Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)- 8-O-Debutanoylthapsigargin

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In spite of the impressing cytotoxicity of thapsigargin (Tg), this compound cannot be used
as a chemotherapeutic drug because of general toxicity, causing unacceptable side effects. Instead,
a prodrug targeted towards tumors, mipsagargin, was brought into clinical trials. What substantially
reduces the clinical potential is the limited access to Tg and its derivatives and cost-inefficient syntheses
with unacceptably low yields. Laser trilobum, which contains a structurally related sesquiterpene
lactone, trilobolide (Tb), is successfully cultivated. Here, we report scalable isolation of Tb from
L. trilobum and a transformation of Tb to 8-O-(12-aminododecanoyl)-8-O-debutanoylthapsigargin
in seven steps. The use of cultivated L. trilobum offers an unlimited source of the active principle
in mipsagargin.
Original languageEnglish
Article number1640
Number of pages11
Publication statusPublished - 2020

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