Isolation and characterization of auronlignan derivatives with hepatoprotective and hypolipidemic activities from the fruits of Hippophae rhamnoides L.

Abstract

The fruit of Hippophae rhamnoides L. is not only used as delicious food with nutritional values, but also served as traditional Chinese medicine with multiple bioactivities. In order to find...

Hippophae rhamnoides L.: A Comprehensive Review on the Botany, Traditional Uses, Phytonutrients, Health Benefits, Quality Markers, and Applications

“…There are also lignan derivatives combined with other natural products, and they are the important chemical components in H. rhamnoides L. Up to now, there are 2 kinds of lignans isolated from H. rhamnoides L., including flavonolignans ( 100 – 123 ) and auronlignans ( 124 – 143 ). These compounds were identified as ( E )-2-(4-hydroxyphenyl)-3-hydroxy-8-isopentenol-4″,5″-dimethoxyphenyl-9″-(4‴,5‴-dimethylallyl)­dipyranoxanthene-4,10″-dione ( 100 ), 2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxy-12,13-dimethylchromene-3″,4″,5″-trimethoxyphenyl-8″-(4‴,5‴-dimethylallyl)-dipyranoxanthene-4,9″-dione ( 101 ), 2-(4′-hydroxy-3′,5′-dimethoxyphenyl)-3,7-dihydroxy-8-(12,13-dimethylbutan-10-one)-7″-(4″-methoxyphenyl)-8″-(4‴,5‴-dimethylallyl)-dipyranoxanthene-4,9″-dione ( 102 ), 2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxy-8-(13,14-dimethylfuran-12-one)-4″,5″-dimethoxyphenyl-9″-(4‴,5‴-dimethylallyl)-dipyranoxanthene-4,10″-dione ( 103 ), 2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxy-7,8-furan-10-isopropanol-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione ( 104 ), 2-(4′-hydroxy-3′,5′-dimethoxyphenyl)-3-hydroxy-12,13-dimethylchromene-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione ( 105 ), ( E )-2-(4′-hydroxy-3′,5′-dimethoxyphenyl)-3,7-dihydroxy-8-isopropenylated-isobutyrate-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione ( 106 ), 2-(4′-hydroxyphenyl)-3,7-dihydroxy-8-(12,13-dimethylallyl)-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione ( 107 ), ( E )-2-(4′-hydroxy-3′,5′-dihydroxyphenyl)-3,7-dihydroxy-8-geranyl-3″,4″-dihydroxyphenyl-pyrano-chromene-4,7″-dione ( 108 ), ( E )-2-(4′-hydroxy-3′-hydroxyphenyl)-3,7-dihydroxy-8-geranyl-3″,4″-dioxolophenylpyranochromene-4,7″-dione ( 109 ), ent-mururin A ( 110 ), mururin A ( 111 ), mururin B ( 112 ), ent-vaccinin A ( 113 ), silybin A ( 114 ), silybin B ( 115 ), hydnocarpin D ( 116 ), 5′-methoxyhydnocarpin D ( 117 ), vaccinin A ( 118 ), cinchonain Ia ( 119 ), cinchonain Ib ( 120 ), 2,3-dehydrosily christin ( 121 ), silychristin A ( 122 ), silychristin B ( 123 ), 3,3′,4‴,6,6″-tetrahydroxy-7‴′,8‴′-(4‴′-hydroxy-1‴′-cinnamyl alcohol)-10,10″-biauronlignan ( 124 ), 3′,4‴,6,6″-tetrahydroxy-7‴′,8‴′-(4‴′-hydroxy-5‴′-methoxy-1‴′-cinnamyl alcohol)-10, 10″-biauronlignan ( 125 ), 3′,4‴,6,6″-tetrahydroxy-4′-(4‴′-hydroxy-3‴′,5‴′-dimethoxy-1‴′-cinnamyl alcohol)-10,10″-biauronlignan ( 126 ), 3′,6-dihydroxy-7-prenyl-7‴,8‴-(4‴-hydroxy-1‴-cinnamyl alcohol)-10-(4″-hydroxy-benzyl)-auronlignan ( 127 ), 3′-hydroxy-6,7-(14,15-dimethyl-11-cyclohexanone)-7‴,8‴-(4‴-hydroxy-5‴′-methoxy-1‴-cinnamyl alcohol)-10-(4″-hydroxy-benzyl)-auronlignan ( 128 ), 3′/5′/6-trihydroxy-7-(14,15-dimethylbutan-12-one)-4′-(4‴-hydroxy-3‴,5‴-methoxy-1‴-cinnamyl alcohol)-10-(4″-hydroxy-benzyl)-auronlignan ( 129 ), 3′,6-dihydroxy-7-prenyl-7‴,8‴-(4‴-hydroxy-1‴-cinnamyl alcohol)-10- O -β- d -glucopyranosyl-auronlignan ( 130 ), 3′-hydroxy-6,7-(14,15-dimethylchromeneprenyl)-7‴,8‴-(4‴-hydroxy-5‴′-methoxy-1‴-cinnamyl alcohol)-10- O - β- d -glucopyranosyl-auronlignan ( 131 ),…”

