Phragmalin-type Limonoids from Heynea trijuga

Abstract

Nine new phragmalin-type limonoids, heytrijumalins A-I (1-9), together with the known 15-acetyltrichagmalin E (10) were isolated from the branches and leaves of Heynea trijuga. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis. Compounds 6 and 10 showed insecticidal activity at 100 ppm, with corrected mortalities of 82.94 % and 96.02 %, respectively. Compounds 2 and 10 showed weak cytotoxicity against HL-60 and A-549 human tumor cell lines, with IC₅₀ values ranging from 14.55 to 25.27 µM.

Analysis of mexicanolide‐ and phragmalin‐type limonoids from Heynea trijuga using high‐performance liquid chromatography/electrospray tandem mass spectrometry

“…The branches and leaves of H. trijuga were collected from Changjiang County, Hainan Province, China, in December, 2010. The plant was identified by Dr. Guangwan Hu (Kunming Institute of Botany, Chinese Academy of Sciences) . Ethanol (EtOH), petroleum ether (PE), ethyl acetate (EtOAc), and n‐butanol (Bodi Corp., Tianjin, China) were used to prepare the extract.…”

“…Limonoids, a class of tetranortriterpenoids, are mainly found in plants belonging to the families Rutaceae and Meliaceae . These compounds have attracted attention in the fields of nutrition and medicine due to their diverse structures and significant biological activities.…”

“…The biological effects of limonoids include insect antifeedant and growth‐regulating activities, antimicrobial activity, potent cell adhesion inhibitory effects, antimalarial activity against Plasmodium falciparum , anticancer activities, and antioxidant activity . Phragmalin‐ and mexicanolide‐type limonoids show moderate cytotoxicity against HL‐60 cells and insecticidal activity . The potential application necessitates the development of a method for the reliable, fast and low‐cost analysis for this class of compounds.…”

“…In our laboratory, nine phragmalin‐ and mexicanolide‐type limonoids, (15‐acetyltrichagmalin E, heytrijumalin A, heytrijumalin B, heytrijumalin D, heytrijumalin E, heytrijumalin F, heytrijunolide A, heytrijunolide C and heytrijunolide D; Fig. ) were isolated and identified from Heynea trijuga Roxburgh (Meliaceae) . To our knowledge, phragmalin‐ and mexicanolide‐type limonoids have not been studied by electrospray ionization tandem mass spectrometry (ESI‐MS/MS).…”

Triterpenoids

“…Heytrijumalins A 485-I 493 have been isolated from the twigs and leaves of Heynea trijuga. 157 Other new compounds in this group include hisomicines D 494 and E 495 from Chisocheton ceramicus, 158 malayanines A 496 and B 497 from Chisocheton erythrocarpus, 159 senegalensions A 498-C 500 from Khaya senegalensis, 160 kotschyins D 501-H 505 from Pseudocedrela kotschyi, 161 soymidins A 506 and B 507 from Soymida febrifuga 162 and swietenin J 508 from Swietenia macrophylla. 163 Five new mexicanolide derivatives, heytrijunolides A 509-E 513, have been obtained from Heynea trijuga.…”