reticuline and higenamine

reticuline has been researched along with higenamine* in 2 studies

Other Studies

2 other study(ies) available for reticuline and higenamine

Article	Year
Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids. The Journal of organic chemistry, 2015, May-15, Volume: 80, Issue:10 A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine. Topics: Alkaloids; Benzylisoquinolines; Biological Products; Catalysis; Cyclization; Ethylamines; Isoquinolines; Molecular Structure; Organic Chemistry Phenomena; Stereoisomerism; Tetrahydroisoquinolines	2015
Inotropic effects of (+/-)-higenamine and its chemically related components, (+)-R-coclaurine and (+)-S-reticuline, contained in the traditional sino-Japanese medicines "bushi" and "shin-i" in isolated guinea pig papillary muscle. Japanese journal of pharmacology, 1989, Volume: 50, Issue:1 (+/-)-Higenamine (Hig. demethylcoclaurine) is a cardiotonic principle from aconite root. (+)-R-Coclaurine (Coc) and (+)-S-reticuline (Ret) are compounds contained in the dried buds of Magnolia salicifolia MAXIM. All of these alkaloids possess a common chemical structure: tetrahydroisoquinoline. Coc and Ret showed negative inotropic effects in contrast to the positive inotropic effects of Hig in papillary muscles of guinea pigs. Coc and Ret shifted to the right the concentration-contraction curves of Hig. Hig shifted in parallel to the left the Ca2+ curve, and it tended to shift to the left the isoproterenol (Isp)-induced response curve. In contrast, Coc and Ret inhibited the Ca2+ curve and the low concentration range of the Isp-induced curve, and it potentiated the high concentration ranges of Ca2+ and Isp. Coc and Ret showed actions that were reversed in direction to those of Hig, as clearly demonstrated in the Ca2+ curve. Topics: Alkaloids; Animals; Benzylisoquinolines; Cardiotonic Agents; Guinea Pigs; In Vitro Techniques; Isoquinolines; Male; Medicine, East Asian Traditional; Myocardial Contraction; Papillary Muscles; Plant Extracts; Stereoisomerism; Tetrahydroisoquinolines	1989

Article

Year

Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids.

The Journal of organic chemistry, 2015, May-15, Volume: 80, Issue:10

A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

Topics: Alkaloids; Benzylisoquinolines; Biological Products; Catalysis; Cyclization; Ethylamines; Isoquinolines; Molecular Structure; Organic Chemistry Phenomena; Stereoisomerism; Tetrahydroisoquinolines

2015

Inotropic effects of (+/-)-higenamine and its chemically related components, (+)-R-coclaurine and (+)-S-reticuline, contained in the traditional sino-Japanese medicines "bushi" and "shin-i" in isolated guinea pig papillary muscle.

Japanese journal of pharmacology, 1989, Volume: 50, Issue:1

(+/-)-Higenamine (Hig. demethylcoclaurine) is a cardiotonic principle from aconite root. (+)-R-Coclaurine (Coc) and (+)-S-reticuline (Ret) are compounds contained in the dried buds of Magnolia salicifolia MAXIM. All of these alkaloids possess a common chemical structure: tetrahydroisoquinoline. Coc and Ret showed negative inotropic effects in contrast to the positive inotropic effects of Hig in papillary muscles of guinea pigs. Coc and Ret shifted to the right the concentration-contraction curves of Hig. Hig shifted in parallel to the left the Ca2+ curve, and it tended to shift to the left the isoproterenol (Isp)-induced response curve. In contrast, Coc and Ret inhibited the Ca2+ curve and the low concentration range of the Isp-induced curve, and it potentiated the high concentration ranges of Ca2+ and Isp. Coc and Ret showed actions that were reversed in direction to those of Hig, as clearly demonstrated in the Ca2+ curve.

Topics: Alkaloids; Animals; Benzylisoquinolines; Cardiotonic Agents; Guinea Pigs; In Vitro Techniques; Isoquinolines; Male; Medicine, East Asian Traditional; Myocardial Contraction; Papillary Muscles; Plant Extracts; Stereoisomerism; Tetrahydroisoquinolines

1989