Die Alkaloide von Veratrum album. 2. Mitteilung<sup>1</sup>): Die einzelnen Alkaloide und ihre Beziehungen zueinander. Protoveratridin, Germerin, Protoveratrin

Poethke, W

doi:10.1002/ardp.19372750803

Cited by 21 publications

(3 citation statements)

References 9 publications

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“…Specific location at Cm, Cm, Cm is made possible by the following results. When the crude product of periodic acid oxidation of germine diacetate was exposed to dilute ammonia, an unsaturated ketone was obtained, \max 238 .µ (e 10,000); \max 2.90(s), 5.78-5.85(s), 5.92(s), 6.05( )µ. The ultraviolet spectrum of the product is incompatible with the presence of a Cm-, Cm-, Cn-triol system in germine.28 The ultraviolet spectrum is, however, compatible with two alternative enones derived from a Cm-, Cm-Cirtriol (V and VI).23 The infrared spectral V VI characteristics of the product indicate that the 8•9-14structure V is the correct one.…”

mentioning

confidence: 99%

Veratrum Alkaloids. XXVIII.¹ The Structure and Configuration of Germine^2-4

Kupchan¹,

Narayanan²

1959

J. Am. Chem. Soc.

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The alkaloid germine has been shown to have structure and configuration I. Alkaline isomerization of I leads to isogermine (XI) and thence to pseudogermine (XII). Acetic anhydride-pyridine acetylation of I affords a tetraacetate (XIII); acetylation under more vigorous conditions gives a pentaacetate (XIV). I forms an acetonide (XV) which is oxidized by periodic acid to an aldehydo--lactone (XVI) also obtained from pseudogermine acetonide (XVII); XVI yields a diacetate (XX). The oxime XIX derived from XVI also yields a diacetate (XXII). Compound XI yields an acetonide Germine undergoes a series of isomerizations (germine-isogermine-¡ pseudogermine) which parallels those of zygadenine16 and veracevine.17-19

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confidence: 99%

Veratrum Alkaloids. XXVIII.¹ The Structure and Configuration of Germine^2-4

Kupchan¹,

Narayanan²

1959

J. Am. Chem. Soc.

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“…album and V . viride , the German investigator W. Poethke was the first modern chemist to successfully purify Veratrum alkaloids of the cevanine type, 1,2 procuring the ester-alkaloids protoveratrine and germerine in addition to the alkamines germine and protoverine from the rhizomes of V. album in 1937 (Poethke 1937a, b). Poethke’s work caught the attention of researchers Lyman Craig and Walter Jacobs at the Rockefeller Institute for Medical Research in New York City, New York, who had been working on the degradation of the related alkaloid veracevine (the alkamine base of the ester alkaloids found in veratrine obtained from the seeds of S. officiale ).…”

Section: Modern Phytochemistry and Use Of Veratrum Alkaloids In The Tmentioning

confidence: 99%

Medicinal history of North American Veratrum

Chandler

McDougal

2013

Phytochem Rev

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Plants belonging to the genus Veratrum have been used throughout history for their medicinal properties. During the nineteenth and twentieth centuries, phytochemical investigations revealed a host of steroidal alkaloids in Veratrum species, some of which are potent bioactives. This review discusses Veratrum species that grow in North America with a focus on the medicinal history of these plants and the steroidal alkaloids they contain. While significant reviews have been devoted to singularly describing the plant species within the genus Veratrum (botany), the staggering breadth of alkaloids isolated from these and related plants (phytochemistry), and the intricacies of how the various alkaloids act on their biological targets (physiology and biochemistry), this review will straddle the margins of the aforementioned disciplines in an attempt to provide a unified, coherent picture of the Veratrum plants of North America and the medicinal uses of their bioactive steroidal alkaloids.

