Macrocarpal B

Bioorg Med Chem Lett. 2007 Feb 15;17(4):1107-11.

Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.[Pubmed: 17118653]

The uptake and transepithelial transport of the three main constituents macrocarpal A (M-A), Macrocarpal B (M-B), and cypellocarpa C (Cy-C) from the fruits of Eucalyptus globulus Labill. were investigated.
METHODS AND RESULTS:
Monolayers of the human intestinal epithelial cancer cell line Caco-2 were incubated with M-A, Macrocarpal B, and Cy-C to model its intestinal absorption and transport, respectively. The determination of compounds was performed by HPLC. The apparent permeability coefficients (P(app)) for M-A, Macrocarpal B, and Cy-C in the apical-to-basolateral direction of a Caco-2 monolayer were (1.70+/-0.06)x10(-6), (1.99+/-0.10)x10(-6), and (6.08+/-0.41)x10(-6)cm/s, respectively. In the presence of iodoacetamide, the P(app) of Cy-C were both reducted in apical-to-basolateral and basolateral-to-apical directions. M-A and Macrocarpal B appear to accumulate in the epithelial cells.
CONCLUSIONS:
The intestinal absorption of M-A, Macrocarpal B, and Cy-C was passive diffusion as the dominating process and Cy-C was partly ATP-dependent.

Zhongguo Zhong Yao Za Zhi. 2007 Mar;32(6):496-500.

[Studies on chemical constituents in fruits of Eucalyptus globulus].[Pubmed: 17552153]

To study the chemical constituents in the fruits of Eucalyptus globulus Labill.
METHODS AND RESULTS:
The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by IR, NMR and MS evidences. Fifteen compounds were obtained and identified as beta-sitosterol (1), betulinic acid (2), stigmasterol (3), euscaphic acid (4), 2a-Hydroxybetulinic acid (5), Macrocarpal B (6), macrocarpal A (7), oleanolic acid (8), 3,4,3'-O-trimethylellagic acid (9), 3-O-methylellagic acid 4'-O-(2"-O-acetyl )-alpha-L-rhamnopyranoside (10), camaldulenside (cypellocarpin C, 11), 3-O-methylellagic acid 4'-O-alpha-L-rhamnopyranoside (12), 3-O-methylellagic acid (13), ellagic acid (14), and gallic acid (15).
CONCLUSIONS:
Compounds 4 and 5 from genera Eucalyptus, 1, 3 and 11 from plant E. globulus, and 6, 7, 9 and 15 from the fruits of E. globulus were isolated for the first time.

Biosci. Biotech. Biochem., 1995, 59(12):2330-2.

New Macrocarpal-am-1 from Eucalyptus amplifolia.[Reference: WebLink]

METHODS AND RESULTS:
Four macrocarpals (macrocarpal A, Macrocarpal B, Macrocarpal E, and macrocarpal am-1) were isolated from the leaves of Eucalyptus amplifolia.
CONCLUSIONS:
Macrocarpal-am-1 is a new macrocarpal in which the isopentyl phloroglucinol chromophore is coupled with the 1,10-secoaromadendrane skeleton. Its structure is elucidated by spectral techniques.