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Review
. 2023 May 4;28(9):3873.
doi: 10.3390/molecules28093873.

Antibacterial and Antifungal Terpenes from the Medicinal Angiosperms of Asia and the Pacific: Haystacks and Gold Needles

Christophe Wiart  1 , Geethanjali Kathirvalu  2 , Chandramathi Samudi Raju  2 , Veeranoot Nissapatorn  3 , Mohammed Rahmatullah  4 , Alok K Paul  5 , Mogana Rajagopal  6 , Jaya Seelan Sathiya Seelan  1 , Nor Azizun Rusdi  1 , Scholastica Lanting  1 , Mazdida Sulaiman  7
Affiliations
Review

Antibacterial and Antifungal Terpenes from the Medicinal Angiosperms of Asia and the Pacific: Haystacks and Gold Needles

Christophe Wiart et al. Molecules. .

Abstract

This review identifies terpenes isolated from the medicinal Angiosperms of Asia and the Pacific with antibacterial and/or antifungal activities and analyses their distribution, molecular mass, solubility, and modes of action. All data in this review were compiled from Google Scholar, PubMed, Science Direct, Web of Science, ChemSpider, PubChem, and library searches from 1968 to 2022. About 300 antibacterial and/or antifungal terpenes were identified during this period. Terpenes with a MIC ≤ 2 µg/mL are mostly amphiphilic and active against Gram-positive bacteria, with a molecular mass ranging from about 150 to 550 g/mol, and a polar surface area around 20 Ų. Carvacrol, celastrol, cuminol, dysoxyhainic acid I, ent-1β,14β-diacetoxy-7α-hydroxykaur-16-en-15-one, ergosterol-5,8-endoperoxide, geranylgeraniol, gossypol, 16α-hydroxy-cleroda-3,13 (14)Z-diene-15,16-olide, 7-hydroxycadalene, 17-hydroxyjolkinolide B, (20R)-3β-hydroxy-24,25,26,27-tetranor-5α cycloartan-23,21-olide, mansonone F, (+)-6,6'-methoxygossypol, polygodial, pristimerin, terpinen-4-ol, and α-terpineol are chemical frameworks that could be candidates for the further development of lead antibacterial or antifungal drugs.

Keywords: Asia; Pacific; antibacterial terpenes; antifungal terpenes; medicinal plants.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Antibacterial and antifungal linear monoterpenes. (1) geraniol, (2) nerol, (3) neral, (4) geranyl acetate, (5) geranial, (6) citronellol, (7) citronellal, (8) citronellic acid, (9) linalool, (10) myrcene.
Figure 2
Figure 2
Antibacterial and antifungal cyclic monoterpenes. Borneol (11), isoborneol (12), camphor (13), α-pinene (14), α-pinene-7β-O-β-D-2,6-diacetylglucopyranoside (15), limonene (16), isomenthone (17), piperitone (18), menthol (19), carvone (20), car-3-ene (21), car-3-ene-2,5-dione (22), asarinol A (23), α-terpineol (24), terpinen-4-ol (25), δ-terpineol (26), 1,8-cineole (27), γ-terpinene (28), α-terpinene (29), ascaridole (30), p-cymene (31), cuminol (32), thymol (33), 7-acetyl-8,9-dihydroxy thymol (34), 7,8-dihydroxy-9-butyryl thymol (35), carvacrol (37).
Figure 3
Figure 3
Antibacterial and antifungal linear sesquiterpenes. Farnesol (38), farnesal (39).
Figure 4
Figure 4
Antibacterial and antifungal cyclic sesquiterpenes. Germacrone (40), dehydrocurdione (41), 1(10),4(5)-diepoxygermacrone (42), c urdione (43), β-elemene (44), costunolide (45),cynaropicrin (46), deacetylxanthumine (47), isoalantolactone (48), microjaponin (49), 8-acetoxymutangin (50), monichinine H (51), gossypol (52), (+)-6,6′-methoxygossypol (53), 7-hydroxycadalene (54), mansonone E (55), mansonone F (56), cedrelanol (57),(+)-8-hydroxy calamenen (58), 4-(1,5-dimethyl-3-oxo-4-hexenyl) benzoic acid (59), artemisinin (60), α-humulene (61), α-santalol (62), β-santalol (63), and polygodial (64).
Figure 5
Figure 5
Antibacterial and antifungal linear diterpenes. Geranylgeraniol (65), (E)-phytol (66).
Figure 6
Figure 6
Antibacterial and antifungal cyclic diterpenes. Toonaciliatin M (67), 17-hydroxyjolkinolide B (68), cryptotanshinone (69), dihydrotanshinone I (70), carnosic acid (71), carnosol (72), is 6β-cinnamoyl-7β-hydroxyvouacapen-5α-ol (73), Niloticane (74), neocaesalpin P (75), phytocassane B (76), E)-8β, 17-epoxylabd-12-ene-15,16-dial (77), ent-trachyloban-19-oic acid (78), ent-kaur-16-en-19-oic acid (79), ent-18-acetoxy-7α-hydroxykaur-16-en-15-one (80), ent-1β,14β-diacetoxy-7α-hydroxykaur-16-en-15-one (81), lasiodin (82), bafoudiosbulbin C (83), 16α-hydroxy-cleroda-3,13 (14)Z-diene-15,16-olide (84), 16-oxo-cleroda-3, 13(14) E-diene-15 oic acid (85), euphoheliosnoid E (86), ovatodiolide (87), and dehydroabietylamine (88).
Figure 7
Figure 7
Antibacterial and antifungal cyclic triterpenes. 4-Seco-mansumbinoic acid (90), β-amyrin (91), aceriphyllic acid A (92), gypsogenin (93), dysoxyhainic acid I (94), taraxerone (95), friedelin (96), pristimerin (97), celastrol (98), zeylasterone (99), (20R)-3β-hydroxy-24,25,26,27-tetranor-5α cycloartan-23,21-olide (100), bryononic acid (101), 7-cinnamoyltoosendanin (102), swietenolide (103), mulavanin D (104), 2-hydroxyfissinolide (105), (6R)-methoxyjavanicin B (106), ergosterol-5,8-endoperoxide (107), stigmasterol 3–O–β–D–glucopyranoside (108), and dioscin (109).
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