11-Deoxojervine, A New Alkaloid from <i>Veratrum</i> Species

Masamune, Tadashi; Mori, Yoichi; Takasugi, Mitsuo; Murai, Akio; Ohuchi, Shigehiro; Satô, Norio; Katsui, Nobukatsu

doi:10.1246/bcsj.38.1374

Cited by 62 publications

(27 citation statements)

References 14 publications

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“…35 While synthetic studies by Johnson et al 36 and Masamune et al . 37 in the 1960s provided approaches towards cyclopamine ( 9 ), it was not until 2009 that Giannis and co-workers provided its expedient, biomimetic total synthesis (Scheme 2b). 25 Starting with dehydro- epi -androsterone ( 46 ), benzyl protection and condensation gave the 2-picolylimine directing group (Schönecker directing group) 33 on 52 .…”

Section: Steroid-alkaloidsmentioning

confidence: 99%

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

Cherney

Baran

2011

Israel Journal of Chemistry

101

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Terpenes and alkaloids are ever-growing classes of natural products that provide new molecular structures which inspire chemists and possess a broad range of biological activity. Terpenoid-alkaloids originate from the same prenyl units that construct terpene skeletons. However, during biosynthesis, a nitrogen atom (or atoms) is introduced in the form of β-aminoethanol, ethylamine, or methylamine. Nitrogen incorporation can occur either before, during, or after the cyclase phase. The outcome of this unique biosynthesis is the formation of natural products containing unprecedented structures. These complex structural motifs expose current limitations in organic chemistry, thus providing opportunities for invention. This review focuses on total syntheses of terpenoid-alkaloids and unique issues presented by this class of natural products. More specifically, it examines how these syntheses relate to the way terpenoid-alkaloids are made in Nature. Developments in chemistry that have facilitated these syntheses are emphasized, as well as chemical technology needed to conquer those that evade synthesis.

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Section: Steroid-alkaloidsmentioning

confidence: 99%

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

Cherney

Baran

2011

Israel Journal of Chemistry

101

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“…The anhydrous alcoholic extract (1.25 g) and total alkaloids (82 mg) and 10 isolates were prepared by the method reported previously (Tang et al, 2008b). The chloroform extract (125 g) was submitted to silica gel and Sephadex LH-20 column chromatography, to yield cyclopamine (1) (18 mg) (Masamune et al, 1965), veratramine (2) (107 mg) (Tezuka et al, 1998) and jervine (3) (84 mg) (Tezuka et al, 1998), 3, 15-diangeloylgermine (4) (41 mg) (Yang et al, 1987), 3-angeloylzygadenine (5) (105 mg) (Zhao et al, 1989), and 3-veratroylzygadenine (6) (62 mg,) (Bondarenko, 1985), 15-angeloylgermine (7) (59 mg) (Zhou et al, 1999). The ethyl acetate extract (152 g) was purifi ed over the silica gel, polyamide and Sephadex LH-20 column chromatography to give germine (8) (26 mg) (El Sayed et al, 1996), veratrosine (9) (57 mg) (Quan et al, 2003) and pseudojevine (10) (15 mg) (Atta-ur-Rahman et al, 1996).…”

Section: Preparation Of Samples the Powdered Rhizomes Ofmentioning

confidence: 99%

Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum

Tang

Shen

et al. 2010

Phytotherapy Research

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Ten steroidal alkaloids - cyclopamine, veratramine, jervine, 3, 15-diangyloylgermine, 3-angyloylzygadenine, 3-veratroyl zygadenine, 15-veratroylgermine, germine, veratrosine and pseudojervine - from Veratrum dahuricum, together with the ethanol extract and total alkaloids, were evaluated for their antitumor and antiplatelet activities. Cyclopamine, veratramine and germine significantly inhibited the hedgehog pathway in NIH/3T3 cells. Cyclopamine exerted a potent inhibitory effect against the growth of PANC-1 tumors in mice, with inhibition rates of 40.64%, 44.37%, 46.77% at doses of 5.0, 15.0 and 50.0 mg kg-1, respectively. Veratroylgermine was found to produce the strongest inhibition against the platelet aggregation induced by arachidonic acid, with inhibition rate of 92.0% at 100 microM.

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“…it was decided to extend the above strategy to encompass some of the more oxygenated Veratrum alkaloids and .5a,6-dihydroveratramine (56) became the target compound. Since the latter had already been converted to veratramine (14) (13), jenine (32) (14,15), veratrobasine (33) (15,16), and 11-deoxojervine (34) (17), a synthesis of this intermediate represents in a formal sense the total synthesis of these natural products.…”

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confidence: 99%

Synthetic Studies in the Veratrum Alkaloid Series. II. The Total Synthesis of Verarine, Veratramine, Jervine, and Veratrobasine

Kutney¹,

Cable²,

Gladstone³

et al. 1975

Can. J. Chem.

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Coupling of 3β-acetoxy-5α-etiojerv-12(13)-en-17-one (1) with the lithio derivative of 2-ethyl-5-methylpyridine provides the crucial intermediate (3) for the subsequent elaboration to verarine. Aromatization of 3 to 4 and reduction of the latter provides a mixture from which N-acetyl-5α,6-dihydroverarine (11) was isolated. Subsequent introduction of the 5,6-double bond in the latter and removal of the N-acetate function completed the synthesis of verarine (31). In a similar sequence of reactions employing 1 and the lithio derivative of 2-ethyl-3-methoxy-5-methyl-pyridine, the resultant intermediate (54), was elaborated to 5α,6-dihydroveratramine (56). Due to known conversions of the latter to veratramine (14), jervine (32), veratrobasine (33), and 11-deoxojervine (34), the formal total synthesis of these natural products is complete.

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11-Deoxojervine, A New Alkaloid from Veratrum Species

Cited by 62 publications

References 14 publications

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum

Synthetic Studies in the Veratrum Alkaloid Series. II. The Total Synthesis of Verarine, Veratramine, Jervine, and Veratrobasine

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