10351-88-9

Usage

Uses

Used in Pharmaceutical Industry:
Phyllanthin is used as an anti-diabetic agent for its ability to regulate blood sugar levels and improve insulin sensitivity. It has been found to be effective in managing type 2 diabetes and its associated complications.
Used in Anti-arthritic Applications:
Phyllanthin is used as an anti-arthritic agent for its potential to alleviate pain, reduce inflammation, and improve joint function in conditions such as rheumatoid arthritis and osteoarthritis.
Used in Cancer Therapy:
Phyllanthin is used as a P-glycoprotein (P-gp) inhibitor, which can help overcome multidrug resistance in cancer treatment. By inhibiting P-gp, Phyllanthin can increase the bioavailability and effectiveness of chemotherapeutic drugs, improving treatment outcomes for cancer patients.

Synthetic route

Dg-threo-2,3-bis-(3,4-dimethoxy-benzyl)-butanediol-(1,4) (10352-25-7) + methyl iodide (74-88-4) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
With silver(l) oxide In N,N-dimethyl-formamide

C22H26O6 + methyl iodide (74-88-4) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
(i) Li, EtOH, liq. NH3, (ii) NaH, benzene, (iii) /BRN= 969135/; Multistep reaction;

methyl iodide (74-88-4) + (-)-tetrahydroeudesmyne → (+)-phyllanthin (10351-88-9)

Conditions	Yield
With sodium hydride

Dg-threo-2.3-bis-(3.4-dimethoxy-benzyl)-succinic acid (15813-34-0, 15905-29-0, 93609-04-2, 126965-32-0) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: LiAlH4 / tetrahydrofuran 3: Ag2O / dimethylformamide View Scheme

D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid (15813-34-0, 15905-29-0, 93609-04-2, 126965-32-0) → (+)-phyllanthin (10351-88-9)

Conditions	Yield
Multi-step reaction with 4 steps 3: LiAlH4 / tetrahydrofuran 4: Ag2O / dimethylformamide View Scheme

(+)-2,3-Diveratryl-bernsteinsaeure-dimethylester → (+)-phyllanthin (10351-88-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran 2: Ag2O / dimethylformamide View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carbaldehyde (79606-73-8)

Conditions	Yield
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 50℃; for 0.666667h; sonication;	92%

(+)-phyllanthin (10351-88-9) → 3,4,3',4'-tetramethoxy-9,9'-epoxylignan (10352-26-8)

Conditions	Yield
With trifluoroacetic anhydride; trichlorophosphate In benzene for 6h; Heating;	45%

(+)-phyllanthin (10351-88-9) → (S:S)-1,4-dimethoxy-2,3-bis-(6-bromo-3,4-dimethoxy-benzyl)-butane (138737-28-7)

Conditions	Yield
With chloroform; bromine

(+)-phyllanthin (10351-88-9) → Dinitrophyllanthin

Conditions	Yield
With nitric acid In acetic acid

chloroform (67-66-3) + (+)-phyllanthin (10351-88-9) + bromine (7726-95-6) → (S:S)-1,4-dimethoxy-2,3-bis-(6-bromo-3,4-dimethoxy-benzyl)-butane (138737-28-7)

(+)-phyllanthin (10351-88-9) → 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene (5811-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 92 percent / H2; acetic acid / Pd/C / ethyl acetate / 18 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → dehydrodimethylconidendrin (6258-38-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 85 percent / NaClO2; 2-methylbutene; NaH2PO4 / H2O; 2-methyl-propan-2-ol / 20 °C 3: 98 percent / trifluoroacetic acid / acetonitrile / 24 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4,5,3',4'-tetrahydroxy-2,7'-cycloligna-7,7'-diene-9,9'-lactone (741292-75-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 85 percent / NaClO2; 2-methylbutene; NaH2PO4 / H2O; 2-methyl-propan-2-ol / 20 °C 3: 98 percent / trifluoroacetic acid / acetonitrile / 24 h / 20 °C 4: 79 percent / pyridinium hydrochloride / 0.5 h / 190 °C View Scheme

