472-11-7

Basic information

• Product Name: RUSCOGENIN
• Synonyms: FlebopoM;HeModren;Rectolander;Ruscogenin, froM Ophiopogon japonicus;(1B,3B,25R)-SPIROST-5-ENE-1,3-DIOL;RUSCOGENIN;RUSCOGENINE;(25R)-spirost-5-ene-1-beta,3-beta-diol
• CAS NO: 472-11-7
• Molecular Formula: C₂₇H₄₂O₄
• Molecular Weight: 430.62
• EINECS: 207-447-2
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Miscellaneous Natural Products;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 472-11-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 198-202℃
• Boiling Point: 563.1 °C at 760 mmHg
• Flash Point: 294.3 °C
• Appearance: /
• Density: 1.18
• Vapor Pressure: 5.03E-15mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 14.56±0.70(Predicted)
• CAS DataBase Reference: RUSCOGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: RUSCOGENIN(472-11-7)
• EPA Substance Registry System: RUSCOGENIN(472-11-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 472-11-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 472-11-7 differently. You can refer to the following data:
1. A major steroidal sapogenin from Radix ophiopogon japonicus with robust anti-inflammatory and anti-thrombotic activities. Studies suggest that it inhibits adhesion of leukocytes to a human umbilical v ein endothelial cell line (ECV304) injured by tumor necrosis factor-α (TNF-α) in a concentration-dependent manner.
2. A major steroidal sapogenin from Radix ophiopogon japonicus with robust anti-inflammatory and anti-thrombotic activities. Studies suggest that it inhibits adhesion of leukocytes to a human umbilical vein endothelial cell line (ECV304) injured by tumor necrosis factor-α (TNF-α) in a concentration-dependent manner.

InChI:InChI=1/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27?/m1/s1

Synthetic route

(25R)-26-O-β-D-glucopyranosyl-furosta-5,20(22)-diene-1β,3β,26-triol 1-O-[α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside] (1307292-22-3) → (25R)-ruscogenin (472-11-7)

Conditions	Yield
With β-glucosidase In phosphoric acid at 37℃; for 24h; Enzymatic reaction;

β-D-xylopyranoside → D-xylose (58-86-6) + (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;	A n/a B 3.8 mg

(25R)-3β-hydroxyspitost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-xylopyranoside → D-xylose (58-86-6) + L-Rhamnose (3615-41-6) + (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;	A n/a B n/a C 2.8 mg

(25R)-3β-hydroxyspitost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside → L-Rhamnose (3615-41-6) + D-glucose (50-99-7) + (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;	A n/a B n/a C 1.5 mg

3β-O-tert-butyldimethylsilyl-(25R)-ruscogenin (201858-23-3) → (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In acetone for 1h; Ambient temperature;	96%
With hydrogenchloride at 20℃; for 1h;	96%

3β-acetoxyspirost-5-ene-1-one (90802-64-5) → (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene (79037-17-5) + (25R)-ruscogenin (472-11-7)

Conditions	Yield
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran cooling 1 h, r.t., 1 h;	A 66% B 34%
With LTBH In tetrahydrofuran cooling 1 h, r.t., 1 h;	A 66% B 34%

(25R)-3β-hydroxyspirost-5-en-1β-yl 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside → (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 95℃; for 1h;	11.2 mg
With hydrogenchloride In methanol at 80℃; for 10h; Sealed tube;	0.6 mg

spirost-5-ene-1-oxo-3β-ol (14414-62-1) → (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene (79037-17-5) + (25R)-ruscogenin (472-11-7)

Conditions	Yield
With sodium tetrahydroborate In methanol for 2h; Ambient temperature;	A 70% B 30%
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran cooling 1 h, r.t., 1 h;	A 60% B 40%

ruscogenin 1-O-α-L-arabinopyranosyl-(1-2)-β-D-glucopyranoside → (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In methanol for 3h; Heating;

spirosta-5(6),25(27)-diene-1β,3β-diol (17676-33-4) → (25R)-ruscogenin (472-11-7)

Conditions	Yield
palladium on activated charcoal In ethanol; cyclohexene for 16h; Heating; Yield given;

26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1<*>2)-4-O-sulfo-α-L-arabinopyran... → (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;

ruscogenin 1-O-α-L-rhamnopyranosyl(1<*>2)-4-O-sulfo-α-L-arabinopyranoside → (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;

(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[(1S,2S,4S,5′R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2′-oxane]-14-yl]oxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol (125150-67-6) → (25R)-ruscogenin (472-11-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;

ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (94898-61-0) → (25R)-ruscogenin (472-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; dioxane / 7 h / 80 °C 2: 2 N HCl / dioxane; H2O / 2 h / Heating View Scheme

26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (94901-57-2) → (25R)-ruscogenin (472-11-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O / 24 h / 37 °C / almond emulsin 2: pyridine; dioxane / 7 h / 80 °C 3: 2 N HCl / dioxane; H2O / 2 h / Heating View Scheme

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + (25S)-ruscogenin (35882-30-5) → (25R)-ruscogenin (472-11-7)

(25R)-ruscogenin (472-11-7) → 25(R,S)-spirost-5-en-1β,3β,7β-triol

Conditions	Yield
With hydrogenchloride; dipotassium hydrogenphosphate; 2,3,4,5,6-pentahydroxy-hexanal; sodium chloride In water; dimethyl sulfoxide at 120℃; pH=7; Autoclave; Microbiological reaction;

(25R)-ruscogenin (472-11-7) → 25(R,S)-spirost-5-en-1β,3β,7β,12β-tetraol

Conditions	Yield
With hydrogenchloride; dipotassium hydrogenphosphate; 2,3,4,5,6-pentahydroxy-hexanal; sodium chloride In water; dimethyl sulfoxide at 120℃; pH=7; Autoclave; Microbiological reaction;