“…These compounds were identified as (E)-2-(4-hydroxyphenyl)-3-hydroxy-8-isopentenol-4″,5″-dimethoxyphenyl-9″-(4‴,5‴-dimethylallyl)dipyranoxanthene-4,10″-dione (100), 47 2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxy-12,13-dimethylchromene-3″,4″,5″-trimethoxyphenyl-8″-(4‴,5‴-dimethylallyl)-dipyranoxanthene-4,9″-dione (101), 47 2-(4′-hydroxy-3′,5′dimethoxyphenyl)-3,7-dihydroxy-8-(12,13-dimethylbutan-10one)-7″-(4″-methoxyphenyl)-8″-(4‴,5‴-dimethylallyl)-dipyranoxanthene-4,9″-dione (102), 47 2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxy-8-(13,14-dimethylfuran-12-one)-4″,5″-dimethoxyphenyl-9″-(4‴,5‴-dimethylallyl)-dipyranoxanthene-4,10″-dione (103), 47 2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxy-7,8-furan-10-isopropanol-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione (104), 47 2-(4′-hydroxy-3′,5′-dimethoxyphenyl)-3-hydroxy-12,13-dimethylchromene-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione (105), 47 (E)-2-(4′-hydroxy-3′,5′-dimethoxyphenyl)-3,7-dihydroxy-8-isopropenylated-isobutyrate-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione (106), 47 2-(4′-hydroxyphenyl)-3,7-dihydroxy-8-(12,13-dimethylallyl)-1″,5″-isopropylpentenonepyranochromene-2″,4,6″-trione (107), 47 (E)-2-(4′-hydroxy-3′,5′dihydroxyphenyl)-3,7-dihydroxy-8-geranyl-3″,4″-dihydroxyphenyl-pyrano-chromene-4,7″-dione (108), 47 (E)-2-(4′-hydroxy-3′-hydroxyphenyl)-3,7-dihydroxy-8-geranyl-3″,4″-dioxolophenylpyranochromene-4,7″-dione (109), 47 ent-mururin A (110), 47 mururin A (111), 47 mururin B (112), 47 ent-vaccinin A (113), 47 silybin A (114), 47 silybin B (115), 47 hydnocarpin D (116), 47 5′-methoxyhydnocarpin D (117), 47 vaccinin A (118), 47 cinchonain Ia (119), 47 cinchonain Ib (120), 47 2,3dehydrosily christin (121), 47 silychristin A (122), 47 silychristin B (123), 47 48 aulacomnium-biaureusidin (139), 48 altilisin H (140), 48 altilisin J (141), 48 7,2′,5′trihydroxy-8-prenylaurone (142), 48 and damaurone C (143). 48 Among them, compounds …”

Study of the influence of stratification on germination of sea buckthorn seeds (Hippophae rhamnoides L.) in the conditions of the Moscow region

“…Hippophae rhamnoides L. is one of the most economically valuable species of the Loch family (Elaeagnaceae), which is widely used for reclamation of disturbed lands and improvement of soil fertility [3][4][5][6][7][8][9].…”

A Comprehensive Review on Extraction, Structure, Detection, Bioactivity, and Metabolism of Flavonoids from Sea Buckthorn (Hippophae rhamnoides L.)

“…Sea buckthorn (Hippophae rhamnoides L.) belongs to the Elaeagnaceae family [1]. It is not only used as a favorite fruit with rich nutrients but also served as a medicinal plant with multiple medical functions of invigorating spleen, relieving cough, eliminating food, eliminating phlegm, dispersing blood stasis, and promoting blood circulation [2].…”

“…Te favonoids(1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) were isolated from sea buckthorn (Hippophae rhamnoides L.).…”