2,6,4'-Trihydroxy-4-methoxybenzophenone

Biol Pharm Bull. 2005 Sep;28(9):1798-800.

7-hydroxy-3-(4-hydroxybenzyl)chroman and broussonin b: neurotrophic compounds, isolated from Anemarrhena asphodeloides BUNGE, function as proteasome inhibitors.[Pubmed: 16141565]

METHODS AND RESULTS:
The extract of Anemarrhenae Rhizoma (rhizomes of Anemarrhena asphodeloides BUNGE) showed neurotrophic activity toward rat pheochromocytoma (PC-12) cells. Bioassay-guided purification afforded four compounds, 2,6,4'-Trihydroxy-4-methoxybenzophenone (1), 7-hydroxy-3-(4-hydroxybenzyl)chroman (2), broussonin B (3), and cis-hinokiresinol (4).
CONCLUSIONS:
Compounds 1-3 induced neurite outgrowth in PC-12 cells at concentration of 50 microg/ml, while 4 was less active. In addition, compounds 2-4 showed moderate inhibitory activities against a chymotrypsin-like activity of the proteasome.

Biol Pharm Bull. 2001 May;24(5):586-7.

Testosterone 5alpha-reductase inhibitory active constituents from Anemarrhenae Rhizoma.[Pubmed: 11379787]

METHODS AND RESULTS:
The diethyl ether extract of Anemarrhenae Rhizoma (rhizomes of Anemarrhena asphodeloides Bunge) showed testosterone 5alpha-reductase inhibitory activity.
CONCLUSIONS:
Two major constituents, cis-hinokiresinol (1) and 2,6,4'-Trihydroxy-4-methoxybenzophenone (2) were identified as the active principles. The inhibitory activity of 1 was superior to that of ethinylestradiol, but that of 2 was weak.

Jurnal Teknologi, 2013, 64(2).

Cytotoxic Activity of Major Compounds from Phaleria macrocarpa (Scheff.) Boerl. Fruits.[Reference: WebLink]

P. macrocarpa is a well known Indonesian medicinal plant which is traditionally claimed to have anticancer properties. To date, there are numerous cytotoxic studies conducted on crude extracts of this plant. However, there are limited informations available regarding cytotoxic activity of the compounds isolated from this plant.
METHODS AND RESULTS:
Thus, this study investigated cytotoxic activity of two benzophenones derivatives identified as 2,6,4'-Trihydroxy-4-methoxybenzophenone(1) and 6,4′-dihydroxy-4-methoxybenzophenone-2-O-β-D-glucopyranoside (2) isolated from the ethyl acetate extract. Cytotoxic activities of these compounds were performed against human cervical carcinoma cell line (HeLa) and mouse embryonic fibroblast cell line (3T3) using MTT assay.
CONCLUSIONS:
The result showed that benzophenone (1) exhibited low cytotoxic effect against HeLa and 3T3 cell lines with IC50 values of 132 μg/ml and 158 μg/ml, repectively while benzophenone (2) was non toxic against HeLa and 3T3 cell lines are because the IC50 is more than 250 μg/ml. These findings may sheds light on the actual properties of this plant.

Nat Prod Commun. 2013 Apr;8(4):481-3.

Inhibitory activity of benzophenones from Anemarrhena asphodeloides on pancreatic lipase.[Pubmed: 23738459]

