A new 3,4-seco-lupane derivative from Lasianthus gardneri

Sabrina Dallavalle; Lalith Jayasinghe; B M M Kumarihamy; Lucio Merlini; Loana Musso; Leonardo Scaglioni

doi:10.1021/np030374g

A new 3,4-seco-lupane derivative from Lasianthus gardneri

J Nat Prod. 2004 May;67(5):911-3. doi: 10.1021/np030374g.

Authors

Sabrina Dallavalle¹, Lalith Jayasinghe, B M M Kumarihamy, Lucio Merlini, Loana Musso, Leonardo Scaglioni

Affiliation

¹ Dipartimento di Scienze Molecolari Agroalimentari, Università di Milano, Via Celoria 2, 20133 Milano, Italy.

PMID: 15165165
DOI: 10.1021/np030374g

Abstract

A new seco-ring A lupane triterpene derivative (1), along with lupenone, lupeol, beta-sitosterol, ursolic acid, and stigmasterol 3-O-beta-d-glucoside, were isolated from a methanol extract of mature stems of Lasianthus gardneri, a shrub from the family Rubiaceae growing in Sri Lanka. The structure and stereochemistry of the new compound were determined using a combination of (13)C and (1)H homo- and heteronuclear 2D NMR experiments and from mass spectral data. The structure of 1 was confirmed by partial synthesis from lupeol.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Glucosides / chemistry
Glucosides / isolation & purification
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pentacyclic Triterpenes
Plant Stems / chemistry
Rubiaceae / chemistry*
Sitosterols / chemistry
Sitosterols / isolation & purification
Sri Lanka
Stigmasterol / analogs & derivatives*
Stigmasterol / chemistry
Stigmasterol / isolation & purification
Triterpenes / chemical synthesis
Triterpenes / chemistry
Triterpenes / isolation & purification*
Ursolic Acid

Substances

3,4-seco-lupa-4(23),20(29)-dien-3-ol
Glucosides
Pentacyclic Triterpenes
Sitosterols
Triterpenes
lupenone
stigmasterol glucoside
gamma-sitosterol
Stigmasterol
lupeol