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“…Protoverine 3,6,15-triisobutyrate 7-acetate {VII). Methanolysis of (V) (1)(2)(3)(4)(5)(6)(7)(8) g) by the procedure described for the preparation of (VI) yielded (VII) (760 mg) in the form of colourless needles.…”

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confidence: 99%

Veratrum Alkaloids--XLIV. Structure-Activity Relationships in a Series of Synthetic Hypotensive Esters of Protoverine

Kupchan¹,

Hensler²,

Weaver³

1961

J. Med. Chem.

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A study aimed at further elucidation of the relationship between hypotensive activity and structure among analogs of the protoveratrines is reported. A series of synthetic protoverine tetraesters, which differ from each other only in the nature of the acid residue affixed at 6 5 , have been prepared and subjected to preliminary phatmacological evaluation. The results indicate that alteration in the structure of the ester affixed at C16 in analogs of the protoveratrines profoundly affects hypotensive potency.wo recent developments have stimulated Tstudies involving the synthesis and pharmacological evaluation of analogs of the protoveratrines. On the chemical side, our elucidation of the complete structures and configurations of protoveratrine A (I) and protoveratrine B (11) (1) and several related hypotensive ester alkaloids (2, 3) made feasible the systematic alteration of the molecules. On the clinical side, recent work has demonstrated significant differences between protoveratrine A and protoveratrine B when the substances are administered orally, particularly with regard to hypotensive-emetic relationships (4-6). Since protoveratrines A and B differ only in the nature of the ester moiety a t C3, it was deemed desirable that new protoverine (111) (7) esters, which differ from the protoveratrines solely in the nature of the acid residues, should he prepared and subjected to pharmacological evaluation.In our previous studies the compounds examined were protoverine derivatives with varying substitution a t positions 3, 4, 6, 7, 14, 15, and 16 (8-10). The results supported the following generalizations (a) esterification a t position 16 with acetate or isobutyrate is accompanied by a profound loss in activity, (b) esterification a t positions 3 and 15 is required for high activity, chain acid may be disadvantageous, (g) oxidation of the alcohol group at position 16 to a ketone group is accompanied hy a loss in activity, (lz) acetonide formation a t positions 14 and 1.5 is accompanied by a profound loss in activity, (i) esterification a t position 3 may he disadvantageous, and ( j ) considerable alteration can be made in the structure of the ester affixed a t 3 without greatly altering hypotensive potency. In view of the aforementioned facts that minor differences in the ester affixed a t 3 significantly affect the hypotensive-emetic ratio of the protoveratrines and that changes in the structure of the ester at C3 do not greatly alter hypotensive potency, it was deemed desirable that additional compounds which differ from each other only in the nature of the ester a t C15 should be prepared and subjected to pharmacological evaluation. The present report details the synthesis and preliminary pharmacological evaluation of three new analogs of the protoveratrines In the new analogs, the isohutyrate residue, previously demonstrated to he an effective suhstitute for the naturally-occurring substituted a-niethylhutyrate residues (S), is affixed a t C3 Treatment of protoverine (111) with acetone and hydrochloric ac...

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Die Alkaloide von Veratrum album. 2. Mitteilung¹): Die einzelnen Alkaloide und ihre Beziehungen zueinander. Protoveratridin, Germerin, Protoveratrin

Cited by 21 publications

References 9 publications

Veratrum Alkaloids. XXVIII.¹ The Structure and Configuration of Germine^2-4

Veratrum Alkaloids. XXVIII.¹ The Structure and Configuration of Germine^2-4

Medicinal history of North American Veratrum

Veratrum Alkaloids--XLIV. Structure-Activity Relationships in a Series of Synthetic Hypotensive Esters of Protoverine

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Die Alkaloide von Veratrum album. 2. Mitteilung1): Die einzelnen Alkaloide und ihre Beziehungen zueinander. Protoveratridin, Germerin, Protoveratrin

Cited by 21 publications

References 9 publications

Veratrum Alkaloids. XXVIII.1 The Structure and Configuration of Germine2-4

Veratrum Alkaloids. XXVIII.1 The Structure and Configuration of Germine2-4

Medicinal history of North American Veratrum

Veratrum Alkaloids--XLIV. Structure-Activity Relationships in a Series of Synthetic Hypotensive Esters of Protoverine

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Die Alkaloide von Veratrum album. 2. Mitteilung¹): Die einzelnen Alkaloide und ihre Beziehungen zueinander. Protoveratridin, Germerin, Protoveratrin

Veratrum Alkaloids. XXVIII.¹ The Structure and Configuration of Germine^2-4

Veratrum Alkaloids. XXVIII.¹ The Structure and Configuration of Germine^2-4