Withanolides from Aureliana fasciculata var. fasciculata

Abstract

In the first phytochemical study of the Aureliana genus (Solanaceae), two new withanolides, 1 and 2, together with two known sterols, were isolated from the MeOH extract of the leaves of Aureliana fasciculata var. fasciculata. The structures were established as (4S,22R)-16a-acetoxy-5b,6b-epoxy-4b,17a-dihydroxy-1-oxowitha-2,24-dienolide (aurelianolide A) and (4S,22R)-16a-acetoxy-4b,17a-dihydroxy-1-oxowitha-2,5,24-trienolide (aurelianolide B). The new compounds possessed the unusual 16a,17a-dioxygenated group and were fully characterized by spectroscopic techniques, including 1 H-and Introduction. -The withasteroids comprise a group of naturally occurring C 28 -steroids characterized by an unaltered or a modified ergostane skeleton with a lactone or potential lactone ring in the C 9 side chain [1]. The most abundant type is designated usually as withanolide, and these compounds possess an a,b-unsaturated d-lactone ring in the side chain of the molecule. These steroid derivatives are frequently polyoxygenated, and biogenetic transformations can produce highly modified structures, both in the steroid nucleus and in the side chain, such as physalins, withaphysalins, acnistins, withanolides, ixocarpalactones, and perulactones [2]. To date, over 400 withasteroids have been reported which are restricted in distribution to the plant family Solanaceae occurring primarily in ca. 20 genera [1] [2]. However, the occurrence of steroidal lactones is not completely restricted to Solanaceae, whereas these compounds have also been found in soft coral from Minabea sp.

Antiproliferative withanolides from the Solanaceae: A structure–activity study

“…Over the last 46 years, approximately 750 withanolides, exhibiting more than 22 carbon skeletons (Figure 2), have been reported from various plant sources. As listed in Table 1, withanolides are predominant in 25 genera (including Acnistus , Datura , Deprea , Discopodium , Dunalia , Iochroma, Jaborosa , Lycium , Nicandra , Physalis , Solanum , Trechonaetes , Tubocapsicum , Vassobia , Withania and Witheringia ) of the Solanaceae family [2—7, 10—12]. Not limited to the Solanaceae, withanolides have also been isolated from a smaller number of species in the Dioscoreaceae [13], Fabaceae [7], Lamiaceae [2], Myrtaceae [14], Taccaceae [2], and from two genera in the marine Alcyoniidae [15, 16].…”

Antiproliferative withanolides from the solanaceae: A structure-activity study

“…2), have been reported from various plant sources. As listed in Table 1, withanolides are predominant in 25 genera (including Acnistus, Datura, Deprea, Discopodium, Dunalia, Iochroma, Jaborosa, Lycium, Nicandra, Physalis, Solanum, Trechonaetes, Tubocapsicum, Vassobia, Withania, and Witheringia) of the Solanaceae family [2][3][4][5][6][7][10][11][12]. Not limited to the Solanaceae, withanolides have also been isolated from a smaller number of species in the Dioscoreaceae [13], Fabaceae [7], Lamiaceae [2], Myrtaceae [14], Taccaceae [2], and from two genera in the marine Alcyoniidae [15,16].…”

Athenolide A, a New Steroidal Lactone from the Leaves of Athenaea martiana (Solanaceae) Determined by Means of HPLC‐HR‐MS‐SPE‐NMR Analysis

“…[8] This chemotaxonomic information is in agreement with previous phytochemical studies of the genus Aurealina, which reported the isolation of withanolides. [7] Similarly, here we describe the structural elucidation of athenolides in the genus Athenaea. Therefore, in this study, the phytochemical study of A. martiana supported its positon in the subfamily Solanoideae as well as the chemical relationships between the Athenaea and Aureliana genera by the occurrence of steroidal lactones.…”

“…[2] [3] The taxonomic knowledge of the Athenaea genus has been the subject of several reviews, [4 -6] and recently botanical studies suggested the re-evaluation of the generic status of this genus as a synonym of Aureliana. [1] [3] Previous phytochemical investigations of species of the genus Aureliana led to identification of withanolides, [7] whereas there are no studies of Athenaea species. Withanolides are a class of naturally occurring C(28) steroidal lactones structurally based on the ergostane-type skeleton, and recognized as chemotaxonomy markers of Solanaceae.…”