New 9β-Lanostane-Type Triterpenic and 13,14-seco-Steroidal Esters from the Roots of Artemisia scoparia

Abstract

Phytochemical studies on the roots of Artemisia scoparia, collected from the Kullu Valley region of Himachal Pradesh, India, resulted in the isolation of one lanostane-type triterpenoid 1 and two 13,14-seco-steroids 4 and 8. Their structures have been established as 9β-lanosta-5-ene-3α,27-diol 3α-palmitoleate, 13,14-seco-cholest-7-ene-3,6α,27-triol 3,27-diocta-8‘,6‘-dienoate, and 13,14-seco-cholest-5-ene-3β,27-diol 27-methanoate 3β-hexadeca-11‘,13‘,15‘-trien-1‘-oate on the basis of the spectroscopic techniques and chemical means.

Glutathione S-Transferase Inhibiting Chemical Constituents of Caesalpinia bonduc

“…This indicated that the newly isolated compounds have more or less same activity as that of the standard inhibitor. Nearly half a dozen of 13,14-seco-steroids have been reported in the literature, [12][13][14] and no comments on their biosynthetic origin have been published. We hereby propose a plausible biogenetic pathway that could lead to the formation of the C/D seco ring of the 13,14-seco-steroids.…”

“…Compounds 2-5 were characterized as 13,14-seco-stigmasta-5,14-dien-3a-ol (2), 13,14-seco-stigmasta-9(11),14-dien-3a-ol (3), caesaldekarin J (4) and pipataline (5) by comparison of their 1 H-, 13 C-NMR and mass spectra data with those of reported compounds. 3,[12][13][14]18) 2D NMR spectra (COSY, HSQC, HMBC, NOESY) were also used to confirm their structures.…”

“…3,[12][13][14]18) 2D NMR spectra (COSY, HSQC, HMBC, NOESY) were also used to confirm their structures. Our 2D NMR spectral data of 2 suggested that C-14 and C-15 protons resonated at d 5.00 and 5.12, re- C-NMR chemical shift assignments of C-14 and C-15 for compounds 2 and 3 need to be revised.…”

“…About half a dozen compounds have been previously reported in the class of 13,14-seco-steroids. [12][13][14] Biogenetically, the C/D seco ring may be produced in nature as illustrated in Chart 1.…”

New (9βH)‐Lanostanes and Lanostanes from Mikania aff. jeffreyi (Asteraceae)

“…Only pentacyclic triterpenes were found in the species of Mikania genus until the present work. As mentioned before, (9bH)-lanostanes were isolated from dicotyledone angiosperms only from the plants Santiria trimera (Burseraceae) (two compounds [9]), Pistacia integerrima (Anacardiaceae) (two compounds [11] [12]), and Artemisia escoparia (Asteraceae) (one compound [10]). Finally, this is the second study about acetyl-lanosterol from higher plants [22].…”