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C17H26O4
APtclcactv08042321262D 0   0.00000     0.00000
 
 47 47  0  0  0  0  0  0  0  0999 V2000
    4.2690   -1.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -1.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -0.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    0.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    1.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8671    1.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8671    2.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7331    3.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7331    4.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991    4.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991    5.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -3.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -5.5600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -2.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -4.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -2.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -4.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -2.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -3.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -3.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -4.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -4.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -4.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0569   -1.3574    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584   -2.0477    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3471   -2.0226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7456   -1.3323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -5.5600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    0.1426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5244   -0.5477    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2131   -0.5226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6116    0.1677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890    1.6426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3905    0.9523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0791    0.9774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4776    1.6677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6550    3.1426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2565    2.4523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9451    2.4774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3437    3.1677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5210    4.6426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1225    3.9523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8112    3.9774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2097    4.6677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2191    5.5600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991    6.1800    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9791    5.5600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  1 18  1  0  0  0  0
 19 21  1  0  0  0  0
 14 19  2  0  0  0  0
 20 22  1  0  0  0  0
 16 20  1  0  0  0  0
  1  2  1  0  0  0  0
 21 23  2  0  0  0  0
 17 21  1  0  0  0  0
 15 22  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 22 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 12 16  1  0  0  0  0
  2 26  1  0  0  0  0
  2 27  1  0  0  0  0
 23 28  1  0  0  0  0
 13 17  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
 10 43  1  0  0  0  0
 10 44  1  0  0  0  0
 11 45  1  0  0  0  0
 11 46  1  0  0  0  0
 11 47  1  0  0  0  0
M  END
$$$$

MOL SMILES InChIKey

Compound Description

A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease.

Identification

IUPAC Names

2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione

Molecular Formula

C17H26O4

Mass

294.38590

Monoisotopic Mass

294.18311

Charge

InChI

InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3

InChIKey

IRSFLDGTOHBADP-UHFFFAOYSA-N

SMILES

CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O

Synonyms

2,5-dihydroxy-3-undecyl-1,4-benzoquinone

embelic acid

Embelin

emberine

Species

oxalis erythrorhiza

IPNI:177985-2 12963150

embelia schimperi

IPNI:588468-1 11054840

lysimachia punctata

NCBI:txid213289 15890461

embelia ribes

NCBI:txid459629 17124632

aegiceras corniculatum

NCBI:txid59970 10.1021/np50063a031

myrsine africana

NCBI:txid59982 ELECTRON J FOOD PLANTS CHEM, 2007, 2, 20

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Europe PubMed Central results

Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease.

Author: Hussein G, Miyashiro H, Nakamura N, Hattori M, Kakiuchi N, Shimotohno K.

Abstract: One hundred fifty-two methanol and water extracts of different parts of 71 plants commonly used in Sudanese traditional medicine were screened for their inhibitory effects on hepatitis C virus (HCV) protease (PR) using in vitro assay methods. Thirty-four extracts showed significant inhibitory activity (>/=60% inhibition at 100 microg/mL). Of these, eight extracts, methanol extracts of Acacia nilotica, Boswellia carterii, Embelia schimperi, Quercus infectoria, Trachyspermum ammi and water extracts of Piper cubeba, Q. infectoria and Syzygium aromaticum, were the most active (>/=90% inhibition at 100 microg/mL). From the E. schimperi extract, two benzoquinones, embelin (I) and 5-O-methylembelin (II), were isolated and found as potent HCV-PR inhibitors with IC(50) values of 21 and 46 microM, respectively. Inhibitory activities of derivatives of I against HCV-PR as well as their effects on other serine proteases were also investigated.

DOI: 10.1002/1099-1573(200011)14:7<510::aid-ptr646>3.0.co;2-b

Bioactive alkyl phenols and embelin from Oxalis erythrorhiza.

Author: Feresin GE, Tapia A, Sortino M, Zacchino S, de Arias AR, Inchausti A, Yaluff G, Rodriguez J, Theoduloz C, Schmeda-Hirschmann G.

Abstract: The benzoquinone embelin and four alkyl phenols were isolated from an Argentinean collection of Oxalis erythrorhiza. 3-Heptadecyl-5-methoxy-phenol is reported for the first time. The structures were determined by spectroscopic methods. Embelin presented inhibitory effect on methicillin-resistant Staphylococcus aureus, Escherichia coli and the dermatophytic fungi Epidermophyton floccosum, Microsporum canis, Microsporum gypseum, Trichophyton mentagrophytes and Trichophyton rubrum with MICs ranging between 50 and 100 microg/ml. Furthermore, embelin was active against Trypanosoma cruzi trypomastigotes with 100% lysis at 100 microg/ml and cytotoxicity below the trypanocidal concentration. The new alkyl phenol 3-heptadecyl-5-methoxy-phenol was active towards Leishmania amazonensis and Leishmania donovani promastigotes with 100% lysis at 100 microg/ml. The cytotoxicity (IC50) of embelin and the new alkyl phenol on human lung fibroblasts were 739 and 366 microM, respectively. The plant is used to treat heart complains, a symptomatology related to Chagas' disease which is endemic in the San Juan Province, Argentine.

DOI: 10.1016/s0378-8741(03)00258-7

Cytotoxic activity of embelin from Lysimachia punctata.

Author: Podolak I, Galanty A, Janeczko Z.

Abstract: A major benzoquinone pigment, embelin (1), was isolated from the underground parts of Lysimachia punctata. Compound 1 showed a significant cytotoxic activity in vitro against B16 and XC cell lines with ED50 values of 13 microg/ml and 8 microg/ml, respectively.

DOI: 10.1016/j.fitote.2005.02.006

Microwave-assisted extraction of embelin from Embelia ribes.

Author: Latha C.

Abstract: A rapid and efficient microwave-assisted extraction (MAE) process for the selective extraction of embelin from Embelia ribes was developed. Solvent selection, microwave energy input and solid loading were optimized. The rate of extraction and purity of embelin depended upon the solvent used and exposure time to microwaves. Maximum MAE was achieved in acetone with total yield of 92% (w/w) embelin with 90% (w/w) purity with 1% (w/v) raw material loading at 150 W power level in 80 s. Non-polar solvents, such as hexane and dichloromethane, were not effective for the selective extraction of embelin.

DOI: 10.1007/s10529-006-9243-z

Connect to another EMBL location

MTBLC4778: embelin