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Formation of Triterpenoids throughout Olea europaea Fruit Ontogeny

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Lipids

Abstract

Drupes were handpicked from olive (Olea europaea L.) trees, cv chemlali, at 13 distinct stages of fruit development, referred to as weeks after flowering (WAF), and analyzed for their free and esterified sterols and triterpenoids content. These two classes of compounds are synthesized via the acetate/mevalonate pathway and share common precursors up to oxidosqualene (OS). Cyclization of OS in either cycloartenol or β-amyrin constitutes a branch point between primary (sterol pathway) and secondary (triterpenoid pathway) metabolisms. At the onset of fruit development, i.e., between 12 and 18 WAF, drupes were found to contain high amounts of α- and β-amyrins as well as more-oxygenated compounds such as triterpenic diols (erythrodiol and uvaol) and acids (oleanolic, ursolic and maslinic acids). Concomitantly, sterol precursors were barely detectable. From 21 WAF, when the olive fruit reached its final size and began to turn from green to purple, α- and β-amyrins were no longer present, while 4,4-dimethyl- and 4α-methylsterols started to be formed, indicating a redirection of the carbon flux from the triterpenoid pathway towards the sterol pathway. Between 21 and 30 WAF, sterol end products, mainly represented by sitosterol, progressively accumulated and triterpenic diols were replaced by triterpenic acids, essentially maslinic acid. Interestingly, the developing olive fruit was found to accumulate significant amounts of parkeol as an ester conjugate. Whatever the stage of development, triterpenoids represent the major triterpenic compounds of the olive fruit.

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Abbreviations

βAS:

β-Amyrin synthase

CAS:

Cycloartenol synthase

HPTA:

Hydroxy pentacyclic triterpenic acid

OS:

Oxidosqualene

RRT:

Relative retention time

TAG:

Triacylglycerol

WAF:

Week after flowering

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Acknowledgment

We thank Prof. Z. Mighri (Faculté des Sciences, Monastir, Tunisia) for providing us with an authentic sample of maslinic acid and Dr. Pierrette Bouvier-Navé (IBMP, Strasbourg, France) for critical analysis of the work.

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Authors and Affiliations

  1. Département des Isoprénoïdes, Institut de Biologie Moléculaire des Plantes (CNRS UPR 2357), 28 rue Goethe, 67083, Strasbourg Cedex, France

    Marie-Andrée Hartmann

  2. Laboratoire de Biochimie des Lipides, Faculté des Sciences, 1060, Tunis, Tunisia

    Naïm Stiti & Saïda Triki

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  1. Naïm Stiti
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  2. Saïda Triki
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  3. Marie-Andrée Hartmann
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Correspondence to Marie-Andrée Hartmann.

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Part of this work was presented at the 97th Annual Meeting of the AOCS in Saint Louis, Missouri, April 30–May 3, 2006.

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Stiti, N., Triki, S. & Hartmann, MA. Formation of Triterpenoids throughout Olea europaea Fruit Ontogeny. Lipids 42, 55–67 (2007). https://doi.org/10.1007/s11745-006-3002-8

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