(+)-phyllanthin (10351-88-9) → 5-(3,4-dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol (741292-76-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 92 percent / H2; acetic acid / Pd/C / ethyl acetate / 18 h / 20 °C 3: 57 percent / pyridinium hydrochloride / 0.5 h / 190 °C View Scheme

(+)-phyllanthin (10351-88-9) → 3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde (741292-78-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-methyl-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 51 percent / CH2Cl2 / 3 h 4: 74 percent / sodium borohydride / methanol / 0.5 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-yl]-methanol

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 75 percent / NaBH4 / CH2Cl2; methanol / 10 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carboxylic acid (741292-74-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 85 percent / NaClO2; 2-methylbutene; NaH2PO4 / H2O; 2-methyl-propan-2-ol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-2-isopropyl-6,7-dimethoxy-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 46 percent / CH2Cl2 4: 74 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-methyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol / 0.17 h 2.2: 99 percent / NaBH4 / methanol / 0.5 h / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 6',9'-dibromo-4,5,3',4'-tetramethoxy-9-oxo-2,7'-cycloligna-7,7'-diene

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 10 mg / Br2 View Scheme

(+)-phyllanthin (10351-88-9) → 8-bromo-3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde (741292-79-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 61 mg / Br2 View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-2-isobutyl-6,7-dimethoxy-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 58 percent / CH2Cl2 4: 72 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-isopropyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol 2.2: 98 percent / NaBH4 / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 5-bromo-1-(3',4'-dihydroxyphenyl)-6,7-dimethoxy-N-methyl-2'',5''H-pyrrolo[4,3-b]naphthalene

Conditions	Yield
Multi-step reaction with 5 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 61 mg / Br2 4: 65 percent / CH2Cl2 5: 75 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-propyl-2,3-dihydro-1H-benzo[f]isoindole

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 41 percent / CH2Cl2 4: 66 percent / sodium borohydride / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-propyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol 2.2: 98 percent / NaBH4 / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → [4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalen-2-ylmethyl]-isobutyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2.1: methanol 2.2: 98 percent / NaBH4 / methanol / 20 °C View Scheme

(+)-phyllanthin (10351-88-9) → 9-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-methyl-3-methylamino-1H-benzo[f]isoindolium; bromide

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 51 percent / CH2Cl2 / 3 h View Scheme

(+)-phyllanthin (10351-88-9) → 5-bromo-9-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2-methyl-3-methylamino-1H-benzo[f]isoindolium; bromide

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 61 mg / Br2 4: 65 percent / CH2Cl2 View Scheme

(+)-phyllanthin (10351-88-9) → 9-(3,4-dimethoxy-phenyl)-2-isopropyl-3-isopropylamino-6,7-dimethoxy-1H-benzo[f]isoindolium; bromide

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / DDQ; acetic acid / 0.67 h / 50 °C / sonication 2: 89 percent / HBr / CH2Cl2 / 3 h / 20 °C 3: 46 percent / CH2Cl2 View Scheme

Upstream product

• 10352-25-7 D_g-threo-2,3-bis-(3,4-dimethoxy-benzyl)-butanediol-(1,4) 
• 74-88-4 methyl iodide 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 15813-34-0 D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid 
• 15813-34-0 (1R,2R)-1,2-bis[(3,4-dimethoxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 15813-34-0 D_g-threo-2.3-bis-(3.4-dimethoxy-benzyl)-succinic acid 
• 138737-28-7 bromophyllanthin 

Downstream Products

• 138737-28-7 (S:S)-1,4-dimethoxy-2,3-bis-(6-bromo-3,4-dimethoxy-benzyl)-butane 
• 79606-73-8 4-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carbaldehyde 
• 10352-26-8 3,4,3',4'-tetramethoxy-9,9'-epoxylignan 
• 5811-91-6 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene 
• 6258-38-4 dehydrodimethylconidendrin 
• 741292-75-1 4,5,3',4'-tetrahydroxy-2,7'-cycloligna-7,7'-diene-9,9'-lactone 
• 741292-78-4 3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde 
• 741292-74-0 4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-naphthalene-2-carboxylic acid 
• 741292-79-5 8-bromo-3-bromomethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-naphthalene-2-carbaldehyde 

