8abeta,10alpha,12aalpha,14abeta,14balpha))-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-Eicosahydro-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-2-picenecarboxylic acid

InChi Key: BHVJSLPLFOAMEV-UHIFYLTQSA-N

InChi Code: InChI=1S/C30H48O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h21-23,31H,8-18H2,1-7H3,(H,32,33)/t21-,22+,23-,26+,27-,28+,29+,30-/m0/s1

SMILES Code: O=C([C@]1(C)C[C@@]2([H])[C@]3(C)CCC4=C(CC[C@@]5([H])C(C)(C)[C@@H](O)CC[C@@]54C)[C@@]3(C)CC[C@@]2(C)CC1)O

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: >2 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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 456.71 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tabata M, Tanaka S, Cho HJ, Uno C, Shimakura J, Ito M, Kamisako W, Honda C. Production of an anti-allergic triterpene bryonolic acid, by plant cell cultures. J Nat Prod. 1993 Feb;56(2):165-74. PubMed PMID: 8463793.

2: Gatbonton-Schwager TN, Letterio JJ, Tochtrop GP. Bryonolic acid transcriptional control of anti-inflammatory and antioxidant genes in macrophages in vitro and in vivo. J Nat Prod. 2012 Apr 27;75(4):591-8. doi: 10.1021/np200823p. Epub 2012 Feb 16. PubMed PMID: 22339499; PubMed Central PMCID: PMC4089864.

3: Kondo T, Inoue M, Mizukami H, Ogihara Y. Cytotoxic activity of bryonolic acid isolated from transformed hairy roots of Trichosanthes kirilowii var. japonica. Biol Pharm Bull. 1995 May;18(5):726-9. PubMed PMID: 7492990.

4: Barker EC, Gatbonton-Schwager TN, Han Y, Clay JE, Letterio JJ, Tochtrop GP. Bryonolic acid: a large-scale isolation and evaluation of heme oxygenase 1 expression in activated macrophages. J Nat Prod. 2010 Jun 25;73(6):1064-8. doi: 10.1021/np1000076. PubMed PMID: 20481554; PubMed Central PMCID: PMC2905313.

5: Tanaka S, Uno C, Akimoto M, Tabata M, Honda C, Kamisako W. Anti-allergic effect of bryonolic acid from Luffa cylindrica cell suspension cultures. Planta Med. 1991 Dec;57(6):527-30. PubMed PMID: 1818343.

6: Honda C, Suwa K, Takeyama S, Kamisako W. Relative population of S-form and F-form conformers of bryonolic acid and its derivatives in equilibrium in CdCl3 solutions. Chem Pharm Bull (Tokyo). 2002 Apr;50(4):467-74. PubMed PMID: 11963992.

7: Hayashi H, Huang P, Inoue K, Hiraoka N, Ikeshiro Y, Yazaki K, Tanaka S, Kushiro T, Shibuya M, Ebizuka Y. Molecular cloning and characterization of isomultiflorenol synthase, a new triterpene synthase from Luffa cylindrica, involved in biosynthesis of bryonolic acid. Eur J Biochem. 2001 Dec;268(23):6311-7. PubMed PMID: 11733028.

8: Takeda T, Kondo T, Mizukami H, Ogihara Y. Bryonolic acid production in hairy roots of Trichosanthes kirilowii Max. var Japonica Kitam. Transformed with Agrobacterium rhizogenes and its cytotoxic activity. Chem Pharm Bull (Tokyo). 1994 Mar;42(3):730-2. PubMed PMID: 8004724.

9: Que J, Ye M, Zhang Y, Xu W, Li H, Xu W, Chu K. Bryonolic Acid, a Triterpenoid, Protect Against N-methyl-d-Aspartate-Induced Neurotoxicity in PC12 Cells. Molecules. 2016 Mar 28;21(4):418. doi: 10.3390/molecules21040418. PubMed PMID: 27043504.

10: Shimakura J, Cho HJ, Tanaka S, Fukui H, Kamisako W, Tabata M. Intracellular distribution of the hydrophobic triterpene, bryonolic acid, in cultured cells of Luffa cylindrica L. Plant Cell Rep. 1993 Mar;12(5):264-7. doi: 10.1007/BF00237132. PubMed PMID: 24197154.

11: Kongtun S, Jiratchariyakul W, Kummalue T, Tan-ariya P, Kunnachak S, Frahm AW. Cytotoxic properties of root extract and fruit juice of Trichosanthes cucumerina. Planta Med. 2009 Jun;75(8):839-42. doi: 10.1055/s-0029-1185455. Epub 2009 Mar 13. PubMed PMID: 19288406.

12: Khallouki F, Hull WE, Owen RW. Characterization of a rare triterpenoid and minor phenolic compounds in the root bark of Anisophyllea dichostyla R. Br. Food Chem Toxicol. 2009 Aug;47(8):2007-12. doi: 10.1016/j.fct.2009.05.018. Epub 2009 May 19. PubMed PMID: 19460411.

13: Biglino G, Cattel L, Caputo O. Structure of bryonolic acid. Ric Sci. 1969 Mar;39(3):207-9. PubMed PMID: 5371843.

14: Akiyama K, Hayashi H. Arbuscular mycorrhizal fungus-promoted accumulation of two new triterpenoids in cucumber roots. Biosci Biotechnol Biochem. 2002 Apr;66(4):762-9. PubMed PMID: 12036048.

15: Ignatenko VA, Tochtrop GP. Approach for expanding triterpenoid complexity via divergent Norrish-Yang photocyclization. J Org Chem. 2013 Apr 19;78(8):3821-31. doi: 10.1021/jo400275p. Epub 2013 Apr 11. PubMed PMID: 23544445; PubMed Central PMCID: PMC3903659.

16: Akihisa T, Kokke WC, Tamura T, Nambara T. 7-Oxodihydrokarounidiol [7-oxo-D:C-friedo-olean-8-ene-3 alpha,29-diol], a novel triterpene from Trichosanthes kirilowii. Chem Pharm Bull (Tokyo). 1992 May;40(5):1199-202. PubMed PMID: 1394634.

17: Sahranavard S, Naghibi F, Siems K, Jenett-Siems K. New cucurbitane-type triterpenoids from Bryonia aspera. Planta Med. 2010 Jul;76(10):1014-7. doi: 10.1055/s-0029-1240840. Epub 2010 Jan 27. PubMed PMID: 20108178.

18: Kitajima J, Mukai A, Masuda Y, Tanaka Y. [Studies on the constituents of trichosanthes root. III. Constituents of roots of Trichosanthes bracteata Voigt]. Yakugaku Zasshi. 1989 Apr;109(4):265-70. Japanese. PubMed PMID: 2760813.

19: Kitajima J, Tanaka Y. [Studies on the constituents of trichosanthes root. I. Constituents of roots of Trichosanthes kirilowii Maxim. var. japonicum Kitam]. Yakugaku Zasshi. 1989 Apr;109(4):250-5. Japanese. PubMed PMID: 2760811.

20: Honda C, Kamisako W, Miwa Y. Crystal structure of acetyl 29-methyl-29-methylidene-D:C-friedoolean-8-en-3beta-ol. Anal Sci. 2003 Mar;19(3):473-4. PubMed PMID: 12675365.