2.4.10. Clade Lamiids

The Lamiids produce various types of antimicrobials (Table S2).

*Order Boraginales:* The *Cordia dichotoma* G. Forst. (Boraginaceae) methanol extract restrained *S. pyogenes*, *S. aureus*, *E. coli*, *P. aeruginosa*, *A. niger*, and *C. albicans* [213]. *Merrilliodendron megacarpum* Sleumer (Icacinaceae) yields the strongly antifungal pyranoindolizinoquinoline alkaloid camptothecin (**66**) which also restrains a broad spectrum of virus in vitro (Table S2) [214–219].

*Order Gentianales:* Plants in the genus *Cerbera* L. (Apocynaceae) are antimicrobial. The ethanol extract of *Cerbera manghas* L. very strongly restrained *E. coli* and *P. aeruginosa* (MIC: 4 μg/mL) [17] and VSV (IC50: 0.01 μg/mL) [220]. The methanol extract of seeds of *Cerbera odollam* Gaertn. developed halos with a broad-spectrum of bacteria [221] and the ethanol extract of fruits suppressed *Aspergillus flavus*, *Fusarium oxysporum*, and *Penicillium citrum* [222]. Note that Apocynaceous indole alkaloids are often antistaphylococcal [223]. The ethanol extract of the leaves (500 μg/well) of *Hoya parasitica* (Roxb.) Wall. ex Wight (Asclepiadaceae) inhibited the growth of *S. aureus*, *Proteus sp*., *E. coli*, and *S. sonnei*, and *Shigella dysenteriae* with the IZD of 23, 19, 10, 8, and 20 mm, respectively [224].

In the Rubiaceae, the organic polar and mid-polar extracts of *Guettarda speciosa* L., *Hydnophytum formicarum* Jack, *Morinda citrifolia* L., and *Myrmecodia tuberosa* Jack, and *Guettarda speciosa* L. are antibacterial and antifungal [82,225–228] (Table S2) [81,162,229–231].Plants in this family yield antimicrobial water soluble iridoid glycosides such as in loganic acid (**67**) from *G. speciosa,* which strongly repressed HCV [228], and asperuloside (**68**) from *M. citrifolia* (Table S2) [77,91,93,220,232–234]. Other antimicrobial principles are caffeic acid derivatives including the antiviral 4,5-di-*O*-caffeoylquinic acid (**69**) [229,235] as well as *5*,4--dihydroxy-6,7,8,-trimethoxyflavone (**70**) in *Gardenia lucida Roxb*. [91,234,236], antimycobacterial monoterpene indole alkaloids [230], the chalcone butein (**71**) from *H. formicarum* [22] (Table S2) [88,237], and the anthraquinones damnacanthal (**72**) and 1,3-dihydroxy-5-methoxy-2,6-bismethoxymethyl-9,10-anthraquinone [233] (Table S2) [81,229,230,232]. (*E*)-phytol (**73**) is strongly antimycobacterial [232]. The ethanol extract of *M. citrifolia* is weakly active with the FMDV [238] and the methanol extract of *Psychotria serpens* L. with HSV [155]. The essential oil of the latter is strongly bactericidal with *S. aureus* (MIC/MBC: 39/39 μg/mL) [239].

*Order Lamiales:* In the family Acanthaceae, the chloroform extract of the leaves of *Acanthus ebracteatus* Vahl inhibited the growth of *B. cereus*, *S. aureus*, *P. aeruginosa*, and *Proteus vulgaris, C. albicans*, *Aspergillus fumigatus*, and *A. niger* [240]. This true mangrove herb yields the antibacterial 3,5-dimethoxy-4-hydroxy methyl benzoic acid (**74**), (Z)-4-coumaric acid 4-*O*-β-D-glucopyranoside (**75**), and 6-hydroxy-benzoxazolinone (**76**) (Table S2) [241]. The alcohol extract given to ducklings orally at a dose of 2 g/kg/day for 14 days evoked a decrease in serum hepatitis B surface antigen, AST, ALT, and improved the hepatic cytoarchitecture [242]. The ethanol extract of roots inhibited the replication of the NDV, Vaccinia virus, ECMV, and SFV [130].

*Avicennia* species (Avicenniaceae) are true mangrove trees yielding broad-spectrum antibacterials [243–245] such as the diterpenes excoecarin A (**77**), *ent*-16-hydrozy-3-oxo-13- *epi*-manoyl-oxide (**78**), *ent*-15-hydroxy-labda-8(17), 13*E*-dien-3-one (**79**), which repressed *Rhizopus orizae* and *A. niger* and rhizophorin B with *B. subtilis* (Table S2) [246]. The ethanol extract of *Avicennia alba* L. and *Avicennia officinalis* L. restrained ECMV [130].

*Dolichandrone spathacea* (Burm. f.) Bedd. (Bignoniaceae) is a true mangrove tree yielding the hydroxycinnamic acid glycoside derivatives decaffeoyl acteoside (**80**) and verbascoside (**81**) active against *E. faecalis* (ATCC 1034) and *S. sonnei* (Table S2) [247]. Verbascoside (**81**) very strongly hindered RSV (Table S2) [248].

An extract of the stems and leaves of *Myoporum bontioides* (Siebold & Zucc.) A. Gray (Myoporaceae) moderately inhibited the growth of *F. oxysporum*, *Pestalotia mangiferae*, *Thielaviopsis paradoxa*, *Colletotrichum musae*, *Alternaria alternata*, *Mycosphaerella sentina*, and *Sphaceloma fawcettii* [249]. From this plant, the sesquiterpenes myoporumine A (**82**) and B (**83**), (-)-epingaione (**84**), and (–)-dehydroepingaione (**85**) strongly repressed MRSA (Table S2) [250]. (-)-Epingaione is a strong inhibitor of filamentous fungi [249]. Other antifungal principles in this plant are homomonoterpenes (Table S2) [251]

In the Verbenaceae, *Premna odorata* Blanco produces the strong antimycobacterial long chain alkane 1-heneicosyl formate (**86**) (Table S2) [252]. *Essential oil of plants in this family like in the Lamiaceae are often antifungal* [253]. *The methanol extract (200 μg/disc) developed halos with A. niger and Penicillium cyclopium* [254,255].

*Order Solanales*: The ethanol extract of the flowers of *Ipomoea pes-caprae* (L.) R. Br. (Convolvulaceae) inhibited the growth of *S. aureus*, *B. subtilis*, *Streptococcus mutans*, *P. vulgaris*, *K. pneumoniae*, *E. coli*, *A. flavus*, *A. niger*, and *Penicillium* sp [256]. The methanol extract of the leaves of *Solanum viride* R. Br. (Solanaceae) was weakly active against *S. aureus* and *C. albicans* [257].
