Über Podophyllin

Borsche, W.; Niemann, J.

doi:10.1002/jlac.19324940113

Cited by 32 publications

(12 citation statements)

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“…Podophyllic acid showed impressive in vitro activity against ovarian and melanoma cell lines [23], furthermore, the biotransformation product could be used as a leading compound to synthesize its hydrazide derivates with stronger anti-cancer and antioxidative activity [24,25]. It has been reported that podophyllic acid could be prepared from podophyllotoxin by chemical transformation [26,27]. However, it is the first time that podophyllotoxin was transformed into podophyllic acid by biotransformation in this work.…”

Section: Introductionmentioning

confidence: 89%

Novel biotransformation process of podophyllotoxin to produce podophyllic acid and picropodophyllotoxin by Pseudomonas aeruginosa CCTCC AB93066. Part I: Process development

Tang

Zhong

2008

Bioprocess Biosyst Eng

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A novel biotransformation process of podophyllotoxin (1) to produce picropodophyllotoxin (2) and podophyllic acid (3) was developed in this work. Eight bacteria which could modify the structure of podophyllotoxin were screened out from the tested fourteen bacteria. The highest conversion of podophyllotoxin (i.e., 70.2 +/- 8.0%) was obtained when Pseudomonas aeruginosa CCTCC AB93066 was used as biocatalyst, so P. aeruginosa was selected as a typical biocatalyst in the following study. Product (2) and (3) were separated through D312 macroporous resin and sephadex LH-20 gel column chromatograph. On the basis of (1)H NMR, (13)C NMR, ESI-MS and Elemental Analysis, product (2) and (3) were identified as picropodophyllotoxin (2) and podophyllic acid (3), respectively. This suggested the site-specific isomerization and hydrolization of podophyllotoxin occurred during its biotransformation process by P. aeruginosa. For the first time, podophyllotoxin was biotransformed into its hydrolytic derivate (i.e., podophyllic acid).

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Section: Introductionmentioning

confidence: 89%

Novel biotransformation process of podophyllotoxin to produce podophyllic acid and picropodophyllotoxin by Pseudomonas aeruginosa CCTCC AB93066. Part I: Process development

Tang

Zhong

2008

Bioprocess Biosyst Eng

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“…The isolation of the most abundant active principle, podophyllotoxin (▶ Fig. 1), in the 1880s was first reported by Podwyssotzki [74], though it was not until 1932 that the base structure was reported by Borsche and Niemann [75]. Podophyllotoxin was reported to have antitumor, antiviral, insecticidal, and anti-inflammatory activities, and based on these activities, two of the many semisynthetic derivatives, etoposide (VM 26) and teniposide (VP 16-213) (▶ Fig.…”

Section: Podophyllotoxinmentioning

confidence: 99%

Plant Endophytes and Epiphytes: Burgeoning Sources of Known and “Unknown” Cytotoxic and Antibiotic Agents?

Newman¹,

Cragg²

2020

Planta Med

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In the last 20 or so years, the influence of endophytes and, quite recently, epiphytes of plants upon the compounds found in those plants, which were usually assumed to be phytochemicals produced by the plant for a variety of reasons, often as a defense against predators, is becoming more evident, in particular in the case of antitumor agents originally isolated from plant sources, though antibiotic agents might also be found, particularly from epiphytes. In this review, we started with the first report in 1993 of a taxol-producing endophyte and then expanded the compounds discussed to include camptothecin, the vinca alkaloids, podophyllotoxin, and homoharringtonine from endophytic microbes and then the realization that maytansine is not a plant secondary metabolite at all, and that even such a well-studied plant such as Arabidopsis thaliana has a vast repertoire of potential bioactive agents in its leaf epiphytic bacteria. We have taken data from a variety of sources, including a reasonable history of these discoveries that were not given in recent papers by us, nor in other papers covering this topic. The sources included the Scopus database, but we also performed other searches using bibliographic tools, thus, the majority of the papers referenced are the originals, though we note some very recent papers that have built on previous results. We concluded with a discussion of the more modern techniques that can be utilized to “persuade” endophytes and epiphytes to switch on silent biosynthetic pathways and how current analytical techniques may aid in evaluating such programs. We also comment at times on some findings, particularly in the case of homoharringtonine, where there are repetitious data reports differing by a few years claiming the same endophyte as the producer.

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“…,, 64, 4 ,, 5,3 ,, 29,6 ,, 28,9% 6.2. Epipodophyllotoxin-methyllither (22). Die wie unter 6.1. durchgefuhrte Methylierung von Gef.…”

Section: Uberfiihrung Von Podophyllotoxin In Die Verbindungen 1 Und 3unclassified

“…163-165" 11) Fruhere Bezcichnung : Desoxypikrosikkimotoxin [6].(Zers. ), rollD = -103" (Alkohol)[22].…”

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Zur Struktur des Sikkmotoxins II. Partialsynthese der 6,7‐Dimethoxy‐Analogen von Podophyllotoxin, Epi‐, Neo‐ und Desoxy‐podophyllotoxin 17. Mitteilung über mitosehemmende Naturstoffe [1]

Schreier

1964

Helvetica Chimica Acta

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Im Verlaufe unserer Arbeiten uber Struktur-Wirkungsbeziehungen auf dem Gebiet der Podophyllum-Lignane haben sich Befunde ergeben, die starke Zweifel an der Richtigkeit der fur Sikkimotoxin [ Z ] , einen Inhaltsstoff von PodoPhyllum szkkimensis CHATTER JEE et MUKER JEE [3], vorgeschlagenen Struktur 1 [4] [5] aufkommen lassen. In einer ersten Publikation [6] haben wir bereits auf Unterschiede hingewiesen, die zwischen natiirlichen und synthetischen Produkten aus der Sikkimotoxin-Reihe festgestellt worden waren. Von den seinerzeit synthetisch hergestellten Lignanlactonen sollte das von uns mit (-)-Pikrosikkimotoxin benannte 6,7-Dimethoxy-Analoge des Pikropodophyllins der gesicherten Struktur 2 mit dem aus naturlichem Sikkimotoxin durch Basenkatalyse gebildeten Epimerisierungsprodukt, dem Isosikkimotoxin von CHATTER JEE & CHAKRAVARTI [4], identisch sein. Beim Vergleich des synthetischen Pikrosikkimotoxins und seines Acetylderivats mit Isosikkimotoxin und Acetylisosikkimotoxin zeigten sich jedoch bedeutende Unter-OH OH 1) Dic Zahlen in eckigcn Klammcrn verweiscn auf das Literaturverzeichnis, S. 1555.

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Über Podophyllin

Cited by 32 publications

References 1 publication

Novel biotransformation process of podophyllotoxin to produce podophyllic acid and picropodophyllotoxin by Pseudomonas aeruginosa CCTCC AB93066. Part I: Process development

Novel biotransformation process of podophyllotoxin to produce podophyllic acid and picropodophyllotoxin by Pseudomonas aeruginosa CCTCC AB93066. Part I: Process development

Plant Endophytes and Epiphytes: Burgeoning Sources of Known and “Unknown” Cytotoxic and Antibiotic Agents?

Zur Struktur des Sikkmotoxins II. Partialsynthese der 6,7‐Dimethoxy‐Analogen von Podophyllotoxin, Epi‐, Neo‐ und Desoxy‐podophyllotoxin 17. Mitteilung über mitosehemmende Naturstoffe [1]

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