Artabotryols A – E, New Lanostane Triterpenes from the Seeds of Artabotrys odoratissimus

Abstract

Six new lanostane triterpenes, artabotryols A, B, C1, C2, D, and E (1, 2, 3a, 3b, 4, and 5, resp.) have been isolated from the seeds of Artabotrys odoratissimus (Annonaceae). Their structures have been established as (3a,22S,25R)-3-hydroxy-22,26-epoxylanost-8-en-26-one (1), (3a,22S,25R)-22,26-epoxylanost-8-ene-3,26-diol (2), (3a,22S,25R,26R)-26-methoxy-22,26-epoxylanost-8-en-3-ol (3a), (3a,22S,25R, 26S)-26-methoxy-22,26-epoxylanost-8-en-3-ol (3b), (3a,22S,25R)-3,22-dihydroxylanost-8-en-26-oic acid (4) and (3a,7a,11a,22S,25R)-3,7,11-trihydroxy-22,26-epoxylanost-8-en-26-one (5) by spectroscopic studies and chemical correlations. . A Chinese group recently reported the isolation of more than 30 secondary metabolites, including steroids and alkaloids, as well as two terpenoids, 24-methylenelanosta-7,9(11)-dien-3b-ol and its 3-oxo analog [10]. In the previous article, we reported the isolation of flavonol glycosides from the leaves of the plant [11]. The isolation of decaffeoylacetosides, 6-hydroxyluteolin-7-O-rutenoside, and verbascoside were reported from the seeds of this plant [12]. As a continuation of this study, we have now investigated the hexane as well as MeOH extracts of the seeds of the plant. In this article, we report the isolation and structure elucidation of six new lanostane triterpenes, named artabotryols A, B, C1, C2, D, and E (1, 2, 3a, 3b, 4, and 5, resp.).

Astraodoric Acids A–D: New Lanostane Triterpenes from Edible Mushroom Astraeus odoratus and Their Anti-Mycobacterium tuberculosis H37Ra and Cytotoxic Activity

“…The result showed that the 1 H NMR of compound 2 agreed 21 As a result, compound 2 was identified to be a C-25 epimer of 3-epi-astrahygrol named astraodorol, found for the first time in Astraeus spp. However, a similar structure had been reported as an Artabotryols A, 17 isolated from the seeds of Artabotrys odoratissimus. Therefore, compound 2 is a known compound.…”

The isolation of two new lanostane triterpenoid derivatives from the edible mushroom Astraeus asiaticus

“…1). The analysis of the above data and a comparison of the 1 H and 13 C NMR spectral data with literature, showed that compound 2 was a C-3 oxidative of the known artabotryol C1, isolated from the seeds of Artabotrys odoratissimus (Gupta et al, 2010). The correlation between HC-OMe and H-20 in NOESY suggested an R configuration at C-26.…”

“…1). Spectroscopic data suggested that 3 was a new methylation form of artabotryol D (Gupta et al, 2010). The stereochemistry at C-3, C-20, C-22 and C-25 were assigned as 3a, 22S, 25R, according to its identical 1 H and 13 C NMR data to that of artabotryol D.…”

“…The spectral data of 4 and 5 were carefully compared to some of the compounds found by Gupta et al, (2010) and the result showed that 4 was artabotryol B, which appeared as an epimers mixture. This was confirmed by selecting the relevant 1 H and 13 C NMR data, i.e, the signal that appeared at d c 101.8 and 95.2 for C-26, and d c 78.6 and 69.8 for C-22.…”

“…A modified astraodorol also exhibited the antimalarial activity that had been reported by Nasomjai et al, 2014. Further research of the bioactive chemical constituents in these genera has led to the isolation of two lanostane triterpenoids derivatives (2-3) and six known compounds including astraodorol (Arpha et al, 2012), artabotryol B (Gupta et al, 2010), artabotryol C1 (Gupta et al, 2010), 6-dehydrocerevisterol (Lee et al, 2010), ergosterol (Arpha et al, 2012) and hypaphorine (Arpha et al, 2012) from the edible mushroom A. asiaticus, which are described below.…”