Pancreatic lipase is a key enzyme for lipid absorption by hydrolysis of total dietary fats. Therefore, inhibition of pancreatic lipase is suggested to be an effective therapy in the regulation of obesity. The EtOAc-soluble fraction of Anemarrhena asphodeloides rhizomes significantly inhibited pancreatic lipase activity as assessed using porcine pancreatic lipase as an in vitro assay system. Further fractionation of the EtOAc-soluble fraction of A. asphodeloides led to the isolation of a new benzophenone glycoside, zimoside A (1), together with the eleven known compounds iriflophenone (2), 2,4',6-trihydroxy-4-methoxybenzophenone (2,6,4'-Trihydroxy-4-methoxybenzophenone ,3), foliamangiferoside A (4), (2,3-dihydroxy-4-methoxyphenyl)(4-hydroxyphenyl)-methanone (5), 1,4,5,6,-tetrahydroxyxanthone (6), isosakuranetin (7), 4-hydroxybenzoic acid (8), 4-hydroxyacetophenone (9), vanillic acid (10), tyrosol (11) and 5-hydroxymethyl-2-furaldehyde (12). Among the isolated compounds, 3, 5 and 10 showed significant inhibition of pancreatic lipase activity.

Biomed Res Int. 2014;2014:468157.

Induction of apoptosis of 2,4',6-trihydroxybenzophenone in HT-29 colon carcinoma cell line.[Pubmed: 24579081]

2,4',6-Trihydroxy-4-methoxybenzophenone(2,6,4'-Trihydroxy-4-methoxybenzophenone ) was isolated from the ethyl acetate fraction of Phaleria macrocarpa (Scheff.) Boerl. fruits.
METHODS AND RESULTS:
It was found to inhibit cell proliferation in HT-29 human colon carcinoma cell line but caused little damage to WRL-68 normal human liver and MRC-5 normal human fibroblast lung cell lines. The compound was found to sharply affect the viability of HT-29 cells in a dose- and time-dependent manner. HT-29 cells treated with the compound showed morphological changes under microscopic examination such as cell shrinkage, membrane blebbing, DNA fragmentation, and the occurrence of apoptotic nuclei. The percentage of early apoptotic, late apoptotic, and dead or necrotic cells was determined by flow cytometry using annexin V-FTIC/PI staining. In addition, flow cytometry showed that, when the HT-29 cells were treated with 115 μM of the compound, it resulted in G0/G1 phase arrest in a time-dependent manner. Western blot revealed an upregulation of PUMA, Bak, Bcl-2, and Mcl-1 proteins suggesting that the compound induced apoptosis in HT-29 cells by regulating these proteins.

Indonesian Journal of Chemistry, 2011, 11(2):180-185.

Antioxidant Activity of 2,6,4'-trihydroxy-4-methoxybenzophenone from Ethyl Acetate Extract of Leaves of Mahkota Dewa (Phaleria macrocarpa (Scheff.) Boerl)[Reference: WebLink]

Mahkota dewa plant (Phaleria macrocarpa (Scheff.) Boerl.) which is included into family of Thymelaeaceae is one of Indonesia's traditional medicines. Chemical constituent has been isolated from ethyl acetate extract of leaves of mahkota dewa.
METHODS AND RESULTS:
Sample was extracted with methanol, concentrated then extracted by n-hexane, chloroform and ethyl acetate. The ethyl acetate extract was separated and fractionated by column chromatography. The first fraction was purified by TLC preparative and recrystalization. Compound was isolated as red-brown spherical crystal in 8 mg (m.p. 129-131 °C). Its spot gave dark fluoroscence at TLC plate (UV366) with Rf of 0.3 at TLC chromatogram with eluent of n-hexane : ethyl acetate (7:3); 0.6 with n-hexane : ethyl acetate (1:1); 0.9 with -hexane : ethyl acetate (4:6). This compound was dissolved in methanol. Compound was identified by UV, IR, 1H NMR, 13C NMR and NMR 2 dimension (HMQC, COSY, HMBC and DEPT-135) spectroscopic as 2,6,4'-Trihydroxy-4-methoxybenzophenone.
CONCLUSIONS:
This compound as well as the ethyl acetate extract showed antioxidant activity on DPPH with IC50 was 10.57 and 101.06 μg/mL, respectively. This compound showed strong antioxidant activity on DPPH, almost to the standard antioxidant activity of quercetin (IC50 of 2.93 μg/mL)