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Investigation of anticancer potential of hypoPHYLLANTHIN (cas 10351-88-9) and PHYLLANTHIN (cas 10351-88-9) against breast cancer by in vitro and in vivo methods08/06/2019

ObjectiveTo investigate the in vitro and in vivo anticancer activities of hypophyllanthin and phyllanthin isolated from Phyllanthus amarus Schum & Thonn against breast cancer.detailed

Immobilization mediated enhancement of PHYLLANTHIN (cas 10351-88-9) and hypoPHYLLANTHIN (cas 10351-88-9) from Phyllanthus amarus08/05/2019

ABSTRACTPhyllanthus amarus plant is used in the traditional system of medicine as a hepatoprotective drug for which the major lignans phyllanthin and hypophyllanthin are responsible. So far, no significant work has been done on the culture of this plant. Realizing the hepatoprotective potential,...detailed

Determination of PHYLLANTHIN (cas 10351-88-9) and Gallic Acid In Herbal Hepatoprotective Formulation By TLC-Densitometry Analysis08/04/2019

Introduction: Phyllanthus niruri, Andrographis paniculata and Embilica officinalis are most important and high value medicinal plant known for its hepatoprotective activity. Several analytical methods including HPTLC and HPLC are reported for respective phytoconstituents. However, there is no si...detailed

Endothelium-independent effects of PHYLLANTHIN (cas 10351-88-9) and hypoPHYLLANTHIN (cas 10351-88-9) on vascular tension08/03/2019

The purpose of this study was to investigate the modulating effects of phyllanthin and hypophyllanthin on vascular tension, using in the in vitro model of isolated rat aorta. Our results indicated that both phyllanthin and hypophyllanthin significantly relaxed the sustained contraction induced b...detailed

Ameliorative effects of PHYLLANTHIN (cas 10351-88-9) on carbon tetrachloride-induced hepatic oxidative damage in mice08/01/2019

ObjectiveTo evaluate the liver protecting efficacy of phyllanthin, a lignin, isolated from the leaves of Phyllanthus amarus using mice model.detailed

PHYLLANTHIN (cas 10351-88-9) from Phyllanthus amarus inhibits cellular and humoral immune responses in Balb/C mice07/31/2019

BackgroundPhyllanthin found in many Phyllanthus species has various biochemical and pharmacological properties especially on its hepatoprotective effects. However, its effect on the immune system has not been well documented.detailed

HPLC fingerprint and simultaneous quantitative analysis of PHYLLANTHIN (cas 10351-88-9) and hypoPHYLLANTHIN (cas 10351-88-9) for identification and authentication of Phyllanthus niruri from related species07/30/2019

A precise and accurate method for the identification and authentication of Phyllanthus niruri L. from P. debilis Klein ex Willd. and P. urinaria L., Phyllanthaceae, was developed using high-performance liquid chromatography. Chromatographic fingerprint analysis was combined with simultaneous qua...detailed

Relevant academic research and scientific papers

Oxidative aryl-aryl, aryl-benzyl coupling of lignans-reactions of phyllanthin and haloderivatives with TTFA, DDQ, Li/THF)))): Synthesis of dibenzocyclooctadiene system and phyltetralin

Treatment of phyllanthin (1) with TTFA in TFA gives dibenzocyclooctadiene (2) and phyltetralin (3). Treatment of (1) with DDQ in TFA also affords (2) while with DDQ in acetic acid gives 1-phenylnaphthalenic lignan (4). Synthesis of halophyllanthins (5,6,7) and its Ullmann reaction in ultrasonic condition affords reductive dehalogenated product (1) instead of (2). Treatment of (1) with POCl3 in TCA gives (+) 3,4-diveratryltetrahydrofuran (8) and its conversion to (9) also reported. Treatment of (5) with TTFA/TFA gives (9).