(25R)-ruscogenin (472-11-7) → spirost-5-ene-1-oxo-3β-ol (14414-62-1)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 2.5h; Ambient temperature;	95%
With chromium(VI) oxide; acetic acid

UDP-glucose (133-89-1) + (25R)-ruscogenin (472-11-7) → C33H52O9

Conditions	Yield
With UGT74AN1; magnesium chloride In aq. buffer at 37℃; for 12h; pH=8; Enzymatic reaction;

(25R)-ruscogenin (472-11-7) → Cholest-5-ene-1β,3β,16β,26-tetrol (79037-11-9, 79037-16-4)

Conditions	Yield
With hydrogenchloride; amalgamated zinc In ethanol for 2.5h; Heating;	33%

(25R)-ruscogenin (472-11-7) → 3β-acetoxyspirost-5-ene-1-one (90802-64-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation View Scheme
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; aqueous acetic acid View Scheme

(25R)-ruscogenin (472-11-7) → (20S,22R,25R)-1α,3β-diacetoxyspirost-5-ene (861674-94-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 72 percent / acetylation View Scheme
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 72 percent / acetylation View Scheme

(25R)-ruscogenin (472-11-7) → C41H58O8S2

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme

(25R)-ruscogenin (472-11-7) → cholest-5-ene-1α,16β-diol (79037-09-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme

(25R)-ruscogenin (472-11-7) → cholest-5-ene-1α,3β,16β-triol (79037-10-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme

(25R)-ruscogenin (472-11-7) → cholest-5-ene-1α,3β,16β,26-tetrol (79037-11-9, 79037-16-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating View Scheme
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating View Scheme

(25R)-ruscogenin (472-11-7) → (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene (79037-17-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h View Scheme

(25R)-ruscogenin (472-11-7) → 1α,16β-diacetoxycholest-5-ene (79037-01-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether 5: 80 percent View Scheme
Multi-step reaction with 6 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether 6: 80 percent View Scheme

(25R)-ruscogenin (472-11-7) → Toluene-4-sulfonic acid (2R,6R)-2-methyl-6-((1S,3R,8S,9S,10R,13S,14S,16S,17R)-1,3,16-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-heptyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C, View Scheme

(25R)-ruscogenin (472-11-7) → 1α,3β,16β-triacetoxycholest-5-ene (79037-02-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme
Multi-step reaction with 6 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether View Scheme

(25R)-ruscogenin (472-11-7) → 1α,3β,16β,26-tetraacetoxycholest-5-ene (79037-03-9, 79037-08-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature 3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 4: 87 percent View Scheme
Multi-step reaction with 5 steps 1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 87.5 percent / acetylation 3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h 4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating 5: 87 percent View Scheme

(25R)-ruscogenin (472-11-7) → cholest-5-ene-1β,3β-diol (63908-96-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 33 percent / amalgamated Zn, HCl / aq. ethanol / 2.5 h / Heating 2: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether 3: 0.158 g / pyridine 4: 0.544 g / pyridine / 0 °C 5: 0.346 g / LAH / diethyl ether / Heating View Scheme

Upstream product

• 201858-23-3 3β-O-tert-butyldimethylsilyl-(25R)-ruscogenin 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 35882-30-5 25(S) ruscogenin 
• 14414-62-1 spirost-5-ene-1-oxo-3β-ol 
• 39491-38-8 alliospiroside A 
• 17676-33-4 spirosta-5(6),25(27)-diene-1β,3β-diol 
• 105798-62-7 alliofuroside A 
• 105822-00-2 22-O-methyl ether of alliofuroside A 
• 87425-34-1 25(S)-ruscogenin 1-O-β-D-fucopyranosido-3-O-α-L-rhamnopyranoside 
• 87436-70-2 25(S)-ruscogenin 3-O-L-rhamnopyranoside 
• 38971-41-4 25(S)-ruscogenin 1-O-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 87436-70-2 ruscogenin 3-O-α-L-rhamnopyranoside 
• 87425-36-3 ruscogenin 3-O-β-D-glucopyranosyl(1->3)-α-L-rhamnopyranoside 

Downstream Products

• 6155-50-6 ruscogenin acetate 
• 79037-17-5 (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene 
• 79037-07-3 1β,3β,16β,26-tetrabenzoyloxycholest-5-ene 
• 79037-04-0 1β,3β,16β-tribenzoyloxycholest-5-ene 
• 79037-12-0 C₄₂H₅₆O₇S 
• 79037-13-1 1β,3β-dibenzoyloxycholest-5-ene-16β-ol 
• 35882-30-5 25(S) ruscogenin 
• 6155-50-6 25(S)-ruscogenin 1,3-diacetate 
• 6155-50-6 25(S)-ruscogenin diacetate 

Relevant articles and documents

Synthesis of (25R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)- [β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside

The synthesis of (25R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)- [β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, a saponin from the tuber of Liriope muscari (Decne.) Bailey, is described.

A SPIROSTANOL GLYCOSIDE FROM THE RHIZOMES OF OPHIOPOGON INTERMEDIUS

A new ruscogenin glycoside has been characterized from the rhizomes of Ophiopogon intermedius.Key Word Index - Ophiopogon intermedius; Haemodoraceae; rhizomes; spirostanol glycoside; ruscogenin; spermicidal potential.

First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an Ophiopogonis saponin from the tuber of Liriope muscari (Decne.)

The first total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside (1), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of Liriope muscari (Decne.), is described. The glycosylation of a highly hindered alcohol by Schmidt's 'inverse procedure' is demonstrated.

Steroidal glycosides from the bulbs of Ornithogalum thyrsoides

Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.