Cycloartanes from the gum resin of Gardenia gummifera L.f.

The gum resin exuding from the leaf buds of Gardenia gummifera was investigated. Eight new cycloartane triterpenes, 1-6, 8, and 10, together with two known triterpenes, 25-hydroxycycloart-23-en-3-one (7) and cycloartenone (9), were isolated and identified by extensive NMR spectroscopy. For cycloartenone (9), full NMR assignments are given as these data were not available in the literature. Eight compounds possess a C(3)=O group, two are 3,4-secocycloartanes bearing a free C(3)OOH group; in one of the cycloartanes, gummiferartane-9 (10), ring A occurs as a seven-membered lactone.

Differentiating the gum resins of two closely related Indian Gardenia species, G. gummifera and G. lucida, and establishing the source of dikamali gum resin using high-performance thin-layer chromatography and ultra-performance liquid chromatography-UV/MS.

Dikamali is a gum resin obtained from the leaf buds of Gardenia lucida or G. gummifera. There is controversy regarding the botanical source of this gum resin with some stating it to be from G. lucida while others claim it to be from G. gummifera. Analytical methods including UPLC and HPTLC were developed for the qualitative analysis of Gardenia species and various commercial samples. The separation using a UPLC method was achieved within 12.0 min by using C18 column material, a water/acetonitrile mobile phase, both containing formic acid, a gradient system, and a temperature of 40 degrees C. Extensive studies of dikamali collected from various parts of India in comparison with the gum resins collected from G. lucida and G. gummifera clearly indicated that the botanical source of commercially available dikamali is G. lucida, not G. gummifera. The marker compounds isolated from a market sample of dikamali were present only in the gum resin of G. lucida and the compounds isolated from G. gummifera were not present in any of the dikamali samples, confirming the botanical source of dikamali. This work is of utmost importance, given the ambiguity regarding the botanical source of the gum resin dikamali. LC/MS coupled with electrospray ionization is described for the identification and confirmation of nine compounds from various samples of the gum resin. An HPTLC method was also developed for the fast chemical fingerprint analysis of Gardenia samples.